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Botanical Journal of the Linnean Sociely (1987)94: 293-326. With 10 figures
The chemical constituents and economic
plants of the Euphorbiaceae
ABDEL-FATTAH M. RIZK
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Chemistry Department, Faculty of Science, Qatar University, P.O. Box 2713, Doha, Qatar
Received November 1986, accepted for publication November 1986
RIZK, A.-F. M., 1987. T h e chemical conmtitucntm and economic phtm of the
Euphorbiaceae. A chemical review of the different classes of compounds which have been isolated
from the Euphorbiaceae (other than the diterpenoids) is given. This includes triterpenoids and
related compounds (sterols, alcohols and hydrocarbons), phenolic compounds (flavonoids, lignans,
coumarins, tannins, phenanthrenes, quinones, phenolic acids, etc.), alkaloids, cyanogenic glucosides
and glucosinolates. A summary of the industrial and medicinal uses of members of the
Euphorbiaceae is provided.
ADDITIONAL KEY WORDS:-alcohols
- alkaloids - anthraquinones - arrow poison coumarins - cyanogenic glucosides - fish poison - flavonoids - glucosinolates - lignans - medicinal
plants - naphthaquinones - oils - paper - petroleum plants - phenanthrenes - phenolic acids rubber - steroids - tannins - triterpenoids - ubiquinones - waxes - woods.
CONTENTS
Introduction . . . . . . . .
Chemical constituents . . . . . .
Terpenoids and related substances . .
Fatty acids . . . . . . .
Phenolic substances . . . . .
Alkaloids . . . . . . . .
Economic plants . . . . . . .
Industrial plants and/or their products.
Medicinal plants . . . . . .
References.
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293
294
294
295
298
306
313
313
31 7
321
INTRODUCTION
The plants of the Euphorbiaceae contain acrid, milky or colourless juice.
Chemical data are available for several genera, especially Eubhorbia, where more
than 120 species have been investigated. A survey of this data showed that the
triterpenoids, followed by flavonoids and alkaloids are the main classes of
substances of interest to phytochemists. However, the presence of other
substances, e.g. coumarins, cyanogenic glucosides and tannins are also reported.
0024-4074/87/020293
+ 34 $03.00/0
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293
01987 The Linnean Society of London
294
A.-F. M. RIZK
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The family contains several species of considerable economic importance used
as foodstuffs, as medicinal plants and in industry.
CHEMICAL CONSTITUENTS
Terpenoids and related substances
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More than 55 triterpenoids (tetra- and pentacyclic) have been identified from
the Euphorbiaceae. A review has been given recently by Rizk & El-Missiry
(1986) who discussed the distribution of triterpenoids in this family. Table 1
summarizes the triterpenoids identified in plants of the Euphorbiaceae; see also
Fig. 1. They have been isolated from the latex as well as from the different parts
(bark, cortex, flowers, leaves, roots and stems). Some of the triterpenes (e.g. aand 8-amyrin) have been found either free or as their esters (acetates). Some
also occurred as glycosides, e.g. geniculatin (a triterpenoid saponin) isolated
from Euphorbia geniculata Orteg. (Tripathi & Tiwari, 1980). Another
triterpenoid glycoside (gypsogenic acid derivative) was found in some Euphorbia
species (Soboleva, 1979).
The major constituents of the latex of many Euphorbia species are triterpenes
and their esters. Monoesters and diesters are also found in the latex of Euphorbia
species but they are only minor components (Warnaar, 1981).
The stem bark of Croton oblongiflius Roxb. contains, besides other
components, a group of six compounds having the pimarane skeleton, viz.
oblongifoliol, deoxyoblongifoliol, oblongifolic acid, ent-iso-pirnara-7,15-diene,
ent-isopirnara-7,15-dien10-aldehyde and 19-hydroxy-ent-isopimaradiene (Aiyar
& Seshadri, 1971).
The analysis of the essential oils in several Croton species was reported by
Craveiro et al. (1978, 1981) and the following compounds were identified:
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MONOTERPENOIDS: car-3-ene, a-phellandrene, myrcene, a-pinene, 8-pinene,
sabinene, v-terpinene, a-terpinoline, a-thujene, p-cymene, borneol, camphor,
1,8-cineole, geranial, linalool, neral, a-terpineol, terpinen-4-01, ascaridol and
isoscaridol;
PHENYLPROPANOIDS: t-anethole, estragol, eugenol, methyl eugenol, n-propyl
catechol and elemicin;
SESQUITERPENOIDS: aromadendrene, a-bergamoptene, v-cadinene, b-caryophyllene, a-copaene, 8-elemene, v-elemene, 8-elemene, a-farnesene, 8-farnesene,
germacrene B, 8-guayene, a-humulene and v-muurolene.
The essential oil of Euphorbia monostyla Prokh. contains the following
compounds: thymol, a-pinene, a-thujene, camphene, a-phellandrene, myrcene,
a-cardinene, 8-cardinene, p-cymene, linalool, citronellol and geraniol (Baslas,
1982).
8-Sitosterol has been identified in the sterol fraction of the different species of
the Euphorbiaceae studied. Other sterols also occur, but in relatively small
amounts, e.g. stigmasterol, campesterol, dihydrobrassicasterol, 28-isofucosterol,
A7-i~ofuco~tero1and cholesterol (Rizk & El-Missiry, 1986). 7-Oxo-,
7-a-hydroxy- and 7-j?-hydroxy- derivatives of campesterol, stigmasterol and
sitosterol were isolated from the roots of Euphorbiafzscheriana Steud. ( = E. pallasii
Turcz.), a drug used for its anti-tumour properties in Chinese traditional
medicine (Schroeder, Rohmer, Beck & Anton, 1980).
CHEMICAL CONSTITUENTS OF EUPHORBIACEAE
HO
HO
Cycloaudenol
295
HO
HO
Cmllotodiol
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Cycloeucolenol
CyclDcuphMnol
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CHZ
HO
Ho
H
Cycloroylenol
Euphol
Euphorbol
Euphubinol
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Glochidinol
Hopenme-8
Glafhilocudol:
R iOH; R'= H
Golchidol:
HO
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Geniculotin
Tirucallol
HO OH
Figure I . Some triterpenoids of the Euphorbiaceae.
In the genus Euphorbia, squalene oxide leads both to 4,4-dimethylleuphoids
and 4,4-dimethylsteroids, but it is not clear from the literature whether both or
only one of these is metabolized further to 4-desmethyl compounds. The
existence of 4,4-dimethylleuphoids and a 24-methylene group, as in the case of
euphorbol in E. triangularis Desf., E. ingens E. Mey and E. resinifera Berg, shows
that the (2-24 alkylation can actually occur after cyclization to the euphoidal
structure (Sekula & Nes, 1980).
Long-chain fatty alcohols (particularly n-octacosanol and n-hexacosanol) and
hydrocarbons have been identified from the different genera especially Euphorbia
spp. (Rizk & El-Missiry, 1986). The latter species have been reported to yield a
considerable amount of hydrocarbons and alcohols, and a number of them have
been suggested as potential hydrocarbon-producing crops (Calvin, 1980, 1982).
Fatty acids
The fatty acid composition and characterization has been reported for
relatively few species of the Euphorbiaceae. In addition to the usual saturated
and unsaturated fatty acids, several others were obtained from the seeds oils.
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Table 1. Triterpenoids isolated from the Euphorbiaceae
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Triterpenes
I. Alnusenone
2. a-Amyrin
3. B-Amyrin
4.B-Amyrenone
5. 6-Arnyrenone
Euphorbia wahnabk Mark.
Euphorbia spp., Macaranga tanaritu Muell.-Arg.
Euphorbia spp., Phyllanthus a d u s Skeel.
Macaranga hnnrius Muell.-Arg.
Euphorbia csula L., E. parvijlora L.
6. Betulin
7. Betuliaic acid
8. Butyrospermol
9. Corollatadiol
10. Cycloartenol
1 1. Cycloart-25-ene-3-j3-24-diols
Euphorbia spp., Sarcoccoa prunifrmis Lindl.
Phyllanthus discoides Muell., P. reticulatus Poir.
Euphorbia SQP., Hura crepitans L.
Euphorbia corollata L.
Euphorbia spp.
Euphorbia SQP.
12. Cycloaudenol, and 3-epi-cycloaudenol
13. Cycloeucalenol
14. Cycloeuphornol
15. Cycloroylenol
16. Darninara-20,24-diene-3-B-01
17. Euphadienol
18. Euphol (a- & B-)
19. Euphorbinol
20. Euphorbol and iso-euphorbol
2 1. Friedelan-3-a-01
Euphorbia caudkzolia Mans.
Euphorbia roylcana Boiss, E. paralias L.
Euphorbia timalli L.
Euphorbia roylcana Boiss.
Antidcsma b u n k Spreng.
Euphorbia condyocarpa Bieb.
Euphorbia spp.
Euphorbia tirucalli L.
Euphorbia spp.
BischoJa trifoliata (Roxb.)-Hook. fil., Euphorbia spp., Glochidion
macrophyllum Miill.-Arg.
Bischoja triyoliata (Roxb.) Hk.fil., Euphorbia hirh L., Glochidion
macrophyllum, Phyllanthus reticulatus Poir, Sapium sebijicmm Roxb.
Bischoja tntoliah, Euphorbia spp.
Anlidesma b u n k Spreng., Baccaurea sepida Muell., Bischojia tnjCliata
(Roxb.) Hook fil., Bri&lia spp., Euphorbia spp., Sapium discolor
Muell.-Arg.
Eujhorbia spp.
22. Friedelin
23. Fridelinol (Friedelan-3-/J-ol)
24. epi-Fridelinol
25. Germanicol (and 3-epz-germanicol)
Takemoto & Ishiguro (1966)
Rizk & El-Misery (1986), Hui ct al. (1975
Rizk & El-Missiry (1986)
Hui cf al. (1975)
Manners & Davis (1984), Rizk & El-Missiry
(1986)
Chopra et al. (1969), Rizk & El-Missiry (1986)
Rizk & El-Missiry (1986)
Rizk & El-Missiry (1986)
Piatak & Reimann (1972)
Rizk & El-Missiry (1986)
Anjaneyulu CI al. (1985), Rizk & El-Missiry
( 19%)
Govardhan ct al. (1984)
Rizk & El-Missiry (1986)
Aha ct al. (1979b)
Bhat ct al. (1982)
Sainsbury (1970)
Roschin & Kir’yalov (1970)
Rizk & El-Missiry (1986)
Afza ct al. (1979a)
Rizk & El-Missiry (1986)
Rizk & El-Missiry (1986)
?
a
7
E
7;
26. Glut-5-(6)-en-3-01
27. Clut-5-(6)-3n-3-one
28. Glochidiol
29. Glochidol
30. Glochidone
31. Glochidonol
32. Glocilocudol
33. Hopenol-B
34. Hopenone-B
35. Lanostadienol
36. Lanostenol
37. Lanosterol
38. Lup-20-en-3-fi-16-fidiol
39. Lup-20(29)-en-1-fi-3-fi-diol
40.Lup-20(29)-en-3-a-23-diol
41. Lupenone
42. Lupeol
43. 3-epi-Lupeol
44. Maculatol
45. 24-Methylenecycloartenol
Euphorbia cyparissias L.
Euphorbia cyparissiac L.
Glochidion spp.
Glochidion spp.
Bridelia moonii Thw., Glochidion spp.
Glochidion spp., Phyllanthus reticulalw Poir.
Glochidion multiloculare Voigt
Euphorbia supina Rafin. ex Boiss.
Euphorbia cyparissias L.
Euphorbia balsamifera Aiton
Euphorbia spp.
Euphorbia spp.
Bayeria spp.
Glochidion spp.
Glochidion thomoni Hook. fil.
Euphorbia spp.
Euphorbia spp., Glochidion spp., Phyllanthus spp.
Euphorbia maddeni Boiss., Glochidion hohcnatkm' Bedd.
Euphorbia maculata L.
Euphorbia spp., Hura crepitans L.
46. Moretenol
47. Moretenone
48. Nerifoliol
49. Obtusifoldienol
50. Obtusifoliol
5 1. Oleanolic acid
52. Phyllanthol
53. Taraxasterol (and pseudo-taraxasterol)
54. Taraxerol
Aleurites moluccana L., Sapium sebiferum
Aleurites moluccana L., Euphorbia spp., Sapium sebifeerum
Euphorbia nenifolia L.
Euphorbia echinus Hook., E. obtusiifolia Poir.
Euphorbia obtusifolia Poir.
Euphorbia paralias L.
Phyllanthw acidus Skeel, P. englen
Euphorbia spp.
Bndelia micrantha Baill., Croton sparsaaoms Morong., Euphorbia spp.
55. Taraxerone
Briddia micrantha Baill., Euphorbia spp., Trewia nudgora L.
56. Tirucallol
57. Unolic acid
58. Uvaol
Euphorbia spp.
Euphorbia paralias L.
Euphorbia paralias L.
Starrat (1966)
Rizk & El-Missiry (1986)
z
z
z
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:
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Matsunaga & Morita (1983)
Starrat (1969)
Rizk & El-Missiry (1986)
Rizk & El-Missiry (1986)
Rizk & El-Missiry (1986), Rizk et al. (1980b)
n
2
z
6
c
Rizk & El-Missiry (1986)
8
Takemoto & Inagaki (1958)
Rizk et al. (1974, 1980b), Rizk & ElMissiry (1986)
Rizk & El-Missiry (1986)
Rizk & El-Missiry (1986)
Rao & Row (1966)
4
Rizk & El-Missiry (1986)
Rizk & Rimpler (1977), Rizk & El-Missiry
I19861
Rizk & El-Missiry (1986), Chopra et al.
( 1969)
Rizk & El-Missiry (1986)
Rizk el al. (1974)
Rizk el al. (1974)
z=!
5z
2
m
0
c5
N
s
298
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A.-F. M.RIZK
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Castor oil contains 80-90y0 of the glycerol ester of ricinoleic acid (Vickery &
Vickery, 1979):
CH,(CH,),CHOHCH,CH=CH(CH,),COOHRicinoleic acid
a-Eleostearic acid has been identified from the seed oil of Trewia nud@ora L.,
(Sarkar & Chakrabarty, 1956a):
CH,(CH,),(CH=CH),(CH,),COOH
u-Eleostearic acid
A new conjugated fatty acid identified as deca-2,4-trienoic acid along with its
four isomers have been detected in the latex of Euphorbia pulcherrima Klotzsch
(Baslas, 1982).
