Marine Natural Product

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REVIEW View Journal | View Issue
Marine natural products‡

Cite this: Nat. Prod. Rep., 2016, 33, 382
John W. Blunt,*a Brent R. Copp,b Robert A. Keyzers,c Murray H. G. Munroa
and Michèle R. Prinsepd
Covering: 2014. Previous review: Nat. Prod. Rep., 2015, 32, 116–211
This review covers the literature published in 2014 for marine natural products (MNPs), with 1116
citations (753 for the period January to December 2014) referring to compounds isolated from
marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians,
bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and
Received 17th December 2015
Accepted 20th January 2016
microorganisms. The emphasis is on new compounds (1378 in 456 papers for 2014), together with
the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic
DOI: 10.1039/c5np00156k
studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries,
www.rsc.org/npr have been included.
1 Introduction
1 Introduction
2 Reviews
3 Marine microorganisms and phytoplankton These annual reviews of marine natural products were initiated
3.1 Marine-sourced bacteria (excluding from mangroves) by the late Professor D. John Faulkner in 19841,2 and continued
3.2 Bacteria from mangroves by the New Zealand group since 2003. A feature of the reviews
3.3 Marine-sourced fungi (excluding from mangroves) has been the inclusion of the structures for all new MNPs, and
3.4 Fungi from mangroves any subsequently revised structures. The number of new MNPs
3.5 Cyanobacteria reported each year has steadily grown from 332 in 1984 to 1378
3.6 Dinoagellates in this present review of the 2014 literature. This has inevitably
4 Green algae resulted in an increased size for each review. With the ever-
5 Brown algae increasing size creating difficulties for preparation of the
6 Red algae annual review, the NPR Editorial Board suggested changing the
7 Sponges format to focus on a selection of highlighted structures. To
8 Cnidarians maintain the usual comprehensive coverage of all new and
9 Bryozoans revised MNPs, we have prepared a ESI‡ document with links
10 Molluscs associated with this review, showing all structures, along with
11 Tunicates (ascidians) their names, taxonomic origins, locations for collections, and
12 Echinoderms biological activities. The numbers for all highlighted structures
13 Mangroves in this review (169) are shown in non-italicised bold font, while
14 Miscellaneous italicised numbers refer to the remaining structures in the ESI
15 Conclusion document.‡ For structures that have their absolute congura-
16 Acknowledgements tions fully described, the compound number in the diagrams is
17 References preceded with †. In addition to the highlighted compounds in
this review, we have retained the inclusion of reference to rst
syntheses of MNPs, and comments on new information on
a
Department of Chemistry, University of Canterbury, Christchurch, New Zealand.
ecological aspects, bioactivities or other relevant data for
E-mail: john.blunt@canterbury.ac.nz
b
previously reported MNPs, all as non-highlighted material. The
School of Chemical Sciences, University of Auckland, Auckland, New Zealand
c
Centre for Biodiscovery, School of Chemical and Physical Sciences, Victoria University
Reviews section (Section 2) has also been reformatted to show
of Wellington, Wellington, New Zealand selected highlights, with all other reviews referenced in
d
Chemistry, School of Science, University of Waikato, Hamilton, New Zealand a section of the ESI document.‡
‡ Electronic supplementary information (ESI) available. See DOI:
10.1039/c5np00156k
382 | Nat. Prod. Rep., 2016, 33, 382–431 This journal is © The Royal Society of Chemistry 2016
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Review Natural Product Reports
signicant reviews (16) are given here while a listing of the

2 Reviews remainder (71) is given in the ESI section.‡ A comprehensive
There continues to be a steady increase in the number of review of MNPs reported in 2012 has appeared.3 ‘Marine-sourced
reviews of various aspects of MNP studies. Some of the more anticancer and cancer pain control agents in clinical and late
preclinical development’ have been reviewed,4 and ‘New horizons

for old drugs and drug leads’ were described.5 The implications of
John Blunt obtained his BSc
the Convention on Biological Diversity (1999) and its Nagoya
(Hons) and PhD degrees from the
Protocol (2010) on the collection of marine genetic resources
University of Canterbury, fol-
has been discussed and should be noted by all who collect
lowed by postdoctoral appoint-
marine organisms for MNP studies.6 The putative microbial
ments in Biochemistry at the
origin of sponge metabolites has been the subject of several
University of Wisconsin–Madi-
reviews and articles.7–11 Developments in chemical ecology for
son, and with Sir Ewart Jones at
sh and benthic algae and invertebrates for 2010–2012 have
Oxford University. He took up
been reviewed, with comment on the biosynthesis of bioactive
a lectureship at the University of
MNPs by symbiotic microorganisms.12 Polyketide biosynthesis
Canterbury in 1970, from where
in dinoagellates has been reviewed.13 There have been
he retired as an Emeritus
comprehensive reviews for marine nucleosides,14 saxitoxin,15
Professor in 2008. His research
and tetrodotoxin.16 A review of ‘Emerging strategies and inte-
interests are with natural prod-
grated systems microbiology technologies for biodiscovery of marine
ucts, the application of NMR techniques to structural problems, and
bioactive compounds’ provides a very useful oversight of
the construction of databases to facilitate natural product investi-
a number of developing techniques.17 ‘AlgaeBase: an on-line
gations.
Brent Copp received his BSc Murray Munro, Emeritus

(Hons) and PhD degrees from the Professor in Chemistry at the
University of Canterbury, where University of Canterbury, has
he studied the isolation, structure worked on natural products right
elucidation and structure– through his career. This started
activity relationships of biologi- with diterpenoids (PhD; Peter
cally active marine natural Grant, University of Otago), fol-
products under the guidance of lowed by alkaloids during a post-
Professors Blunt and Munro. He doctoral spell with Alan
undertook postdoctoral research Battersby at Liverpool. A sabbat-
with Jon Clardy at Cornell and ical with Ken Rinehart at the
Chris Ireland at the University of University of Illinois in 1973 led
Utah. 1992–93 was spent to an interest in marine natural
working in industry as an isolation chemist with Xenova Plc, before products with a particular focus on bioactive compounds which has
returning to New Zealand to take a lectureship at the University of continued to this day. In recent years his research interests have
Auckland, where he is currently an Associate Professor. widened to include terrestrial/marine fungi and actinomycetes.
Rob Keyzers carried out his BSc Michèle Prinsep received her BSc
(Hons) and PhD studies at (Hons) and PhD degrees from the
Victoria University of Wellington. University of Canterbury, where
His thesis research, carried out she studied the isolation and
under the guidance of Assoc. Prof. structural elucidation of biologi-
Peter Northcote, a former cally active secondary metabo-
contributor to this review, lites from sponges and bryozoans
focused on spectroscopy-guided under the supervision of Profes-
isolation of sponge metabolites. sors Blunt and Munro. She
He then carried out post-doctoral undertook postdoctoral research
research with Mike Davies-Cole- on cyanobacteria with Richard
man (Rhodes University, South Moore at the University of
Africa) and Raymond Andersen Hawaii before returning to New
(University of British Columbia, Canada) before a short role as Zealand to take up a lectureship at the University of Waikato, where
a avour and aroma chemist at CSIRO in Adelaide, Australia. He she is currently an Associate Professor.
was appointed to the faculty at his alma mater in 2009 where he is
currently a Senior Lecturer.
This journal is © The Royal Society of Chemistry 2016 Nat. Prod. Rep., 2016, 33, 382–431 | 383
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resource for algae’ is an article describing a very comprehensive method resulting in isolation of the O-glycosylated angucyclines
algal database.18 As in previous years, the MarinLit database19 actinosporin A 4 and B 5 of which actinosporin A 4 possessed
has been updated and used as the literature source for the moderate activity against the causative agent of sleeping sick-
preparation of this present review. ness, Trypanosoma brucei (T. brucei).25
3 Marine microorganisms and

phytoplankton
Even considering the trend of recent years that many marine
natural products research efforts are directed towards micro-
organisms, there has been a sharp upward swing in the number
of new metabolites reported from marine microorganisms (677
vs. 493 in 2013). Unless otherwise stated, compounds described
in this section were obtained from cultures of the named
microorganisms.
3.1 Marine-sourced bacteria (excluding from mangroves)

The number of new compounds reported from marine bacteria
(164) is similar to the 158 reported in 2013. A metagenomic
approach has identied the gene cassette responsible for the
biosynthesis of calyculin A, originally isolated from the sponge
Discodermia calyx,20 as microbial in origin, arising from Candi-
datus Entotheonella sp. Functional analysis of the biosynthetic A Korean sediment-derived strain of Bacillus subtilis (B.
pathway has shown that the end product is actually a diphos- subtilis) has yielded a variety of linear lipopeptides with
phate protoxin, phosphocalyculin A 1 rather than calyculin A, differing biological properties, the gageopeptides A–D 6–9,26
suggesting a phosphorylation/dephosphorylation mechanism gageostatins A–C 10–1227 and gageotetrins A–C 13–15.28 Most
for the active chemical defence of the host sponge.21 A further are non-cytotoxic with good antibacterial activity, but better
diphosphate, protoxin phosphocalyculin C 2, has been isolated antifungal activity especially against the late blight pathogen
from D. calyx but can be assumed to have arisen from the same Phytophthora capsici in the case of gageotetrins A–C. A trans-
microbial source. Phosphocalyculin C, although potent (IC50 ¼ formation-associated recombination (TAR) cloning approach
36 nM vs. P388), is 5000 times less toxic than calyculin C itself.22 was used to capture, activate and express a 67-kb non-ribosomal
peptide synthetase (NRPS) biosynthetic gene cluster from Sac-
charomonospora sp., resulting in isolation of the dichlorinated
lipopeptide antibiotic taromycin A 16.29
Solwaraspora sp. (ascidian, Trididemnum orbiculatum, Flor-
ida Keys, U.S.A.) produced the trialkyl-substituted aromatic
acids, solwaric acids A 17 and B 18. Enrichment with 13C-
labelled glucose followed by acquisition of a 13C–13C COSY
enabled unambiguous determination of the position of the
methyl group on the phenyl ring, an approach which could be
very useful for structural determination of molecules with
multiple quaternary carbons.30
Heronapyrroles A–C are nitropyrrole metabolites with
a partially oxidised farnesyl chain appended that were obtained
from a Streptomyces sp.31 Biosynthetic considerations prompted
A Chinese sediment-derived Actinoalloteichus cyanogriseus23 the hypothesis that a mono-tetrahydrofuran-diol, heronapyrrole
was the source of cyanogramide 3, an unprecedented spirocyclic D might be an as yet unidentied metabolite of the bacterium.
alkaloid with multidrug-resistance (MDR) reversing activity.24 Following a putative biomimetic synthesis of heronapyrrole D
An interesting dereplication strategy was utilised in the study of 19 the metabolite was then detected in cultures of the bacte-
sponge-associated Actinokineospora sp. Principal Component rium, thus validating this approach.32 Total synthesis of her-
Analysis (PCA), hierarchical clustering (HCA) and orthogonal onapyrrole C31 has also been reported.33 Mollemycin A 20 is
partial least square-discriminant analysis (OPLS-DA) were a rst-in-class glycol-hexadepsipeptide-polyketide from a Strep-
employed to evaluate HRFTMS and NMR data of crude extracts tomyces sp. (sediment, South Molle Is., Queensland, Australia)
arising from four different fermentation regimes. Statistical and active against certain Gram-positive and Gram negative
analysis enabled identication of the most suitable one-strain- bacteria, in addition to extremely potent antimalarial activity
many-compounds (OSMAC) culture conditions and extraction
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has now led to isolation of a number of bisindole alkaloids;

indimicins A–E 21–25, lynamycins F 26 and G 2737 and pier-
icidin E1 2836 using the same modied A1BFe + C medium.
Piericidin E1 28 was shown to be an intermediate in the
biosynthesis of piericidin A138 during identication of the

biosynthetic gene cluster.
against drug sensitive and MDR Plasmodium falciparum (P. fal- Growth of the strain in modied ISP3 medium yielded her-
ciparum) clones.34 onamides D–F 29–31.39 Violapyrones H 32, I 33, B 34 and C 3540
A deep-sea strain of Streptomyces, previously a source of were obtained from Streptomyces sp. (starsh, Acanthaster
spiroindimicins A–D,35 lynamycins A and D35 and piericidins36 planci, Chuuk, Federated States of Micronesia).41 Violapyrone C
35 has since been synthesised and the absolute conguration
determined.42
A study of the biosynthetic pathway for marineosins43 in

