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Article

Premna Species in Vietnam: Essential Oil Compositions and Mosquito Larvicidal Activities

1
Center for Advanced Chemistry, Institute of Research and Development, Duy Tan University, 03 Quang Trung, Da Nang 550000, Vietnam
2
Department of Pharmacy, Duy Tan University, 03 Quang Trung, Da Nang 550000, Vietnam
3
School of Natural Science Education, Vinh University, 182 Le Duan, Vinh City 43000, Nghe An Province, Vietnam
4
Graduate University of Science and Technology, Vietnam Academy of Science and Technology, 18-Hoang Quoc Viet, Cau Giay, Hanoi 10000, Vietnam
5
Faculty of Agriculture, Forestry and Fishery, Nghe An College of Economics, 51-Ly Tu Trong, Vinh City 43000, Nghe An Province, Vietnam
6
Aromatic Plant Research Center, 230 N 1200 E, Suite 102, Lehi, UT 84043, USA
7
Faculty of Hydrometerology, Ho Chi Minh City University of Natural Resources and Environment, Ho Chi Minh City 70000, Vietnam
8
Department of Chemistry, University of Alabama in Huntsville, Huntsville, AL 35899, USA
*
Authors to whom correspondence should be addressed.
Plants 2020, 9(9), 1130; https://doi.org/10.3390/plants9091130
Submission received: 13 August 2020 / Revised: 22 August 2020 / Accepted: 31 August 2020 / Published: 31 August 2020

Abstract

:
Essential oils have emerged as viable alternatives to synthetic insecticides for control of mosquito-borne pathogens. The leaf essential oils of eight species of Premna (Lamiaceae) growing in central Vietnam have been obtained by hydrodistillation and analyzed by gas chromatography–mass spectrometry. Sesquiterpene hydrocarbons dominated most of the Premna essential oils, with the notable exception of Premna mekongensis from Ngoc Linh Nature Reserve, which had α-pinene as the major component. Larvicidal activities against Aedes aegypti have been determined and all of the Premna essential oils showed larvicidal activity with 24-h LC50 < 65 μg/mL. The leaf essential oils of Premna cambodiana from Chu Mom Ray National Park and Premna mekongensis from Ngoc Linh Nature Reserve showed the best larvicidal activities with 24-h LC50 of 16.8 and 18.0 μg/mL, respectively. The essential oil compositions and larvicidal activities of P. cambodiana, Premna flavescens, Premna maclurei, P. mekongensis, and Premna puberula are reported for the first time. Although the larvicidal activities of Premna leaf essential oils are promising, the essential oil yields are relatively low (0.10–0.25%).

Graphical Abstract

1. Introduction

Mosquito-borne infectious diseases have been a persistent problem in Vietnam. Dengue fever and dengue hemorrhagic fever are especially problematic and chikungunya fever is an emerging threat in the country [1,2]. Aedes aegypti (L.) (Diptera: Culicidae), the yellow fever mosquito, and Aedes albopictus (Skuse) (Diptera: Culicidae), the Asian tiger mosquito, are important vectors of several viral pathogens, including dengue fever virus [3], yellow fever virus [4], chikungunya fever virus [5], and possibly Zika virus [6]. Culex quinquefasciatus Say (Diptera: Culicidae), the southern house mosquito, is a vector of lymphatic filariasis [7] as well as several arboviruses such as West Nile virus and St. Louis encephalitis virus [8], and possibly Zika virus [9].
Insecticide resistance has been emerging in many insect disease vectors, including mosquitoes [10,11,12,13,14]. Furthermore, the environmental impacts of synthetic insecticides have been felt for many years [15,16]. It has been reported that insecticide use has detrimental effects on non-target organisms, for example imidacloprid on honey bee (Apis mellifera) [17], damselfly (Ischnura senegalensis) [18], fathead minnow (Pimephales promelas), or the amphipod (Hyalella azteca) [19]. Thus, there is a need for new and complementary methods for controlling insect vectors, and essential oils have shown promise as renewable and environmentally-safe alternatives to the use of synthetic insecticides [20,21,22,23,24,25].
The Lamiaceae has been an important family in terms of biologically active essential oils. Essential oils from members of this family have demonstrated potential as natural insect pest control agents [24,26,27,28,29,30,31,32]. The genus Premna L. was formerly included in the family Verbenaceae, but has been reassigned to the Lamiaceae [33]. The genus is distributed in tropical regions of the Old World, from Africa, eastward through China, Southeast Asia and Malesia, to Australia and islands in the Pacific [34]. The number of species has been estimated to be as few as 50, or as many as 200 [34]. The ethnopharmacology, pharmacognosy, and phytochemistry of the genus have been reviewed [33,35,36,37]. As part of our ongoing efforts in identifying readily-available essential oils for mosquito control, we have examined the leaf essential oils of eight species of Premna (Table 1) found growing wild in central Vietnam for larvicidal activity against Aedes aegyptae, Aedes albopictus, and Culex quinquefasciatus. Several of these Premna species have been used traditionally in Vietnam (Table 1).
A perusal of the literature has revealed no previous phytochemical reports on P. cambodiana, P. flavescens, P. maclurei, P. mekongensis, or P. puberula.