Euphorbia lagascae Spreng. seed contains a unique epoxy-bearing oil (58-62y0,
12,13-epoxyoleic acid) (Krewson & Scott, 1966). The fatty acids of the
triacylglycerol fraction of the latex of Hevea brusiliensis Muell. Arg. consists of
97% of a C, furanoid fatty acid, 1O713-epoxy-1 1-methyloctadeca- 10,12dienoic. A dioxy fatty acid, 1O713-dioxy-1 1-methyloctadecanoic acid was also
isolated from the free fatty acid fraction of the same plant (Li Ken Jie & Sinha,
1981).
Although the terpenes of the latex of Euphorbiu species have been extensively
studied, much less attention has been given to the saponifiable part of the
terpene esters (Warnaar, 1981). Triterpene esters in the latex of E . pulcherrimu
appeared to be esterified mainly with conjugated decatrienoic acid (Warnaar,
1981). Diterpenes isolated from the latices of E . tirucalli L. (Fuerstenberger &
Hecker, 1971a, b; Kinghorn, 1979) and E. lathyris L. (Adolf & Hecker, 1971)
were also esterified with conjugated fatty acids. These acids have eight to 14
carbon atoms in the chain which has two to five double bonds conjugated with
carboxylic groups. The fatty acids esterified with the triterpene alcohols of
E . lathyris were analysed by Warnaar (1981); 77% of the fatty acids were
conjugated, the main components of which were decadienoic and decatrienoic
acids.
Phenolic substances
Flavonoids
The family Euphorbiaceae is rich in flavonoids, particularly flavones and
flavonols, which have been identified from several genera. They occur both as
0- and C-glycosides and as methyl ethers. Flavanones also occur, but in
relatively few plants (Table 2 & Fig. 2). The flavonoids were detected in
different parts of the plant other than the roots. The two common flavonols
kaempferol and quercetin (and their glycosides) are most widely distributed in
the different genera of the family.
Robidanol (3,7,3',4'5'-pentahydroxyflavene) was identified in Euphorbia
palustris L. and E . stepposa Zoz (Bondarenko et al., 1971). Robidanol-3-gallate7
also occurred in E . palustris (Rizk & El-Missiry, 1986). A chalcone identified as
2',4',6'4-tetrahydroxychalcone was isolated from the stem wood of Excoecaria
agallocha L. (Prakash, Khan, Khan & Zaman, 1983).
Anthocyanins (e.g. cyanidin, delphinidin, and pelargonidin glucosides) were
identified in several Euphorbia species (Yoshitama, Ishii & Yasudo, 1980; Baslas,
1982; Rizk, 1986).
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299
CHEMICAL CONSTITUENTS OF EUPHORBIACEAE
H
o
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W
0
OH
O
H
glucosyl \
6H6
on
glucosyl
H
Orienlin
Irovilexin
(Sapmarelin) R = H
Saponarin: R = glum5e
Apigenin
OH
,OH
zyxwvutsrqpon
o
W
O
H
H
I
I
-O
W
H
on
0
OH
0
OH
o
Viieiin
0
Myricelin: R = H
Isornyrialrin: R = glumse
Gassypelin
OH
OH
Rharnnelin
Kaernpferol
0
Ericdiciyol
"0.
H
o
P
O
H
m
W
O
H
HO
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OH
0
Noringenin
OH
0
Slewyenin: R = H
Slepposide: R = glumse
Robidaml
Figure 2. Some flavonoids of the Euphorbiaceae.
Coumarins
These have been isolated from relatively few plants. The seeds of Euphorbia
lathyris have been reported to contain two bicoumarins (euphorbetin and
isoeuphorbetin) (Table 3 & Fig. 3). Three bergenin derivatives were isolated
from the bark of Mallotus japonicus Mue1l.-Arg. and identified as 11-0-galloylbergenin, 4-0-galloylbergenin and 1 1-0-galloyldemethylbergenin (Yoshida,
Seno, Takamo & Okuda, 1982).
Euphorbia royleana Boiss. contains three benzocoumarins identified as
7-hydroxy-3,4-benzocoumarin, 7-methoxy-3,4-benzocoumarin and 2,7-dihydroxy-3,4-benzocoumarin (Baslas, 1982).Table 3 summarizes the other coumarins
isolated from the Euphorbiaceae.
Lignans
Lignans have been, so far, identified in only two genera, viz. Jatropha and
Phyllanthus. The leaves of Phyllanthus niruri L., contain phyllanthin and
hypophyllanthin (Rizk & El-Missiry, 1986) (Fig. 4). Jatropha gossypifolia L.
(stem, root and the seeds) yielded 2-piperonylidene-3-veratryl-3R-v-butyrolactone (I) (Chatterjee, Das, Pascard & Prange, 1981) and gadain
Flavonoids
Species
I. Flauones
z
z
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Table 2. Flavonoids of the Euphorbiaceae
w
0
References
1. Apigenin
Jatropha mrcas L.,J . gossypifolia L.
Rizk & El-Missiry (1986)
2. Apigenin 7-0-glucoside
(Cosmosiin)
Euphorbia spp.
Ismail et al. (1977), Rizk ct 01. (1982), Rizk
& El-Missiry (1986)
Jefferies (1979), Rizk & El-Missiry (1986)
zyxwvutsrqpon
zyxwvutsrqponm
zyxwvutsrqponmlkjih
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3. 5,4'-LXhydroxy-3,7,8trimethoxyflavone
4. Isoorientin
5. Isovitexin (Apigenin-6C-glucoside, Saponaretin
6. Orientin
7. 5,7,3',4'-Tetrahydroxy-3,&
dimethoxyflavone
8. 5,7,3'-Trihydroxy-3,8,4',5'tetramethoxyfiavone
9. Vicenin-1
10. Vitexin
Be-
leschenaultii Baill., Ricincarpos muricatus Muell.-Arg.
Croton zambezicus Muell.
Croton zambezicus Muell., Jatropha spp., Hevea brasiliensis Muell.-
4.
Wagner et al. (1970)
Rizk & El-Missiry (1986)
Croton zambezicus Muell.
Ricinocarpos muricatus
Wagner et al., (1970)
Jefferies (1979), Rizk & El-Missiry (1986)
B y m a brcvifolia Baill.
Jefferies (1979), Rizk & El-Missiry (1986)
Croton ambtzicus Muell.
Croton zambezicus Muell., Heuea brasilimis Muell.-Arg., Jatropha
SPP.
Wagner et al. (1970)
Rizk & El-Missiry (1986)
II. Flauonols
1 I . Gossypetin hexamethyl ether
12. lsomyricitrin
13. Isoquercitrin
14. Isorhamnetin
15. Isorhamnetin-3-rutinoside
( Narcissin)
16. Kaempferol
17. Kaempferol 3-0-galactoside
(Trifolin)
18. Kaempferol 3-0-glucoside
(Astragalin)
19. Kaempferol 4'-O-glucoside
20. Kaempferol 3-0-glucuronide
21. Kaempferol 3-0-rhamnoside
22. Kaempferol 3-0-rutinoside
23. Myricetin
24. Myricetin hexamethyl ether
Ricinocarpos sglosus Diels
Euphorbia spp.
Euphorbia seguieriana Neck., E. semiuillosa Prokh.
Crotm oblongifolius Roxb., Euphorbia kalenuznkii Czern. ex Trautv.
Mercurialis annua L.
Rizk & El-Missiry (1986)
Euphorbia spp., Phyllanthus emblica
Euphorbia mysinitis L.
Euphorbia spp., Phyllanthus emblica
Euphorbia d e n i Boiss.
Euphorbia spp.
Euphorbia lunulata Bunge, E. mysinites L.
Euphorbia spp., Mercurialis perennis L.
Euphorbia spp., Ricinocarpos splosus
Ricinocarpos splosus
Rizk et a1 (1980a, b ) ,Rizk & El-Missiry
( 1986)
Sahai et al. (1981)
Rizk & El-Missiry (1986)
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zyxwvutsrqpon
zyxwv
zyxwvu
25. Quercetin
26. Quercetin 3-0-arabinoside
27. Quercetin-3-0-galactoside
(Hyperoside, Hyperin)
28. Quercetin-3-digalactoside
(Heliosin)
29. Quercetin-3,5-0-di-galactoside (Tithymalin)
30. Quercetin-3-0-galactoside2”-gallate
3 I . Quercetin-3-0-galactoside6-gallate
32. Quercetin-3-0-glucuronide
33. Quercetin-3-0-glucoside
34. Quercetin-3-0-rhamnoside
(Quercitrin)
35. Quercetin-3-0-rhamnoglucoside (Quercetin-3-0-rutinoside,
Rutin)
36. Quercetin-3’-0-xyloside
37. Rhamnetin
38. Rhamnetin-3-0-arabinoside
39. Rhamnetin-3-0-diarabinoside
40. Rhamnetin-3-0-galactoside
4 I . Rhamnetin-3-0-rhamnoside
42. Rhamnetin-3-0-dirhamnoside
Crofon oblongifolius Roxb., Euphorbia spp. Jafropha hqnii Bal.,
Ricinus communis L.
Euphorbia paralias L., E. sfricfa L.
Croton oblongiflius Roxb., Euphorbia spp., jatropha heynii Bal.,
Ricinus communis L.
Rizk rt al. (1976. 1982), Rizk & El-Missiry
( 1986)
Rizk el al. (1979), Rizk & El-Missiry
( 1986)
Rizk et al. (1980), Rizk & El-Missiry
( 1986)
Euphorbia heliosropia L
Chen el al. (1979), Rizk & El-Missiry
( 1986)
Euphorbia hclioscopia L., E. uerrucosa Lam.
Pohl el al. (1975)
Euphorbia dulcis L., E. plafiphyllos L.
Euphorbia cyparissias L., E. lathyris L.
Euphorbia spp., Sapium sebiferum
Aleuritis cordafa Stand., Euphorbia spp.
Rizk & El-Missiry (1986)
Aleurifes cordafa Stand., Crofon sparsijorus Motong., Euphorbia spp.,
Manihof ufilissima Pohl., Mercurialis spp., Ricinus communis L.
Ismail el al. (1977), Rizk ef al. (1982), Rizk
& El-Missiry (1986)
Rizk el al. (1982), Rizk & El-Missiry
(1986)
Euphorbia paralias L.
Euphorbia spp.
Euphorbia amygdaloides L.
Euphorbia amygdaloidcs L.
Euphorbia peplus L., E. prosfrab Aiton
Euphorbia amygdaloides L.
Euphorbia amygdaloides L.
Rizk el al. (1976)
Rizk & El-Missiry ( 1986)
Mueller & Pohl (1970)
Mueller & Pohl (1970)
Ismail ef al. (1977), Rizk ef al. (1980a, b)
Mueller & Pohl (1970)
Mueller & Pohl (1970)
Sapium sebzyerum Roxb.
Bhat et al. (1981)
zyxwvutsrqponm
zyxwvutsrqp
zyxwvutsrqponmlkjihgfed
zyxwvutsrqponmlk
III. Flavanones
43. 5-methylericdictyol 7-0xyloarabinoside
44. Naringenin
45. Naringenin-3-p-coumarylglucoside
46. Naringenin-3,6-dicoumaroylglucoside
47. Naringenin-7-0-glucoside
48. Steppogenin
49. Stepposide
Mobca caudafa Peth.
Mobea caudafa
Barros el al. (1982)
Mobea caudafa
Euphorbia condylocarpa Bieb.
Euphorbia palusfris L., E. sfepposa Zoz.
Euphorbia spp.
Rizk & El-Missiry (1986)
W
N
0
zyxwvutsrqponm
zyxwvutsrqpo
zyxwvutsrqp
zyxwvutsrqpon
zyxwvuts
zyxwvutsrqpo
zyxwvutsrqpon
Table 3. Some coumarins of the Euphorbiaceae
~~
Coumarins
zy
z
z
~
Species
References
FLwgga minoCarpa BI., Mallotu j a p o h Muell.-Arg.
Euphorbia dranrnculoidcs Lam.
Euphorbia tmacina L.
Euphorbia lunulata Bunge.
Ricinur cmnrmurir L.
Ahmad d al. (1972), Shigematsu et al(1983)
Chawla ct al. ( 1980)
Mahmoud & Abdel Salem (1979)
Rizk & El-Missiry (1986)
Khafagy ct al. (1979)
1. Bergenin
2. Daphnetin
3. 3,7-Dihydroxycoumarin
4. 6,7-Dihydroxycoumarin
5. 6,7-Dihydroxy-8-methoxy
(or 6,8-Dihydroxy-7methoxy) coumarin
6. 3,4-Dimethoxy-6,8dihydroxycoumarin
7. Esculin
8. Esculetin
9. Euphorbetin
(and Isoeuphorbetin)
10. Fraxetin
1 1. 3-Hydroxy-7-methoxycoumarin
12. Maoyancaosu
13. Scopoletin
Euphrbia acanthohnmnos Heldr. & Sart.
Euphorbia spp.
Euphmbicr l o ~ y i L.
s
KaUimanis & Philianos ( I 980)
Rizk & El-Missiry (1986)
Dutta cf al. (1972, 1975)
Jatropha gh&l@ra
Euphbia paralias L.
Eiphorbia lunulota Bunge.
Euphorbia acanthothamnos, Nealchoma yapurmis Huber.
14. Scopolin
Euphorbia acanlllothamnos
Parthasarathy & Saradhi (1984)
Mahmoud & Abdel Salam (1979)
Shang ct al. (1979)
Gunasekera et al. (1W),
Rizk & El-Missiry
(1986)
Kallimanis & Philianos (1980)
Ricirnrr can&
L.
Khafagy ct al. (1979)
CHEMICAL CONSTITUENTS OF EUPHORBIACEAE
zy
zyxw
303
zyxwvu
zyxw
OH
HO
EuphWDelln
ls0euwhorDetin
Mooyonmow
Figure 3. Some coumarins of the Euphorbiaceae.
(Banerji, Das, Chatterjee & Shoolery, 1984) A coumarino-lignan (11),
involving a dioxan type link between a coumarin and a phenyl propane
precursor, similar to the one found in the flavano-lignans, silymarin and
hyndocarpin, was isolated from the roots of Jatropha glandulifera Roxb.
(Parthasarathy & Saradhi, 1984).
Tannins
Hydrolysable tannins have been detected in several species of the
Euphorbiaceae, e.g. Euphorbia maculata L., Gleditsia japonica Miq., Mallotus
japonicus Muel1.-Arg., Phyllanthus emblica L. and Sapium sebiferum Roxb. (Rizk &
El-Missiry, 1986). The bark of Phyllanthus sebiferum contains 16.64% tannins.