Streptomyces sp. led to isolation of 23-hydrox-
yundecylprodiginine 36, 23-ketoundecylprodiginine 37, pre-
marineosin A 38 and 16-ketopremarineosin A 39.44 Syntheses of
23-hydroxyundecylprodiginine 36 (both enantiomers and the
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perdeuterated version) and of 23-ketoundecylprodiginine 37 Escherichia, Jejua, Micrococcus, Micromonospora, Nocardiopsis,

were reported, as was the feeding of synthetic prodiginine Pelomonas, Pseudoalteromonas, Rapidithrix, Salinispora and
analogues which led to the production of novel premarineosins, Shewanella.57–80 As usual, many new metabolites, and some with
although these were not fully characterised.45 revised structures, were also obtained from the genus Strepto-
myces including 104–172.81–103 The genera Verrucosispora and

Vibrio also yielded new metabolites 173 and 174.104,105 Investi-
gation of an octocoral-associated Pseudoalteromonas sp. by
MALDI-imaging mass spectrometry (IMS) and molecular
network analyses indicated that the strain produces higher
levels of the antifungal polyketides, alteramides106,107 in the dark
than in the light and also led to revision of the conguration at
C-6 for 175 and 176.108 In the light, these compounds were
inactivated through a photoinduced intramolecular cyclisation
and production of higher levels of these antifungal metabolites
in the dark was proposed as a strategy to protect the host corals
during night feeding, when they are more exposed.108 Synthesis
of the proposed structure of heronamide C109 has indicated that
the actual structure of the natural product needs to be re-
examined110 and the structure of anthracimycin111 has also been
corrected to 177.112 Total syntheses of indoxamycins113 has led
to stereochemical revision for the indoxamycins B,114 D113 and
The structure of merochlorin A46,47 has been revised to 4048
E113 to 178–180.115 A number of other total syntheses of bacterial
and a biomimetic synthesis of ()-merochlorin B46 has been
metabolites have been reported. These include syntheses of the
achieved,49 while a study of the biosynthesis of the merochlorins
depsipeptides, solanamides A116 and B116,117 and arenamides B118
revealed that just four enzymes are involved50 and that a vana-
and C,118,119 and synthesis120 of the nucleoside antibiotic
dium-dependent chloroperoxidase mediated a complex series
A201A.121,122 Total synthesis of dixiamycin B123 was achieved
of unprecedented transformations in the biosynthesis. Devel-
utilising electrochemical oxidation.124 The alkaloid mansour-
opment of a chlorination method paralleling the biocatalytic
amycin D125,126 was synthesised, as was 5-deoxyte-
process led to the identication of previously undiscovered
trodotoxin.127,128 New biological activities have been reported for
merochlorins 41–43.51 The known synthetic compound ser-
sporolide B129 from Salinispora tropica,130 for some buteno-
iniquinone 4452 has now been obtained as a natural product
lides131,132 and undecylprodigiosin133 from Streptomyces
from Serinicoccus sp. and displayed potent and selective anti-
strains.134,135 Biosynthetic studies have been conducted into
tumour activity.53
various bacterial metabolites including arachidonic acid (in
Aureispira marina),136,137 macrolactins138 and bacillaene139 (in
Bacillus marinus),140 polybrominated aromatics141 (in Mar-
inomonas mediterranea142 and Pseudoalteromonas spp.143),
lomaiviticins144 (in Salinispora pacica145,146 (formerly Micro-
monospora lomaivitiensis)), tropodithietic acid147 (in Phaeobacter
inhibens),148 sulfur volatiles149 (in the Roseobacter clade)150 and
avaroferrin151 and putrebactin152 (in Shewanella sp.).153 Biosyn-
thetic studies within the genus Streptomyces include those on
thiocoraline154 (in S. albus),155 ikarugamycin,156–158 anti-
mycins159,160 and polyhydroxylated saturated fatty acids,161
marinophenazines162–164 and the isoprenylated phenazines,165,166
JBIR-46, JBIR-47 and JBIR-48.167
3.2 Bacteria from mangroves

Investigation of the biosynthesis of sulfur-containing rose- There has been an increase in the number of new metabolites
obacticides54,55 produced by Phaeobacter inhibens indicated that reported from bacteria associated with mangroves (23 in 2014
these compounds arise from three subunits – dimethylsulfo- vs. 10 in 2013). Lechevalieria aerocolonigenes yielded the cyclo-
niopropionate, phenylacetic acid and p-coumaric acid and that pentadecane metabolites, mangromicins A 181, B 182168 and
roseobacticides regulate the symbiosis between P. inhibens and D–I 183–188,169 with mangromicin A 181 exhibiting potent
the microalga Emiliana huxleyi.56 Further new metabolites 45– antitrypanosomal and radical scavenging (DPPH) activi-
103 were obtained from the genera Actinoalloteichus, Actino- ties.168,169 New divergolide congeners 189–192 were obtained
madura, Actinokineospora, Amycolatopsis, Bacillus, Dermacoccus, from an endophytic Streptomyces strain170 and the biosynthetic
gene cluster for divergolides171 identied and characterised.172
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Other metabolites 193–203 were isolated from the genera Jish- penilumamide C 210 led to speculation that these compounds
engella, Micromonospora, Streptomyces and Verrucosispora,173–176 were derived from oxidation of a putative metabolite containing
and a bio-inspired total synthesis of the indole sesquiterpenoid a methionine residue. This led to a feeding experiment with L-
sespenine177 completed.178 methionine resulting in isolation of the sulde, penilumamide
B 209. Yields of penilumamide B 209 and penilumamide

increased with increasing concentration of L-methionine and
when penilumamide B 209 was exposed to air, penilumamide
was detected aer a few days whilst penilumamide C 210 was
formed several days later.189
3.3 Marine-sourced fungi (excluding from mangroves) Of the two prenylated hydroquinone derivatives 213 and 214
obtained from a gorgonian-derived Aspergillus sp., 214 exhibited
Studies of fungi continue to rise with 318 new compounds re- very potent activity against respiratory syncytial virus (RSV).190
ported in 2014 compared to 223 in 2013. Sponge-associated These two metabolites differ only in the conguration of
Aspergillus similanensis yielded two isocoumarin derivatives 204 a methyl group on a cyclohexane ring yet given that 214 is an
and 205, and a deacetyl analogue of chevalone C,179 chevalone E extremely potent anti-RSV agent whilst its epimer 213 is
206, in addition to pyripyropene S 207.180 While chevalone E 206 completely inactive, indicating the importance of the congu-
itself did not display signicant antibacterial activity, it did ration of this ring for anti RSV-activity.
exhibit synergy with the antibiotics oxacillin and ampicillin
against MRSA.181 Ultrasonication of Aspergillus versicolor spores
led to the isolation of a mutant with neomycin resistance from
which six metabolites not present in the parent strain,
including 208 were obtained. Although several patents exist for
synthesis of the planar structure of this compound,182–184 this is
the rst natural product (NP) isolation and establishment of
stereochemistry.
So-coral associated Chondrostereum sp. has previously been

reported to produce hirsutane-framed sesquiterpenes.191–193
Cultivation of the fungus in a medium with glycerol as the
carbon source led to the isolation of the sesquiterpenes chon-
drosterin I 215 and J 216 of which chondrosterin J 216 displayed
potent activity against HTCLs.194 Chemical epigenetic modi-
cation of Cochliobolus lunatus (sea anemone Palythoa haddoni)
Cyclo(D-Tyr-D-Pro) was also claimed as a rst NP isolation but
with inhibitors of histone deacetylase (HDAC) resulted in
this has previously been obtained from both terrestrial185 and
isolation of two brominated 14-membered resorcylic acid
marine186 sources.187 Lumazine peptides, penilumamide B–D
lactones 217 and 218, but only in the presence of an HDAC
209–211 and a cyclic pentapeptide, asperpeptide A 212 were
inhibitor.195
obtained from a gorgonian-derived Aspergillus sp. The presence
of the sulfone penilumamide188 and the derived sulfoxide
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The chromones engyodontiumone A–H 219–226 and the

phenol derivatives 227–229 were derived from deep-sea derived
Engyodontium album. Of these, engyodontiumones E–G 223–225
were obtained as racemates.196 The known polyketide aspergillus
one B197 was also isolated and was a potent inhibitor of settle-
ment of Balanus amphitrite (B. amphitrite) larvae.196 Fermentation
of a lamentous fungus of the Eurotiomycetes class (ascidian,
Lissoclinum patella, Papua New Guinea) produced the pentacyclic Biosynthetic feeding experiments on Penicillium citrinum
oxazinin A 230, derived from a combination of benzoxazine, using 13C labelled glucose, anthranilic acid and ornithine resul-
isoquinoline and pyran rings. Oxazinin A 230 occurred as ted in isolation of two new citrinalins, 17-hydroxycitrinalin B 240
a racemate and was antimycobacterial.198 and citrinalin C 241 and supported the proposition that the cit-
rinalins arise from a bicyclo[2.2.2]diazaoctane precursor. Also in
this investigation, synthesis of the enantiomer of citrinalin B201
led to revision of the structure of citrinalin B to 242.202 Pen-
icillipyrones A 243 and B 244 are meroterpenoids obtained from
a sediment-derived Penicillium strain and represent a new skel-
etal class with a unique linkage between the drimane sesquiter-
pene and pyrone moieties. Penicillipyrone B 244 elicited
signicant induction of quinone reductase in murine hepatoma
cells, indicating a possible cancer preventative role.203
Neosartorya pseudoscheri (starsh Acanthaster planci,