2. Results and Discussion

2.1. Plant Collection and Essential Oils

The leaves of eight species of Premna were collected from several sites in Vietnam. The collection sites, voucher numbers, and essential oil yields are summarized in Table 2.

2.2. Essential Oil Compositions

The Premna leaf essential oils were analyzed by gas chromatography–mass spectrometry and the chemical compositions are summarized in Table 3.

2.2.1. Premna cambodiana

A total of 72 compounds were tentatively identified in the leaf essential oil of P. cambodiana, accounting for 97.4% of the total composition (Table 3). Sesquiterpene hydrocarbons dominated P. cambodiana leaf essential oil with α-copaene (23.3%), α-gurjunene (11.3%), (E)-caryophyllene (12.8%), and δ-cadinene (5.5%) as the major sesquiterpene components. There have been no previous phytochemical investigations on P. cambodiana reported in the literature; this is the first report on its essential oil composition.

2.2.2. Premna chevalieri

Eighty-five components (99.8% of the composition) were tentatively identified in P. chevalieri essential oil. The major components in the leaf essential oil of P. chevalieri were the sesquiterpenes (E)-caryophyllene (31.5%) and α-humulene (7.5%) and the monoterpenes α-pinene (12.2%) and β-pinene (16.8%) (Table 3). There have been no previous phytochemical investigations on P. chevalieri reported in the literature; this is the first report on the leaf essential oil composition of this plant.

2.2.3. Premna corymbosa (syn. P. integrifolia, P. serratifolia)

Leaves of P. corymbosa were collected from two different sites (i.e., Nậm Giải Commune, Quế Phong district, Pu Hoat Nature Reserve, Nghe An province, and Son Tra Peninsula, Da Nang province). Although the two essential oil compositions are qualitatively similar, there are notable quantitative differences (Table 3). The sample from Nghe An province was rich in oxygenated sesquiterpenoids, e.g., spathulenol (17.3%) and caryophyllene oxide (16.8%), while the sample from Da Nang was dominated by sesquiterpene hydrocarbons, including allo-aromadendrene (39.7%), (E)-caryophyllene (13.3%), and α-copaene (8.1%).
The major components of the leaf essential oil of P. corymbosa (reported as P. integrifolia) from Bangladesh were phytol (27.3%), α-humulene (14.2%), spathulenol (12.1%), 1-octen-3-ol (8.2%), eugenol (6.7%), and phenylethyl alcohol (5.8%) [46]. Neither 1-octen-3-ol, phenylethyl alcohol, nor eugenol were detected in the samples from Vietnam. Likewise, neither α-copaene nor allo-aromadendrene were reported from the Bangladeshi sample. In contrast, P. corymbosa leaf essential oil (reported as P. serratifolia) displayed a very simple composition of eugenol (47.9%), eugenyl acetate (9.1%), massoialactone (32.9%), and a compound identified as cis-2-oxabicyclo[4.4.0]decane (12.4%) (likely incorrect based on relative retention times) [47]. Thus, there is wide variation in the essential oil compositions of this plant, which suggests different chemotypes are possible or these three plants represent different species.

2.2.4. Premna flavescens

Leaves of P. flavescens were collected from two different sites (i.e., Nậm Giải Commune, Quế Phong district, Pu Hoat Nature Reserve, Nghe An province, and Đồng Văn Commune, Quế Phong District, Pu Hoat Nature Reserve, Nghe An province). The leaf essential oils from the two sites showed notable differences in compositions (Table 3). (E)-Caryophyllene was abundant in both samples (41.0% and 11.8% in the Nậm Giải and Đồng Văn samples, respectively), as was trans-β-elemene (9.9% and 8.7%, respectively). The sample from Đồng Văn was rich in α-gurjunene (19.6%), but only a minor component (0.1%) in the sample from Nậm Giải. Likewise, α-guaiene and α-bulnesene were relatively abundant in the Đồng Văn sample (6.1% and 5.4%), but minor in the sample from Nậm Giải (0.5% and 0.2%, respectively). Interestingly, bicyclogermacrene (7.8%) and an unidentified component (RI 1759, 14.7%) in the sample from Nậm Giải, were not detected in the sample from Đồng Văn. Conversely, α-selinene, 8.7% in the sample from Đồng Văn, was not detected in the sample from Nậm Giải. As far as we are aware, there have been no previous reports on the essential oil chemistry of P. flavescens.

