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Article

Essential Oils from Vietnamese Asteraceae for Environmentally Friendly Control of Aedes Mosquitoes

by
Tran Minh Hoi
1,
Prabodh Satyal
2,
Le Thi Huong
3,
Dang Viet Hau
4,
Tran Duc Binh
1,
Dang Thi Hong Duyen
4,
Do Ngoc Dai
5,
Ngo Gia Huy
6,
Hoang Van Chinh
7,
Vo Van Hoa
8,
Nguyen Huy Hung
6,8,* and
William N. Setzer
2,9,*
1
Department of Plant Resources, Institute of Ecology and Biological Resources, Vietnam Academy of Science and Technology, Hanoi 100000, Vietnam
2
Aromatic Plant Research Center, Lehi, UT 84043, USA
3
School of Natural Science Education, Vinh University, Vinh City 43000, Vietnam
4
Center for Research and Technology Transfer, Vietnam Academy of Science and Technology, Hanoi 100000, Vietnam
5
Faculty of Agriculture, Forestry and Fishery, Nghe An College of Economics, Vinh City 43000, Vietnam
6
Center for Advanced Chemistry, Institute of Research and Development, Duy Tan University, Da Nang 550000, Vietnam
7
Faculty of Natural Sciences, Hong Duc University, Thanh Hoa 440000, Vietnam
8
Department of Pharmacy, Duy Tan University, Da Nang 550000, Vietnam
9
Department of Chemistry, University of Alabama in Huntsville, Huntsville, AL 35899, USA
*
Authors to whom correspondence should be addressed.
Molecules 2022, 27(22), 7961; https://doi.org/10.3390/molecules27227961
Submission received: 6 October 2022 / Revised: 27 October 2022 / Accepted: 14 November 2022 / Published: 17 November 2022
(This article belongs to the Special Issue Essential Oils II)
Browse Figure
Review Reports Versions Notes

Abstract

:
Mosquitoes, in addition to being a biting nuisance, are vectors of several pathogenic viruses and parasites. As a continuation of our work identifying abundant and/or invasive plant species in Vietnam for use as ecologically friendly pesticidal agents, we obtained the essential oils of Blumea lacera, Blumea sinuata, Emilia sonchifolia, Parthenium hysterophorus, and Sphaeranthus africanus; analyzed the essential oils using gas chromatographic techniques; and screened the essential oils for mosquito larvicidal activity against Aedes aegypti and Aedes albopictus. The most active larvicidal essential oils were B. sinuata, which was rich in thymohydroquinone dimethyl ether (29.4%), (E)-β-caryophyllene (19.7%), α-pinene (8.8%), germacrene D (7.8%), and α-humulene (4.3%), (24-h LC50 23.4 and 29.1 μg/mL) on Ae. aegypti and Ae. albopictus, respectively, and Emilia sonchifolia, dominated by 1-undecene (41.9%) and germacrene D (11.0%), (24-h LC50 30.1 and 29.6 μg/mL) on the two mosquito species. The essential oils of P. hysterophorus and S. africanus were also active against mosquito larvae. Notably, B. sinuata, P. hysterophorus, and S. africanus essential oils were not toxic to the non-target water bug, Diplonychus rusticus. However, E. sonchifolia essential oil showed insecticidal activity (24-h LC50 48.1 μg/mL) on D. rusticus. Based on these results, B. sinuata, P. hysterophorus, and S. africanus essential oils appear promising for further investigations.