Hainan, China) produced different suites of metabolites when
cultured in different media. When cultured in glycerol–
peptone–yeast extract (GlyPy), the diketopiperazines neosartin A
231 and B 232 were produced along with six known diketopi-
perazines and a precursor alkaloid but when fermented in
glucose–peptone–yeast extract (GluPy), a tetracyclic-fused alka-
loid neosartin C 233 was produced along with a known mer- Metabolites 245–254 were also obtained from the genera
oterpenoid and ve known gliotoxin analogues 234–238, Acremonium, Arthrinium, Ascotricha and Astrocystis.204–207 As usual,
obtained here for the rst time as NPs.199 Endophytic Paecilo- a large number of metabolites were obtained from species of the
myces variotii (red alga, Grateloupia turuturu, Qingdao, China) Aspergillus genus. Two indole diterpenoids 255 and 256, and an
yielded varioxepine A 239, an alkaloid with an unprecedented isocoumarin 257 were obtained from A. avus. The known
3,6,8-trioxabicyclo[3.2.1]octane unit.200 compounds b-aatrem,208 paspalinine209,210 and leporine B211 were
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isolated and leporine A212 was prepared from the last of these. metabolites that were not produced under normal culture
Congurations were established for each as 258–261 respectively conditions: A. sclerotiorum produced aspochracin340,341 when
and b-aatrem and leporine B were isolated for the rst time as stressed with copper and produced stephacidin A342 and notoa-
MNPs.213 Other metabolites isolated from the genus Aspergillus mides B342 and F343 under normal culture conditions whilst A.
include 262–327 (the last obtained from co-culture with an clavatus produced the acetophenone derivative clavatol344,345 under
unidentied bacterium).214–237 New metabolites 328–371 were also stress conditions and deoxytryptoquivaline346 and tryptoquivaline
obtained from the genera Beauveria, Cladosporium, Cochliobolus, A346 in metal-free culture.347
Curvularia, Dendrodochium, Diaporthaceae, Dichotomomyces,
Emericella and Eurotium.238–250 A pyrrolidinoindoline diketopiper-
azine dimer, cristatumin E, isolated from Eurotium herbariorum,251 3.4 Fungi from mangroves
appears to be identical to the previously reported eurocristatine.252 There has been a considerable increase in the number of new
The genera Hansfordia, Humicola, Isaria, Neosartorya, Nigrospora, metabolites reported from mangrove-associated fungi (108 in
Paecilomyces and Paraconiothyrium also yielded the new metabo- 2014 vs. 75 in 2013), with the majority coming from endophytic
lites 372–399.179,253–258 The genus Penicillium was the source of species. Co-culture of Alternaria and Phomopsis species led to
many other metabolites 400–461.259–278 Other genera to yield new isolation of three cyclic peptides 528–530, all of which exhibited
the metabolites 462–520 were Pseudallescheria, Spicaria, Spi- signicant activity against a range of plant pathogenic
romastix, Stachybotrys, Talaromyces, Trichoderma, Xylaria and fungi,348,349 whilst co-culture of two brown alga (Sargassum)-
Xylariaceae,279–291 while 521 was obtained from a strain of the derived Aspergillus species also produced a cyclic peptide, psy-
order Xylariales and also synthesised.292 A number of syntheses of chrophilin E 531.350
fungal metabolites have resulted in structural revisions of the
natural products, including syntheses of ()-protubonine A 522,
()-protubonine B 523 (Aspergillus sp.)293,294 and (+)-cristatumin C
524 (Eurotium cristatum).295,296 Synthesis of the racemate of oxali-
cumone C (Penicillium oxalicum)297 followed by resolution by chiral
HPLC and examination of experimental and calculated ECD data,
resulted in the conguration of the natural product being
assigned as (S)-525.298 Culture of a strain of Aspergillus clavatus
isolated from the hydrothermal vent crab Xenograpsus testudinatus
in the presence of the abiotic stress agent and hydrothermal vent
uid component zinc (as zinc sulfate), elicited production of
a known synthetic cyclic peptide299 that was isolated for the rst
time from a natural source and named as clavatustide C 526. The
fungus did not produce clavatustide C 526 when cultured in the
absence of zinc.300 Pericosine E301 (Periconia byssoides) occurs as an
enantiomeric mixture in nature and synthesis of the preferred
enantiomer ()-pericosine E 527 has been reported.302 First
syntheses of a number of fungal metabolites achieved include
those of secalonic acids A303 (Paecilomyces sp.)304 and D305 (Glio-
cladium sp.)306,307 ()-sorbiterrin A308 (Penicillium terrestre),309
()-auronamide C310 (Penicillium aurantiogriseum),311 calcaripep-
tides A–C312 (Calcarisporium sp.),313 ()-aspergilazine A314 (Asper-
gillus taichungensis),315 aspirin316 (Aspergillus versicolor),317
cochliomycin B318 (Cochliobolus lunatus),319 dendroides320 (Den-
drodochium sp.) A,321 B322 and E,322 paecilocin323 (Paecilomyces
variotii),324 penicimonoterpene325 (Penicillium chrysogenum)326 and
(+)-penostatin E327 (Penicillium sp.).328 The benzaldehyde derivative
isotetrahydro-auroglaucin329,330 has been shown to exhibit anti-
inammatory activity, inhibiting the NF-kB pathway through
suppressing production of both pro-inammatory mediators and
cytokines.331 Oxirapentyns A332,333 and B333 exhibited growth stim-
ulatory effects on seedling roots of barley and wheat334 while iso-
echinulin A335,336 was a strong inhibitor of settlement of larvae of
the barnacle B. amphitrite.337 Methylpenicinoline338 also displayed
anti-inammatory activity, suppressing expression of pro-inam-
matory mediators through the NF-kB and MAPK pathways.339
Heavy metal stress of two strains of hydrothermal vent fungi
(Aspergillus sclerotiorum and A. clavatus) induced biosynthesis of
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Aspergillus avipes was the source of the aromatic butyr- inhibited Mycobacterium tuberculosis protein tyrosine phos-
olactones, avipesin A 532 and B 533 and the previously syn- phatase B (MptpB).358
thesised 534351 and 535,352 of which avipesin A 532 exhibited The polyketides 544 and 545 were obtained from co-culture
moderate to good antibacterial activity. Unlike penicillin, it was of mangrove soil derived Penicillium sp. with the sediment
able to penetrate the biolm matrix to kill live bacteria inside derived bacterium Streptomyces fradiae and were not produced
mature Staphylococcus aureus biolm.353 An endophytic Dia- in discrete bacterial and fungal control cultures, suggesting the
porthe sp. was the source of diaporine 536, an unprecedented activation of silent gene clusters by co-cultivation. These also
symmetric polyketide which induces conversion of tumour occurred as a racemate and were separated by chiral chroma-
associated macrophages from the M2 to the M1 phenotype in tography into 544359 a known terrestrial fungal metabolite
both cellular and animal models.354 (9R,14S)-epoxy-11-deoxyfunicone, but now isolated as a rst-
time MNP, and the enantiomer (9S,14R)-epoxy-11-deoxy-
funicone 545.360 An endophytic Penicillium sp. was the source of
a phenyl ether derivative 546 and a spiroax-4-ene-12-one deriv-
ative 547 with the spiroax-4-ene-12-one derivative 547 more
potent to the MG-63 cell line with in vivo activity and signicant
inhibition of human osteosarcoma in nude mice upon oral
administration.361 The prenylated phenols vaccinol A–G, 548–
554 and the naphthalene derivative vaccinal A 555 were isolated
from Pestalotiopsis vaccinii. Vaccinal A 555 exhibited potent
COX-2 inhibition.362 Other genera or families of fungi associ-
ated with mangroves to yield the new metabolites 556–635 were
Acremonium, Alternaria, Daldinia, Guignardia, Penicillium, Pes-
talotiopsis, Phoma, Phomopsis, Pseudolagarobasidium, Rhy-
tidhysteron, Stemphylium and Xylariaceae.363–388
The polyketides dothiorelone F 537 and I 538 were obtained

from endophytic Dothiorella sp. along with three known
analogues.355 Of these analogues, dothiorelone G356 is actually
the same as the previously reported cytosporone R,357 also ob-
tained from a mangrove associated species (Leucostoma per-
soonii). Peniphenones A–D 539–543 were obtained from
Penicillium dipodomyicola. Of these, peniphenone A 539, 540 3.5 Cyanobacteria
occurs as a racemate and was separated into its enantiomers by There has been an increase in the number of new metabolites
chiral HPLC while peniphenones B 541 and C 542 strongly reported from cyanobacteria since 2013, but the total numbers
are still low overall (20 in 2014 vs. 9 in 2013), seemingly
continuing an overall downward trend. Typical of the phylum,
the vast majority of metabolites reported were peptidic in
nature. Although not peptidic, yoshinone A 636 and the dia-
stereoisomers yoshinone B1 and B2 637 were isolated from
Leptolyngbya sp. Yoshinone A 636 inhibited differentiation of
3T3-L1 cells into adipocytes without accompanying cytotoxicity
suggesting potential as an anti-obesity lead.389 A cyanobacterial
assemblage, consisting mostly of Lyngbya sp. (now renamed as
Moorea sp.) yielded the dolastatin 13 analogue, kurahamide
638, a strong inhibitor of the proteases elastase and chymo-
trypsin390 and the acetylenic lipopeptide kurahyne 639 an
inhibitor of the HeLa cell line and inducer of apoptosis.391
Mooreamide A 640 is a cannabinomimetic lipid obtained
from Moorea bouillonii and is the most potent marine-derived
inhibitor of the neuroreceptor CB1 reported to date.392 Two new
aplysiatoxin analogues, 3-methoxyaplysiatoxin 641 and 3-
methoxydebromoaplysiatoxin 642 were isolated from Tricho-
desmium erythraeum and 642, along with the co-isolated
known debromo analogues debromoaplysiatoxin393 and
View Article Online
for itralamide B415 and coibamide A416 have indicated that the
structures of these natural products require revision.417,418
Grassypeptolides A–C419 were shown to selectively inhibit the
dipeptidyl peptidase (DPP8) protease and molecular docking
studies indicated that grassypeptolide A binds to the enzyme at

two different sites.420 Gallinamide A421 was shown to be a potent
and selective inhibitor of the human cysteine protease
cathepsin L.422 A genome mining approach was utilised to
identify three proteusin rSAM epimerases, enzymes which
install multiple D-amino acids in genetically encoded peptide
chains, from three strains of cyanobacteria including a marine-
derived Pleurocapsa strain.423 A genome mining approach was
also used to show that LanA peptides, linear precursor peptides
of lanthionine-containing peptides (lanthipeptides),424 are
highly diverse among different systems and that closely related
lanthipeptide synthetases can be associated with quite different
substrate sets.425
3.6 Dinoagellates
The number of new metabolites reported from dinoagellates
has remained about the same as for 2013 with 19 compounds
reported in 2014. The linear polyketide, amphirionin-4 658,
from an Amphidinium species displayed very potent and
selective growth promotion activity on murine bone marrow
stromal ST-2 cells. Feeding experiments with 13C single and
anhydrodebromoaplysiatoxin,394 were inhibitors of the Chi- double labelled acetate indicated that polyketide 658
kungunya virus.395 comprises a linear C22 chain with two irregular C1 sites
(in the terahydrofuran moiety) and four C1 branches.426
Dinophysis acuminata was the source of the macrolide
acuminolide A 659 which was non-toxic to human tumour cell
lines (HTCLs) but a potent stimulator of actomyosin ATPase
activity.427 Belizentrin 660, a 25-membered macrolactam ob-
tained from Prorocentrum belizeanum is the rst member of its
class of polyunsaturated and polyhydroxylated macrocycles
and displayed potent effects on neuronal network integrity in
cerebellar cells, ultimately resulting in cell death.428
Other genera of dinoagellates from which the new
metabolites 661–675 were isolated include Amphidinium,
Azadinium, Karenia and Vulcanodinium.429–436 Tentative struc-
tures were assigned to ovatoxin-g 676 and an isomer of paly-
toxin, the so-called isobaric palytoxin.437 The absolute
conguration of amphidinin A438 was determined as 677.439
Synthesis of genetically predicted saxitoxin intermediates
with identication and quantication in the dinoagellate
Alexandrium tamarense and the cyanobacterium Anabaena
cicinalis supports the genetically proposed biosynthetic
Other new metabolites 643–655 were obtained from the
route440 to saxitoxin.441 Metabolomic and proteomic analyses
genera Anabaena, Lyngbya, Moorea, Oscillatoria and Sym-
indicated that Karenia brevis exhibited allelopathy against two
ploca.396–402 The absolute congurations of coibacins A and B403
competitor diatoms Asterionellopsis glacialis and Thalassiosira
have been determined as 656 and 657 respectively by total
pseudonana. The former, which co-occurs with K. brevis,
synthesis.404 Syntheses of biselyngbyolide A405 (Lyngbya (Moorea)
exhibited somewhat more robust metabolism while in the
sp.),406 apratoxin C407 (Lyngbya (Moorea) sp.),408 malevamide D409
latter, energy metabolism was disrupted and cellular protec-
(Symploca hydnoides),410 micromide411 (Symploca sp.),412 and 12-
tion mechanisms were impeded.442 Other studies examined
epi-hapalindole Q isonitrile413 (Hapalosiphon laingii),414 have
the biosynthesis of brevetoxin,443,444 brevisamide445,446 and the
also been achieved. Total syntheses of the proposed structures
genetics of toxin production in Alexandrium catenella.447
View Article Online
algal literature for 2014 was a study on the effect of natural

lycopene (E/Z mixture) on a human prostate cancer cell line,453
while a thought-provoking paper tackled a problem all marine
natural product chemists should be alert to – the misuse of
taxonomic descriptors and the implications that this has.