The main tannin of Triadica sebifera Small ( = Sapium sebiferum Roxb.) is geraniin
(Fig. 5). The latter compound and mallotusinic acid are the main tannins of
Mallotus japonicus (Okuda, Mori & Hatano, 1980a; Okuda, Yoshida & Hatano,
1980b; Okuda & Kaoru, 1981). The leaf of M. juponicus contained a third
tannin identified as mallotinic acid (Okuda & Seno, 1981). Corilagin (a
hydrolysate product of geraniin) was identified in the bark of the same plant
(Yoshida, Seno, Takamo & Okuda, 1982).
0
/
zyxwvutsrqp
zyxwvut
'0
ocH3
Phyllonthin
L
O
L
HypOphyllonlhin
Godain
u
Figure 4. Some lignans of the Euphorbiaceae.
O
I
304
zyxwvutsrqp
zyxwvu
A.-F. M.RIZK
OH OH
HO
OH
Q
60
zyxwvuts
zyxwvut
$+O
'H
OH
HO
0
0
Lo
do
bn
Corilagin
0
Nc-0
zyxwvutsrqp
Gemniin: R H
H
O
HO
Mallatusink acid: R :
W
O
H
O-C=O
Ellagic acid
COOH
COOH
OH
zyxwvutsrqponm
zyxwvutsrq
Chloropnic acid:
R * quinic acid HtO
Gallic acid
-
Vonillic a i d
OH
OH
R*-C
or rn-digoilale
'OH
zyxwvu
Tannic add
Figure 5. Some phenolic compounds of the Euphorbiaceae.
Ellagic acid (a constituent of some tannins) has been identified in several
species, e.g. some species of Euphorbiu (Rizk, Rimpler & Ismail, 1977; Rizk &
El-Missiry, 1986)) Mullotus juponicus (Yoshida et ul., 1982) and Supium sebiferum
(Kouno, Saishoji, Sugiyama & Kawano, 1983). Tri-0-methylellagic acid was
also detected in several species, e.g. Aculyphu indicu L. (Talapatra, Goswami &
Talapatra, 1981) and Mullotus juponicus (Yoshida et ul., 1982). 2,3Dimethylellagic acid and 3,3-di-O-methylellagic acid (and its acetate) have
been isolated from Euphorbiu royleunu Boiss. (Nazir, Ahmad, Bhatty &
Karimullah, 1966) and Euphorbiu wullichii Hook. fil. (Baslas, 1982))respectively.
Gallic and tannic acids were identified from Euphorbiu hirtu L. (Rizk, 1986)
CHEMICAL CONSTITUENTS OF EUPHORBIACEAE
OH
Micmndrol E
OH
zyxw
305
2-Met hylanlhroquinone
Microndrol F
zyxwvu
zyxwvuts
zyxw
zyxwv
H
Ubiquinone-8: n . 8
Ubiquinon-9 n = 9
Ubiquinone-10: n 10
Figure 6. Some phenanthrenes and quinones of the Euphorbiaceae.
zyxw
and phyllembin (ethyl gallate) from Emblica ojicinalis Gaertn. (syn. Phyllanthus
emblica L.) (Chopra, Chopra & Varma, 1969).
Phenanthrenes and quinones
Two micrandrols, E (6-hydroxy-7-methoxy-lY2-dimethylphenanthrene)and
F (6-hydroxy-7-methoxy-172-dimethyl-9,10-dihydrophenanthrene) have been
identified from the trunk wood of Sagotia racemosa Baill. (Fig. 6) (de Alvarenga,
Gottlieb & MagalhPes, 1976). The trunk of Jatropha glandulifera Roxb. contains
3,3-dimethyl-acryl shikonin and acetylshikonin (Ballantine, 1969). 2-Methylanthraquinone was isolated from both Acalypha indica L. (Talapatra et al., 1981)
and Euphorbiu pulcherrima (Baslas, 1982). Ubiquinones (-8, -9 and -10) were
identified from Hevea brasiliensis (Law, Threlfall & Whistance, 1970).
Phenolic acids
In addition to ellagic, gallic and tannic acids, several other phenolic acids
were identified in plants of this family. Examples of these acids are: vanillic and
veratric acids from Euphorbia resinifera (Boe, Wisnes, Nordal & Bernatek, 1969);
p-coumaric acid from Euphorbia acanthothamnos Heldr. & Sart. (Kallimanis &
Philianos, 1980); chlorogenic and neochlorogenic acids from Ricinus communis L.
and Mercurialis perennis L. (Soboleva, 1980); and m-hydroxybenzoic acid from
Euphorbia royleanu (Baslas, 1982).
Other phenolic compounds
Four rottlerin-like phloroglucinol derivatives were isolated from the fruits of
Mallotus japonicus; three of which identified as 3-(3,3-dimethylallyl)-5(3-acetyl-2,4 - dihydroxy -5- methyl -6- methoxybenzyl) - phloroacetophenone,
3-(3-methyl-2-hydroxybut-3-enyl)-5-(3-acetyl-2,4dihydroxy-5-methyl-6-methoxybenzy1)-phloroacetophenone (Shigematsu, Kouno & Kawano, 1983) and
2,6-dihydroxy-3-methyl-4-methoxyacetophenone(Kouno, Shigematsu, Iwagam
& Kawano, 1985). The structures of these compounds resemble rottlerin from
M. phillz$inensis Muell.-Arg. (Shigematsu et al., 1983).
The root bark of the Chinese tallow tree, Sapium sebiferum Roxb. contains the
306
zyxwvutsrqp
zyxw
A.-F. M. RIZK
N'-4'-oxcdecamyl- hinlmnlne
Glomldln
Glochidiclne
Ricinine
Aslrocotine
Sccurinine
m
Vosicine
Vircnccuinin
H Ro@
F
.I
-
I.'
'Norrccurinine
Spanifiorine
R
A1 lorccurininc
zyxwv
zyxwv
Crolsparinin: R = R'* H
N-Mcthylcmtnporinin :
R =H; R ' = CH,
#
Cmhporlne:
N-MetlylcmlsparIne:
R R'' HR = H; R'. CHI
N.O-Dlmelhylao)rporln~:R = R'*CH3
0
Figure 7. Some alkaloids of the Euphorbiaceae.
zy
zyx
zyx
following two compounds: xanthoxylin (2-hydroxy-4,6-dimethoxyacetophenone), and a xylosylglucoside of xanthoxylin identified as 2-acetyl-3,5dimethoxyphenyl-0-fi-xylopyranos
yl- ( 1 +6) -fi-~-glucopyranoside(Kouno el al.,
1983).
Vanillin (p-hydroxy-m-methoxybenzaldehyde) occurred in Croton eluteria
Benn. (Claus, 1961 ) .
Alkaloids
Several classes of alkaloids occur in certain genera of the family
Euphorbiaceae and in particular Croton, Phyllanthu and Securinega species
CHEMICAL CONSTITUENTS OF EUPHORBIACEAE
zyxw
307
OH
cH30%
N-CHI
zyxw
0
0
Flovinanltne: R ' i R3 :CH,; R2; H
Flovinine:R' = R 2 = H; R3= CH,
Crotonorine
Solutoridine: R CH,
N-Nonolubridine: R = H
Linearirine
Sirnutine: R ' = H; R' = CH,
Nminwculine: R' * R z = H
zyxwv
h
zyxwvutsrqp
zyxwvutsrq
CH,
in,
Milliarnine A. R, = X; Rz: COW,
8. Rl = H i R 2 = X
Physosligrniw
HsC-..
HN
k
(+)9-ora-l-methyl
aicyclo- t3.3. I]
nonon-3-cne
zyxwvutsr
zyxwvuts
Daphniphylline
Figure 7 confinucd.
(Fig. 7). Imidazole alkaloids have been detected in only the genus Glochidion.
Croton species contain several types of alkaloids, viz. isoquinolines (aporphines,
e.g. sparsiflorine; proaporphines, e.g. crotsparine; and dihydroproaporphines,
e.g. crotsparinine) , morphinandienones (e.g. crotonosine), quinolines (e.g.
vasicine) a pyrrolidine alkaloid (4-hydroxyhygrinic acid) and others (e.g.
taspine, an alkaloid of unusual structure). Pyrimidine and guanidine alkaloids
were isolated from only one species, viz. Alchornea jauanensis Muell.-Arg.; while
purine nuclei alkaloids were identified in only Jatropha basiacantha Pax & K.
Hoffm. Several quinolizidine alkaloids were identified in the family, but mostly
from Phyllanths and Securinega species. The presence of other classes in plants of
the Euphorbiaceae was also reported, e.g. pyridine, piperidine and indole
alkaloids (Table 4). Glycoalkaloids were reported in Euphorbia dracunculoides
)
zyxwvut
zyxwv
zyxwvutsrqp
zyxwvutsrqponm
Table 4. Alkaloids of the Euphorbiaceae
Alkaloids
I. Imiahzole alkaloidr
1. Na-Cinnamoylhistamine
2. Na-4'-Oxodecanoylhistamine
}
@
Species
References
GlwhidiOn philippicum (Cav. C . B. Rob. ( = C. philippcnse
Benth.)
Johns & Lamberton (1967), Manske (1968)
zyxwv
zyxwvuts
I
zyxwvutsrqp
zyxwvutsrqp
3. Glochidicine
4. Glochidine
II. Pyrintdinc alkaloidr
5. Alchornidine
6. Alchornine (2-Isopropenyl7,7-dimethyl-5-oxo-2,3,5,6,
7,&hexahydroimidazo[ I ,%a]pyrimidine
Glwhidion philippicvnr (Cav.) C . B. Rob. ( = G. philippme
Benth.)
Johns & Lamberton (1967)
Alchornea javanmcis Muell.-Arg.
Hart et al. (1969, 1970)
9
r;
IIZ. Ppnoidine alkaloids
7. CHydroxy-hygrinic acid
Crofon spp.
N.Pydim alkaloidr
8. Ricinine
9. Nudiflorine
Ricinus convnwris L.
Trewia spp.
Rizk & El-Mkiry (1986)
Ponsinet & Ourisson (1965)
Astrocasia phylkanhids Robinson & M a p .
Manske (1968)
Ponsinet & Ourisson (1965)
F
E
R
zyxwvutsrqponmlkji
V. Pipendine alkaloids
10. Astrocasine
1I . 2,4-Dimethoxy-3-#-$dimethylallyl-transcinnamoylpiperidide (111)
12. Julocrotine
Excwchria agallocha L.
M a s h et al. (1983)
Julonoton spp.
Manske (1968), Yamaguchi (1970)
VI. Quidizidirualrtaloidc
13. Allosecurine
14. Dihydrosecurine
Phyllanthur discoides Muell.-Arg., Securinega Sufituosa Rehd.
Phyllanthur spp., Securincga sufiticosa Rehd.
15. Norexcurinine
Fluegga spp., PlyUanthus spp., Securimga uirosa Pax. H o h .
16. Phyllantidine
17. Phyllantine (Metoxysecurinine)
Phyllanthus discoides
Phyllanthus discoides
Bevan et al. (1964)
Ponsinet & Ourisson (1965), Rizk & ElMissiry (1986)
Ponsinet & Ourisson (1965), Yamaguchi
(1970)
Parello & Munavalli (1965)
Parello & Munavalli (1965)
18. Phyllochrysine
19. Securinine
20. Suffruticosine
2 1. Virosecurinine
zyxw
zyxwvutsr
zyxwvutsrqponml
zyxwvutsr
zyxwvutsrq
VII. QUiMZOlOne alkaloids
22. Tumuriquirensine
23. Vasicine
VIII. Isoquinoline alkaloidc
(a) Aporphines
24. Glaucine
25. Orotonsine
26. Pronuciforine
27. Sparsiflorine
Phyllanthus spp.
Phyllanthus spp., Securinega sujhticosa Rehd.
Phyllanthus spp.
FIuegga spp., Securinega virosa Pax. & Hofm.
Ponsinet & Ourisson ( 1 965)
Ponsinet & Ourisson (1965), Yamaguchi
(1970), Rizk & El-Missiry (1986)
Ponsinet & Ourisson (1965)
Ponsinet & Ourisson (1965), Yamaguchi
(1970)
Croton spp.
Croton spp.
Ponsinet & Ourisson (1965)
Ponsinet & Ourisson (1965)
Croton draconoides Muell.-Arg.
Bettolo & Scarpati (1979)
Croton spp.
Ponsinet & Ourisson (1965)
Croton spp.
Ponsinet & Ourisson (1965), Bhakuni et al.
(1970)
Bettolo & Scarpati (1979)
28. Thaliporphine
Croton draconoides Mull.-Arg.
(b) Dihydropoaporphines
29. Crotsparinine (Jacularine)
Croton linearis Jacq., C. sparsillorus Morong.
30. N-Methylcrotsparinine
Croton sparsiJ0m.s Morong.
(c) Proaporphines
3 1. Crotsparine (Crotoflorine)
Croton sparsj7om.s Morong. (C. bonplandium Bail.)
Bhakuni & Dhar (1968), Bhakuni et al.
(1970)
Croton spars$orus
Bhakuni et al. (1970)
32. N,O-Dimethylcrotsparine
33. N-Methylcrotsparine
Bhakuni & Dhar (1969), Bhakuni et al.
(1970)
Bhakuni et al. (1970)
14
zyxwvutsrqponml
zyxwvutsrqpo
Ix. hforphinandienone alkaloidc
34.
35.
36.
37.
38.
Crotonosine
Flavinantine
Flavinine
Linearisine
3-Methoxy-4,6-dihydroxymorphinandien-7-one (IV)
39. N-Norsalutaridine
40.Noninoacutine
Croton linearis Jacq.
Yamaguchi (1970)
Crotonjavm L.
Stuart et al. (1969)
Croton linearir Jacq.
Croton bonplandianum Bail.
Yamaguchi (1970)
Tiwari el al. (1981)
Croton salutaris Casar.
Croton spp.
Barnes & Soeiro (1981)
Manske (1968), Stuart'et al. (1969), Tiwari
et al. (1981)
b
%?
z
zyxwvu
zyxwvuts
zyxwvuts
zyxw
zyxwvutsrqpo
w,
0
z
Table 4. continued.
Alkaloids
41. Salutaridine
42. Salutarine
X.Indole alkaloidc
44. Physostigmine
45. Yohimbine
zyxwvutsrqpon
zyxwvutsrqpo
Species
Croton salutmir
References
Casar.
Croton saluhrir Casar.
*H
SPP.
A l c h a spp.