2.2.5. Premna maclurei

The leaf essential oil composition of P. maclurei is shown in Table 3. The essential oil was dominated by sesquiterpene hydrocarbons (62.5%) and oxygenated sesquiterpenoids (30.1%) with (E)-caryophyllene (30.7%), α-humulene (5.3%), δ-cadinene (8.4%), spathulenol (6.8%), and caryophyllene oxide (12.3%) as the major components. To our knowledge, there have been no previous reports on the essential oil composition of P. maclurei.

2.2.6. Premna mekongensis

Essential oils were obtained from leaves of P. mekongensis from two different locations, Ngoc Linh Nature Reserve in Quang Nam Province, and Chu Mom Ray National Park. The leaf essential oil compositions are listed in Table 3. The two samples showed very different compositions. The Ngoc Linh sample was dominated by α-pinene (66.9%) and (E)-caryophyllene (14.7%). The leaf essential oil from Chu Mom Ray, on the other hand, had relatively low concentrations of α-pinene (1.5%) and (E)-caryophyllene (3.9%). In addition, the Chu Mom Ray essential oil was much more complex with 95 identified components compared to only 37 in the Ngoc Linh sample. The high concentration of α-pinene in P. mekongensis leaf essential oil from Ngoc Linh was unexpected and uncharacteristic of Premna leaf essential oils, which are generally low in monoterpene hydrocarbon concentrations (see below). To our knowledge, there have been no previous studies on the essential oil composition of P. mekongensis.

2.2.7. Premna puberula

The chemical composition of the leaf essential oil of P. puberula is shown in Table 3. The major chemical classes present in the essential oil were sesquiterpene hydrocarbons (22.4%), with α-copaene (5.3%) and allo-aromadendrene (4.1%) as major components, and oxygenated sesquiterpenoids (58.2%), dominated by (E)-caryophyllene oxide (21.2%) along with spathulenol (7.7%) and humulene epoxide II (4.7%). There have been no previous reports on the essential oil of P. puberula.

2.2.8. Premna tomentosa

The leaf essential oil composition of P. tomentosa is shown in Table 3. A total of 82 compounds were tentatively identified in the essential oil accounting for 99.8% of the composition, which was dominated by sesquiterpene hydrocarbons, especially (E)-caryophyllene (22.0%) and germacrene D (11.4%). The only previous examination of the essential oil of P. tomentosa is a relatively old work by Narayan and Muthana in 1953 [48]. These workers identified limonene (57.8%), (E)-caryophyllene (17.2%), an unidentified cadinane sesquiterpene (7.8%), an unidentified sesquiterpene alcohol (5.6%), and an unidentified diterpene hydrocarbon (5.5%) in the leaf essential oil from southern India.

2.2.9. Species Composition Comparison

Analogous to most of the Premna essential oil compositions observed in this study, leaf essential oils of other Premna species have shown compositions dominated by sesquiterpene hydrocarbons, e.g., Premna coriacea (55.2%) [49], Premna latifolia (76.4%) [50], Premna quadrifolia (65.5%) [51], and Premna odorata (62.3%) [52]. On the other hand, other Premna species are particularly rich in low molecular weight alcohols such as 1-octen-3-ol in Premna barbata (37.3%) [53], P. latifolia (35.7%) [54], and Premna angolensis (28.0%) [51]. In contrast, the essential oil of Premna microphylla was dominated by the sesquiterpenoid derivative blumenol C (49.7%) [55].
Compounds common to all eight of the Premna leaf essential oils in this study were α-pinene, β-pinene, p-cymene, limonene, linalool, trans-β-elemene, (E)-caryophyllene, α-humulene, β-selinene, and caryophyllene oxide. These are all relatively common essential oil constituents, and therefore cannot be considered as key compounds defining the genus. Furthermore, leaf essential oils of other Premna species were missing several of these components. The leaf essential oil of P. coriacea from Karnataka, India, was devoid of α-pinene, β-pinene, linalool, and β-selinene [49]. Likewise, the leaf oil from P. microphylla from Zhejiang Province, China, contained no α-pinene, β-pinene, linalool, (E)-caryophyllene, or α-humulene [55]. Premna integrifolia leaf essential oil from Bangladesh did not show p-cymene, limonene, linalool, β-elemene, or β-selinene [46]; P. odorata leaf oil from Giza, Egypt, showed no α-pinene, β-pinene, p-cymene, limonene, β-elemene, or β-selinene [52]; P. angolensis leaf oil from Comé, Benin, contained no β-pinene or caryophyllene oxide, and P. quadrifolia from Comé, Benin, contained no α-pinene, limonene, or linalool [51].