Misuse of such descriptors appears to be a particular problem
with marine algae.454
5 Brown algae
The output of new compounds (17) from brown algae in 2014
was again relatively low and although dominated by terpenoid
chemistry saw the emergence of a new class of brown algal
metabolite. This was the characterisation of a 1-deoxy-
sphingoid, 3-epi-xestoaminol C 681, from a New Zealand
collection of Xiphophora chondrophylla following a M. tubercu-
losis-guided fractionation. A genome-wide screening against
a library of non-essential gene deletion mutants of Saccharo-
myces cerevisiae established the cellular processes that 681
disrupted.455
Some 27 diterpenoids ranging across six classes were iso-

lated from a Chinese collection of Dictyota plectens. These
included seven new diterpenes, belonging to the dolabellanes
682–684, prenylated guaianes 685–687, and a xenicane 688, 19
4 Green algae known analogues and an ethoxylated artifact as well.456 Three
new diterpenoids, a dolabellane 689 a xenicane 690, and a pre-
Research into green algal chemistry continues at low ebb with
nylated guaiane 691 with ve previously characterised
just 13 relevant articles published and just three new
compounds were characterised from Mediterranean collections
compounds published for 2014. The new compounds were the
of several Dictyota spp.457 Three new, 692–694, and three known
racemosines A–C 678–680,448,449 bisindole alkaloids isolated
dolabellane diterpenoids,458,459 were isolated from a Brazilian D.
from Caulerpa racemosa which are biosynthetically related to
pfaffi, and a single crystal X-ray analysis established the absolute
the well-established green algal metabolite caulerpin, also from
conguration of the known 10,18-diacetoxy-8-hydroxy-2,6-dola-
a Caulerpa sp.450 Caulerpin featured in studies of anti-
belladiene.458,460 The meroterpenoids sargachromanol Q 695
nociception mechanisms451 and the antituberculosis activities
and R 696 along with the known sargachromanol J461 resulted
of caulerpin and synthetic analogues.452 Included in the green
from re-examination of the original extract from Sargassum sil-
iquastrum,462 while thunberol, 697, is the only new sterol of ve
isolated from the Chinese Sargassum thunbergii.463 Typical
brown algal phlorotannins such as eckol and dieckol have
stimulated research into a wide range of topics – heme oxy-
genase-1 expression,464 oxidative stress,465 anti-adipogenic
activity,466 anti-HIV-1467 and antibacterial activity.468 Among the
studies on the anti-inammatory properties of phlor-
otannins469,470 was the synthesis of a rhodamine-labelled die-
ckol. Confocal laser microscopy determined that the labeled
dieckol was mainly located in the endoplasmic reticulum and
studies showed that the anti-inammatory activity of the
conjugate was considerably greater than that of dieckol itself.471
The potential therapeutic properties of fucoxanthin and deriv-
atives have been studied,472,473 as have those of polyphenols
such as octaphlorethol,474–476 and mono- and diacylglycerols.477
View Article Online
6 Red algae A synthesis491 of the brominated sesquiterpene aldingenin

492
C showed that the original structure was incorrect, and it was
There continues to be a marked variation in the number of new suggested that aldingenin C was probably the known
compounds obtained from red algae and reported each year, compound caespitol.493 A synthesis494 of the proposed structure
with 42 for 2014 compared to 9 for 2013. There was the usual of prevezol B495 has shown that the original structure was
range of structural types with glycolipids 698478 and 699–701,479 incorrect. Of the 70 polyhalogenated acyclic monoterpenes
halogenated allenes and alkynes 702–704,480 705–709,481 710482 isolated from Plocamium spp., surprisingly none had been
and 711,482 halogenated monoterpenes 712–718,483 sesquiter- synthesised until the use of a broadly applicable approach
penes 719–725,484 726,485 727,485 and 728–730,486 (including the generated four of the naturally occurring compounds and
unusual seco-laurokamurone 719), diterpenes 731–733,487 a number of analogues.496 An asymmetric total synthesis of
brominated aromatics 734488 and 735–737489 and the mahor- (+)-bermudenynol497 has been accomplished,498 while a total
ones 738–739, unusual 2,3-dibrominated 2-cyclopentenones.490 synthesis of the snyderane (+)-luzofuran499 has also been
The use of rapid dereplication tools (UHPLC–PDA–HRMS, 2D made.500 The anti-inammatory potential of 5b-hydrox-
HSQC NMR, soware tools and databases) for identication of ypalisadin B501 from Laurencia snackeyi has been demonstrated
the allenes 710 and 711482 and LC-UV-MS-SPE-NMR for the in LPS-stimulated RAW 264.7 macrophages502 and LPS-induced
monoterpenes 712–718483 were notable features. zebrash embryo.503
7 Sponges
With 283 new structures reported from the phylum Porifera in
2014, sponges have returned again to be a dominant source of
new bioactive metabolites, although the growing realisation
that microbial symbionts are the real producers of “sponge”
specialised metabolites highlights the need for more detailed
metagenomic and biosynthetic analyses of sponge matrices.
View Article Online
Sphingoids 740504 and 741,505 taurinated fatty acids 742– The stellatolides A–G 780–786 are a family of cyclo-
745506,507 and a large number of polyacetylenes 746–765508–513 depsipeptides from a Madagascan Ecionemia acervus. The full
have been reported from the genera Callyspongia, Coscinoderma, stereochemical analyses of several variants were established by
Echinoclathria, Petrosia, Placospongia, Siphonochalina and Xes- Marfey's analysis, and the solid-phase peptide total synthesis of
tospongia. The synthesis of a series of miyakosyne A (Petrosia 780 was also achieved. The unexplained racemisation of L-Thr
sp.)514 diastereomers followed by RP-HPLC separation at 56 C during the Marfey's analysis is a salient warning to all experi-
has revealed that the natural product 766 is actually a mixture of mentalists using this technique. Several of the stellatolides were
two stereoisomers in 96 : 4 (14R) : (14S) ratio.515 A compre- cytotoxic in the nM range against three HTCLs.525
hensive blend of synthesis with NMR, IR and vibrational
circular dichroism (VCD) spectroscopy has allowed for the The genera Asteropus, Discodermia, Pipestela, Reniochalina,
relative congurational assignment of the C-36–C-42 segment Stylissa, Suberites and Theonella have also yielded a large
of hemicalide 767 (Hemimycale sp.), as well as securing the number of peptides 787–806.526–532 Callyspongiolide 807 is an
absolute conguration of C-42. This potent (sub-nM) inhibitor unusual carbamate macrolide with an unprecedented conju-
of mitosis was sourced from a deep water sponge collected at gated dienyne side chain isolated from Callyspongia sp.
the Torres Islands, Vanuatu, but to date has only been reported (Ambon, Indonesia). Evaluation of 807 against three HTCLs
in a patent.516,517 A series of peroxides 768–773,518 halogenated indicated potent cytotoxicity (IC50 ¼ 60–320 nM). Notably, the
alkenes 774 and 775,519 and an amide 776520 have been reported viability of cell lines treated with callyspongiolide was not
from Plakortis simplex, Dysidea sp. and Anoxycalyx (Scolymastra) affected by QVD-OPh, a known caspase-inhibitor, suggesting
joubini, respectively. Sponges continue to be a prolic source of the test compound induces cellular toxicity in a caspase-inde-
peptide natural products. Reisolation of cyclolithistide A from pendent manner.533
a deep sea Discodermia japonica (200 m, Sagami Bay, Japan),
originally reported in 1998,521 allowed in-depth LC-MS/MS and
Marfey's analyses that necessitated a revision of the amino acid
sequence and congurations as shown here 777.522 The simple
substitution of a side-chain Asp for hydroxy-Asp in pipecoli-
depsins A 778 and B 779 (Homophymia lamellosa, Saint Marie
Is., Madagascar) resulted in a greater than ten-fold increase in
activity against three HTCLs.523 The synthesis of 778 had already
been reported in 2013.524
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The total synthesis of halichondrin A has been accomplished. inhibition of both Gram positive and negative bacteria (MIC 0.5–
Halichondrin A is a “phantom” natural product, viz. it is the only 8 mg mL1 vs. eight bacterial cell lines), even though the initial
member of the norhalichondrin/halichondrin/homohalichon- isolation study reported minimal activity. Further detailed
drin family not to have been detected from a natural source, investigation could not determine a specic mode of action but
typically Halichondria okadai,534,535 even though concerted efforts did suggest secondary membrane-disruption as the likely route to
have been made to try and detect this compound for more than activity.563 The comprehensive total synthesis of sceptrin, ageli-
20 years. Use of the synthetic material to guide studies searching ferin and massadine congeners via single electron cycloaddition
for the presence of halichondrin A in legacy extracts of H. okadai reactions has several wide-ranging consequences. Firstly, it
were unsuccessful.536 A diketopiperazine 808,537 a 3-alkylpiper- necessitates the revision of the absolute conguration of sceptrin
idine 809,538 seven manzamine-type alkaloids 810–816539,540 and and its brominated analogues 878–880564–566 and ageliferin and
seven 3-alkylpyridines 817–823541 have been isolated from the congeners 881–883567 as shown here, based upon X-ray crystal
sponge genera Callyspongia, Acanthostrongylophora and Top- structures. Moreover, the massadines had been thought to be
sentia. Axinyssa aculeata (Okinawa) was the source of proto- rearrangement products from the ageliferins,568,569 however the
aculeine B 824 that is a putative novel N-terminal residue for the absolute congurations of the two series of compounds are
peptidic toxins aculeines A–C. The structure of this polyamine antipodal, hence indicating enantiodivergent biosynthetic path-
compound, including identifying its attachment to the peptide ways in vivo to these bromopyrrole alkaloids and invalidating the
toxins themselves, was determined from detailed synthetic and so-called “Scheuer-hypothesis” for their formation.570,571
mass spectrometric studies.542
Other indole 825–829543,544 and b-carboline 830–837544–546