M a d e (1968), Barnes & Soeiro (1981)
Barnes & Soeiro (1981)
Ponsinet & Ourisson (1965)
Ponsinet & Ourisson (1965)
XI. Gnanidinc alkaloiak
46.N' ,N'
-Diisopentenyl-guanidine
47. N ,.W,.P-Triipentenylguanidine
Akhornca jaoannrriC Muell.-Arg.
Hart ct al. (1970)
XII. Dikrpmoidalkaloih
48. Milliamine A
49. Milliamine B
Euphorbia milli Desmoul.
Uemura & Hirata (1971)
Euphorbia atoh Forst.
Hart et al. (1967)
Daphtnphyllum calpinum Benth.
Manske (1968
Daphnaphyllum macropodium Miq.
Flugga microcarpa Blurnc (F. mrosa Baill.)
Daphp;Pnllum macropodium Miq.
Jatropha &L
Pax & K.Hoffm.
Croton spp.
Euphorbia hirh L.
Daphniphyllum macropodium Miq.
Manske (1968)
Paris ct al. (1955), Manske (1968)
Manske ( 1968)
Rizk & El-Missiry (1986)
Bettolo & Scarpati (1979)
Rizk (1986)
M a d e (1968)
XIII. Other alkaloidc
50. 9-ha-1-methyl-bicycle
[3,3, I]-nonan-3-one
5 1. Daphnicadine
52. Daphnicaline
53. Daphnicamine
54. Daphniphylline
55. Nueggeine
56. Neodaphniphylline
57. Purine nuclei alkaloids
58. Taspine
59. Xanthorhamin
60.Yuzurimine
zy
zyxw
zyxwvutsrqp
zyxwv
zyxwvuts
CHEMICAL CONSTITUENTS OF EUPHORBIACEAE
31 1
Table 5. Cyanogenic Glucosides of the Euphorbiaceae
Cyanogenic glucosides
Species
References
I . Aralyphin
2. Linarnarin
(Phaseolunatin =
rnanihotoxin)
3. Lotaustralin
Acalypha indica L.
Cnidoscolus texanus MuelLArg.,
Heuea brasiliensis Muell.-Arg.,
Manihot spp.
Manihot carthaginensis Muell .Arg.
Phyllanthus gastroemii Muell.-Arg.
Nahrstedt et al. (1982)
Valen (1978), Rizk & ElMissiry (1986)
4. Taxiphyllin
(Phyllanthin)
5. Triglochinin
Andrachne colchia Fisch & Mey.,
Securinega suJruficosa (Pall.)
Rehdr.
Valen (1978)
Valen ( 1978)
Valen (1978), Rizk & ElMissiry ( 1986)
Lam. (Singh & Srivastava, 1966) and Euphorbia hirta L. (Rizk & El-Missiry,
1986).
Cyanogenic glucosides
Though several species of the Euphorbiaceae have been reported as
cyanophoric, yet relatively few cyanogenic glucosides have been identified
(Table 5 & Fig. 8). Cyanogensis in the family have been surveyed by Valen
( 1978). Cyanophoric taxa occur frequently in the Euphorbiaceae. Both
subfamilies, i.e. Phyllanthoideae and Euphorbioideae, comprise taxa which are
able to produce hydrocyanic acid (Hegnauer, 1966; Valen, 1978). A number of
species belonging to the following genera have been reported as cyanogenic:
Andrachne, Btyeria, Bridelia, Cnidoscolus, Colliguaja, Elateriosperrnurn, Euphorbia,
Gyrnnanthes, Hevea, Jatropha, Manihot, Mercurialis, Phyllanthus, Poranthera, Securinega
(Valen, 1978) and Slillingia (Lewis & Elvin-Lewis, 1977).
Glucosinolates
Few glucosinolates have been identified from only limited species of the
Euphorbiaceae (Fig. 9). Examples of the glucosinolates detected are
H.C~O-~-GIUC
H,C~O-~-GIUC
H3C
H5Cz
Lolaurtmlin
C E N
CN
H
0&H&zO
:H
OH
I
CGN
Limmain
tH3
Acalyphin
H, ,O-p-GluC.
Hd
Taaiphyllin
Triglochinin
Figure 8. Cyanogenic glucosides of the Euphorbiaceae.
312
zyx
zyx
zyxwvutsrqpon
A.-F. M. RIZK
O
H
Ho
HW
s
$
zyxwvutsrqpon
CHs-CH,-CH-N=C
I
HO
/s--pluc-
CHI
CH,
I
Clnrmin
'OW;
Glucocochlearin
~/~'CH,CH,
OH
Glucocleomin
s-glucae
/
CH3-CH-N=C
I
o' so;
CH3
Glumputranjivin
Figure 9. Some glucosinolates of the Euphorbiaceae
glucoputranjivin, glucocochlearin, glucojaputin and glucocleomin (from kernels
of Putranjiua roxburghii Wall.) and benzylisothiocyanate (an enzymatic
hydrolysate of a glucosinolate from the latex of Jatropha multifida L.) (Kjaer &
Friis, 1962; Rizk & El-Missiry, 1986).
Miscellaneous compounds
zyxwvu
zyx
A number of other compounds have been isolated from plants of the
Euphorbiaceae (Fig. 10). Examples of these substances are: quinic and shikimic
acids from Euphorbia species (Rizk & El-Missiry, 1986); amides, e.g.
acalyphamide (an amide of tyramine and acid; C,,H,,COOH) and
succinimide from Acalypha indica L. (Talapatra et al., 1981); I-methyl-6hydroxy- 1,2,3,4-tetrahydroxyisoquinoline-3-carboxylic acid from Euphorbia
myrsinites L. (Mueller & Schuette, 1968); calcium 5,5-dimethyl-2-oxo-5,6dihydro-2H-pyran-3,4-dicarboxylatefrom Euphorbia biglandulosa Desf. (Falsone
& Spur, 1979); 1-tridecene-3,5,7,9,11-pentyne and trans-dehydromatricaria ester
from Ricinus communis (Schulte, Reisch & Bornfleth, 1964); D-( + ) - a hydroxyglutaric acid, myoinositol, L ( - )-inositol from Euphorbia resinifera (Boe et
al., 1969); cardiac glycosides from Mallotus japonicus (Shigematsu et al., 1983);
laiodiplodin, a potent antileukemic macrolide, from the stems of Euphorbia
splendens Bojer (E. milii Boiss.) (Lee et al., 1982); melissic acid,
CH,(CH,) ,,COOH, from Euphorbia hirla (Rizk, 1986); and diacetylmaderine
from Phyllanthus maderaspatensis L. (Chopra, Chopra & Varma, 1969).
f&
OH
"bco%:,
HO COOH
Ho,*&oH
HO
I',
H;CH
H H
6
OH
Quinic acid
bH
Shikimic acid
Laicdiplodin
Figure 10. Some miscellaneous compounds of the Euphorbiaceae.
zyxwvu
CHEMICAL CONSTITUENTS OF EUPHORBIACEAE
ECONOMIC PLANTS
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313
Several plants of the Euphorbiaceae are of considerable economic
importance, and products obtained from this family include castor oil (Ricinus),
tung oil (Aleurites), cassava, tapioca (Manihot) and rubber (Hevea). By no means
have all of these been shown to contain irritant carcinogens (Kinghorn, 1979).
Many species, and in particular Euphorbia and Croton species, are reported to
cause poisoning of human beings and livestock (Watt & Breyer-Brandwijk,
1962; Kingsbury, 1964). Poisoning is caused by the acrid and irritant substances
(recently identified as diterpenoid esters). Ethnobotanical records (Watt &
Breyher-Brandwijk, 1962) indicate that the toxicological dangers presented by
Euphorbia species have been recognized as far as the succulent species are
concerned.
Many of these toxic plants are ornamental and household plants, including
several Euphorbia species (e.g. E. milii, E. tirucalli L., E. lactea Roxb.), Acalypha
wilksiana Muel1.-Arg., Ricinus communis, Jatropha multiJida L., Sapium sebiferum
and Syndadenium grantii hook. fil.
Industrial plants andlor their products
Food plants
Manihot: Next to the sweet potato, the cassava (Manihot esculenta Crantz) is the
most important of the tropical root crops and furnishes the basic food for
millions of people. Cassava also called manioc, mandioc or yuca is one of the
most wholesome foods. The tubers are eaten raw or cooked. Cassava bread has a
high food value and replaces wheat bread in some diets (Hill, 1952). The tubers
of M . esculenta contain about 77.5-88.5% starch (Chopra et al., 1969) but less
than 1% protein (Vickery & Vickery, 1979). The fresh tubers contain a useful
amount of vitamin C (27 mg per 100 g) and Ca (25 mg per 100 g) (Vickery &
Vickery, 1979). Though sweet varieties of cassava contain linamarin, this
cyanogenic glucoside occurs only in the outer peel and is removed before the
tubers are eaten. Despite its lack of protein, cassava is a useful staple food, as the
mature tubers can be left in the ground for up to two years. West African
villagers like to keep a plot of cassava in case other crops fail (Vickery &
Vickery, 1979).
Cassava starch, Para or Brazilian arrowroot, is the starch obtained from the
thickened roots of the butter cassava (Manihot utilissima Pohl) and the sweet
cassava ( M .palmata Muell.-Arg.). These plants are reported to produce large
roots weighing as much as 5 kg (Hill, 1952).
Cassava is one of the principal crops in much of Africa, India and Brazil. The
latter is the largest world producer of Cassava (Vickery & Vickery, 1979). In
India it is grown as a subsidiary food crop and as an excellent raw material for
sago manufacture (Chopra et al., 1969).
Other plants: The otaheite gooseberry (Phyllanthus acidus) yields yellow
cherrylike fruits (Hill, 1952). The dried bark of Croton eluteria Benn. is used in
flavouring liquors and in scenting tobacco. It contains 1-1.5y0 volatile oil
containing eugenol, limonene, cascarillin, tannin and vanillin (Claus, 1961).
The nuts of Cnidoscolus marcgravii Pohl., a tree identical with Jatropha oligandra
314
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A.-F. M. RIZK
Muel1.-Arg. are used by the natives in Rio de Janeiro as food and the oil is
pressed from them for cooking (Bondar, 1942).
Fatty oils and waxes
Castor oil: The seeds of Ricinus communis L., are the source of castor oil, the
yield being up to 54%. Castor oil contains 1% tocopherol, 21.6% non-sterol
fraction of the unsaponifiable matter and 0.9% castor germ oil. The main
constituents of the oil are glycerin esters of ricinoleic acid (Rizk, 1986).
Castor oil has been put to many industrial uses, in addition to its traditional
use as a soothing local application and as a successful local application to get rid
of warts. I t is useful as a plasticizer in the lacquer industry, mixed with oil
derivatives as a lubricant and mixed with alcohol as a brake fluid. I t is also used
in making Turkey red oil, a moistener used in the textile industry (Watt &
Breyer-Brandwijk, 1962). The oil is water resistant and therefore is used for
coating fabrics and for protective coverings for aeroplanes, insulation, food
containers, gums, etc. It is also used in paints, varnishes, soap, inks, plastics and
as an illuminant.
Ricinus zansibarinus G. H. Popova yields 53.7-65.0% oil resembling castor oil
and is usable for the same purposes (Watt & Breyer-Brandwijk, 1962).
Tung oil: Tung oil, sometimes called Chinawood oil is the fixed oil obtained
from the seeds of both Aleurites fordii Hemsl. and A . montana E. H. Wilson. The
oil is not edible but is a quick-drying solvent for paints and varnishes. It is a
good preservative and very resistant to weathering and is therefore valuable for
outside paints. It is also used in the manufacture of linoleum, oilcloth, water
proofing fabrics, brake linings, leather dressings, soap, inks, insulating
compounds and fibreboard. The quick-drying properties of tung oil are due to
its content of eleostearic acid (Hill, 1952; Vickery & Vickery, 1979).
Candlenut oil, also known as lumbang oil, is obtained from the hard-shelled
seeds or roots of Aleurites moluccana Willd. and has similar uses as tung oil. The oil
is also used as a preservative of the hulls of vessels (Hill, 1952).
Aleurites species are a profitable source of income, and have also solved the
problem of eroded and waste land as they grow on soils unsuitable for other
types of agriculture (Hill, 1952).
The seeds of Trewia nudijora L. yield an oil similar to tung oil (Sarkar &
Chakrabarty, 1956a).
Tallow: The seeds of Sapium sebiferum represent the source of Chinese vegetable
tallow (Hill, 1952). An early report suggested its use as a possible substitute of
animal tallows in the manufacture of cotton (Puntambeker & Krishna, 1932).
The outer layer of the seeds of Stillingia sebifeera Trillot contained 54.5% tallow
(Kaufmann & King, 1939).
Candilla wax: Candilla wax is obtained from Euphorbia antisyphilitica Zucc.,
E. cerifera Alcocet, Pedilanthus aphyllus Boiss. and P. pavonis Boiss. (Hill, 1952;
Daugherty et al., 1953). I t is generally used as extender wax mixed with others.
Other oils: The evaluation of the seed oils of several other Euphorbiaceous
plants has been reported. Some of the oils have been reported as equal or
superior to the common oils, e.g. the seed oils of Euphorbia heterophylla L. and
E. marginata Pursh have been stated as equal to, or superior to, linseed as a
drying oil (Earle et al., 1960). Seeds of Jutropha gossypifoolia L. were reported as a
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CHEMICAL CONSTITUENTS OF EUPHORBIACEAE
315
common oilseed crop as compared with palm oil (Husain et al., 1982). The nutkernels of Cnidoscolus margravii contained 28.8% total fat and may serve for the
manufacture of paints, soap and other articles where soybean oil is used
(Bondar, 1942). Chrozophora plicata A. Juss. yields lineolate rich seed oil (Hassan
et al., 1980). The seed oil content of some other species are shown in Table 6.
Rubber plants
Several rubber plants belong to the family Euphorbiaceae. The Hevea or Para
rubber tree (Hevea brasiliensis) is the major source of the rubber produced
throughout the world. Elastica, caoutchouc or India rubber is the prepared
latex or milk of Hevea brasilensis and probably of other species of Hevea (Claus,
1961).
Ceara or manicobe rubber is obtained from Manihot glaziovii Muel1.-Arg.,
while caura rubber of Venezuela is obtained from species of Micandra. Species of
Cnidoscolus yield chilte rubber (Hill, 1952).