Graphical Abstract

1. Introduction

The Asteraceae is the largest family of flora in the world, comprising about 1550 genera and about 23,000 species [1]. In Vietnam, there are about 126 genera and 379 species from this family [2]. Many species are used as medicines, for isolation of essential oils, or as ornamentals [2].
Blumea lacera (Burm. f.) DC. (syn. Conyza lacera Burm. f., Blumea bodinieri Vaniot, Blumea dregeanoides Sch. Bip. ex A. Rich., Blumea duclouxii Vaniot, Blumea glandulosa DC., Blumea subcapitata DC., Blumea velutina (H. Lév. and Vaniot) H. Lév. and Vaniot, Conyza velutina H. Lév., and Senecio velutinus H. Lév. and Vaniot) is found in China, Bhutan, India, Japan, Laos, Malaysia, Myanmar, Nepal, New Guinea, Pakistan, Sri Lanka, Thailand, and Vietnam [1]. The pharmacognosy and phytochemistry of B. lacera have been reviewed [3]. In traditional medicine, B. lacera has been used as an expectorant, diuretic, astringent, antispasmodic, antipyretic, antioxidant, antidiarrheal, liver tonic, and stimulant [4]. The leaves of B. lacera are fragrant, and in Vietnam, are used as a vegetable as well as a medicine to treat boils and stop bleeding [5].
Blumea sinuata (Lour.) Merr. (syn. Blumea laciniata (Wall. ex Roxb.) DC., Conyza laciniata Roxb., Asteraceae) [6] is native to southern China, India, Pakistan, Sri Lanka, Bhutan, Nepal, Myanmar, Malaysia, Indonesia, the Philippines, and Vietnam, naturally ranging from southern China and India, south through Indonesia, Malaysia, Myanmar, Thailand, and Vietnam [1]. Its leaves and stems are used to treat boils, remove toxins from the body, and stop bleeding. Leaves of B. sinuata have been used to treat influenza, rheumatism, bone pain, or pain due to injury or swelling [5]. A review of the medicinal chemistry, phytochemistry, and pharmacology of the Blumea genus has been published [7].
Emilia sonchifolia (L.) DC. (syn. Cacalia sonchifolia L., Crassocephalum sonchifolium Less., Emilia mucronata Wall., Emilia purpurea Cass., Emilia rigidula DC., Emilia scabra DC., Emilia sinica Miq., Senecio ecalyculatus Sch. Bip., Senecio rapae F. Br., Senecio sonchifolius Moench) is a pantropical weed of Old World origin [8]. Ethnomedically, the plant has been used to treat eye sores, convulsion, cuts, wounds, rheumatism, and insect bites [9]. In Vietnam, the leaves and young tops are used as vegetables, and the whole plant is used as medicine to reduce fever [5].
Parthenium hysterophorus L. (syn. Argyrochaeta bipinnatifida Cav., Argyrochaeta parviflora Cav., Echetrosis pentasperma Phil., Parthenium lobatum Buckley, Parthenium pinnatifidum Stokes) is believed to be native to the Gulf of Mexico, including Honduras, Guatemala, and Mexico, as well as the West Indies [10]. The plant was introduced to Australia, India, southern China, and Vietnam, where it became a noxious weed [11,12]. Nevertheless, the plant has shown potential medicinal applications [13,14,15].
Sphaeranthus africanus L. (syn. Sphaeranthus cochinchinensis Lour., Sphaeranthus glaber DC., Sphaeranthus globosus Wall. ex DC., Sphaeranthus hildebrandtii Baker, Sphaeranthus indicus Kurz, Sphaeranthus laevigatus Wall. ex DC., Sphaeranthus microcephalus Vatke, Sphaeranthus microcephalus Willd., Sphaeranthus ovalis Steetz, Sphaeranthus paniculatus Cass., Sphaeranthus sphenocleoides Oliv. and Hiern, Sphaeranthus suberiflorus Hayata) is native to Africa (Kenya, Tanzania, Mozambique, and Madagascar), tropical Asia (Bangladesh, Borneo, Cambodia, south-central and southeastern China, Hainan, India, Malaya, Myanmar, Nepal, Philippines, Sri Lanka, Taiwan, Thailand, and Vietnam), and Australia (Northern Territory, Queensland, and Western Australia) [16]. In Vietnam, a decoction of the leaves of S. africanus is used to prepare a mouthwash to treat sore throats [5]. Several biologically active carvotacetones have been isolated from S. africanus extracts [17,18,19].
Aedes mosquitoes (Culicidae) are acknowledged vectors of numerous pathogenic viruses. Aedes aegypti (L.) is known to transmit the yellow fever, Zika, dengue, and chikungunya viruses [20], whereas Aedes albopictus (Skuse) is a vector for West Nile, Japanese encephalitis, and Eastern equine encephalitis, as well as dengue and chikungunya viral pathogens [21]. Dengue fever is widespread in Southeast Asia, including Vietnam, and causes considerable health and economic burden [22]. Both chikungunya [23] and Zika [24] viral infections are emerging diseases in the region. Though synthetic insecticides have been used to control mosquito populations, there is growing concern regarding insecticidal resistance [25,26], environmental degradation [27,28], and harm to non-target organisms [29,30]. Essential oils have been recognized as potential alternatives to synthetic insecticides for control of insect pests, including mosquitoes [31,32].
As part of our research into the identification of readily available native and invasive plants in Vietnam as sources of essential oils for ecologically friendly pest control agents [33,34,35,36], we investigated B. lacera, B. sinuata, E. sonchifolia, P. hysterophorus, and S. africanus essential oils for mosquito larvicidal activity against Aedes aegypti (L.) and Aedes albopictus (Skuse) (Diptera: Culicidae) mosquitoes. These species of mosquitoes are the principal vectors of the dengue fever virus in Vietnam [37]. To test selectivity, we screened the essential oils against the non-target water bug, Diplonychus rusticus (Fabricius), a predator of mosquito larvae. There have been several reviews on the potential pesticidal utility of essential oils to control mosquito populations [38,39,40,41].

2. Results and Discussion

2.1. Essential Oil Compositions

2.1.1. Blumea lacera

Floral, leaf, and stem essential oils of B. lacera were obtained at 1.10, 1.56, and 0.35%, respectively. The chemical compositions of B. lacera essential oils are presented in Table 1. The most abundant chemical components in the essential oils of B. lacera were (E)-β-caryophyllene (23.8, 27.2, and 11.7%), germacrene D (18.5, 21.0, and 11.2%), thymohydroquinone dimethyl ether (5.0, 4.1, and 28.4%), γ-curcumene (5.9, 7.7, and 4.7%), ar-curcumene (8.0, 3.7, and 1.9%), and α-zingiberene (4.7, 7.1, and 4.6%) in the flowers, leaves, and stems, respectively.
A B. lacera leaf essential oil sample from Idaban, Nigeria, was found to contain thymohydroquinone dimethyl ether (33.9%) and (E)-β-caryophyllene (10.7%) as major components [42]. Similarly, the two essential oil samples from aerial parts of B. lacera from central Vietnam were rich in (E)-β-caryophyllene (12.0 and 8.3%), thymohydroquinone dimethyl ether (11.4 and 6.6%), and caryophyllene oxide (21.7 and 11.9%) [43]. Joshi and co-workers have noted large variations in essential oil compositions in samples from different geographical regions of India with thymohydroquinone dimethyl ether ranging from 0.4 to 28.7% and (E)-β-caryophyllene from 0.5 to 25.5% [44]. In contrast, a previous examination of the essential oil from the aerial parts of B. lacera from Biratnagar, Nepal, found the oil to be dominated by (Z)-lachnophyllum ester (25.5%), (Z)-lachnophyllic acid (17.0%), germacrene D (11.0%), (E)-β-farnesene (10.1%), bicyclogermacrene (5.2%), (E)-caryophyllene (4.8%), and (E)-nerolidol (4.2%) [45]. Both the essential oil and (Z)-lachnophyllum ester showed cytotoxic, antibacterial, and antifungal activity. Interestingly, neither lachnophyllum esters nor lachnophyllic acids were detected in the essential oils from Vietnam. It is not clear what factors contribute to the large variations in essential oil compositions, but environmental influences (climate, altitude, latitude, and edaphic conditions), seasonality, phenology, genotype variation, or extraction method have often been attributed to rationalize essential oil compositional differences [46].