alkaloids were reported from Hyrtios, and Luffariella sponges. A
biomimetic total synthesis of ()-dictazole B, isolated from the
shallow water sponge Smenospongia cerebriformis,547 has been
performed using articial light to facilitate the [2 + 2] photo-
chemical cycloaddition reaction between aplysinopsin mono-
mers, under the presumed high local concentration of the parent
Bromotyrosine metabolites 884–893 have been isolated from
reactant that would be found in the relevant sponge organelle.
Callyspongia,572 Aplysinella573 and Dendrilla574 sponges, while
This biomimetic route is a viable alternative to the [4 + 2] Diels– Haliclona, Petrosia, Phoriospongia and Dragmacidon sponges have
Alder cycloaddition that has been presumed to take place in the
yielded substituted purine/pyrimidine compounds 894–
biosynthesis of the cycloaplysinopsins.548 Fieen new aaptamine
898.504,575–577 As usual, sponges continue to be a valuable reser-
alkaloids 838–852549–551 have been reported from Aaptos sponges
voir of new terpenoid metabolites. Merosesquiterpenoids 899–
while a new polycyclic aromatic alkaloid 853 came from an
930 came from the sponge genera Aka (Siphonodictyon), Dysidea,
Ancorina sp.552 An unbiased screen of a library of 480 sponge
Dactylospongia and Xestosopngia.578–584 In particular, xesto-
extracts identied the surprisingly simple compound girolline553
lactone A 931 and xestosaprol O 932 were isolated from Xesto-
from Stylissa carteri (Mont Pass, Pohnpei, Micronesia) as a potent
spongia vansoesti (Palawan Is., Philippines). Xestosaprol O is
inhibitor of signalling of MyD88-dependent and -independent twenty times more potent as an inhibitor of indoleamine 2,3-
Toll-Like Receptors (TLR) 2, 3, 4, 5 and 7, reducing cytokine
dioxygenase (IDO; IC50 ¼ 4 mM) than 931 (IC50 ¼ 81 mM),
production in peripheral blood mononuclear cells and macro-
making it a lead towards inhibitors of tumour immune escape.
phages, therefore imbuing the molecule with potent anti-
The total syntheses of 932 and two analogues were achieved
inammatory activity. In-depth chemical genetics proling
using the rarely applied silver-catalysed Sato photochemical
identied elongation factor 2 as the molecular target of girolline
coupling, leading to a short and efficient synthesis of the
implying inhibition of protein synthesis as its mode of action.554
natural product. Comparative analysis of 932 and its analogues
Guanidine-derived alkaloids 854–863 were reported from
showed that the 3-OH functional group is highly detrimental for
Monanchora pulchra,555 Acanthella cavernosa556 and Biemna lab- IDO-inhibitory activity.585
outei,557 while several brominated hymenialdisine-type 864–867
and oroidin/oroidin dimer-type 868–877 came from Callyspongia
sp.558 and Agelas sp.,559–561 respectively. A highly scalable, multi-
gram synthesis of axinellamines A and B (Axinella sp.)562 and
analogues has been achieved. Evaluation of the antibacterial
properties of racemic synthetic products highlighted their potent
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A merotetraterpenoid 933 has been reported from Sarco- concentration of marine natural products in sensitive marine
tragus spinosulus.586 Similarly, Axinyssa, Dysidea, Ircinia and ecosystems. A pump is used to suction sponge-matrix particles
Topsentia sponges were the sources of a number of sesqui- that are ltered into a hollow-bre bioreactor. This is used to
terpenoids 934–964,587–591 some of which had been cleaved, cultivate microbial symbionts that produce secondary metabolites
while diterpenoids were obtained from Diacarnus mega- which are, in turn, trapped on reversed-phase cartridges for
spinorhabdosa 965–970,592 Spongia sp. 971–973593 and Darwinella concentration. The articial sponge system was used in three
oxeata 974–982.594 A large number of sesterterpenoids 983–1011 expeditions across 11 locations, two in the Pacic and one in the
were reported in 2014 from the sponge genera Clathria, Cosci- South China Sea, with the deployment at Pulau Lakei (Sarawak,
noderma, Hippospongia, Hyrtios, Petrosaspongia, Phorbas and Malaysia) yielding jasplakinolide, jasplakinolide B and C in
Scalarispongia.506,595–601 As always, sponges yielded a variety of a 18 : 1 : 1 ratio, the same proportions as found from Jaspis
steroids 1012–1019,504,505,602,603 steroidal amines 1020 and splendens collected near Vanuatu.611,612 Metagenomic analyses
1021,604 and degraded steroids 1022–1024605,606 from species of continue to rise in their importance to sponge natural product
Echinoclathria, Corticium, Haliclona, Ircinia, Petrosia, Plakortis biosyntheses. Detailed metagenomic proling of the “High
and Theonella. T. swinhoei (Xisha Is., S. China Sea) yielded Microbial Abundance” (38–57% microbial biomass) sponge Pla-
swinhoeisterols A 1025 and B 1026 with unprecedented 6/6/5/7 kortis halichondrioides (Little San Salvador Is., Caribbean Sea)
tetracyclic frameworks. The absolute congurations of the found characteristic gene sequences of poribacteria (a bacterial
compounds were secured by a combination of X-ray diffraction, phylum found exclusively in sponges) but the known supA and
TDDFT ECD calculations and Mosher's method. Detailed in swfA biosynthetic clusters observed were absent from the por-
silico analysis of both compounds against 211 potential protein ibacteria genomes. Further investigation showed similarity
targets of relevance for cancer therapy revealed 1025 should between these clusters and protist type I polyketide synthetase
exhibit activity against the histone acetyltransferase (h)p300. (PKS) genes hence protists could be a previously overlooked
This was validated in vitro with IC50 ¼ 2.9 mM while 1026 was reservoir of novel bioactive metabolites.613 A comprehensive
almost 100 times less potent (IC50 ¼ 240 mM), indicating the metagenomic survey of the microbial community associated
steric importance of the 9-OH in abrogating activity.607 with the metabolite-rich sponge Theonella swinhoei has uncovered
a new bacterial genus, Entotheonella. This genus is a member of
the new candidate phylum Tectomicrobia and appears to be
a widespread sponge endosymbiont across many diverse sponge
species. Moreover, biosynthetic gene cassettes suitable for
production of many “Theonella swinhoei” NRPS and PKS
compounds, including the onnamide,614 polytheonamide,615 ker-
amamide616 and cyclotheonamide617 classes, have been identied
in the microbial genome.8,9 A metagenomic approach identied
the gene cassette for calyculin A (Discodermia calyx)20 biosynthesis
as being microbial in origin, as described in 3.1 Bacteria, and
resulted in the identication of two diphosphate protoxins (see 1
and 2),21,22 again underscoring the importance of symbiotic
microbial communities in the production of “sponge” metabo-
Cinanthrenol A 1027 is the rst example of a phenanthrene- lites. The microtubule-stabilising mode of action of laulimalide618
containing steroid. It was sourced from Cinachyrella sp. and peloruside A619 has been established through the use of high-
collected by dredging at 160 m (Oshima-Shinsone, Japan) resolution crystal structures of the compounds bound to
where the unique phenanthrene-uorescence signature was tubulin,620 while aaptamine621 has been shown to have protective
used to select the sponge from amongst detritus. As well as effects against cisplatin-induced kidney damage,622 and also
moderate activity against various HTCLs, 1027 was a potent prevents photoageing.623 A polybrominated diphenylether624
estrogen-receptor binder, displacing estradiol in a competitive (Dysidea granulosa) has been shown to inhibit hepatitis C non-
manner with IC50 ¼ 10 nM, as well as altering estrogen- structural protein NS3 helicase, a validated antiviral target.625 The
responsive gene expression.608 four bromotyrosine compounds ianthelliformisamine A–C (Sub-
erea ianthelliformis)626 and spermatinamine (Pseudoceratina sp.)627
were selective and potent inhibitors of human carbonic anhydrase
IX (IC50 ¼ 0.20–0.36 mM), with implications for maintaining
cellular pH homeostasis and hence application in a variety of
disease states.628 The sesterterpenoid heteronemin (Hyrtios sp.)629
inhibited trans-activation response DNA-binding protein 43 kDa
(TDP-43), a key factor of several neurodegenerative states. Heter-
onemin binds to TDP-43 (ki ¼ 270 nM) and altered the aggre-
A series of triterpenoids 1028–1032 have been reported from
gation state and localisation of this important neurochemical
Jaspis stellifera609 and Siphonochalina siphonella.610 An articial
target.630 The rst total syntheses of an all-(Z) octadeca-pentene-
“sponge” has been developed for the non-destructive
3-one (Callyspongia sp.),631,632 strongylodiol G (Strongylophora
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sp.),633,634 bitungolide B (Theonella swinhoei),635,636 plakortone L 42-hydroxypalytoxin diastereomer 1059 from Palythoa tuber-
(Plakortis clathrata),637,638 epiplakinic acid F (Plakinastrella sp.),639 culosa.689 Previous studies of an extract of Palythoa toxica identi-
and its methyl ester (Plakortis halichondrioides),640,641 gracilioether ed the major toxin to be a 42-hydroxy analogue of palytoxin 1060
F (Plakinastrella mamilaris),642,643 taumycins A and B (revised 1033 however the conguration at positions C-41 and C-42 remained
and 1034, Fascaplysinopsis sp.),644,645 polydiscamides B–D (Ircinia unresolved.690 More recent J-based analysis has dened the
sp.),646,647 callipeltin M (Latrunculia sp.),648,649 topsentolide A2 conguration at these stereocentres as (41S) and (42S). The same
(revised 1035, Topsentia sp.),650,651 penarolide sulfate A2 (Penares study also established the absolute conguration of a related
sp.),652,653 haliclorensin C (Haliclona tulearensis),654,655 nakinadine A palytoxin analogue isolated from P. tuberculosa as being (42S)-
(revised 1036, Amphimedon sp.),656,657 thiaplakortone A (Plakortis hydroxy-(50S)-palytoxin 1059. The relative affinity of palytoxin,
lita),658,659 (+)-cylindradine A (Axinella cylindratus),660,661 ianthelli- 1059 and 1060 towards a mouse anti-palytoxin monoclonal
formisamines A–C (Suberea ianthelliformis),626,662,663 tokaradine C antibody identied palytoxin to have the most potent KD (nM),
(Pseudoceratina purpurea),663,664 (+)-hemistularin 3 (revised 1037, while 1059 and 1060 were approximately one and three orders of
Verongia sp.),665,666 trachycladines A and B (Trachycladus laevis- magnitude less potent respectively. Similar relative levels of
pirulifer),667–669 cyclospongiaquinone-1 (Stelospongia conulata),670,671 cytotoxicity towards keratinocytes were also observed, with paly-
deoxyspongiaquinol (revised 1038) and deoxyspongiaquinone toxin being the most potent. Palytoxin is known to be capable of
(revised 1039, Euryspongia sp.),672,673 plakinamine B (Plakina disrupting mechanisms of cellular ion homeostasis: NMR
sp.)674,675 and clionamine D (Cliona celata)676,677 have all been studies have dened the C-25–C-33 and C-47–C-53 fragments of
completed. The total syntheses of the putative structures of 15- palytoxin as being involved with Ca2+ coordination.691
oxopuupehenoic acid (Hyrtios sp.)678,679 and astakolactin (Caco- A series of butenolide and cyclopentenones 1061–1072 were
spongia scalaris)680,681 have also been achieved but the spectro- reported from Subergorgia suberosa and Sinularia sp. so
scopic data call into question the original identied structures, corals.692–694 A comprehensive investigation of a Bahamian
with no alternative suggestions provided. collection of Pseudopterogorgia rigida identied a chamigrane
1073 and seven bisabolanes 1074–1079 as new sesquiter-
penes.695 The study also reported an extensive number of co-
8 Cnidarians metabolites 1080–1083 that had been previously reported from
terrestrial plants or as semi-synthetic derivatives 1084–1090.
The number of new compounds reported from cnidarians in
Other sesquiterpenes 1091–1110 have been reported from
2014 (201) is similar to the previous decadal average. The
Rumphella antipathies,696–698 Lemnalia philippinensis,699 Menella
importance of chemical cues in coral reef remediation have been
kanisa,700 Nephthea erecta,701 an unidentied gorgonian,702 Den-
highlighted in a study that found that coral and sh juveniles
dronephthya sp.,703 Sinularia kavarattiensis,704 Echinogorgia sas-
were repelled from reefs that were overshed and seaweed-
sapo reticulata705 and Anthrogorgia ochracea.706 Of these
dominated.682 A method of recovery of such degraded habitats
sesquiterpenes, rumphellaoic acid A 1093697 contains a unique
was proposed to involve reduction in shing harvest of critical
skeleton, while shagenes A 1102 and B 1103702 and ochracenoid
species of herbivorous shes. The chemistry of both hard and
A 1109706 contain rarely reported skeletons. In the case of the
so corals are dominated by terpenes – alkaloids are only rarely
ochracenoid A, absolute conguration was assigned by use of
isolated. In 2014 there were seven examples of alkaloids isolated
TDDFT calculated ECD data.
from so corals, comprised of an unusual diketopiperazine 1040
A South China Sea collection of Anthrogorgia caerulea yiel-
from Menella kanisa,683 and six tetraprenylated purines, malon-
ded, in addition to two known avermectin macrolides, aver-
ganenone L–Q 1041–1046, from Echinogorgia pseudossapo.684 In
mectin B2a and 22,23-dihydroavermectin A1a,707 two new
contrast, cnidarians of the order Zoantharia (zoanthids) were the
congeners B1c 1111 and B1e 1112.708 All four MNPs exhibited
sources of ve new parazoanthine congeners 1047–1051 (Para-
moderate antifouling activities.
zoanthus axinellae).685 These structures were established using
Of the thirty-six cembrane related metabolites 1113–1149 re-
a metabolomics model, with LCMS/MS fragment analysis being
ported from cnidarians in 2014,709–722 secocrassumol 1113
used to dene structures and LC-ECD employed to assign abso-
(Lobophytun crassum)709 is notable as it is derived from the cem-
lute conguration (to 1047, 1048 and 1050).
brane skeleton via an unusual C-11–C-12 bond cleavage, sinu-
gyrosanolide A 1114 (Sinularia gyrosa) is an unprecedented C-4
norcembranoid,710 tortuosenes A 1146 and B 1147 (Sarcophyton
tortuosum)721 represent the rst examples of cembranoids con-
taining a C-2–C-20 ring closure, and sinularbols A 1148 and B
1149 (Sinularia arborea) contain a rare C-3–C-9 ring closure.722
Cnidarian chemistry is dominated by metabolites derived
from terpene biosynthesis, with particularly large numbers
falling into the diterpenoid classication. Thirty-eight new
briarane-skeletoned MNPs (1150, gemmacolides AS–AY 1151–
1157, briarenolide J 1158, junceellolides M–P 1159–1162, fra-
Other zoanthamine analogues, 1052–1058, were isolated gilisinins A–L 1163–1174, dollfusilins A 1175 and B 1176, bria-
from Zoanthus sp.686,687 and Zoanthus kuroshio688 as well as a new violides A–J 1177–1186 and anthrogonoid A 1187) were reported
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from octocoral species Pennatula aculeata, Dichotella gemmacea,