Many Euphorbia species either yield, or have been reported as a possible source
of, rubber, e.g. E. i n t i v (Hill, 1952). The latex obtained from E. caducifolia
Haines gives marginally better natural rubber than does Calotropis proceru
(Banerji & Millns, 1981). The rubber percentages of some other Euphorbia
lattices are as follows: E. abyssinica J. F. Gmel., 16.7%; E. candelabrum Trem. ex
Klotzsch, 20%; E. dregeana E. Mey., 17.6%; and E. mauritanica L., 15.81%
(Watt & Breyer-Brandwijk, 1962).
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Wood and paper
Few Euphorbiaceous trees have been reported to provide timber suitable for
making furniture and for structural work. Examples of these plants are: the
sandbox tree (Hura crepitans L.) which produces timber suitable for furniture
(Vickery & Vickery, 1979); trees of Bridelia ferruginea Benth., Oldfeldia africana
Benth. & Hook. fil. and Uapaca species provide timber for structural work
(Vickery & Vickery, 1979); Androstachy johnsonii Prain produces a hard timber,
durable and resistant to termites (Watt & Breyer-Brandwijk, 1962); and
Ricinodendron africanus Muell.-Arg. produces a valuable timber (Watt & BreyerBrandwijk, 1962).
Table 6. The seed-oil content of some euphorbiaceous plants
~~
Oil (%)
Species
1 . Anlidesma diandrum Spreng.
2. BischoJiajauanica Blume
3. Euphorbia calycina N. E. Br.
4. E . dracunculoides Lam.
5. E. gregaria Marl.
6. E. helioscopia L.
7. Heuea brasilimsis (A. Juss.) Muell.Arg.
8. Jatropha spp.
9. Ricinodmdron africannum Muell.-Arg.
10. R. rautancnii Schinz.
10.2
21.4
20.8
25.0
40.8
32.6
References
}
Sarkar & Chakrabarty (1965b)
}
Watt & Breyer-Brandwijk (1962)
Singh & Srivastava (1966)
Watt & Breyer-Brandwijk (1962)
~~~
~
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23-32
32.0
15.5
30-40
(edible oil)
Hill (1952)
Sarkar & Chakrabarty (1956b)
}
Watt & Breyer-Brandwijk (1962)
316
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A.-F. M. RIZK
Possibilities of obtaining pulp and paper from many plants of the
Euphorbiaceae are reported, e.g. Hura crepitans (Rojas, 1964), Macaranga tanorius
Muell.-Arg. (Hui, Li & Ng, 1975), Ricinodendron heudelotti Pax (Vickery &
Vickery, 1979) and Sapium sebiferum (Tutiya & Kato, 1940).
Ricinus communis L. yields a fibre suitable for paper making of superior quality,
if made with an admixture of bamboo pulp (Watt & Breyer-Brandwijk, 1962).
The mucilages of Munihot are used for paper making (Oguri & Shinohara,
1957).
Petroleum plants
Some crops have been recently developed for the production of fuels and
materials in addition to food and fibre. Euphorbia species, and in particular
E. lathyris, have been suggested as crops for the production of a whole-plant oil
low in isoprene content. Research on several latex-rich species showed that low
molecular weight hydrocarbons suitable for cracking to liquid fuels occur in
reasonable percentages (10% or more of total dry weight) in many species of the
Euphorbiaceae. The Gopher plant (Euphorbia lathyris), ranked among the
highest species analysed, contains up to 10% reduced hydrocarbons (acetone
extractable material) (Rizk, 1986).
Euphorbia lathyris is one of the plants which pass through summer drought
conditions, overwinter and, with warming temperatures in spring, commence
growth. The plant has been estimated to yield approximately ten barrels of
hydrocarbon material per acre in a 7-month growing period on semiarid land
(Calvin, 1979). The product is a mixture of hydrocarbons consisting mainly of
open-chain and cyclic terpenoid isoprenes (Nemethy, Otvos & Calvin, 1981a).
According to Calvin (1982), 95% of the oil from E . lathyris can be cracked to
useful products, making it very valuable petrochemical feedstock from which
gasoline itself can be made. The evaluation of this species as one of the few
potential hydrocarbon-producing crops has been reported by several authors
(e.g. Calvin, 1979, 1980, 1982, 1983; Calvin, Nemethy, Redenbaugh & Otvos,
1982; Hinman, Hoffman, McLaughlin & Peoples, 1980; Nemethy et al.,
1981a, b; Peoples et al., 1981).
Fish poison
The latex of several genera of the Euphorbiaceae, and in particular species of
Euphorbia, have been used extensively by fishermen in different countries as a
fish poison of high biological activity (Watt & Breyer-Branwijk, 1962; Novack,
Crea & Falsone, 1980). The rhizomes of Euphorbia biglundulosa Desf., for
example, are pounded in order to free the latex and thrown into stagnant waters
or rivers with a lower water level. The rapidly dissolving poison then kills the
fish by an apparent paralysis. However, though the sap causes intensive
irritation of the human skin, surprisingly, no intoxications of the people who
handle the latex and eat the fish were described (Novack, Crea & Falsone,
1980). Examples of the Euphorbiaceous plants used as fish poison are Aleurites
montana E. H. Wilson, Antidesma uenosum E. Mey., Croton sylvaticus Hochst. (Watt
& Breyer-Brandwijk, 1962), Elaeophorbia drupifera Stapf (Vickery & Vickery,
1979) and Euphorbia species (Baslas, 1982).
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CHEMICAL CONSTITUENTS OF EUPHORBIACEAE
317
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Arrow poison
In the past, arrow poisons have been very important to the people of Africa
and other countries, as they were often the only way of killing large animals,
especially in poaching valuable game animals such as leopards and lions
(Vickery & Vickery, 1979). Examples of the plants used as arrow poisons are
Euphorbia species (Watt & Breyer-Brandwijk, 1962) and Hippomane mancinella L.
(Ayensu, 1981).
Other uses
The main toxic principle of the seeds of Ricinus communis is the phytotoxin ricin
(a protein of the globulin type) converted by acid hydrolysis into non-toxic
compounds which are of nutritional value. The seed cake (after removal of the
oil) is used as a fertilizer. The oil cake of Aleurites species is a good fertilizer, but
cannot be used as a feed (Hill, 1952). Androstachysjohnsonii Prain has been used
as an animal feed (Watt & Breyer-Brandwijk, 1962).
Medicinal plants
Since antiquity curative effects have been attributed to many plants of the
Euphorbiaceae; for example Euphorbia jischeriana Steud. ( = E. pallasii Turcz.)
has been used in traditional Chinese medicine for more than 2000 years as
antitumour drug (Schroeder et al., 1980). Plants of this family have been used to
treat cancer, tumours and warts from at least the time of Hippocrates (circa 400
B.c.), and references to their used have appeared in the literature of many
countries (Kupchan et al., 1976). Certain species have been described in
homoeopathic pharmacopoeias, e.g. Acalypha indica (Nahrstedt, Kant & Wray,
1982).
In India, members of the following genera are reported as medicinal plants:
Acalypha, Aleurites, Andrachne, Antidesma, Aporosa, Baliospermum, Bischoja, Breynia,
Bridelia, Chrozophora, Cicca, Cleistanthus, Croton, Euphorbia, Excoecaria, Fluegga,
Glochidion, Hippomane, Homonoia, Hura, Jatropha, Macaranga, Mallotus, Manihot,
Phyllanthus, Putranjiva, Ricinus, Sapium, Sebastiania, Tragia and Trewia (Chopra el
al., 1983; Kirtikar & Basu, 1984). Species of Euphorbiaceae have been used by
local populations of many countries in folk medicines as remedies against several
diseases. Table 7 summarizes the medicinal uses.
The plants of this family are known to be extremely toxic; causing
inflammations of the skin and mucous membranes, conjuctivitis and even
blindness. Several species are toxic to livestock and allelopathic to desirable
forage plants. Examples of the poisonous plants are Aleurites fordii Hemsl., Croton
species, Euphorbia species, Excoecaria venenifera Pax, Hippomane mancinella, Hura
crepitans, Jatropha species, Pedilanthus tithymaloides Poi t., Phyllanthus species, Sapium
species, Stillingia treculeana I. M. Johnston and Syndenium grantii (Watt & BreyerBrandwijk, 1962; Kingsbury, 1964; Lewis & Elvin-Lewis, 1977).
The attempts over 150 years to establish the cathartic principles of Croton
tiglium L. were given a new impetus after the discovery of the tumour-promoting
(carcinogenic) activity of Croton oil (Kinghorm, 1979). These efforts culminated
with the isolation of the irritant cocarcinogenic factors of the oil as esters of
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Table 7. Medicinal uses of some euphorbiaceous plants
W
e
Used as/Treatment of
I . Abdominal pains
2. Abortion
3. Anthelmintic (Vermifuge)
4. Antiasthmatic
Species
Croton spp., Euphorbia spp., Jatropha gossypifolia L., Ricinus
C0mmuni.I L.
AcalVplur wilkcsimra Mud.-@., Cnidoscolus u r m Arthur, Croton
seilowii Baill., EuphorbL spp., Flueggea virosa Baill. (Willd.)
Baill., Souropus rostratus Miq.
6. Anticancer
Croton spp., Euphorbia spp.
7. Antihistaminic
Euphorbia hi& L.
Euphorbia ncrifolia L.
9. Antispasmodic (spasmolytic)
10. Aphrodisiac
1 1. Bronchitis
Eupkorbia spp.
Mallotuc spp., Phyllanthus spp., R i c h grandis Vahl.
Euphbia spp.
12. C h a t complaints
C r o t o n ~ c n sL., E@hrococca r i g d ~ o l i aPax., Euphorbia spp.,
13. Choleretic
14. Conjunctivitis
15. Contraceptive
16. Cough
19. Diaphoretic
zy
Watt & Breyer-Brandwijk (1962)
Ayensu (1978)
Caius & Mhaskar (1923), Watt & BreyerBrandwijk (1962), Lewis & Elvin-Lewis
(1977), Ayensu (1978, 1981), Biswas &
Chopra ( 1982)
Claw (1961), Watt & Breyer-Brandwijk
(1962), Ayensu (1978, 1981), Baslas
(1982), Boulos (1983), Duke & Ayensu
(1985)
Watanabe ct al. (1956), Watt & BreyerBrandwijk (1962), Lewis & Elvin-Lewis
(1977), Adesina ct al. (1980), Duke &
Ayensu (1985)
Kupchan ct d . (1976), Let ct al. (1982),
Baslas (1982)
Duke & A y e ~ u(1985)
Watt & Breyer-Brandwijk (1962), Hallet &
Parks (1953)
Baslas (1982), Duke & Ayensu (1985)
Ayensu (1978), Duke & Ayensu (1985)
Ayensu (1978), Chen ct al. (1979), Baslas
(1982)
Watt & Breyer-Brandwijk (1962), Ayensu
(1978, 1981), Boulos (1983), Duke &
Ayensu (1985)
Baslas (1982)
Ayensu (1978), Duke & Ayensu (1985)
Duke & Ayensu (1985)
Lewis & Elvin-Lewis (1977), Ayensu
(1978)
Lewis & Elvin-Lewis (1977), Duke &
Ayensu (1985)
Gohalons & Fontana (1926), Watt &
Breyer-Brandwijk (1962), Ayensu (1978,
1981), Baslas & Agarwal ( 1980)
Watt & Breyer-Brandwijk (1962)
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8. Antipyretic (antifebrile)
18. Diabetes
W
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Antiahma m s u m E. Mey., Briedilia sclcronncroides Pax
A&homea cord$olia (Schum. & Thonn.) Stapf, Brioklia micrantha
Hochst. (Baill.) (anti-abortive)
Acalypha indica L., Alchomea cord$olia, Andrachnc ovalis Muell.-Arg.,
Croton macrostachys A. Rich., Euphorbia spp., jatropha curcar L.,
Maliotus spp.
5. Antibiotic (mainly antibacterial)
17. Dermatitis
References
Fiueggea mrosa Baill., Mildbracdiafallax Hutch., Monaahium
immustwn N . E. Br., Phyllanthus muell(0.Ktze.) E x d .
Euphorbia spp.
Bride& &antha, Croton tiglium L., PlyllantluLc spp.
Mallohrr philiPpinmriS Muell.-Arg.
Alchomea cord$olia, Elaeophorbia drupiiia (Thonn.), Phyllanthus
mgleri Pax
Croton corlcsionus H. B. & K., Glochidion spp.
Bridclia f-inca
Benth., Croton spp., Euphorbin hirta L.,
Phyllanthus spp.
Euphorbia gmishidcs Berg.
zyxwvutsrqponmlkjih
zyxwv
Acalypha australis L., Alchonua cordifolia, Bridelia femrginea,
Euphmbia spp., Jatropha spp., Phyllanthus spp., ricinus communis
L., Ricinodcndron afncanum Muell.-Arg., Sauropus rostratus Miq.
Acalypha cvrardii Gagnep., Alchonua cordijolia, Bischovia javanica BI.,
Bridelia fermginea, Euphorbia spp., Hippomane mancinclla L.,
Homonoia riparia L., Jatropha curcas L., Kirganelia reticulafa
(Poir.) Baill., Mercurialis amua L., Manihof esculenfa Crantz,
Phyllanthui spp., Sapium sebifrum (L.) Roxb.
Acalypha australis L., Alchornea cordifolia, Brcynia spp., Brihlia
fmuginea, Caloxylon spp., Euphorbia spp., Glochidion spp.,
Mallotus opposififolius (Geisel.) Muell.-Arg.
Euphorbia antiquorum L., Jafropha curcar 1.
Glochidion p u b m m (L.) Hutch., Hura crcpitans L.
Watt & Breyer-Brandwijk (1962), Ayensu
(1978, 1981), Baslas & Aganval (1980),
Boulos ( 1983)
Woerd (1941), Watt & Breyer-Brandwijk
(1962), Chopra el al. (1969), Lewis &
Elvin-Lewis (1977), Baslas (1982), Biswas
& Chopra (1982), Boulos (1983), Kouno
ef al. (1983), Duke & Ayensu (1985)
Watt & Breyer-Brandwijk (1962), Ayensu
(1978, 1981), Duke & Ayensu (1985)
Watt & Breyer-Brandwijk (1962), Ayensu
(1978, 1981), Duke & Ayensu (1985)
35. Hypnotic
36. Hypotensive
37. Influenza
Acalypha indica, Alchonua cordijolia, Euphorbia spp., Hura crepitans,
Jatr~phacurcas, Marcya minanlha Muell.-Arg., Mildraedia fal1a.x
Hutch., Pedilanthus tithymaloides Poit.
Ricinus communis
Jatropha curcar, Mallofus opposififolius Muell.-Arg., Phyllanfhus
mwllcrianus (Kuntze) Exell.
Acdrpha indua
Sarococca prunijomis Lindl.