2.3. Mosquito Larvicidal Activity

The Premna leaf essential oils have been screened for mosquito larvicidal activity against Aedes aegypti and, if sufficient mosquito larvae were available, also against Ae. albopictus and Culex quinquefasciatus. The 24-h and 48-h larvicidal activities are shown in Table 4 and Table 5, respectively. Considering larvicidal activities against Ae. aegypti, the most active Premna leaf essential oils were P. cambodiana (24-h LC50 = 16.8 μg/mL) and P. mekongensis from Nghe An (24-h LC50 = 16.8 μg/mL).
The pronounced larvicidal activity of P. mekongensis (Ngoc Linh) against Ae. aegypti can be attributed to the high concentration of α-pinene. This monoterpene has shown larvicidal activity against Ae. aegypti with LC50 values ranging from 15.4 μg/mL to 79.1 μg/mL [56]. Interestingly, the larvicidal activity of P. mekongensis (Ngoc Linh) against Cx. quinquefasciatus was less (24-h LC50 = 42.7 μg/mL), consistent with the reduced activity of α-pinene against this mosquito larva (LC50 = 95 μg/mL) [57].
The major components in P. cambodiana leaf essential oil were the sesquiterpene hydrocarbons α-copaene (23.3%), (E)-caryophyllene (12.8%), and α-gurjunene (11.3%). (E)-Caryophyllene has shown larvicidal activity against Ae. aegypti with reported LC50 values of 38.6 μg/mL [58] and 88.3 μg/mL [59]. As far as we are aware, there have been no reports on the larvicidal activities of either α-copaene or α-gurjunene. However, essential oils rich in α-copaene have shown notable larvicidal activity. For example, the essential oil from the inflorescences of Piper marginatum Jacq. (Piperaceae) (9.4% α-copaene and 13.1% (E)-caryophyllene) showed larvicidal activity against Ae. aegypti with LC50 of 19.9 μg/mL [60]; the ripe peel essential oil of Hymenaea courbaril L. (Fabaceae) (11.1% α-copaene) had an LC50 of 14.8 μg/mL on Ae. aegypti [61]. Note, however, that the leaf essential oil of P. corymbosa from Da Nang was also rich in α-copaene (8.1%) and (E)-caryophyllene (13.3%), but the larvicidal activity against Ae. aegypti was weaker (LC50 = 61.8 μg/mL). Similarly, the leaf essential oil of P. flavescens from Đồng Văn had α-gurjunene (19.6%) and (E)-caryophyllene (11.8%) as major components, but also showed weak larvicidal activity against Ae. aegypti (LC50 = 64.7 μg/mL). The mere presence of the sesquiterpene hydrocarbons α-copaene, α-gurjunene, and (E)-caryophyllene is not sufficient to impart good larvicidal activity; there are likely synergistic effects of these compounds with minor components that account for the activities.

3. Materials and Methods

3.1. Plant Material

Leaves of Premna species were collected from several different locations in central Vietnam (Table 1). The plants were identified by Dr. Do Ngoc Dai, and voucher specimens (see Table 2) have been deposited in the plant specimen room, Faculty Agriculture, Forestry, and Fishery, Nghe An, College of Economics. The fresh leaves (2.0 kg each), immediately after collection, were shredded and hydrodistilled for 4 h using a Clevenger type apparatus (Witeg Labortechnik, Wertheim, Germany). Essential oil yields are summarized in Table 2. Essential oils were dried over anhydrous Na2SO4 and stored in sealed glass vials at 4 °C until analyzed.

3.2. Gas Chromatography–Mass Spectrometry

The Premna leaf essential oils were analyzed by gas chromatography–mass spectrometry (GC-MS) as described previously [56]: Shimadzu GCMS-QP2010 Ultra, electron impact (EI) mode (electron energy = 70 eV), scan range = 40–400 atomic mass units, scan rate = 3.0 scans/s; ZB-5ms column (30 m length × 0.25 mm inner diameter × 0.25 μm film thickness); He carrier gas, head pressure of 552 kPa, flow rate of 1.37 mL/min; injector temperature was 250 °C, ion source temperature was 200 °C; GC oven temperature program: 50 °C initial temperature, increased 2 °C/min to 260 °C; 5% solution of essential oil in CH2Cl2, 0.1 μL injection, splitting ratio 30:1. Putative identification of the essential oil components was based on their calculated retention indices (RI), based on a homologous series of n-alkanes (C8-C40), and their mass spectral fragmentation patterns compared with those reported in the databases [42,43,44,45], with RI values within ±10 units and with matching factors >80%. The concentrations of the essential oil components were calculated from raw peak areas, normalized to 100%, without standardization.