Junceella gemmacea, J. fragilis, Ellisella dollfusi, Briareum viola-
cea, and Anthrogorgia caerulea.723–730 As usually happens each
year, there is duplication of structure/trivial name amongst
a small number of MNPs. In the set of briaranes reported from
Junceella gemmacea (South China Sea) and J. fragilis (also South
China Sea), junceellolide O 1161726 and fragilisinin G 1169727
share the same assigned structure, however spectroscopic and
photometric data reported for the two compounds are quite
different clearly indicating that one of the structures is in need Examples of eunicellins were reported from Anthrogorgia caer-
of revision. The structure and absolute conguration of bria- ulea (antsimplexin A, 1188),730 Muricella sibogae (sibogins A 1189
violide A 1177729 was secured by single crystal X-ray analysis. and B 1190),731 Cladiella sp. (cladieunicellin J, 1191),732 Klyxum
The second dominant class of diterpenoid metabolites re- molle (klymollins T–X, 1192–1196),733 Cladiella sp. (cladieuni-
ported from so corals contain the eunicellin skeleton. cellin M–Q, 1197–1201),734 Cladiella kremp (krempelins N–R,
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1202–1206),735,736 and Cladiella hirsuta (hirsutalin N–R, 1207– 1265747–753 from species of Schleronephthya, Subergorgia, Sar-
1211).737 Readers should note that cladieunicellin N 1198 is cophyton, Sinularia, Verrucella, Echinogorgia, and Leptogorgia.
a structural duplicate of the previously reported Klyxum molle Noteworthy amongst these compounds, was the enhanced
metabolite klymollin Q,738 exhibiting identical spectroscopic, (synergistic) cytotoxicity observed for paclitaxel in the presence
spectrometric and chiroptical properties and that the structure of punicinols A 1257 and B 1258 (Leptogorgia punicea) and that
elucidation of cladieunicellin M–Q also led to revision of the two sterols were also able to inhibit A549 tumour cell growth
conguration at C-7 of the structure of litophynin I diacetate to in a clonogenic assay over a sustained period of ten days.752
that shown in 1212. In addition to the mildly antiproliferative epoxyergosterols
1266–1271 (Anthopleura midori),754 investigation of MNP chem-
istry of sea anemones and hydrozoa has identied two new
cytolysins (3013 and 3375 Da) from the tentacles of the hydro-
zoan Olindias sambaquiensis755 and PhcrTx1, a 32 amino acid
residue acid-sensing ion channel inhibiting peptide from the
sea anemone Phymanthus crucifer756 that represents the rst
example of a peptide containing an Inhibitor Cysteine Knot
scaffold to be isolated from a cnidarian. Further study of the
biological activities of previously reported anemone toxins has
Further examples of diterpenoids, 1213 and 1214,739 1215
identied Av3 (Anemonia viridis) to show specicity towards
and 1216,740 cespitulones A 1217 and B 1218,741 dihy-
arthropod voltage-gated sodium channels by binding to one of
drosarsolenone 1219, methyldihydrosarsolenoneate 1220, and
the transmembrane cles of the channel a-subunit,757 while
sarsolilides B 1221 and C 1222,742 have been isolated from so
AdE-1 (Aiptasia diasphana) prolongs cardiomyocyte action
corals of the genera Cespitularia, Xenia, and Sarcophyton.
potential duration while lowering peak amplitude via slowing
Structure elucidation and determination of absolute congu-
inactivation of sodium channels and enhancing the transient K+
ration of 1219 and 1220742 led the authors to propose a revision
current.758 Mutation of the pore-forming toxin sticholysin I
of the relative conguration at C-2 of the previously reported
(Stichodactyla helianthus) residue tryptophan 111 to cysteine
MNP sarsolenone (to that shown 1223).743 Absolute congura-
reduced the toxins affinity for membranes by an order of
tion was assigned to 1219 and 1220 using TDDFT calculations of
magnitude,759 cysteine mutants of phenylalanine 15 or arginine
ECD data.
52 did not alter pore-forming activity but did protect the toxin
from peroxynitrite oxidative damage,760 while a third study,
using monolayers of phosphatidycholine and sphingomyelin,
determined that the toxin preferentially binds and penetrates
membranes which have moderate enrichment in sphingomye-
lin and membrane uidity.761 The rst total syntheses of
alkaloids N-(3-guanidinopropyl)-2-(4-hydroxyphenyl)-2-oxoace-
tamide (Campanularia sp.)762,763 and ()-tubastrindole B
(Tubastraea sp.),764,765 butenolide (+)-hydroxyancepsenolide
(Pterogorgia anceps),766,767 and diterpenes sandresolide B,768
amphilectolide769 and (+)-ileabethoxazole770 (Pseudopterogorgia
Sarcophyton ehrenbergi was the source of a number of pros- elisabethae)771,772 have been completed. Conversion of bipinna-
taglandins including sarcoehrendins A–J 1224–1233.744 In tin J (Pseudopterogorgia bipinnata)773 to intricarene (Pseudopter-
addition, three prostaglandins previously reported as synthetic ogorgia kallos)774 via a photochemical pathway has been
compounds 1234–1236 were reported as natural products for demonstrated,775 while a photochemical (E/Z) olen isomer-
the rst time. Relatively potent activity was observed towards isation was a critical step in the total synthesis of the natural
phosphodiesterase-4, a target for CNS, inammatory and product analog 17-deoxyprovidencin.776 Clarication of the
respiratory diseases. So corals also yielded a variety of steroids structure of the cladiellin diterpene sclerophytin F (Scle-
including pregnanes 1237 and 1238,745 seco-sterols 1239– rophytum capitalis)777 has been an ongoing issue, with Frie-
1244746,747 and hydroxylated/polyhydroxylated sterols 1245– drich and Paquette in 2002 proposing the structure should be
revised to be the (3S) diastereomer of sclerophyton A.778
Synthesis of this proposed revised structure gave a product
whose spectroscopic data differed from those reported for the
natural product, suggesting further investigation is needed to
resolve this issue.779 A modular approach to a number of
cladiellin MNPs using a gold-catalysed tandem reaction of
1,7-diynes has been reported.780 Hippuristanol (Isis hippu-
ris)781 analogues have been evaluated as inhibitors of
eukaryotic translation initiation,782 cembranoid and ergosterol
MNPs from Vietnamese cnidarians were found to exhibit
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selective in vitro activity against T. brucei,783 a number of Azaspiracid-1 1291 was isolated from contaminated raw shell-
diterpenes (Sinularia maxima) were found to be modest to sh – the epimer forms spontaneously via an equilibrium and
poor inhibitors of NF-kB transcriptional activation,784 struc- formation, as expected, is accelerated by heating.799 Implication
turally simpler analogues of fuscol/eunicol exhibit compa- of the latter in relationship to the cooking of shellsh is
rable or better anti-inammatory activity in the mouse ear important as 37-epi-AZA1 was 5-fold more toxic towards Jurkat T
edema assay,785 semi-synthetic oxygenated dolabellane diter- lymphocyte cells in vitro than AZA1. Corresponding epimers of
penes exhibit in vitro anti-HIV activity,786 further semi- the related toxins AZA2 and AZA3 were also detected.
synthetic examples of hydoxysterols were found to induce
pregnane X receptor transactivation,787 exibilide788 exhibits
in vivo anti-neuroinammatory activity in rats,789 11-epi-sin-
ulariolide acetate inhibits carcinoma cell migration and
invasion by suppressing a number of phosphorylation-
dependent pathways,790 13-acetoxysarcocrassolide induces
apoptosis in carcinoma cells by activation of p38/JNK and
suppression of PI3K/AKT pathways,791 and cembranoids from
Sarcophyton glaucum exhibit cytotoxicity towards a murine
melanoma cell line.792,793
Specimens of the Mediterranean sacoglossan mollusc Thur-