2.1.2. Blumea sinuata

The fresh aerial parts of B. sinuata were hydrodistilled using a Clevenger apparatus to obtain the essential oil in 0.16% yield. The essential oil composition of B. sinuata is shown in Table 2. The major components in the essential oil of B. sinuata were thymohydroquinone dimethyl ether (29.4%), (E)-β-caryophyllene (19.7%), α-pinene (8.8%), germacrene D (7.8%), and α-humulene (4.3%). As far as we are aware, there is only one previous report on the essential oil of B. sinuata (as B. laciniata, from Dapoli region, Maharashtra, India) [47]. The GC–MS analysis, however, is not reliable, so a meaningful comparison of the compositions is not possible.

2.1.3. Emilia sonchifolia

Hydrodistillation of the fresh aerial parts of E. sonchifolia gave a 0.51% yield of essential oil. A total of 43 compounds were identified, accounting for 93.2% of the total composition (see Table 3). Gas chromatographic analysis of E. sonchifolia essential oils revealed the oil to be dominated by 1-undecene (41.9%) and germacrene D (11.0%). The essential oil composition of E. sonchifolia from Vietnam is in marked contrast to the essential oils from Belagavi, Karnataka, India [48] or Ojo State, Nigeria [49]. The E. sonchifolia sample from India was rich in the sesquiterpene hydrocarbons, (E)-β-caryophyllene (22.7%) and γ-muurolene (32.1%). The essential oil from Nigeria was also rich in sesquiterpene hydrocarbons, namely (E)-β-caryophyllene (15.7%), γ-gurjunene (8.6%), and γ-himachalene (25.2%). The differences in essential oil compositions may be due to genetic or environmental factors.

2.1.4. Parthenium hysterophorus

Hydrodistillation of the fresh aerial parts of P. hysterophorus gave a yield of 0.05% (w/w) as a colorless/pale yellow essential oil. Gas chromatography–mass spectral analysis of the essential oil revealed a total of 75 identified (97.8% of the total) compounds (see Table 4).
The major components in the P. hysterophorus essential oil were germacrene D (23.2%), myrcene (14.4%), (E)-β-caryophyllene (12.6%), cogeijerene (4.8%), (E,E)-α-farnesene (3.3%), (E)-β-ocimene (3.1%), and β-pinene (3.0%). Though most of these compounds are commonly present in essential oils, cogeigerene (1,2,3,7,8,8a-hexahydro-4,8a-dimethylnaphthalene) is a relatively rare component of essential oils. The compound was originally isolated and characterized from Geijera parviflora [50], but it has also been found in the essential oils of Geijera parviflora (4.3%) [51], Scaligeria tripartita (1.0%) [52], and Artemesia annua (0.1%) [53]. The essential oil composition is qualitatively similar to an essential oil sample from Lavras, Minas Gerais, Brazil, with germacrene D (35.9%), myrcene (7.6%), (E)-β-caryophyllene (3.1%), (E)-β-ocimene (8.5%), and β-pinene (7.6%) [54]. However, neither cogeijerene nor (E,E)-α-farnesene were reported from the Brazilian sample.

2.1.5. Sphaeranthus africanus

The essential oil from the aerial parts of S. africanus was obtained at 0.25% yield. The major components in S. africanus essential oil were 1-decen-3-ol (36.9%), α-pinene (21.0%), τ-cadinol (7.5%), 3-octyl propionate (5.6%), and (E)-β-caryophyllene (5.5%) (see Table 5). In contrast, the S. africanus (as S. indicus) essential oil from India was composed of thymohydroquinone dimethyl ether (18.2%), α-agarofuran (11.8%), 10-epi-γ-eudesmol (7.9%), and selin-11-en-4α-ol (12.7%) [55]. The compositional differences in the essential oils from Vietnam and India may be attributed to genetic differences or environmental factors.

2.2. Mosquito Larvicidal Activity

The essential oils of B. lacera, B. sinuata, E. sonchifolia, P. hysterophorus, and S. africanus were screened for mosquito larvicidal activity against Aedes aegypti (the yellow fever mosquito) and Aedes albopictus (the Asian tiger mosquito), as previously described [34,56]. The essential oils were also screened for possible insecticidal activity against the non-targeted water bug, D. rusticus, as previously reported [33,36]. The larvicidal and insecticidal activities for the essential oils are summarized in Table 6.
According to Dias and Moraes [39], essential oils and their components are considered to be active with larvicidal LC50 values less than 100 μg/mL. However, we have recently amended the activity definition: essential oils with 24-h LC50 < 10 μg/mL are considered “exceptionally active”, those with 24-h LC50 between 10 and 50 μg/mL are “very active”, those with 24-h LC50 between 50 and 100 μg/mL are “moderately active”, and LC50 >100 μg/mL are “inactive” [58]. Thus, B. lacera leaf essential oil was only marginally active against Ae. aegypti and inactive against Ae. albopictus.
The essential oil of B. sinuata, on the other hand, showed very good Aedes larvicidal activities with 24-h LC50 values of 23.4 and 29.1 μg/mL against Ae. aegypti and Ae. albopictus, respectively, as well as 48-h LC50 values of 17.4 and 12.4 μg/mL. Importantly, B. sinuata essential oil showed no mortality at the highest concentration tested (100 ug/mL) against the non-target water bug, Diplonychus rusticus. The larvicidal activities observed can be partly attributed to the major components. Ayapana triplinervis essential oil, rich in thymohydroquinone dimethyl ether (84.5%), showed larvicidal activity against Ae. aegypti (24-h LC50 = 86.2 μg/mL) [59]. (E)-β-Caryophyllene has shown insecticidal activity against Ae. aegypti larvae (LC50 39–88 μg/mL), as well as Ae. albopictus larvae (LC50 40–45 μg/mL) [33,35,36]. Likewise, α-pinene has demonstrated larvicidal activities against both Ae. aegypti and Ae. albopictus with LC50 values ranging 40–65 and 29–69 μg/mL, respectively [35], germacrene D showed good larvicidal activity on Ae. aegypti (LC50 = 18.8 μg/mL) [60], and α-humulene was larvicidal with 24-h LC50 values of 44.4 and 43.9 μg/mL against Ae. aegypti and Ae. albopictus, respectively [36].
Although E. sonchifolia essential oil showed moderately active mosquito larvicidal activity (24-h LC50 = 30.1 and 29.6 μg/mL against Ae. aegypti and Ae. albopictus, respectively), it was also insecticidal to the non-target insect, Diplonychus rusticus with a 24-h LC50 of 48.1 μg/mL. Thus, the E. sonchifolia essential oil is not selectively toxic and should not be considered further for this purpose.
The Parthenum hysterophorus essential oil showed good mosquito larvicidal activity with 24-h LC50 values of 47.6 and 44.4 μg/mL against Ae. aegypti and Ae. albopictus, respectively. Notably, the essential oil showed no lethality to the non-target insect, Diplonychus rusticus. Several of the major components of the P. hysterophorus essential oil have previously shown larvicidal activity against Ae. aegypti, including germacrene D (LC50 = 18.8 μg/mL) [60], myrcene (LC50 = 35.8 μg/mL) [61], (E)-β-caryophyllene (LC50 = 61.1 μg/mL) [36], and β-pinene (22.9 μg/mL) [33]. Larvicidal activity on Ae. albopictus has also been reported for myrcene [61] and (E)-β-caryophyllene [33] (LC50 = 27.0 and 56.9 μg/mL, respectively). The larvicidal activities of the major components, therefore, likely account for the observed larvicidal activities of the P. hysterophorus essential oil.
The essential oil of S. africanus showed moderate larvicidal activity with 24-h LC50 values of 50.7 and 36.9 μg/mL, respectively, on Ae. aegypti and Ae. albopictus. In a previous study, the S. africanus (as S. indicus) essential oil from India was screened for mosquito larvicidal activity against Culex quinquefasciatus and Ae. aegypti [62]. The larvicidal activities were very modest, however (24-h LC50 = 130 and 140 μg/mL, respectively). Unfortunately, the essential oil characterization in this study is not reliable.