3.3. Mosquito Larvicidal Assay

Eggs of Aedes aegypti were purchased from Institute of Biotechnology, Vietnam Academy of Science and Technology and maintained at the Laboratory of Department of Pharmacy of Duy Tan University, Da Nang, Vietnam. Adults of Culex quinquefasciatus and Aedes albopictus collected in Hoa Khanh Nam ward, Lien Chieu district, Da Nang city (16°03′14.9″ N, 108°09′31.2″ E) and were identified by National institute of Malariology, Parasitology, and Entomology, Ho Chi Minh City. Adult mosquitoes were maintained in entomological cages (40 × 40 × 40 cm) and fed a 10% sucrose solution and were allowed to blood feed on 1-week-old chicks and mice, respectively. Egg hatchings were induced with tap water. Larvae were reared in plastic trays (24 × 35 × 5 cm). The larvae were fed on Koi fish food. All developmental stages were maintained at 25 ± 2 °C, 65–75% relative humidity and a 12:12 h light:dark cycle at the Laboratory of the Faculty of Environmental and Chemical Engineering of Duy Tan University, Da Nang, Vietnam.
Larvicidal activities of the Premna essential oils were determined following the protocol previously reported [62]: 250-mL beakers, 150 mL of water, and 20 larvae (fourth instar), aliquots of the Premna essential oils dissolved in EtOH (1% stock solution) were added to give final concentrations of 100, 50, 25, 12.5, and 6 μg/mL; EtOH only (negative control) and permethrin (positive control), mortality recorded after 24 h and 48 h of exposure, experiments were carried out at 25 ± 2 °C, each test was conducted with four replicates. The data obtained were subjected to log-probit analysis [63] to obtain LC50 values, LC90 values and 95% confidence limits using Minitab® 19 (Minitab, LLC, State College, PA, USA).
All experimental procedures that involved animals (mice, mosquitoes, chicks, and non-target organisms) were conducted in accordance with the “Guideline for the Care and Use of Laboratory Animals” which was approved by the Medical-Biological Research Ethics Committee of Duy Tan University (DTU/REC2020/NHH01), Vietnam.

4. Conclusions

The leaf essential oils of eight species of Premna have been obtained in yields ranging from 0.10% to 0.25%. The mosquito larvicidal activities of these species have been determined for the first time and this is the first report of the essential oil compositions of P. cambodiana, P. flavescens, P. maclurei, P. mekongensis, and P. puberula. The essential oil compositions were largely dominated by sesquiterpene hydrocarbons and oxygenated sesquiterpenoids. The larvicidal activities against Aedes aegypti (LC50 < 65 μg/mL) are promising and can probably be attributed to these components. The essential oil yields, however, are low and likely preclude their consideration as viable alternatives to other essential oils for control of mosquito vectors. However, potential utility of these essential oils will necessitate exploration of cultivation, including plant breeding aimed at increasing oil yield and/or larvicidal activity, potential detrimental effects of the essential oils on the environment, as well as field experiments on application of the essential oils, effects of environmental conditions and potential formulations on essential oil evaporation rates.

Author Contributions

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

Funding

This research was funded by NAFOSTED (Vietnam), grant number 106.03-2019.25.

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/).

Conflicts of Interest

The authors declare no conflict of interest.