9 Bryozoans idilla hopei afforded new nor-diterpene aldehydes 1292–1294800
in addition to known congeners thuridillin A, B and C.801 The
There were only three reports (containing 19 compounds) of
mollusc feeds on the green alga Derbesia tenuissima, extracts of
new metabolites isolated from bryozoans in 2014, which is
which only contain a known epoxylactone,802 supporting the
a large increase on 2013 when only one new metabolite was
assumption that 1292–1294 are mollusc transformation prod-
reported from this understudied phylum. The bromopyrrole
ucts. Acetylenic alcohols 1295–1299 were isolated from both the
alkaloids aspidostomides A–H 1272–1279 and aspidazide A
Mediterranean dorid nudibranch Peltodoris atromaculata and
1280 were isolated from the Patagonian bryozoan Aspidostoma
one of the nudibranch's common dietary prey, the sponge
giganteum. Aspidostomide E 1276 exhibited moderate inhibi-
Haliclona fulva.803 In a similar manner, renieramycin-related
tion of the 786-O renal carcinoma cell line. Aspidazide A 1280 is
alkaloids fennebricin A 1300 and B 1301 were isolated from
a rare asymmetrical diacylazide and NOE NMR correlations and
both the nudibranch Jorunna funebris and the sponge Xesto-
chemical transformations were utilised in determination of the
spongia sp.804 The substructurally-related isoquinoline 1302 was
structure.794 A series of ceramides neritinaceramide A–E 1281–
only identied in the sponge extract. New diketopiperazines
1285 were obtained from Bugula neritina and exhibited selective
1303–1306 were reported from Pleurobranchus areolatus –
but weak activity against two HTCLs.795 The same sample yiel-
related metabolites have been reported from the ascidian
ded several sterols 1286–1290.796 Convolutamydine A797 dis-
Didemnum sp., a suspected prey of P. areolatus.805 Further
played signicant anti-inammatory activity both in vitro and in
investigation into the origin of tetrodotoxin in Pleurobranchaea
vivo.798
maculata demonstrated that the mollusc can accumulate the
toxin through its diet however there was no identiable tetro-
dotoxin source in the molluscs local environment.806 Two
studies of sea hares identied two moderately cytotoxic
sesquiterpenes oculiferane 1307 and epi-obtusane 1308 (Aplysia
oculifera)807 and an anti-neuroinammatory diterpene dactylo-
diterpenol acetate 1309 (A. dactylomela).808 6-Bromoisatin, typi-
cally isolated from muricid molluscs, is weakly antiproliferative
towards HT29 cells, and enhances apoptosis in an in vivo colon
cancer model.809 Further structure–activity relationship studies
of the cyclic peptide sanguinamide B (Hexabranchus sangui-
neaus)810 have found that antiproliferative activity is dependent
upon both the location of specic amino acids in the macro-
cycle and their conguration.811,812 New synthetic auristatin
analogues, being related to the original MNP dolastatin 10
(Dolabella auricularia),813 bearing changes at the N-terminus
showed pronounced antitumour activity.814 The binding of
three examples to tubulin was investigated by co-crystal X-ray
10 Molluscs studies, identifying an interesting structural feature whereby in
The 23 new metabolites reported from molluscs is the average the solid state the valine-dolaisoleucine fragment exists in
number reported per year over the past decade. 37-epi-
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the cis-conguration, whereas in solution it exists solely in the 1332.838 Noteworthy was the isolation, structure elucidation
trans-conguration. In further studies, cholesterol and other and synthesis of a rare example of a modied nucleoside
simple sterols puried from mussels showed anti-aging bearing a 50 -thiomethyl substituent 1333.839 The same study
and neuroprotective properties,815 synthetic tambjamine also led to the reassignment of structure of a known sponge
analogues show enhanced tumour cell antiproliferative and metabolite hamiguanosinol840 from the enol tautomer to the
chloride transport properties,816 and lamellarin D (Lamellaria guanosine keto tautomer 1334. The tanjungides A 1335 and B
sp.)817 induces senescence in cancer cells, in a process that 1336,841 novel dibromoindole enamide alkaloids isolated
includes the generation of intracellular ROS and requires the from Diazona cf. formosa exhibit potent cytotoxicity (<1–2 mM)
presence of topoisomerase I.818 Biosynthesis of long chain towards a panel of HTCLs. An eleven-step linear synthesis
polyunsaturated fatty acids in the scallop Chlamys nobilis was utilising Buchwald vinyliodide amidation and peptide
investigated, revealing the presence of a new elongase, that synthesis established the absolute conguration of the
can elongate 20:4n-6 and 20:5n-3 to C22 and C24 acids, and alkaloids.
a D8-desaturase.819 A new example of an a4/7-conotoxin, a-
BnIA 1310 was isolated from crude venom of the molluscivo-
rous cone snail Conus bandanus.820 Peptides with the same
sequence, Mr1.1 and Bn1.1, were previously identied by PCR
amplication of venom duct cDNA from molluscs C. marmor-
eus821 and C. bandanus.822 The peptide reversibly inhibited the
human a7 nicotinic acetylcholine receptor (nAChR) and
blocked nerve-evoked skeletal muscle contractions. Conus
bandanus (Vietnam) was also the source of BnIIID 1311, a 15
residue M–1 family peptide containing six cysteines (disulde
Over the years a number of cyclic ribosomal peptides, now
connectivity not determined) and three post-translational
known as the cyanobactins, have been reported from ascid-
modications comprised of a bromotryptophan, g-carboxy
ians, typically of the genus Lissoclinum. The true producers of
glutamate and amidated aspartic acid residues.823 An unusual
these natural products are photosynthetic symbiotic cyano-
a5/5 conotoxin AusIA 1312 was puried from the venom of C.
bacteria of the genus Prochloron. The apparent random
australis – both synthetic globular (natural) and ribbon
distribution of cyanobactins isolated from ascidians has now
(different disulde linkages) congurations inhibited the a7
been credited to host phylogeny, with genetic analysis
nAChR.824 A short cyclic hexapeptide Vi804 1313 was isolated
revealing that ‘Lissoclinum patella’ falls into three phyloge-
from crude venom of C. virgo and the solution structure of it
netic groups that in turn may contain further cryptic
and the DW3 synthetic analogue explored by NMR spectros-
species.842 The implications that local extinctions of such
copy.825 The high hydrophobicity of g-conotoxins make them
cryptic species may reduce marine natural product diversity is
difficult to synthesise by standard peptide synthesis tech-
indeed food-for-thought in the context of climate change. A
niques. A recent report describes the use of a Lys4 solubilising
very interesting demonstration of the use of the biosynthetic
C-terminus tag to enable the synthesis and NaV subtype
machinery of cyanobactin production was recently reported,
selectivity of three previously reported C. consors g-conotoxins,
whereby engineered enzymes of the patellamide pathway, in
g-CnVIB, g-CnVIC and g-CnVID.826 Further studies have re-
combination with enzymes from other cyanobactin-related
ported on the structure and activity of dicarba analogues of a-
pathways, were used for the in vitro production of a small
RgIA,827 the inuence of disulde connectivity on structure and
library of cyclic peptides.843 This proof of principle allowed for
bioactivity of a-TxIA,828 the inuence of acetylcholine to
the preparation of 1–2 mg of each peptide. Total synthesis has
affect the binding of a-MII at nAChRs,829 the neuronal target
led to revision of the original structure proposed for didem-
selectivity of the Conus textile T-superfamily peptide TxVC,830
naketal B (Didemnum sp.)844 to 1337, requiring stereochemical
and the Ca2+-activated K+ (BK) channel selectivity of the
inversion of the C-10–C-20 spiroacetal domain of the MNP.845
unusual M superfamily conotoxin Vt3.1.831
Such a revision may be of relevance to the ongoing revision of
the (stereo)structure of didemnaketal A.846 Syntheses of the
11 Tunicates (ascidians) reported structures of polycitorols A and B (unidentied
ascidian)847,848 and (+)-didemniserinolipid C (Didemnum
The 22 new tunicate-derived natural products presented in this
sp.)849,850 suggest that the structures of all three MNPs require
review is the second lowest number reported in one year
revision. Total synthesis has also led to revision of the struc-
over the last decade. A structurally-diverse range of metabo-
ture of mandelalide A (Lissoclinum sp.)851 to 1338852 and
lites were reported, with examples of glycerides 1314 and
conrmation of the revised structure of haouamine B
1315,832 amino alcohols 1316–1322,833 new didemnaketal
(Aplidium haouarianum),853–855 while the structures of
congeners 1323, 1324834 and 1325, 1326,835 halogenated alka-
distomadines A and B (Pseudodistoma aureum)856,857 and
loids 1327 and 1328,836 a new rubrolide (R) 1329837 (that
synoxazolidinones A and B (Synoicum pulmonaria)858,859 have
unfortunately shares the same letter designation as a related
been conrmed by synthesis. Synoxazolidinones A and C and
metabolite reported from Aspergillus terreus217), pyr-
S. pulmonaria co-metabolites pulmonarins A and B exhibited
idoacridine cnemidine A 1330552 and sulfated sterols 1331 and
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variable levels of anti-biofouling activity against a panel of test of vitellogenin, a nutrient protein present in sea urchin game-
organisms, with synoxazolidinone C being particularly potent togenic cells, suggesting the possibility that echinometrin is
as both a growth and adhesion inhibitor.860 The effects of a cryptide.879
ascidian extracts on the estrogen receptor-negative breast
cancer cell line MDA-MB-231 were investigated by content-rich

screening, leading to the identication of eusynstyelamide B
(Didemnum candidum, originally isolated from Eusynstyela
The rst synthesis of a pyranonaphthazarin pigment isolated
latericus861) as a moderate cytotoxin (IC50 5 mM) causing cell
from the sea urchin Echinothrix diadema880 has been reported.881
cycle arrest in G2/M and inducing apoptosis.862 The potently
Further studies using puried pentahydroxynaphthoquinone
cytotoxic macrolide iejimalide C (Eudistoma cf. rigida)863 joins
echinochrome A882,883 have identied it to enhance mitochon-
congeners iejimalides A and B as being identied as an
drial biogenesis,884 to protect cardiomyocyte mitochondria from
inhibitor of the vacuolar-type ATP-driven proton pump (H+-
the effects of cardiotoxic drugs885 and to inhibit acetylcholin-
ATPase).864 Aer 24 h treatment, cells also exhibited actin
esterase in an irreversible and uncompetitive mode.886 The
aggregates, but as the MNP does not inhibit actin polymeri-
mechanisms of antioxidant reactivity of the structurally related
sation in vitro, it was concluded that actin activity was
echinamines A and B887 has been investigated using DFT
a consequence of disruption of pH homeostasis. Preliminary
methods.888 The benzochromenone comaparvin (Comanthus
data suggesting that trabectedin (Et 743) exhibits anti-angio-
bennetti)889 exhibits anti-inammatory activity in the carra-
genic activity towards breast cancer cell lines has been
geenan-induced rat model.890 A simple synthesis of ovothiol A891
reported.865
from L-hisidine has been reported,892 the role of a non-heme
iron oxidase enzyme in the biosynthesis of ovothiol A investi-
gated,893 NMR-pH titrations used to investigate the micro-
12 Echinoderms speciation of the amino acid,894 and the antiproliferative activity
The 35 new metabolites reported from echinoderms in this towards Hep-G2 cell line via an autophagy mechanism identi-
review is 25% lower than the average number reported per ed.895 Sterols and fatty acids from the spiny sea-star Marthas-
annum over the last decade. Beyond the simple sulfonic acid terias glacialis exhibit both anti-inammatory896 and cell cycle
derivative 1339 isolated from the sea urchin Brisaster latifrons866 arrest properties,897 while sterols from an urchin and a starsh
and the highly substituted unsymmetrical binaphthoquinone exhibit selective antiparasitic activity towards T. brucei.783
mirabiquinone 1340 (sea urchin Scaphechinus mirabilis),867 the Investigation of the structure and bioactivity of chimeric
natural product chemistry of echinoderms is dominated by analogues of the starsh cardiac-stomach relaxing SALMFa-
steroidal tri- (1341868 and 1342869), tetra- (1343–1352870–873), mide neuropeptides S1 and S2 has highlighted the importance
penta- and hexaoses (1353–1371).873–875 The aglycone 1372 was of the C-terminus for bioactivity and that the N-terminus
also isolated.874 In many cases these MNPs exhibited biological confers structural stability.898 Treatment of pancreatic cancer in
activity including anti-inammatory,866 cytotoxic,870,872,874 vivo in athymic mice using a combination of frondoside A
hemolytic870 and antifungal873,875 properties. (Cucumaria frondosa)899 and the nucleoside anticancer agent
gemcitabine was signicantly more effective than with either
drug alone.900 The cytotoxic and apoptotic-inducing abilities of
steroids from the cold water starsh Ctenodiscus crispatus901 and
the triterpene glycosides, including echinoside A, from Hol-
othuria scabra and Cucumaria frondosa have been reported.902
Echinoside A and related saponin holothurin A inhibit dietary
fat absorption and decrease the adipose tissue accumulation in
mice,903 and typicosides (Actinocucumis typica)904 exhibit a strong
immunostimulatory effect on mouse macrophages with marked
increase in lysosomal activity and ROS formation.905 Complete
A number of new saponins were identied in extracts of the
NMR assignments have been reported for four pentaoside
Australian sea cucumber Holothuria lessoni using solely LC-MS/
asterosaponins: thornasteroside A, versicoside A, anasteroside
MS metabolomic techniques.876 In a conceptually similar
B and asteronylpentaglycoside sulfate (Asterias amurensis).906
manner, the chemical diversity of saponins present in different
organs of the starsh Asterias rubens was investigated by
combinations of MALDI-TOF and LC-MS(/MS) techniques.877 13 Mangroves
The latter study concluded that different organs are charac-
terised by different saponin mixtures and inter-specimen vari- In addition to a series of mildly antioxidant glycosides, mar-
ability exists suggesting inuence of sex and/or collecting inoids F–M 1374–1381, reported from the whole fruits of the
season on saponin prole. A short octapeptide echinometrin mangrove Avicennia marina,907,908 seco-diterpene 1382 (Ceriops
1373 (sea urchin Echinometra lucunter) was found to exhibit decandra),909 cinnamides 1383–1387 (Micromelum falcatum,
ability to degranulate mast cells leading to an inammatory mangrove associate),910 protolimonoids 1388–1394 (Xylocarpus
reaction.878 The sequence of the peptide is an internal fragment granatum),911 and limonoids 1395–1401,912 1402–1404,913 1405–
View Article Online
1408,914 1409–1418,915 1419–1422916 and 1423917 (X. rumphii and relative conguration of the alkaloid was determined by
X. granatum) were also isolated from mangroves or their asso- a combination of heteronuclear J-based congurational analysis
ciates. The absolute conguration of the unusual spiro-seco- and GIAO calculated chemical shis and DP4 probability
abietane decandrinin 1382 was secured via analysis of experi- analysis. Mild cytotoxicity towards a leukemia cell line was also
mental and calculated ECD and ORD chiroptical data909 while of observed. The arenicins, antimicrobial peptides produced by
the limonoids reported, the structures of xylorumphiin G the polychaete worm Arenicola marina,931 are constitutively
1398,912 xylogranatopyridine A 1402,913 granatumin L 1409915 expressed in a range of tissues in the organism suggestive that
and granatumin Y 1422916 were established by single crystal X- the peptides play a front-line role in defense against infec-
ray diffraction studies. tions.932 Cypridina luciferyl sulfate 1427 appears to be a more
stable storage form of cypridina luciferin, the luminescence
precursor of the ostracod Cypridina (Vargula) hilgendori.933 The
luciferin could be converted to luciferyl sulfate by action of
crude extract of the organism, presumably containing a sulfo-
transferase, in the presence of 30 -phosphoadenosine 50 -phos-
phosulfate (PAPS, a sulfate donor), while the reverse reaction
took place in the presence of adenosine 30 ,50 -diphosphate,
a sulfate acceptor.
Extracts of ovary tissue from Takifugu pardalis yielded a new