3. Materials and Methods

3.1. Plant Material

The details of plant material collection and hydrodistillation are summarized in Table 7. During this process, botanical identification and confirmation was conducted by Dr. Huong, L.T., Faculty of Biology, College of Natural Science Education, Vinh University, Vietnam. In addition, voucher specimens with codes LTH 881, LTH 284, LTH 286, LTH 327, and LTH 332 were preserved in the plant specimen room, Vinh University, Vietnam. Aerial parts were shredded and hydrodistilled for 5 h using a Clevenger-type apparatus (Witeg Labortechnik, Wertheim, Germany). Essential oil isolation yields of three consecutive replicates were used to calculate the average yield. The essential oils were dried over anhydrous Na2SO4 and stored in sealed glass vials at 4 °C until use in analysis and bioactivity assays.

3.2. Gas Chromatography–Mass Spectral Analysis

Gas chromatography–mass spectral analyses (GC–MS) of B. lacera, B. sinuata, E. sonchifolia, P. hysterophorus, and S. africanus essential oils were carried out using the instrumentation and protocols previously published [36,56,63]. A Shimadzu GCMS-QP2010 Ultra, with a ZB-5 ms fused silica capillary column (60 m length, 0.25 mm diameter, 0.25 μm film thickness) was used, He carrier gas, 2.0 mL/min flow rate, injection and ion source temperatures of 260 °C, and a GC oven program of 50 to 260 °C at 2.0 °C/min. Injection volumes of 0.1 μL of 5% (w/v) samples of essential oil in CH2Cl2 were injected in split mode, with a 24.5:1 split ratio. Identification of the essential oil components was carried out with a comparison of MS fragmentation and retention indices (RI) with those available in the databases [64,65,66,67]. The peak areas were corrected for response using external standards of representative compounds from each compound class.

3.3. Mosquito Larvicidal Activity Screening

Mosquito larvicidal activity screening against Ae. aegypti and Ae. albopictus was carried out as previously described [34,56]. Quadruplicate assays using 20 fourth-instar mosquito larvae and five essential oil concentrations (100, 75, 50, 25, and 12.5 μg/mL) and a permethrin positive control. Mortality was recorded after 24 h and again after 48 h of exposure. Lethality data were subjected to log-probit analysis to obtain LC50 values, LC90 values, and 95% confidence limits using Minitab® version 19.2020.1 (Minitab, LLC, State College, PA, USA).

3.4. Diplonychus Rusticus Insecticidal Assay

Insecticidal activity against D. rusticus was carried out as previously described [33]. Quadruplicate assays were conducted, using 20 adult D. rusticus, and five essential oil concentrations (100, 75, 50, 25, and 12.5 μg/mL), with mortality recorded after 24 h and 48 h exposure times.

4. Conclusions

The essential oils of B. sinuata, rich in thymohydroquinone dimethyl ether, (E)-β-caryophyllene, α-pinene, and germacrene D; P. hysterophorus, rich in germacrene D, myrcene, and (E)-β-caryophyllene; and S. africanus, dominated by 1-decen-3-ol and α-pinene, all showed good mosquito larvicidal activities without toxicity to a non-target aquatic species. Based on these encouraging results, B. sinuata, P. hysterophorus, and S. africanus essential oils should be further investigated for use as eco-friendly botanical pesticides. Field trials and formulations are needed to enhance the environmental lifetime of the essential oils and determine whether they are a viable alternative pest-control agents in aquatic systems.

Author Contributions

Conceptualization, N.H.H. and W.N.S.; methodology, N.H.H. and P.S.; software, P.S.; validation, W.N.S. and N.H.H.; formal analysis, W.N.S. and N.H.H.; investigation, T.M.H., P.S., L.T.H., D.V.H., T.D.B., D.T.H.D., D.N.D., N.G.H., H.V.C., V.V.H. and N.H.H.; resources, T.M.H.; data curation, T.M.H., N.H.H., P.S. and W.N.S.; writing—original draft preparation, N.H.H. and W.N.S.; writing—review and editing, W.N.S.; visualization, T.M.H.; supervision, T.M.H.; project administration, T.M.H.; funding acquisition, T.M.H. All authors have read and agreed to the published version of the manuscript.

Funding

This research was funded by NAFOSTED (Vietnam), grant number 106.03-2019.315.