Acal.ha ausfralis, Alchonua cordijolia, Breynia spp., Bridclia
fmuginea, Croton linearis, Euphorbia spp., jatropha spp.,
Phyllanthus spp., Sauropus rosfratus, Miq., Saussurea lappa C. B.
Clarke, Tefrorchidium didyostemon (Baill.) Pox & K. Hoffm.,
Trigonostrmon l o n g i f o h Baill.
Euphorbia spp.
Euphorbia hirta L.
Acalypha australis, Alchonua cordgolia, Breynia spp.
Euphorbia sp1enden.s Bojer (E. millii Desmoulins), Mallofus apclta
(Lour.) Muell.-Arg., Phyllanthus urinaria L.
Euphorbia spp.
Alcurites fordii, Euphorbia maddmi
Clufia abyssinica Spach., Glochidion purpureum (L.) Hutch.
38. Insecticides
Croton spp., Hura ncpitans, Mallofus rapandus (Willd.) Muell.-Arg.
39. Jaundice
Euphorbia humijiusa Willd., Jatropha curcas, Ricinus communis
40. Lactogogue
4 1. Leprosy
Euphorbia f h F y o l i a L., Jatropha curcar
Hura ncpitans, Marcya micranfha, Ricinus communis
42. Malaria
Alchonua cordifolia, Crofon spp., Glochidion puberum Hutch.:
20. Diarrhoea
21. Diuretic
22. Dysentry
23. Dyspepsia
24. Elephantiansis
Ayensu (1978), Duke & Ayensu (1985)
Chopra et al. (1969), Duke & Ayensu
(1985)
25. Emetic
26. Emmenagogue
27. Enema
31.
32.
33.
34.
n
0
s
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zyxwvutsrqpon
zyxwvutsrqponmlk
zyxwvutsr
28. Expectorant
29. Febrifuge
30. Fevers
Watt & Breyer-Brandwijk (1962)
Ayensu (1978)
Galactogogue
Heart diseases
Haemorrhage
Hepatitis
Lewis & Elvin-Lewis (1977)
Chopra el al. (1969)
Serra (1944), Chopra el al. (1969), Lewis &
Elvin-Lewis (1977), Ayensu (1978,
1981), Duke & Ayensu (1985)
Watt & Breyer-Brandwijk (1962)
Ayensu (1978)
Ayensu (1978), Duke & Ayensu (1985)
Lce el al. (1982), Duke & Ayensu (1985)
Baslas (1982)
Claw (1961), Sahai cl al. (1981)
Watt & Breyer-Brandwijk (1962), Duke &
Ayensu (1985)
Lewis & Elvin-Lewis (1977), Duke &
Ayensu (1985)
Ayensu (1978), Boulos (1983), Duke &
Ayensu (1985)
Ayensu (1978, 1981)
Chopra cl al. (1969), Ayensu (1978), Boulos
(1983)
Watt & Breyer-Brandwijk (1962), Ayensu
(1978), Duke & Ayensu (1985)
w
X
0
m
bm
&
zyxwvu
zyxwvutsr
z
zyxwv
zyxwvutsrqpo
Table 7. continued
Used as/Treatment of
Species
43. Menstruation
44. Nephritis
45. Neuralgia
Euphorbia atoto Forst.
Euphorbia spp., Phyllanthus urinaria L.
Euphorbia tirucalli
Bridc[ia fmuginea
Acaltha spp., Alchornea cordgolia, Euphorbia spp., Jatropha ncrcas,
Phyllanthur mueNnianuF
Alchornea cord$olia, Atnamnus lucidus (Sw.) Rohrn., Homonia riparia
Lour., Mallotur of@ositifolius (Geisel.) Muell.-Arg.
Acaltha spp., Alchornea cord$olia, Bridelia spp., Claoxylonpolot
Merr., Clutia atgssinica Spach., Croton spp., Elaeophorbia durpijina
Stapf., Euphorbia spp., Hippomane mancinClla L., Homaia riparia
Lour., Hura crcpitonr, Jatropha spp., Mallotus philippirumis
Muell.-Arg., Mapouna a f i a n a Muell.-Arg., Mareya micrantha
(Benth.), Muell.-Arg., Mercurialis annua L., Midbraedia fallax
Hutch., Phyllanth spp., Pseudolachnosrylis spp., Ricinur
comnutnis, Sapium sebifmtm, Tetrochidium diapostenwn (Baill.) Pax
& K. Hoffm.
Alchonuo cordifoh, Bridelia fmuginea, Croton spp., Euphrbia spp.,
Jarropha spp., Mareya micrantha, Mncurialis annua, Ricinus
communis, Sarococca pruniformis Lindl., Spnanskia tubnculata
(Bunge) Baill.
Bridclio micrantha (Hochst.) Baill.
Euphorbia pekinmcis Rupr.
Pedilanthus tithymaloides Poit.
Kirganelia retidata (Poir.) Baa. ( = Phyllanthus reticulatus Poir.)
A c d t h a spp., Cluytia similis Muell.-Arg., Eiaeophorbia drupifera,
Erythrococca rigidgolia Pax, Euphorbia spp.> Manihot esculenh
Crantz., Mareya micrantha, Sapium sebifcrum
Alchonua spp., Bischoja jauanica, Brey’na spp., Croton alamosanum N.
E. Rose, Euphorbia spp,, Ricinus communis
Croton eluuria (L.) Sw., Euphorbia spp.
Alchornea cordgolia, Bri&lia f m g i n e a , Breyia spp., Euphorbia spp.,
Hippomane mancinella, Homonia riparia, Jatrobha curcas, Kirganeiia
reticulata Baill., Mallotus spp., Mareya micrantha, Monadenium
lugardac N. E. Br., Phyllanthur spp., Ricinodmdron afkanum
Muell.-Arg.
Croton humilis L.
46. Oedema
47. Ophthalmic diseases
48. Piles
49. Purgative (Cathartic,
Laxative)
50. Rheumatism
5 1. Scabies
52. Schistosomicidal
53. Scorpion-bite
54. Smallpox
55. Snake-bite
56. Toothache
57. Tonic
58. Veneral diseases
References
Lewis & Elvin-Lewis (1977)
Duke & Ayensu (1985)
Baslas (1982)
Ayensu (1978)
Ayensu (1978), Boulos (1983), Duke &
Ayensu ( 1985)
Ayensu (1978, 1981), Biswas & Chopra
zyxwvutsrq
zyxwvu
( 1982)
Clam (1961), Watt & Breyer-Brandwijk
(1962), Chopra et al. (1969), Ayensu
(1978, 1981), Biswas & Chopra (1982),
Baslas (1982), Lewis & Elvin-Lewis
(1977), Kouno et al. (1983), Duke &
Ayensu (1985)
?
t;
F
Ballantine ( 1969), Chopra et al. ( 1969),
Ayensu (1978, 1981), Baslas (1982),
Boulos (1983), Duke & Ayensu (1985)
E
F
Ayensu (1978)
Duke & Ayensu (1985)
Chopra et aI. (1969)
Chopra ct al. (1969)
Watt & Breyer-Brandwijk (1962), Lewis &
Elvin-Lewis (1977), Ayensu (1978,
1981), Duke & Ayensu (1985)
Lewis & Elvin-Lewis (1977), Ayensu (1978,
zyxwvuts
1981)
Ayensu (1978, 1981)
Watt & Breyer-Brandwijk (1962), Chopra
et ul. (1969), Ayensu (1978, 1981),
Biswas & Chopra (1982), Duke &
Ayensu (1985)
zyxwvutsrqponmlk
(Gonorrhoea and syphilis)
59. Urinary diseases
u
Lewis & Elvin-Lewis (1977)
zyx
zyxwvu
CHEMICAL CONSTITUENTS O F EUPHORBIACEAE
32 1
tetracyclic diterpenoid phorbol (Hecker, 1968). After the structure elucidation
of phorbol, many related diterpene esters have been identified from the family
Euphorbiaceae, especially from Euphorbia species (Evans & Soper, 1978;
Kinghorn, 1979). Certain of these compounds are tumour promoters while
others have anti-tumour action. However, all of them are extremely potent
direct primary irritants on mammalian skin (Rizk, 1986). Investigation of
Euphorbia esula L. and Crolon liglium L. which have been used widely in folk
medicine for treating cancers led to the isolation of two diterpenoid esters which
showed antileukemic activity (Kupchan, 1976). O n the other hand there are
several genera which have been reported either responsible for irritant
dermatitis (e.g. Cnidoscolus, Dalechampia, Jatropha and Trugia) or causing allergic
reactions (e.g. Codiaeum, Croton, Euphorbia, Hippomane, Hura and Phyllanthus)
(Lewis & Elvin-Lewis, 1977).
zyx
zyx
zyxwvutsr
REFERENCES
ADESINA, S. K., OGANTIMEIN, B. J. & AKINWUSHI, D. D., 1980. Phytochemical and biological
evaluation of the leaves of Acalypha wikesiana (red acalypha, Euphorbiaceae). Qprterly Journal of Crude Drug
Research, 18: 45-48.
ADOLF, W. & HECKER, E., 1971. Further new diterpene esters from the irritant and co-carcinogenic seed
oil and latex of the caper spurge. Experientia, 27: 1393-1394.
AFZA, N., MALIK, A. & SIDDIQUI, S., 1979a. A new triterpenoid from Euphorbia tirucelli. Pakistan Journal
of Scientific and Industrial Research, 22: 124-127.
AFZA, N.,MALIK, A. & SIDDIQUI, S., 1979b. Isolation and structure of cycloeuphornol, a new triterpene
from Euphorbia tirucalli. Pakistan Journal of Scientific and Industrial Research, 22: 173-1 76.
AHMAD, S. A., KAPOOR, S. K. & ZAMAN, A., 1972. Bergenin in Fluegga microcarpa. Phytochemistry, 11: 452.
AIYAR, V. N. & SESHADRI, T. R., 1971. Chemical components of Croton oblongifolius Roxb. Part V. Indian
Journal of Chemistry 9: 613.
DE ALVARENGA, M. A., GOTTLIEB, 0. R. & MAGALHAES, M. T., 1976. Methyl-phenanthrenes from
Sagotia racemosa. Phytochemisty, 15: 844-845.
ANJANEYULU, V., RAO, G. S. & CONNOLLY, J. D., 1985. Occurrence of 24-epimers of cycloart-25-ene3, 24-diols in the stem of Euphorbia trigona. Phytochemistry, 24: 1610-1612.
AYENSU, E. S., 1978. Medicinal Plants of West Africa. Algonac, Michigan, U.S.A.: Reference Publications,
Inc.
AYENSU, E. S., 1981. Medicinal Plants of West Indies. Algonac, Michigan, U.S.A.: Reference Publications Inc.
BALLANTINE, J. A., 1969. The isolation of two esters of the naphthaquinone alcohol, shikonin, from the
shrub Jatropha glandulifua. Phytochemistry, 8: 1587-1590.
BANERJI, M. S. & MILLNS, W., 1981. Rubber India, 33(1): 13-18, (via Chemical Abstracts, 96: 105549).
BANERJI, J., DAS, B., CHATTERJEE, A. & SHOOLERY, J. N., 1984. Gadain, a lignan from Jatropha
gossrpijolia, Phytochemistry, 23: 2323-2327.
BARNES, R. A., & SOEIRO, 0. M., 1981. The alkaloids of Croton salutaris. Phytochemistry, 20: 543-544.
BARROS, D. A. D., DE ALVARENGA, M. A., GOTTLIEB, 0. R. & GOTTLIEB, H. E., 1982. Naringenin
coumaroylglucosides from Mobea caudata, Phytochemistry, 21: 2 107-2109.
BASLAS, P. K. & AGARWAL, R., 1980. Isolation and characterization of different constituents of Euphorbia
hirta Linn. Current Science. 49: 311-312.
BASLAS, R. K., 1982. Phyiochemical studies of the plants of the genera Euphorbia. Part 11. Herba Hungarica,
21: 115-126.
BENTLEY, R. & TRIMEN, H., 1880. Medicinal Plants, 4 . London: J. A. Churchill.
BETTOLO, R. M. & SCARPATI, M. L., 1979. Alkaloids of Croton draconoides. Phytochemistry, 18: 520.
BEVAN, C. W. L., PATEL, M. B. & REES, A. H., 1964. Minor alkaloids of Phyllanthus discoides. Chemistry and
Industry, 2054.
BHAKUNI, D. S. & DHAR, M. M., 1968. Crotsparine, a new proaporphine alkaloid from Croton sparsijlorus
Morong. Experientia, 24: 10-1 1.
BHAKUNI, D. S. & DHAR, M. M., 1969. Crotsparinine, a dihydroaporphine alkaloid from Croton sparsijorus.
Exberientia. 25: 354.
BHAKUNI, D. S., SATISH, S. & DHAR, M. M., 1970. The alkaloids of Croton sparsijlorus. Phytochemistry, 9:
2573-2580.
BHAT, S. K., DIXIT, V. & SINGH, K. V., 1981. A flavanone glycoside from seeds of Sapium scbiferum.
Plylochemistry, 20: 2442.
zyxw
zyx
322
zyxwvutsr
zyxwvutsrqp
zyx
zy
zy
A.-F. M. RlZK
BHAT, V. S., JOSHI, V. S. & NANAVATI, D. D., 1982. Cycloroylenol, a cyclopropane containing euphoid
from Euphorbia roylana. Tetrahedrom Letters, 5207-52 10.
BHUSHAN, D., RAM, A. & PRAKASH, O., 1951. Mandara seed and its oil. Journal and Proceedings of the Oil
Technologists Association, Kanpur, India, 7: 68-73; (via Chemical Abstracts, 48: 9720).
BISWAS, K. & CHOPRA, R. N., 1982. Common Medicinal Plants of Darjeeling and the Sikkim Himalayas. Delhi:
Periodical Experts Book Agency.
BOE, J. E., WINSNES, R., NORDAL, A. & BERNATEK, E., 1969. New constituents of Euphorbia resinifera.
Acia Chemica Scandinavica, 23: 3609.
BONDARENKO, 0. M., CHAGOVETS, R. K., LITVINENKO, V. I., OBOLENTSEVA, G . V., SILA, V.
1. & KIGEL, T. B., 1971. Euphorbia palustris and Euphorbia stepposa flavonoids and their pharmacological
properties. Farmatscvticheskii <hurnal (Kiev), 26(6): 46-48; (via Chemical Abstracts, 76: 121697).