References

  1. Kim Lien, P.T.; Briant, L.; Tang, T.B.; Trang, B.M.; Gavotte, L.; Cornillot, E.; Duoc, V.T.; Duong, T.N.; Frutos, R.; Nga, P.T. Surveillance of dengue and chikungunya infection in Dong Thap, Vietnam: A 13-month study. Asian Pac. J. Trop. Med. 2016, 9, 39–43. [Google Scholar] [CrossRef] [PubMed]
  2. Pham Thi, K.L.; Briant, L.; Gavotte, L.; Labbe, P.; Perriat-Sanguinet, M.; Cornillot, E.; Vu, T.D.; Nguyen, T.Y.; Tran, V.P.; Nguyen, V.S.; et al. Incidence of dengue and chikungunya viruses in mosquitoes and human patients in border provinces of Vietnam. Parasites Vectors 2017, 10, 556. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  3. Lambrechts, L.; Scott, T.W.; Gubler, D.J. Consequences of the expanding global distribution of Aedes albopictus for dengue virus transmission. PLoS Negl. Trop. Dis. 2010, 4, e646. [Google Scholar] [CrossRef] [PubMed]
  4. Lourenço de Oliveira, R.; Vazeille, M.; de Filippis, A.M.B.; Failloux, A.B. Large genetic differentiation and low variation in vector competence for dengue and yellow fever viruses of Aedes albopictus from Brazil, the United States, and the Cayman Islands. Am. J. Trop. Med. Hyg. 2003, 69, 105–114. [Google Scholar] [CrossRef] [Green Version]
  5. Vazeille, M.; Moutailler, S.; Coudrier, D.; Rousseaux, C.; Khun, H.; Huerre, M.; Thiria, J.; Dehecq, J.S.; Fontenille, D.; Schuffenecker, I.; et al. Two Chikungunya isolates from the outbreak of La Reunion (Indian Ocean) exhibit different patterns of infection in the mosquito, Aedes albopictus. PLoS ONE 2007, 2, e1168. [Google Scholar] [CrossRef] [PubMed]
  6. Wong, P.-S.J.; Li, M.I.; Chong, C.-S.; Ng, L.-C.; Tan, C.-H. Aedes (Stegomyia) albopictus (Skuse): A potential vector of Zika virus in Singapore. PLoS Negl. Trop. Dis. 2013, 7, e2348. [Google Scholar] [CrossRef]
  7. Albuquerque, C.M.R.; Cavalcanti, V.M.S.; Melo, M.A.V.; Verçosa, P.; Regis, L.N.; Hurd, H. Bloodmeal microfilariae density and the uptake and establishment of Wuchereria bancrofti infections in Culex quinquefasciatus and Aedes aegypti. Mem. Inst. Oswaldo Cruz 1999, 94, 591–596. [Google Scholar] [CrossRef] [Green Version]
  8. Turell, M.J. Members of the Culex pipiens complex as vectors of viruses. J. Am. Mosq. Control Assoc. 2012, 28, 123–127. [Google Scholar] [CrossRef]
  9. Van den Hurk, A.F.; Hall-Mendelin, S.; Jansen, C.C.; Higgs, S. Zika virus and Culex quinquefasciatus mosquitoes: A tenuous link. Lancet Infect. Dis. 2017, 17, 1014–1016. [Google Scholar] [CrossRef] [Green Version]
  10. Hemingway, J.; Ranson, H. Insecticide resistance in insect vectors of human disease. Annu. Rev. Entomol. 2000, 45, 371–391. [Google Scholar] [CrossRef]
  11. Vontas, J.; Kioulos, E.; Pavlidi, N.; Morou, E.; della Torre, A.; Ranson, H. Insecticide resistance in the major dengue vectors Aedes albopictus and Aedes aegypti. Pestic. Biochem. Physiol. 2012, 104, 126–131. [Google Scholar] [CrossRef]
  12. Liu, N. Insecticide resistance in mosquitoes: Impact, mechanisms, and research directions. Annu. Rev. Entomol. 2015, 60, 537–559. [Google Scholar] [CrossRef] [PubMed]
  13. Smith, L.B.; Kasai, S.; Scott, J.G. Pyrethroid resistance in Aedes aegypti and Aedes albopictus: Important mosquito vectors of human diseases. Pestic. Biochem. Physiol. 2016, 133, 1–12. [Google Scholar] [CrossRef] [PubMed]
  14. Naqqash, M.N.; Gökçe, A.; Bakhsh, A.; Salim, M. Insecticide resistance and its molecular basis in urban insect pests. Parasitol. Res. 2016, 115, 1363–1373. [Google Scholar] [CrossRef] [PubMed]
  15. Kamrin, M.A. Pesticide Profiles: Toxicity, Environmental Impact, and Fate; CRC Press: Boca Raton, FL, USA, 1997; ISBN 0-56670-190-2. [Google Scholar]
  16. Goulson, D. An overview of the environmental risks posed by neonicotinoid insecticides. J. Appl. Ecol. 2013, 50, 977–987. [Google Scholar] [CrossRef]
  17. Suchail, S.; Guez, D.; Belzunces, L.P. Characteristics of imidacloprid toxicity in two Apis mellifera subspecies. Environ. Toxicol. Chem. 2000, 19, 1901. [Google Scholar] [CrossRef] [Green Version]
  18. Sugita, N.; Agemori, H.; Goka, K. Acute toxicity of neonicotinoids and some insecticides to first instar nymphs of a non-target damselfly, Ischnura senegalensis (Odonata: Coenagrionidae), in Japanese paddy fields. Appl. Entomol. Zool. 2018, 53, 519–524. [Google Scholar] [CrossRef]