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

All data are available upon reasonable request from the corresponding authors (N.H.H. and W.N.S.).

Acknowledgments

P.S. and W.N.S. participated in this work as part of the activities of the Aromatic Plant Research Center (APRC, https://aromaticplant.org/ (accessed on 13 November 2022)).

Conflicts of Interest

The authors declare no conflict of interest.

Sample Availability

Samples of the essential oils are available from the corresponding author N.H.H.

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Table
Table 1. Chemical compositions of Blumea lacera essential oils.
Table 1. Chemical compositions of Blumea lacera essential oils.
RIcalcRIdbCompound%
FloralLeafStem
931933α-Pinene0.50.10.1
949950Camphenetrtr---
971972Sabinene0.1tr---
990986Safranal0.10.4tr
10241025p-Cymene0.1trtr
10281030Limonenetrtr---
10571054γ-Terpinenetrtr---
106310862,6,6-Trimethyl-1,4-cyclohexadiene-1-carboxaldehyde0.1trtr
10991101Linalool0.20.1tr
11011106Filifolone1.20.90.1
11051107Nonanal0.10.1---
11081106iso-Chrysanthenone0.10.1---
11121110(E)-4,8-Dimethylnona-1,3,7-triene0.1trtr
11221124Chrysanthenone1.31.00.1
112911291,3,8-p-Menthatriene------0.1
11371136trans-Chrysanthenol0.30.20.1
11591152Albenetrtr0.2
12231215Isothymyl methyl ether ------tr
12291229Thymyl methyl ether0.10.11.0
12381239Carvacryl methyl ethertrtr0.1
12561261cis-Chrysanthenyl acetate0.1------
12841285Bornyl acetate------0.1
12901289Thymol------tr
13451345Silphinene------tr
13741375α-Copaene0.10.1tr
13801381cis-β-Elemenetr0.10.1
13821382β-Bourbonenetrtrtr
13861387β-Cubebene0.10.1tr
13881390trans-β-Elemene1.62.11.1
139413922-Ethylidene-6-methyl-3,5-heptadienal0.90.6---
14131411Thymohydroquinone dimethyl ether5.04.128.4
14191417(E)-β-Caryophyllene 23.827.211.7
14281430β-Copaene0.20.10.1
14311432trans-α-Bergamotene0.30.20.2
14341443Dimethoxy-p-cymenene0.1tr0.5
14451446epi-β-Santene------0.1
14461453Geranyl acetone0.1trtr
14511452(E)-β-Farnesene0.90.80.5
14551454α-Humulene3.73.51.5
14591457allo-Aromadendrene 0.10.1tr
14611461cis-Cadina-1(6),4-diene0.10.1---
14711475trans-Cadina-1(6),4-dienetr------
1473---Unidentified (43, 148, 218)0.40.21.0
14751480Thymyl isobutyrate0.90.52.7
14771481γ-Curcumene5.97.74.7
14801479ar-Curcumene8.03.71.9
14821483Germacrene D18.521.011.2
14821490Neryl isobutyratetr---5.2
14881489β-Selinene 0.40.30.2
14911492trans-Muurola-4(14),5-diene tr0.10.1
14931493α-Zingiberene5.77.14.6
14971497α-Muurolene 0.50.40.2
15021504(E,E)-α-Farnesene 0.60.20.1
15061508β-Bisabolenetr0.10.1
15121514γ-Cadinene0.50.30.3
15161518δ-Cadinene1.71.00.6
15221521β-Sesquiphellandrene 3.63.82.4
15591562(E)-Nerolidol0.40.20.1
15651571Thymyl 2-methylbutanoate0.90.41.1
15681571Neryl 2-methylbutanoate0.90.83.3
15761580Neryl isovalerate0.80.51.3
15821587Caryophyllene oxide1.41.40.5
15981598Humulene epoxide I0.20.20.1
16101611Humulene epoxide II0.10.1tr
16131611Zingiberenol0.30.20.3
163016327-epi-cis-Sesquisabinene hydrate0.20.10.3
16341635Caryophylla-4(12),8(13)-dien-5α-ol0.10.10.1
16371636Caryophylla-4(12),8(13)-dien-5β-ol0.10.30.1
16391638(2S,5E)-Caryophyll-5-en-12-al1.01.10.4
16421643τ-Cadinol0.80.83.0
16441645τ-Muurolol 0.40.30.4
16461645δ-Cadinol 0.10.10.1
16511650β-Eudesmol------0.1
16551655α-Cadinol1.21.01.3
16591658Selin-11-en-4α-oltr0.10.1
16651665Intermedeoltr---0.1
166716736-Methoxythymyl isobutyrate 0.20.10.9
1670167114-Hydroxy-9-epi-(E)-caryophyllene---0.1---
168516874-Himachalen-1β-ol (2-Himachalen-6β-ol)0.70.50.8
16871685α-Bisabolol0.10.1---
16941713(2Z,6Z)-Farnesal0.1------
17131715Pentadecanal---0.20.2
17451751Xanthorrhizol------0.1
17801780(Z)-Nerolidyl isobutyrate0.2------
2013---Unidentified (43, 71, 145, 162)0.30.21.8
2098---Unidentified (43, 57, 71, 85, 145, 162)0.50.31.0
21032106(E)-Phytoltr0.20.1
25002500Pentacosane trtr0.1
Monoterpene hydrocarbons0.60.10.1
Oxygenated monoterpenoids13.09.344.9
Sesquiterpene hydrocarbons76.180.141.5
Oxygenated sesquiterpenoids7.66.87.7
Others0.40.90.6
Total identified97.797.394.7
RIcalc. = Retention indices determined with reference to a homologous series of n-alkanes on a ZB-5 ms column. RIdb = Retention indices from the databases. tr = trace (<0.05%). % = percent of total essential oil composition.
Table
Table 2. Essential oil composition of Blumea sinuata from Vietnam.