BONDAR, G., 1942. PenHo, a new source of oil (in the province) of Bahia; Cnidoscolus marcgravii Pohl. Revista
de quimica industrial (Rio de Janeiro), lI(128): 15-18; (via C h i c a l Abstracts, 37: 4267).
BOULOS, L., 1983. Medicinal Plants of North Africa. Algonac, Michigan: Reference Publications, Inc.
CAIUS, J. F. & MHASKAR, K. S., 1923. The correlation between the chemical composition of
anthelmintics and their therapeutic value in connection with the hookworm inquiry in the Madras
Presidency. XXI. Miscellaneous anthelmintics. Indian J o u m l of Medical Research, I I : 353-370.
CALVIN, M., 1979. Petroleum plantations. In R. R. Hautala, R. B. King & C. Kutal (Eds), Solar Energy:
Chemical Conversion and Storage. U.S.A.: The Humana Press.
CALVIN, M., 1980. Hydrocarbons from plants; analytical method and observations. Natunuissmschaflm, 67:
525-533.
CALVIN, M., 1982. Energy agriculture. Presented at the Symposium on Con17Or~er~d
Topics in Agricultural and
Food Chemistry, American Chemical Society, Kansas City, Mo, U.S.A., 7-12 Sept.: 1-46.
CALVIN, M., 1983. New sources for fuel materials. Science, 219: 24-26.
CALVIN, M., NEMETHY, E. K., REDENBAUGH, K. & OTVOS, J. W., 1982. Plants as a direct source of
fuel. Experientia, 38: 18-22.
CHATTERJEE, A., DAS, B., PASCARD, C. & PRANGE, T., 1981. Crystal structure of a lignan from
jatropha gossypifolia. Phytochemistry 20: 2047-2048.
CHAWLA, H. M., CHAKRABARTY, K., CHIBBER, S. S., KALIA, A. N. & CHAUDHURY, N. C., 1980.
Daphnetin from Euphorbia dracunculoides. Indian Journal of Pharmaceutical Science, 42: 138- 139.
CHEN, Y., TANG, Z.-J., JIANG, F.-X., ZHANG, X.-X. & LAO, AI-NA., 1979. Studies on the active
principles of Ze-Qi (Euphorbia helioscopia L.), a drug used for chronic bronchitis. Tao Hsueh Hsueh Pao, 14(2):
91-95. (via Chnical Abstracts; 92: 72680).
CHOPRA, R. N., CHOPRA, I. C. & VARMA, B. S., 1969. Supplement to Glossary of Indian Medicinal Plants.
New Delhi: Publications & Information Directorate.
CHOPRA, I. C., ABROL, B. K., HANDA, K. L.,PARIS, R. & DILLEMAN, G., 1983. Medicinal Plants of
the Arid <ones. New Delhi: Today and Tomorrow’s Printers & Publishers.
CLAUS, E. P., 1961. Pharmacognosy, 4th edition. Philadelphia: Lea & Febiger.
CRAVEIRO, A. A., MONTE, F. J., MATOS, F. J. A. & ALENCAR, J. W., 1978. Volatile constituents of
Croton aff. agyrophylloids Muell.-Arg. Revista latinoamericann dc quimica, 9: 98-99.
CRAVEIRO, A. A., RODRIGUEZ, A. S., ANDRADE, C. H. S., MATOS, F. J. A., ALENCAR, J. W. &
MACHADO, M. I. L., 1981. Volatile constituents of Brazilian Euphorbiaceae. Genus Croton. Journal of
Natural Products, 44: 602-608.
DAUGHERTY, P. M., SINEATH, H. H. & WASTLER, T. A., 1953. Industrial raw material of plant
origin, 111. Candelilla and candilella wax. Feth und Scifm, 55: 113-1 18.
DUKE, J. A. & AYENSU, E. S., 1985. Medicinal Plants of China, 1. Algonac, Michigan: Reference
Publications, Inc.
DUTTA, P. K., BANERJEE, D. & DUTTA, N. L., 1972. Euphorbetin: A new bicoumarin from Euphorbia
l a t h y i L., Tetrahedron Letters, 601-604.
DUTTA, P. K., MAJUMDER, P. C. & DUTTA, N. L., 1975. Synthetic approaches towards bicoumarins.
Synthesis of euphorbetin and isoeuphorbetin. Tetrahedron, 31: 1 167-1 170.
EARLE, F. R., MCGUIRE, T. A., MALLAN, J., BAGBY, M. 0. & WOLFF, I. A., 1960. Search for new
industrial oils. 11. Oils with high iodine value. Journal of the American Oil Chemists’ Sociely, 37: 48-50.
EVANS, F. J. & SOPER, C. J., 1978. The tigliane, daphnane and ingnane diterpenes, their chemistry,
distribution and biological activities. A review. Lloydia, 41: 193-233.
FALSONE, G. & SPUR, B., 1979. Constituents of Euphorbiaceae. V. Synthesis of calcium 5,5-dimethyl-Zoxo-5,6-dihydro-2H-pyran3,4-dicarboxyiate.
Liebigs Annalm die Chemie, 923-926.
FUERSTENBERGER, G . & HECKER, E., 1977a. New highly irritant Euphorbia factors from the latex of
Euphorbia timalli L. Experimtia, 33: 986-988.
FUERSTENBERGER, G . & HECKER, E., 1977b. The new diterpene 4-deoxyphorbol and its highly
unsaturated irritant esters. Tetrahedron Letters, 11: 925-928.
GORALONS, G. P. & FONTANA, A., 1926. Effect of Phyllanthus sellowianus Muell. on blood sugar
concentration. Archives argentinos de mfemdades del aparato digestivo y de la nutricidn, I : 993-998 (via Chemical
Abstracts, 22: 988).
GOVARDHAN, CH., REDDY, P. R. & SUNDRARARAMAIAH, T., 1984. 3-Epicycloaudenol and known
triterpenes from Euphorbia caudicijioolia. Phytochemisty, 23: 41 1 4 1 3 .
zyxwvutsrq
zyxwv
zyxwvut
zyx
zyx
zyxwv
zyxwvu
zyxwvu
zyx
zyxwvuts
zyx
CHEMICAL CONSTITUENTS O F EUPHORBIACEAE
323
GUNASEKERA, S. P., CORDELL, G. A. & FARNSWORTH, N. R., 1980. Constituents of Nealchornea
yapurensis (Euphorbiaceae). Journal of Natural Products, 43: 285-287.
HELLETT, F. P. & PARKS, L. M., 1953. The antispasmodic principle of Euphorbia PiluliJzra. Journal of the
American Pharmaceutical Association 42: 607-609.
HAMMOUDA, F. M., RIZK, A. M., EL-MISSIRY, M. M. & RADWAN, H. M., 1984. Constituents of the
latex of Euphorbia roykana. Fitoterapia, 55: 245-247.
HART, N. K., JONES, S. R. & LAMBERTON, J. A,, 1967. (+)-9-Aza-I-methyl-bicyclo[3,3,1] nonan-3~
20: 561-563.
one, a new alkaloid from Euphorbia atoto Forst. Australian J o uof ~Chnnishy,
HART, N. K., JONES, S. R. & LAMBERTON, J. A., 1969. Hexahydroimidazo-pyrimidines, a new class
alkaloids from Alchomea javanensis. Journal of the Chnnical Sociep, D: 1484-1485.
HART, N. K., JONES, S. R., LAMBERTON, J. A. & WILLIG, R. J., 1970. Alkaloids of Alchomea javanmris:
the isolation of hexahydroimidazo [ 1,2a] pyrimidines and guanidines. Australian ,journal of Chemistry, 23:
1679-1693.
HASSAN, S . Q.,AHMED, I., SHERWANI, M. R. K., ANSARI, A. A. & OSMAN, S. M., 1980. Studies on
herbaceous seed oils. X. Fette, SeiJen, Anstrichmittel, 82: 204-205.
HECKER, E., 1968. Cocarcinogenic principles from the seed oil of Croton tiglium and from other
Euphorbiaceae. Cancer Research, 28: 2338-2349.
HEGNAUER, R., 1966. Chemotaxonomie der VanZen, Bd. 4. Dicotyledoneae: Daphniphyllaceae-Lythraceae,
Basel & Stuttgart: Birkhaeuser Verlag.
HILL. A. F., 1952. Economic Botany-A Textbook of Useful
Plants and Plant Products. 2nd edition. Bombav. New
"
Delhi: Tata McGraw-Hill Pubiishing Co. Ltd:
HINMAN. C. W.. HOFFMAN, 1. P.. MCLAUGHLIN, S. P. & PEOPLES, T. R.. 1980. Hvdrocarbon
production from arid land p l k t species. Proceedings
the 1980 Annual Meeting, American Siction of the
International Solar Energy SocieLy, Inc.: 110-1 14.
HUI, W.-H., LI, M.-M. & NG, K.K., 1975. Terpenoids and steroids from Macarango tanarius. Phytochemistry
14: 816-817.
HUSAIN, S. R., AHMAD, M. S., AHMAD, S. M., AHMAD, M. & OSMAN, S. M., 1982. Studies on
herbaceous seed oils. XIII. Journal of the Oil Technologists Association of India, 14(2): 61-63.
ISMAIL, S. I., EL-MISSIRY, M. M., HAMMOUDA, F. M. & RIZK, A. M., 1977. Flavonoids of Euphorbia
gmiculata and Euphorbia prostrata. Pharmazie, 32: 538.
JEFFERIES, P. R., 1979. Studies on the resin chemistry of some Western Australian plants. Journal of the
Royal Sociep of Western Australia, 62: 95-107.
JOHNS, S. R. & LAMBERTON, J. A., 1967. New imidazole alkaloids from a Clochidion species (family
Euphorbiaceae). Australian Journal of Chemistry, 20: 555-560.
KALLIMANIS, G. & PHILIANOS, S., 1980. Constituants chimiques des feuilles d'Euphorbia acanthofhamnos
Heldr. st Start. Plantes medicinales Phytothnapie, 14: 233-237.
KAUFMANN, H. P. & KING, B.-W., 1939. Fats from the seeds of Stillingia scbvera Trillot. Fette und SeiJm,46:
388-390.
KHAFAGY, S. M., MAHMOUD, 2. F. & ABDEL SALAM, N. A., 1979. Coumarins and flavonoids of
Ricinus communis growing in Egypt. Planta Medica, 37: 191.
KINGHORN, A. D., 1979. Carcinogenic irritant Euphorbiaceae. In A. D.Kinghorn, (Ed.), Toxic Plants;
137-159. New York: Columbia University Press.
KINGSBURY, J. M., 1964. Poisonous Plants of the United States and Canada. New Jersey: Prentice Hall, Inc.
KIRTIKAR, K. R. & BASU, B. D., 1984. Indian Medicinal Plants, 2: 21W2290. Allahabad, India: Lalit
Mohan Basu Publisher.
KJAER, A. & FRIIS, P., 1962. Isothiocyanates XLIII. Isothiocyanates from Putranjiua roxburghii Wall.
including (S)-2-methylbutyl isothiocyanate, a new mustard oil of natural derivation. Acta Chemica
Scandinauica, 10: 936-946.
KOUNO, I., SAISHOJI, T., SUGIYAMA, M. & KAWANO, N., 1983. A xylosyl-glucoside of xanthoxylin
from Sapium sebiJerum root bark. Phytochernistry, 22: 790-791.
KUONO, I., SHIGEMATSU, N., IWAGAM, M. & KAWANO, N., 1985. Further phloroglucinol
derivatives in the fruits of Mallotus japonicus, Phytochemistv, 24: 620-621.
KREWSON, C. F. & SCOTT, W. E., 1966. Euphorbia lagascae Spreng., an abundant source of epoxyloeic
acid; seed extraction and oil composition. Journal of the American Oil Chemists' Sociep, 43: 171-174.
KUPCHAN, S. M., UCHIDA, I., BRANFMAN, A. R., DAILEY, R. G., JR. & FEI, B. Y., 1976.
Antileukemic principles isolated from Euphorbiaceae plants. Science, 191: 571-572.
LAW, AH., THRELFALL, D. R. & WHISTANCE, G. R., 1970. Ubiquinones of Heva brasiliensis.
Phytochernistry, 9: 246 I .
LEE, Y. C. & NOBLES, W. L., 1959. Journal of the American Pharmaceutical Association, ScientiJic Edition, 48:
162- 165.
LEE, K.-H., HAYASHI, N., OKANO, M., HALL, I. H., WU, R.-Y., & MCPHAIL, A., 1982.
Lasiodiplodin, a potent antileukemic macrolide from Euphorbia splendenr. Phytochemistry, 21: I 1 19-1 121.
LEWIS, W. H. & ELVIN-LEWIS, M. P. F., 1977. Medical Botany. New York, London: John Wiley & Sons.
LI KEN JIE, M. S. F. & SINHA, S., 1981. Fatty acid composition and the characterisation of a novel dioxo
C , fatty acid in the latex of Heva brasiliensis. Phytochemistry, 20: 1863-1866.
I .
2
324
zyxwvutsrqp
zyxwvutsrq
zyxwvu
A.-F. M.R I Z K
zyxwvutsr
zyxwvut
zyx
zyxwvutsr
MAHMOUD, Z. F. & ABDEL SALAM, N. A., 1979. Coumarins of Euphorbia lerracina and Euphorbia paralias
growing in Egypt. Phamazie, 34: 446-447.
MANNERS, G. D. & DAVIS, D. G., 1984. Epicuticular wax constituents of north American and European
Euphorbia esula biotype. Phytochemistry, 23: 1059-1062.
MANSKE, R.H.F., 1968.Alkaloids unclassified and of unknown structure. In R. H. F. Manske (Ed.), The
Alkaloids, Chemistry and Physiology, 10: 545-595.New York, London: Academic Press.
MATSUNAGO, S. & MORITA, R., 1983. Hopenol-B, a triterpene alcohol from Euphorbia supina.
Phytochemistry, 22: 605-606.
MUELLER, R. & POHL, R., 1970. Die Flavonolglykoside von Euphorbia amygdaloides und ihre Quantitative
Bestimmung in Verschieden Entwicklungsstadien der Pfanze. 5. Mitteilung ueber die Flavonoide
einheimisher Euphorbiaceen. Planta Medica, 18: 1 14- 129.
MUELLER, P. & SCHUETTE, H. R., 1968. Biochemistry and physiology of latex. XVIII. I-Methyl-6hydroxy-l,2,3,4-tetrahydroxyisoquinoline-3-carboxy~ic
acid in Euphorbia myrsinites latex. Zeitschrvt fur
Naturforschung, B, 23: 491-493.