  19. Lanteigne, M.; Whiting, S.A.; Lydy, M.J. Mixture toxicity of imidacloprid and cyfluthrin to two non-target species, the fathead minnow Pimephales promelas and the amphipod Hyalella azteca. Arch. Environ. Contam. Toxicol. 2015, 68, 354–361. [Google Scholar] [CrossRef]
  20. Silva, W.J.; Dória, G.A.A.; Maia, R.T.; Nunes, R.S.; Carvalho, G.A.; Blank, A.F.; Alves, P.B.; Marçal, R.M.; Cavalcanti, S.C.H. Effects of essential oils on Aedes aegypti larvae: Alternatives to environmentally safe insecticides. Bioresour. Technol. 2008, 99, 3251–3255. [Google Scholar] [CrossRef]
  21. Benelli, G. Research in mosquito control: Current challenges for a brighter future. Parasitol. Res. 2015, 114, 2801–2805. [Google Scholar] [CrossRef]
  22. Masetti, A. The potential use of essential oils against mosquito larvae: A short review. Bull. Insectology 2016, 69, 307–310. [Google Scholar]
  23. Pavela, R.; Benelli, G. Essential oils as ecofriendly biopesticides? Challenges and constraints. Trends Plant Sci. 2016, 21, 1000–1007. [Google Scholar] [CrossRef] [PubMed]
  24. Senthil-Nathan, S. A review of resistance mechanisms of synthetic insecticides and botanicals, phytochemicals, and essential oils as alternative larvicidal agents against mosquitoes. Front. Physiol. 2020, 10, 1591. [Google Scholar] [CrossRef] [PubMed]
  25. Ntalli, N.; Koliopoulos, G.; Giatropoulos, A.; Menkissoglu-Spiroudi, U. Plant secondary metabolites against arthropods of medical importance. Phytochem. Rev. 2019, 18, 1255–1275. [Google Scholar] [CrossRef]
  26. Ebadollahi, A. Iranian plant essential oils as sources of natural insecticide agents. Int. J. Biol. Chem. 2011, 5, 266–290. [Google Scholar] [CrossRef]
  27. Yildirim, E.; Kordali, S.; Yazici, G. Insecticidal effects of essential oils of eleven plant species from Lamiaceae on Sitophilus granarius (L.) (Coleoptera: Curculionidae). Rom. Biotechnol. Lett. 2011, 16, 6702–6709. [Google Scholar]
  28. Dias, C.N.; Moraes, D.F.C. Essential oils and their compounds as Aedes aegypti L. (Diptera: Culicidae) larvicide: Review. Parasitol. Res. 2014, 113, 565–592. [Google Scholar] [CrossRef]
  29. Pavela, R. Essential oils for the development of eco-friendly mosquito larvicides: A review. Ind. Crop. Prod. 2015, 76, 174–187. [Google Scholar] [CrossRef]
  30. Andrade-Ochoa, S.; Sánchez-Torres, L.E.; Nevárez-Moorillón, G.V.; Camacho, A.D.; Nogueda-Torres, B. Aceites esenciales y sus constituyentes como una alternativa en el control de mosquitos vectores de enfermedades. Biomedica 2017, 37, 224–243. [Google Scholar]
  31. Giatropoulos, A.; Kimbaris, A.; Michaelakis, A.; Papachristos, D.P.; Polissiou, M.G.; Emmanouel, N. Chemical composition and assessment of larvicidal and repellent capacity of 14 Lamiaceae essential oils against Aedes albopictus. Parasitol. Res. 2018, 117, 1953–1964. [Google Scholar] [CrossRef]
  32. Ebadollahi, A.; Ziaee, M.; Palla, F. Essential oils extracted from different species of the Lamiaceae plant family as prospective bioagents against several detrimental pests. Molecules 2020, 25, 1556. [Google Scholar] [CrossRef] [Green Version]
  33. Dianita, R.; Jantan, I. Ethnomedicinal uses, phytochemistry and pharmacological aspects of the genus Premna: A review. Pharm. Biol. 2017, 55, 1715–1739. [Google Scholar] [CrossRef] [Green Version]
  34. De Kok, R. The genus Premna L. (Lamiaceae) in the Flora Malesiana area. Kew Bull. 2013, 68, 55–84. [Google Scholar] [CrossRef]
  35. Thirumalai, D.; Paridhavi, M.; Gowtham, M. A phytochemical review on Premna species. Int. J. Res. Phytochem. Pharmacol. 2011, 1, 196–200. [Google Scholar]
  36. Kabra, A.; Kabra, R.; Baghel, U.S. Premna species: A review. J. Biol. Chem. Chronicles 2015, 1, 55–59. [Google Scholar]
  37. Rekha, K.; Richa, P.K.; Babu, S.; Rao, M. A phytochemistry of the genus Premna: A review. Int. J. Pharm. Chem. Sci. 2015, 4, 317–325. [Google Scholar]
  38. WCSP World Checklist of Selected Plant Families. Available online: https://wcsp.science.kew.org/home.do (accessed on 26 May 2020).
  39. Ho, P.-H. An Illustrated Flora of Vietnam; Youth Publishing House: Ho Chi Minh City, Vietnam, 2000; Volume 3. [Google Scholar]
  40. Phuông, V.X. Flora of Vietnam, Volume 6—Verbenaceae; Science & Technics Publishing House: Hanoi, Vietnam, 2007. [Google Scholar]
  41. Wu, Z.Y.; Raven, P.H. Flora of China. Vol. 17 (Verbenaceae through Solanaceae); Science Press: Beijing, China; Missouri Botanical Garden Press: St. Louis, MO, USA, 1994; pp. 1–49. Available online: http://www.efloras.org/flora_page.aspx?flora_id=2 (accessed on 26 May 2020).