Table 2. Essential oil composition of Blumea sinuata from Vietnam.
RIcalcRIdbCompound%
925925α-Thujenetr
933933α-Pinene8.8
949950Camphenetr
952953Thuja-2,4(10)-dienetr
970969Dimethyltrisulfidetr
972972Sabinenetr
977978β-Pinenetr
9859866-Methylhept-5-en-2-onetr
988989Myrcene0.1
9899892-Pentylfurantr
10071007α-Phellandrenetr
10251025p-Cymene0.1
10291030Limonene0.1
10311031β-Phellandrenetr
10451045(E)-β-Ocimenetr
11001101Linalool0.1
11061107Nonanal0.1
110711071-Octen-3-yl acetatetr
11101108p-Mentha-2,8-dien-1-oltr
11131113(E)-1,5-Dimethylnona-1,3,7-trienetr
11461145trans-Verbenoltr
11591161Albene0.3
11961195α-Terpineoltr
12071206Decanaltr
12301229Thymyl methyl ether0.4
12391239Carvacryl methyl ethertr
12661272Nonanoic acid0.1
12841285Bornyl acetate0.3
13231326Myrtenyl acetatetr
13461348α-Cubebene 0.1
13501348α-Longipinenetr
13591361Neryl acetate0.3
13711371Decanoic acid1.5
13751375α-Copaene 1.2
13831382β-Bourbonene0.1
13871387β-Cubebene 0.4
13891390trans-β-Elemene 0.3
14151411Thymohydroquinone dimethyl ether29.4
14201417(E)-β-Caryophyllene 19.7
14301430β-Copaene0.2
14331432trans-α-Bergamotene0.1
14411439(Z)-β-Farnesene0.1
14471446epi-β-Santalene0.1
14531452(E)-β-Farnesene3.5
14561454α-Humulene 4.3
14601457allo-Aromadendrene0.5
14751478γ-Muurolene0.1
14791481(E)-β-Ionone0.1
14821483Germacrene D7.8
14841483trans-β-Bergamotene0.5
14891489β-Selinene0.1
14921492trans-Muurola-4(14),5-diene0.1
14961497α-Selinene 0.7
14981497α-Muurolene0.2
15041504(E,E)-α-Farnesene1.1
15081508β-Bisabolene0.1
15131514γ-Cadinene0.1
15181515Dihydrolachnophyllum ester B1.0
15181518δ-Cadinene0.8
15221519trans-Calamenene0.1
152415237-epi-cis-Sesquisabinene hydrate0.2
15611562(E)-Nerolidol0.4
156415617-Hydroxyfarnesene0.2
15711568Palustrol0.2
15791580Neryl isovalerate0.6
15831587Caryophyllene oxide3.6
15931593Salvial-4(14)-en-1-one0.1
16051605Ledol0.2
16111611Humulene epoxide II0.4
16131610(Z)-Sesquilavandulol0.2
16171611β-Atlantol0.2
162916281-epi-Cubenol0.1
16351635Caryophylla-4(12),8(13)-dien-5α-ol0.1
16381636Caryophylla-4(12),8(13)-dien-5β-ol0.5
16401639allo-Aromadendrene epoxide0.1
16431643τ-Cadinol 0.3
16451645τ-Muurolol 0.2
16471653Pogostol0.2
16561655α-Cadinol 0.8
1671167114-Hydroxy-9-epi-(E)-caryophyllene0.3
1680168315-Hydroxy-α-muurolene0.3
16861683Germacra-4(15),5,10(14)-trien-1α-ol0.5
17161715Pentadecanal0.4
18411841Phytone0.1
18621856(Z)-Lanceol acetate2.6
Monoterpene hydrocarbons9.1
Oxygenated monoterpenoids30.5
Sesquiterpene hydrocarbons42.4
Oxygenated sesquiterpenoids12.2
Others3.5
Total identified97.8
RIcalc. = Retention indices determined with reference to a homologous series of n-alkanes on a ZB-5 ms column. RIdb = Retention indices from the databases. tr = trace (<0.05%). % = percent of total essential oil composition.
Table
Table 3. Essential oil composition of Emilia sonchifolia from Vietnam.
Table 3. Essential oil composition of Emilia sonchifolia from Vietnam.
RIcalcRIdbCompound%
8828802-Butylfuran0.3
933932α-Pinene2.4
949950Camphene0.2
977978β-Pinene1.2
989989Myrcene0.8
9919871-Decene0.4
10241024p-Cymene1.7
10291030Limonene1.5
10461045(E)-β-Ocimene0.8
109210911-Undecene41.9
13351335δ-Elemene0.6
13691367Cyclosativene0.3
13751375α-Copaene0.3
13871387β-Cubebene0.4
13891390trans-β-Elemene1.4
14181417(E)-β-Caryophyllene2.2
14281427γ-Elemene0.6
14521452(E)-β-Farnesene0.2
14541454α-Humulene2.8
14591461Precocene I (=6-Demethoxyageratochromene)0.8
14741475γ-Muurolene0.6
14801480Germacrene D11.0
149214921-Pentadecene0.2
14971497α-Muurolene0.5
15031503(E,E)-α-Farnesene0.3
15061508β-Bisabolene1.4
15111512γ-Cadinene0.4
15171518δ-Cadinene0.8
15271528Kessane0.5
15571557Germacrene B0.6
15591561(E)-Nerolidol1.1
156615661,5-Epoxysalvial-4(14)-ene0.9
15751576Spathulenol1.0
15801577Caryophyllene oxide1.3
16071607Humulene epoxide I1.2
16261629iso-Spathulenol0.7
16371644allo-Aromadendrene epoxide0.8
16401640τ-Cadinol0.3
16421644τ-Muurolol0.5
16531655α-Cadinol3.8
1659---Unidentified (43, 79, 91, 105, 133(100%), 163, 206)1.1
1666---Unidentified (41, 55, 81(100%), 93, 164, 206)1.2
1827---Unidentified (41, 55, 81, 123(100%), 151, 191)2.8
18391841Phytone0.8
21132109Phytol3.8
Monoterpene hydrocarbons8.7
Oxygenated monoterpenoids0.0
Sesquiterpene hydrocarbons24.7
Oxygenated sesquiterpenoids11.6
Diterpenoids3.8
Others44.4
Total identified93.2