tetrodotoxin analogue, 6-deoxyTTX 1428.934 The potent voltage-
gated sodium channel blocker was also detected by LC-MSMS in
other marine animals including snail and octopus. Alanine
scanning of the hagsh (Myxine glutinosa)935 12-amino acid
residue antimicrobial peptide myxinidin has identied
a number of critical residues for the observed biological activ-
ities and that judicious substitution with arginine led to the
identication of more potent analogues.936 The 33-amino-acid
Further investigation of previously reported mangrove residue peptide pardaxin (atsh Pardachirus marmoratus)
MNPs has identied avicequinone C (Avicennia marina)918 as exhibited in vivo activity towards MRSA dermal infection and
a 5a-reductase-type 1 inhibitor,919 catunaregin (Micromelum enhanced wound healing.937 A range of arsenic-containing
falcatum)920 as an angiogenesis inhibitor,921 the cardiac lipids have been synthesised, providing valuable reference
glycoside neriifolin (Cerbera manghas)922 as the acaricidal standards for future studies directed towards understanding
component of Panonychus citri,923 and that leaf extracts and the uptake, biotransformation and toxicity of these unusual
puried components of Avicennia marina exhibit antibacterial MNPs.938
activity with relevance to urinary tract infections.924 Finally,
a new biomimetic synthesis925 and a structure–activity rela-
tionship study of the protein tyrosine phosphatase 1B inhib- 15 Conclusion
iting properties926 of the unusual dimeric alkylbutenolide
paracaseolide A (Sonneratia paracaseolaris)927 have been In a recent review the number of new MNPs reported from
reported. a range of countries was analysed based on the location of the
principal author for each publication.3 What is not apparent
from this analysis is the location of the collecting sites for the
14 Miscellaneous organisms. This can be problematical as shown in an extreme
example: one prominent MNP chemist based in the Mid-West of
Two studies of sea grass from the Egyptian Red Sea led to the the USA, thousands of km from any coastal resource, collected
identication of avone xyloside 1424 (Thalassia hemprichii)928 widely (see Fig. 1).
and dihydrochalcone diglycoside 1425 (Thalassodendron cil- With the biogeographic aspect of the MarinLit database19
iatum)929 as antimicrobial and anti-inuenza A virus MNPs now widely available an alternative perspective is available for
respectively. Thelepamide 1426 is an unusual ketide-amino acid viewing the collection data. It is now possible to search by
isolated from the annelid worm Thelepus crispus.930 The region showing who is collecting where and hence the
View Article Online
Table 1 The 22 oceanic regions or countries used in the survey giving

numbers of publications and new compounds discovered in each
region/country over the period 1965–2014
# #
Country or Oceanic region Compounds Papers
Pacic Russia, sea of Japan 377 167

China 2915 942
South China sea and Yellow sea 525 203
Taiwan 1350 376
Japan, including Okinawa 3877 1570
South Korea 848 239
North Pacic islands and atolls 1539 576
South Pacic islands and atolls 1548 522
Fig. 1 Collection sites (red stars) for a US MNP chemist. Maritime SE Asia, Papua-New Guinea 1340 502
Australia 1854 677
Mainland SE Asia (including East Malaysia) 457 173
South Asia 714 333
interests that MNP chemists have in the various regions of the Indian ocean and islands 326 155
globe. The 50 years of collecting effort globally is depicted in Mediterranean, Arabian Peninsula, Black sea 2358 876
Fig. 2. The red stars in Fig. 2 represent the collecting sites, Other African countries 456 154
Atlantic Europe and the Baltic sea 476 210
described in 9000 papers, from which 25 700 new
Atlantic ocean and islands 361 140
compounds have been obtained. The actual number of unique South American countries 538 210
collection sites is less than the number of papers as multiple Central America 245 86
collections have oen been made at the same sites. Fig. 2 Gulf of Mexico, Caribbean sea and islands 1524 571
displays those areas that have had high collecting pressures North America 1382 520
Arctic and Antarctica 330 105
and those where there has been, for whatever reason, lower
collecting pressures. An analysis has been made of the col-
lecting effort globally by semi-decade since 1965. For conve-
nience the globe was divided up into 22 regions or countries followed closely by China with 2915 compounds from the
(see Table 1) and the published papers for each region mainland with a further 525 compounds to be included if the
compiled. Totals for papers (citing collection sites) describing regions of the South China Sea and Yellow Sea are also
new compounds from 1965 are also listed in Table 1 while considered. But what is remarkable here is the rapid emergence
Fig. 3 shows the incidence of discovery of new compounds in of MNP chemistry using Chinese-based collections as seen in
each region or country by semi-decade since 1965. It is worth Fig. 3. Other regions where there have been extensive collec-
noting that since 1965–280 papers contained no biogeo- tions are in the Mediterranean (2358) (which includes the
graphic data, not even a country or an ocean, to describe the Mediterranean coasts of Spain and France, Italy, the islands of
origin of new compounds being reported. Fortunately, recent the Mediterranean, Greece, Turkey, Israel, Egypt, the Arabian
years have seen the increasing use of exact coordinates. The Peninsula, Black Sea and the Mediterranean African coastlines),
Japanese region, including Okinawa, has been the most Australia (1854), the North (1539) and South (1548) Pacic
productive region with 3877 compounds described. This was islands and atolls, and the Gulf of Mexico, Caribbean Sea and
islands (1524). Other regions that have been well explored
include Taiwan (1350) and Maritime SE-Asia and Papua-New
Guinea (1340).
The graph shows very clearly those countries that were most
closely studied in the early years. Compounds of Japanese origin
were prominent from the 1960s, but the search for MNPs was
quickly taken up with compounds from the Mediterranean,
North Pacic and North American regions appearing in the
early 1970s, followed by Australian and Maritime SE-Asian
compounds later in that decade. Prospecting activity in other
parts of Asia was relatively slow to start and it was not really
until the 1990s that compounds of Mainland SE-Asian, South
Korean, Taiwan and Chinese origin started to appear. The
output from these regions has rapidly accelerated since,
particularly so in the case of compounds of Chinese origin.
Fig. 2 and 3, taken in combination, provide a snapshot of the
past efforts in marine natural products as well as current
endeavours and highlights those areas of the globe that are
currently under-explored.
Fig. 2 All collection sites for MNP discovery, 1965–2014.
View Article Online

Fig. 3 The count of new compounds by region/country over the period 1965–2014, by semi-decade.
16 Acknowledgements 6 L. E. Lallier, O. McMeel, T. Greiber, T. Vanagt,

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Marine natural products‡

Review Natural Product Reports

signicant reviews (16) are given here while a listing of the

preclinical development’ have been reviewed,4 and ‘New horizons

Brent Copp received his BSc Murray Munro, Emeritus

Natural Product Reports Review

3 Marine microorganisms and

3.1 Marine-sourced bacteria (excluding from mangroves)

Review Natural Product Reports

Natural Product Reports Review

has now led to isolation of a number of bisindole alkaloids;

biosynthesis of piericidin A138 during identication of the

A study of the biosynthetic pathway for marineosins43 in

Review Natural Product Reports

perdeuterated version) and of 23-ketoundecylprodiginine 37 Escherichia, Jejua, Micrococcus, Micromonospora, Nocardiopsis,

myces including 104–172.81–103 The genera Verrucosispora and

3.2 Bacteria from mangroves

Natural Product Reports Review

B 209. Yields of penilumamide B 209 and penilumamide

So-coral associated Chondrostereum sp. has previously been

Review Natural Product Reports

The chromones engyodontiumone A–H 219–226 and the

Neosartorya pseudoscheri (starsh Acanthaster planci,

Natural Product Reports Review

Review Natural Product Reports

The polyketides dothiorelone F 537 and I 538 were obtained

Natural Product Reports Review

studies indicated that grassypeptolide A binds to the enzyme at

Review Natural Product Reports

algal literature for 2014 was a study on the eﬀect of natural

taxonomic descriptors and the implications that this has.

Some 27 diterpenoids ranging across six classes were iso-

Natural Product Reports Review

6 Red algae A synthesis491 of the brominated sesquiterpene aldingenin

Review Natural Product Reports

Natural Product Reports Review

Other indole 825–829543,544 and b-carboline 830–837544–546

Review Natural Product Reports

Natural Product Reports Review

Review Natural Product Reports

from octocoral species Pennatula aculeata, Dichotella gemmacea,

Natural Product Reports Review

Review Natural Product Reports

Specimens of the Mediterranean sacoglossan mollusc Thur-

Natural Product Reports Review

Review Natural Product Reports

cancer cell line MDA-MB-231 were investigated by content-rich

Natural Product Reports Review

Extracts of ovary tissue from Takifugu pardalis yielded a new

Review Natural Product Reports

Table 1 The 22 oceanic regions or countries used in the survey giving

Pacic Russia, sea of Japan 377 167

Natural Product Reports Review

16 Acknowledgements 6 L. E. Lallier, O. McMeel, T. Greiber, T. Vanagt,

Review Natural Product Reports

12 M. P. Puglisi, J. M. Sneed, K. H. Sharp, R. Ritson-Williams 31 R. Raju, A. M. Piggott, L. X. B. Diaz, Z. Khalil and

Natural Product Reports Review

Review Natural Product Reports

4. J. Rubio, M. Sanchez-Hidalgo, A. F. Brana, C. Mendez and

Natural Product Reports Review

Review Natural Product Reports

Natural Product Reports Review

Review Natural Product Reports

Natural Product Reports Review