NAHRSTEDT, A., KANT, J.-D. & WRAY, V., 1982.Acaiyphic, a cyanogenic glucoside from Acabpha indica.
Phytochemistry, 21: 101-105.
NAZIR, M., AHMAD, I., BHATTY, M. K. & KARIMULLAH, 1966. Chemical constituents of Euphorbia
royleana. Pakistan Journal of Scientijc and Industrial Research, 9: 38-40.
NEMETHY, E. K., OTVOS, J. W. & CALVIN, M., 1979. Analysis of extractables from one Euphorbia.
Journal of the American Oil Chemists’ Sociep, 56: 957-960.
NEMETHY, E. K., OTVOS, J. W. & CALVIN, M., 1981a.Natural production of high-energy liquid fuels
from plants. In D. L. Klass & G. H. Emert (Eds), Furisfrom Biomass and Wastes: 405419.Michigan: Ann
Arbor Publishers Inc.
NEMETHY, E. K., OTVOS, J. W. & CALVIN, M., 1981b. Hydrocarbons from Euphorbio lathyris. Pure and
Applied Chemistry, 53: 1101-1 108.
NOVACK, E. A., CREA, A. E. G. & FALSONE, G., 1980. Inhibition of mitochondria1 oxidative
phosporylation by 4-deoxyphorbol triesters, a poisonous constituent of the latex of Euphorbio biglandulosa
Desf. Toxicon, 18: 165-174.
OGURI, S. & SHINOHARA, I., 1957. Effects of standing, heating and stirring on mucilage for Japanese
paper making. Kogyo Kagaku <asshi, @
467-469;
I:
(via Chemical Abstracts, 53: 7592).
OKUDA, T. & KARU S., 1981. Studies of the tannins and polyphenols of Mallotus japonicus. I. Mallotus
japonicus leaf tannins. Nippon Kagaku Kaishi: 671-677. (via Chemical Abstracts, 95: 3440).
OKUDA, T. & SENO, K., 1981.Cited in Yoshida et al., 1982.
OKUDA, T., MORI, K. & HATANO, T., 1980a.T h e distribution of geraniin and mallotusinic acid in the
order Geraniales. Phytochemistry, 19: 547-55 I.
OKUDA, T., YOSHIDA, T. & HATANO, T., 1980b. Equilibrated stereo-structures of hydrated geraniin
and mallotusinic acid. Tetrahedron Letters, 21: 2561-2564.
PARELLO, J. & MUNAVALLI, S., 1965. Phyllantine and phyllantidine, alkaloids of Phyllanthus discozdes.
Comptes Rendus, 260: 337-340.
PARIS, R. A., MOYSE-MIGNON, H. & MEN, J. LE., 1955. Alkaloids of Flueggea wirosa. Annales
pharmaceutiquesfrancaises, 13: 245-249.
PARTHASARATHY, M. R. & SARADHI, K. P., 1984. A Coumarino-lignan from Jatropha glandul$era.
Phytochemistry, 23: 867-869.
PEOPLES, T. R., ALCORN, S., BLOSS, H. E., CLAY, W. F., FLUG, M., HOFFMAN, J. J., LEE, C. W.,
LUNA, S., MCLAUGHLIN, S. P. el al., 1981.Euphorbia lathyris L.: A future source of extractable liquid
fuels. Biosources Digest 3: 1 17-123; (via Chemical Abstracts, 95: 222769).
PIATAK, M. D., & REIMANN, K., 1972. Plant investigation. IV. Corollatadiol, a new triterpene from
Euphorbio corollala. Tetrahedron Lttcrs, 44: 45254528.
POHL, R., JANISTYN, B. & NAHRSTEDT, A,, 1975. Die Flavonolglykoside von Euphorbia helioscopia, E .
stricta, E. uerrucosa and E . dulcis. 9. Mitteilung ueber die Flavonoide eimheimisher Euphorbiaceen. Planta
Medica, 27: 301-303.
PONSINET, G . & OURISSON, G., 1965. etudes chimico-taxonomiques dans la famille des
Euphorbiacees-I.
Introduction gCnOrale et separation et identification des triterpknes titracycliques
monohydroxyles naturels. Phytochemistry, 4: 799-81 I.
PRAKASH, S., KHAN, M. A., KHAN, H. & ZAMAN, A., 1983. A piperidine alkaloid from Excnecharia
agallocha. Phyfochemistry, 22: 1836-1837.
PUNTAMBEKAR, S. V. & KRISHNA, S., 1932. The seeds of Valeria indica Linn. as a source of vegetable
tallow. Indian Forester, 58: 68-74; (via Chemical Abstracts, 28: 6005).
RAO, D. N. & ROW, L. R., 1966. Crystalline constituents of Euphorbiaceae. 111. The triterpenes of
Euphorbia nerifolia. Current Science, 34: 432.
RIZK, A. M., 1986. The Phytochemistry of the Flora of Qatar. The Scientific and Applied Research Centre, Qatar
University. London: Kingprint Press.
RIZK, A. M. & EL-MISSIRY, M. M., 1986. Non-diterpenoid constituents of Euphorbiaceae and
Thymelaeaceae. In F. J. Evans (Ed.), Naturalb Occurring Phorbol Esters: 107-138. Boca Raton: C R C Prcss.
RIZK, A. M. & RIMPLER, H.,1977.Investigation of Euphorbia indica. Planta Mcdica, 32: 177-180.
RIZK, A. M., YOUSSEF, A. M., DIAB, M. A. & SALEM, H. M., 1974. Constituents of Egyptian
zyxwvutsrq
zyxw
zyxwvutsrq
zyxwvu
zyx
zyxwvuts
CHEMICAL CONSTITUENTS OF EUPHORBIACEAE
325
Euphorbiaceae. 1. Triterpenoids and related substances of Euphorbia paralias. zeitschrft fur Naturfrschung,
29C: 529-531.
RIZK, A. M., YOUSSEF, A. M., DIAB, M. A. & SALEM, H. M., 1976. Flavonoids of Euphorbia paralias.
Pharmazie, 31: 405.
RIZK, A. M., RIMPLER, H. & ISMAIL, S. I., 1977.Flavonoids and ellagic acid from Euphorbia hypericiiolia
( = E . indica). Fitoterapia, 48: 99-100.
RIZK, A. M., HAMMOUDA, F. M., SEIF EL-NASR, M. M. & EL-MISSIRY, M. M., 1978.
Phytochemical investigation of Euphorbia geniculata and E . prostrata. Pharmazic, 33: 540-54 1.
RIZK, A. M., AHMED, S. S. & DIM, M. M., 1979. Further investigation of the flavonoids of Euphorbia
paralias L. Planta Medico, 36: 189-190.
RIZK, A. M., HAMMOUDA, F. M., SEIF EL-NASR, M. M. & ABOU-YOUSSEF, A. A., 1980a.
Phytochemical investigation of Euphorbia pcplu. Fitoterapia, 51: 223-227.
RIZK, A. M., HAMMOUDA, F. M., EL-SHAMY, A. M. & EL-MISSIRY, M. M., 1980b. Triterpenoids
from latices of Euphorbia paralias and E. geniculata, Fitoterapia, 51: 31 3-31 6.
RIZK, A. M., AL-NAGDY, S. A. & EL-MISSIRY, M. M., 1982. Investigation of Euphorbia granulata.
Phannazie, 37: 737-738.
ROJAS, H. C., 1964. Possibilities of obtaining pulp and paper from some national raw materials. Tccnologia,
6: 26-32; (via Chemical Abstracts, 66: 66932).
ROSHCHIN, YU. V. & KIR'YALOV, N. P., 1970. Tetracyclic triterpenoid compounds from Euphorbia
condylocarpa. Khimiya prirodnykh soedinenij, 6: 483 (via Chemical Abstracts, 74: 10351).
SAHAI, R., DUBE, M. P. & RASTOGI, R. P., 1981. Chemical and pharmacological study of Euphorbia
maddeni. Indian Journal of Pharmaceutical Science, 43: 216-2 19.
SAINSBURY, M., 1970. Fridelin and epifriedlinol from the bark of Prunus and a review of their natural
distribution. Phytochemistry, 9 : 2209-2215.
SARKAR, S. & CHAKRABARTY, M. M., 1956a. Seed fats of the Euphorbiaceae family. I. Chemical
examination of the seed fat from Trewia nudiflra. Science and Culture, 21: 473-474; (via Chemical Abstracts, 50:
10427).
SARKAR, S. & CHAKRABARTY, M. M., 1956b. Seed fats of the Euphorbiaceae 11. The chemical
composition of the seeds fats from BischoJia javanica and Antidesma diandrum. Science and Culture, 22: 336-337;
(via Chemical Abstracts, 51: 12511).
SCHROEDER, G., ROHMER, M., BECK, J. P. & ANTON, R., 1980. 7-Oxo-,7 a-hydroxy- and 7 8hydroxysterols from Euphorbiafircheriana, Phytochemistry, 19: 2213-2215.
SCHULTE, K. E., REISCH, J. & BORNFLETH, H., 1964.The occurrence of tram-dehydromatricaria ester
and I-tridecene-3,5,7,9,1 I-pentyne in Ricinus communis, Archiv der Phannaie, 297: 443.
SEKULA, B. C. & NES, W., 1980.The identification of cholesterol and other sterols in Euphorbia pulchcrrima.
Phytomistry, 19: 1509- 1512.
SERRA, R. M., 1944. Investigation of quinine in Phyllanthus nururi L. Anales Uniuersidad Santo Domingo, 8:
295-297; (via Chemical Abstracts, 41: 1812).
SHANG, T.-M., WANG, L., LIANG, H.-T., LIN, X.-Y., XIAO, J.-M. & NIU, S.-L., 1979. Studies on the
constituents of Mao-Yan-Cao (Euphorbia lunulata Bge). Hua Hsueh Hsueh Pao, 37: 119-128; (via Chnical
Abstracts, 92: 3 184).
SHIGEMATSU, N., KOUNO, I. & KAWANO, N., 1983. Phloroglucinol derivatives from fruits of Mallotu
japonicus. Phytochemistry, 22: 323-325.
SINGH, A. & SRIVASTAVA, S. N., 1966. Chemical examination of Euphorbia dracunculoides Lam. Indian
Journal of Chemistry, 4: 420.
SOBOLEVA, V. A., 1979.Flavonoids of some Euphorbia species. Khimiya Prirodnykh Soedinenij, 5: 855-856; (via
Chemical Abstracts, 93: 3899).
SOBOLEVA, V. A., 1980. Polyphenol compounds of Ricinus communis and Mercurialis perennis. Khimiya
Prirodnykh Soedinenij, 123- 124; (via Chemical Abstracts, 92: 177454).
STARRAT, A. N., 1966.Triterpenoid constituents of Euphorbia cyparissias. Phytochemistry, 5: 1341-1 344.
STARRAT, A. N., 1969. Isolation of Hopenone-B from Euphorbia cyparissias. Phytochemistry, 8: 1831-1832.
STUART, K. L., CHAMBERS, C. & BYFIELD, D., 1969. Morphinandienone alkaloids from CrotonJavcm
L., Journal of the Chemical Society ( C ) , 168-1684.
TAKEMOTO, T. PC INGAKI, M., 1958.Constituents of Euphorbia marulata. rakugaku zasshi, 78: 292-294.
TAKEMOTO, T. & ISHIGURO, T., 1966. Constituents of Euphorbia watanabei. I. rakugaku zusshi, 86:
530-533.
TALAPATRA, B., GOSWAMI, S. & TALAPATRA, S. K., 1981. Acalyphamide, a new amide and other
constituents of Acalypha indica Linn. Indian Journal of Chemistry, 20B: 974-977.
TIWARI, K. P., CHOUDHARY, R. N. & PANDY, G. D., 1981.3-Methoxy-4,6-dihydroxymorphinandien7-one,an alkaloid from Croton bonpalandianum. Phytochemistry, 20: 863-864.
TIPATHI, R. D. & TIWARI, K. P., 1980. Geniculatin, a triterpenoid saponin from Euphorbia geniculata.
Phytochemistry, 19: 2163-2 166.
TUTIYA, M. & KATO, Y.,1940. Foliaceous woods as raw material from pulp in Formosa. Journal of thc
Agricultural Chemical Society of Japan, 16: 224-226.
UEMURA, D. & HIRA'IA, Y.,1971.The isolation and structures of two new alkaloids milliamines A and B,
obtained from Euphorbia millii. Tetrahedron Letters, 3673-3676.
zyxwvut
326
zyxwvutsrqpo
zyxwvu
zyxwvutsrq
zyxwvutsr
zyxw
A.-F. M. RIZK
VALEN, F., VAN., 1978. Contribution to the knowledge of cyanogenesis in Angiosperms. 10.
Communication. Cyanogenesis in Euphorbiaceae. Planta Medica, H: 408-413.
VICKERY, M. L. & VICKERY, B., 1979. Plant Products of Tropical A f k a . London: MacMillan.
WAGNER, H., HOERHAMMER, L. & KIRALY, I. C., 1970. Flavon-C-Glykoside in Crolon zambezicw.
Phytochnutry, 9: 897.
WARNAAR, F., 1981. Conjugated fatty acids from latex of Euphorbia lathyris. Phytochrmistry: 20: 89-91.
WATANABE, T. A., ARAKI, T., OGATA, K., GOTO, M. & HOMU, I., 1956. Antibiotic components of
plants. 11. Takeda Knutyusho Nrmpo, 15: 129-139. (via Chemical Abstracts, 51: 8367).
WATT, J. M. & BREYER-BRANDWIJK, M. G., 1962. The Medicinal and Poisonous Plants of Southern and Eastern
Africa, 2nd edition. Edinburgh, London: E. & S. Livingstone Ltd.
WOERD, L. A., VAN DER., 1941. The native medicines of the East Indian Archipelago. VII. The diuretic
action of the most common herbs used in the Netherland East Indies in native medicine against diseases of
the urinary system. Geneeskundif Tijhchrifr uoor Nederlandsch-Indie, 81: 1963-1980. (via Chemical Abstracts, 36:
160).
zyxwvut
zyxwvutsrq
YAMAGUCHI, K., 1970. Spectral Data of Natural Products, I. Amsterdam: Elsevier.
YOSHIDA, T., SENO, K., TAKAMO, Y. & OKUDA, T., 1982. Bergenin derivatives from Malloltu
japonicus. P&tochemistry, 21: 118&1182.
YOSHITAMA, K., ISHII, K. & YASUDO, H., 1980. A chromatographic survey of anthocyanins in the flora
of Japan. journal of the Facully of Science of Shinrhu Universily, 15: 19-25.
Abdel Fattah Rizk