RIcalc. = Retention indices determined with reference to a homologous series of n-alkanes on a ZB-5 ms column. RIdb = Retention indices from the databases. tr = trace (<0.05%). % = percent of total essential oil composition.
Table
Table 4. Essential oil composition of Parthenium hysterophorus from Vietnam.
Table 4. Essential oil composition of Parthenium hysterophorus from Vietnam.
RIcalcRIdbCompound%
922923Tricyclene0.1
925925α-Thujenetr
932932α-Pinene1.0
949950Camphene2.2
972972Sabinene0.6
978978β-Pinene3.0
9799781-Octen-3-ol0.3
986986Octan-3-onetr
990989Myrcene14.4
10251025p-Cymene0.1
10301030Limonene1.0
10311031β-Phellandrene0.5
10361035(Z)-β-Ocimenetr
10461046(E)-β-Ocimene3.1
105210512,3,6-Trimethylhepta-1,5-diene0.1
10581058γ-Terpinenetr
108110791-Nonen-3-ol0.2
10861086Terpinolenetr
10991098Perillene0.1
11011101Linalool0.1
111411144,8 Dimethylnona-1,3,7-triene0.4
11401139(E)-Myroxidetr
11821180Terpinen-4-ol0.1
11891187Cryptonetr
12861286Cogeijerene4.8
13321331Bicycloelemene0.1
13351335δ-Elemene0.3
13471348α-Cubebene0.1
13701367Cyclosativene0.2
13761375α-Copaene0.3
13791380Daucene0.2
13821383cis-β-Elemene0.4
13841385β-Bourbonene 0.5
13881387β-Cubebene 0.7
13901390trans-β-Elemene0.9
13921392Sativene0.1
14161414α-Cedrene0.1
14211418(E)-β-Caryophyllene12.6
14301432γ-Elemene0.7
14331432trans-α-Bergamotene0.1
14411439(Z)-β-Farnesene0.1
14421442Guaia-6,9-diene0.1
14451447iso-Germacrene D0.1
14541452(E)-β-Farnesene0.2
14561454α-Humulene1.5
14761478γ-Muurolene2.5
14841483Germacrene D23.2
14901489β-Selinene0.2
14931492trans-Muurola-4(15),5-diene0.1
14961497Bicyclogermacrene0.8
14991500α-Muurolene0.5
15051504(E,E)-α-Farnesene3.3
15081508β-Bisabolene 0.1
15141514γ-Cadinene0.1
15161515Cubebol0.2
15191520δ-Cadinene 0.6
15251524β-Sesquiphellandrene0.2
15331532Selina-4(15),7(11)-diene0.4
15601560Germacrene B0.4
15621560(E)-Nerolidol 0.6
15661571iso-Shyobunol2.8
15781576Spathulenol0.5
15841587Caryophyllene oxide2.4
16041609Carotol1.8
16111611Humulene epoxide II0.2
16281624Muurola-4,10(14)-dien-1α-ol0.6
16301629iso-Spathulenol 0.3
16341632Muurola-4,10(14)-dien-1β-ol1.4
16411644allo-Aromadendrene epoxide0.7
16441643τ-Cadinol0.1
16461645τ-Murrolol0.1
16481651α-Muurolol (=δ-Cadinol)0.6
16571655α-Cadinol0.6
18651860Platambin0.3
21092109Phytol0.5
Monoterpene hydrocarbons26.1
Oxygenated monoterpenoids0.2
Sesquiterpene hydrocarbons51.9
Oxygenated sesquiterpenoids13.2
Diterpenoids0.5
Others5.7
Total identified97.8
RIcalc. = Retention indices determined with reference to a homologous series of n-alkanes on a ZB-5 ms column. RIdb = Retention indices from the databases. tr = trace (<0.05%). % = percent of total essential oil composition.
Table
Table 5. Essential oil composition of Sphaeranthus africanus from Vietnam.
Table 5. Essential oil composition of Sphaeranthus africanus from Vietnam.
RIcalcRIdbCompound%
926925α-Thujenetr
934933α-Pinene21.0
950950Camphene0.1
953953Thuja-2,4(10)-dienetr
973972Sabinene0.1
978978β-Pinene0.2
9799821-Octen-3-ol0.2
989989Myrcene0.1
10251025p-Cymene0.2
10291030Limonene0.1
10461045(E)-β-Ocimene0.2
108110791-Nonen-3-ol0.1
10991099(2Z)-Hexenyl propanoate0.9
11061107Nonanal0.1
110811071-Octen-3-yl acetate0.7
11111109Vinyl 2-ethylhexanoate0.3
112011183-Octyl acetate0.4
119411841-Decen-3-ol36.9
120512183-Octyl propionate5.6
121612183-Nonyl acetate0.1
12291229Thymyl methyl ether0.2
12421242Cuminaldehyde0.1
125012496-Methyldodecane0.2
129012942,2,4,4,6,8,8-Heptamethylnonane2.6
12951294trans-Pinocarvyl acetate0.1
13221322Myrtenyl acetate0.1
134513497-epi-Silphiperfol-5-ene0.3
13801382Modheph-2-ene2.4
13871385α-Isocomene0.4
14091413β-Isocomene0.4
14111411Thymohydroquinone dimethyl ether0.4
14181417(E)-β-Caryophyllene5.5
14521452(E)-β-Farnesene0.1
14541454α-Humulene0.4
14581458allo-Aromadendrene0.5
14601461Precocene 1 (=6-Demethoxyageratochromene)0.5
14791480Germacrene D0.1
14961497α-Muurolene0.1
15111512γ-Cadinene0.8
15151518Isoshyobunone0.5
15161518δ-Cadinene0.3
15791577Caryophyllene oxide1.1
15951597Dimethyl-α-ionone0.2
16001600β-Oplopenone0.1
16011604Geranyl isovalerate0.1
16231624Muurola-4,10(14)-dien-1β-ol0.1
16311631Caryophylla-4(12),8(13)-dien-5α-ol0.1
16341636Caryophylla-4(12),8(13)-dien-5β-ol0.2
16401641τ-Cadinol7.5
16511652β-Himachalol1.5
16621660Selin-11-en-4β-ol0.1
16711672Jatamansone2.0
18341836Neophytadiene0.4
18391841Phytone0.3
21032102Phytol2.0
Monoterpene hydrocarbons22.0
Oxygenated monoterpenoids1.1
Sesquiterpene hydrocarbons10.9
Oxygenated sesquiterpenoids13.4
Diterpenoids2.3
Others48.9
Total identified98.5
RIcalc. = Retention indices determined with reference to a homologous series of n-alkanes on a ZB-5 ms column. RIdb = Retention indices from the databases. tr = trace (<0.05%). % = percent of total essential oil composition.
Table
Table 6. Aedes larvicidal and Diplonychus rusticus insecticidal activities of Vietnamese Asteraceae essential oils.
Table 6. Aedes larvicidal and Diplonychus rusticus insecticidal activities of Vietnamese Asteraceae essential oils.
Aedes Aegypti
Essential Oil24 h48 h
LC50LC90LC50LC90
Blumea lacera leaf64.7 (59.8–70.1)96.4 (89.4–105.3)55.1 (50.5–60.2)83.4 (76.6–92.1)
Blumea sinuata aerial parts23.4 (21.2–25.8)36.2 (32.6–41.9)17.4 (15.6–19.1)27.3 (24.8–31.3)
Emilia sonchifolia aerial parts30.1 (27.9–32.9)40.8 (37.3–46.0)26.2 (24.2–28.8)36.6 (33.1–42.1)
Parthenium hysterophorus aerial parts47.6 (44.7–50.5)63.4 (59.7–68.5)36.3 (33.2–39.6)57.7 (53.1–63.9)
Sphaeranthus africanus aerial parts50.7 (46.6–55.9)74.4 (67.4–84.6)44.2 (40.8–48.4)65.3 (59.4–73.6)
Aedes albopictus
24 h48 h
LC50LC90LC50LC90
Blumea lacera leaf116.7 (110.3–123.7)155.8 (146.4–168.5)99.4 (92.5–107.0)147.4 (136.8–161.3)
Blumea sinuata aerial parts29.1 (24.7–33.4)104.7 (85.0–239.3)12.4 (9.6–14.9)36.5 (31.0–45.5)
Emilia sonchifolia aerial parts29.6 (27.4–32.0)46.3 (42.8–50.9)23.4 (21.3–25.7)40.7 (37.2–45.5)
Parthenium hysterophorus aerial parts44.4 (41.2–47.8)66.4 (61.7–72.4)33.8 (29.9–37.6)63.6 (57.9–71.2)
Sphaeranthus africanus aerial parts36.9 (34.3–39.6)56.4 (52.5–61.3)28.8 (26.6–31.2)44.4 (40.9–49.0)
Diplonychus rusticus
24 h48 h
LC50LC90LC50LC90
Blumea lacera leaf>50>50>50>50
Blumea sinuata aerial parts>100>100>100>100
Emilia sonchifolia aerial parts48.1 (±8.9) a---34.4 (±8.9) a---
Parthenum hysterophorus aerial parts>100>100>100>100
Sphaeranthus africanus aerial parts>50>50>50>50
a Due to insufficient data for probit analysis, the LC50 was determined using the Reed–Muench method [57].
Table
Table 7. Details for collecting essential oils of Blumea lacera, Blumea sinuata, Emilia sonchifolia, Parthenium hysterophorus, and Sphaeranthus africanus.
Table 7. Details for collecting essential oils of Blumea lacera, Blumea sinuata, Emilia sonchifolia, Parthenium hysterophorus, and Sphaeranthus africanus.
Plant
Species		Collection Location (GPS)PartMass Plant Material (kg)Extraction Yield (%w/w)Collection Time
B. laceraNghia Dan District, Nghe An Province (19°23′05″ N, 105°25′51″ E).Aerial parts3.01.2August 2021
Leaves0.31.56August 2021
Flowers0.31.10August 2021
Stems0.30.35August 2021
B. sinuataNghia Dan District, Nghe An Province (19°20′06″ N, 105°25′59″ E).Aerial parts4.00.16August 2021
E. sonchifoliaDiên Lãm Commune, Pù Huống Natural Reserve, Nghệ An Province (19°26′44″ N, 104°58′40″ E).Aerial parts3.00.51August 2021
P. hysterophorusBình Chuẩn Commune, Pù Huống Natural Reserve, Nghệ An Province (19°16′53″ N, 104°55′16″ E).Aerial parts5.00.05August 2021
S. africanusDiên Lãm Commune, Pù Huống Natural Reserve, Nghệ An Province (19°26′44″ N, 104°58′40″ E).Aerial parts4.00.25August 2021
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Hoi, T.M.; Satyal, P.; Huong, L.T.; Hau, D.V.; Binh, T.D.; Duyen, D.T.H.; Dai, D.N.; Huy, N.G.; Chinh, H.V.; Hoa, V.V.; et al. Essential Oils from Vietnamese Asteraceae for Environmentally Friendly Control of Aedes Mosquitoes. Molecules 2022, 27, 7961. https://doi.org/10.3390/molecules27227961

AMA Style

Hoi TM, Satyal P, Huong LT, Hau DV, Binh TD, Duyen DTH, Dai DN, Huy NG, Chinh HV, Hoa VV, et al. Essential Oils from Vietnamese Asteraceae for Environmentally Friendly Control of Aedes Mosquitoes. Molecules. 2022; 27(22):7961. https://doi.org/10.3390/molecules27227961

Chicago/Turabian Style

Hoi, Tran Minh, Prabodh Satyal, Le Thi Huong, Dang Viet Hau, Tran Duc Binh, Dang Thi Hong Duyen, Do Ngoc Dai, Ngo Gia Huy, Hoang Van Chinh, Vo Van Hoa, and et al. 2022. "Essential Oils from Vietnamese Asteraceae for Environmentally Friendly Control of Aedes Mosquitoes" Molecules 27, no. 22: 7961. https://doi.org/10.3390/molecules27227961

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