  42. Adams, R.P. Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry, 4th ed.; Allured Publishing: Carol Stream, IL, USA, 2007. [Google Scholar]
  43. Mondello, L. FFNSC 3; Shimadzu Scientific Instruments: Columbia, MD, USA, 2016. [Google Scholar]
  44. NIST17; National Institute of Standards and Technology: Gaithersburg, MD, USA, 2017.
  45. Satyal, P. Development of GC-MS Database of Essential Oil Components by the Analysis of Natural Essential Oils and Synthetic Compounds and Discovery of Biologically Active Novel Chemotypes in Essential Oils. Ph.D. Thesis, University of Alabama in Huntsville, Huntsville, AL, USA, 2015. [Google Scholar]
  46. Rahman, A.; Sultana Shanta, Z.; Rashid, M.A.; Parvin, T.; Afrin, S.; Khodeza Khatun, M.; Sattar, M.A. In vitro antibacterial properties of essential oil and organic extracts of Premna integrifolia Linn. Arab. J. Chem. 2016, 9, S475–S479. [Google Scholar] [CrossRef] [Green Version]
  47. Nurliana, L.; Musta, R.; Rudi, L. Microencapsulation of essential oil from rogo plant (Premna serratifolia L.) as antibactery Escherichia coli. Int. J. Eng. Sci. Res. Technol. 2018, 7, 314–323. [Google Scholar]
  48. Narayan, V.L.; Muthana, M.S. Essential oil from Premna tomentosa. J. Indian Inst. Sci. 1953, 35, 55–67. [Google Scholar]
  49. Sadashiva, C.T.; Sharanappa, P.; Naidoo, Y.; Balachandran, I. Chemical composition of essential oil from the leaves of Premna coriacea Clarke. Afr. J. Biotechnol. 2013, 12, 2914–2916. [Google Scholar]
  50. Renjana, P.K.; Thoppil, J.E. Larvicidal activities of the leaf extracts and essential oil of Premna latifolia Roxb. (Verbenaceae) against Aedes albopictus Skuse (Diptera: Culicidae). J. Appl. Pharm. Sci. 2013, 3, 101–105. [Google Scholar]
  51. Adjalian, E.; Sessou, P.; Odjo, T.; Figueredo, G.; Kossou, D.; Avlessi, F.; Menut, C.; Sohounhloué, D. Chemical composition and insecticidal and repellent effect of essential oils of two Premna species against Sitotroga cerealella. J. Insects 2015, 2015, 319045. [Google Scholar] [CrossRef] [PubMed]
  52. Elmaidomy, A.; Hassan, H.; Amin, E.; Mohamed, W.; Hetta, M. Premna odorata volatile oil as a new Mycobacterium tuberculosis growth inhibitor for the control of tuberculosis disease. Eur. J. Med. Plants 2017, 21, 1–11. [Google Scholar] [CrossRef]
  53. Chanotiya, C.S.; Yadav, A.K.; Singh, A.K. Leaf oil composition of Premna barbata Wall. ex. Sch. from Kumaon region of Uttarakhand. J. Essent. Oil Res. 2009, 21, 76–77. [Google Scholar] [CrossRef]
  54. Kumar, A.; Tamta, M.L.; Negi, N.; Chandrasekhar, K.; Negi, D.S. Phytochemical investigation and antifeedant activity of Premna latifolia leaves. Nat. Prod. Res. 2011, 25, 1680–1686. [Google Scholar] [CrossRef]
  55. Zhang, H.Y.; Gao, Y.; Lai, P.X. Chemical composition, antioxidant, antimicrobial and cytotoxic activities of essential oil from Premna microphylla Turczaninow. Molecules 2017, 22, 381. [Google Scholar] [CrossRef] [Green Version]
  56. Hung, N.H.; Satyal, P.; Hieu, H.V.; Chuong, N.T.H.; Dai, D.N.; Huong, L.T.; Tai, T.A.; Setzer, W.N. Mosquito larvicidal activity of the essential oils of Erechtites species growing wild in Vietnam. Insects 2019, 10, 47. [Google Scholar] [CrossRef] [Green Version]
  57. Pavela, R. Acute toxicity and synergistic and antagonistic effects of the aromatic compounds of some essential oils against Culex quinquefasciatus Say larvae. Parasitol. Res. 2015, 114, 3835–3853. [Google Scholar] [CrossRef]
  58. Lee, D.C.; Ahn, Y.J. Laboratory and simulated field bioassays to evaluate larvicidal activity of Pinus densiflora hydrodistillate, its constituents and structurally related compounds against Aedes albopictus, Aedes aegypti and Culex pipiens pallens in relation to their inhibitory effects on acetylcholinesterase activity. Insects 2013, 4, 217–229. [Google Scholar]
  59. Perumalsamy, H.; Kim, N.-J.; Ahn, Y.-J. Larvicidal activity of compounds isolated from Asarum heterotropoides against Culex pipiens pallens, Aedes aegypti, and Ochlerotatus togoi (Diptera: Culicidae). J. Med. Entomol. 2009, 46, 1420–1423. [Google Scholar] [CrossRef]
  60. Autran, E.S.; Neves, I.A.; da Silva, C.S.B.; Santos, G.K.N.; da Câmara, C.A.G.; Navarro, D.M.A.F. Chemical composition, oviposition deterrent and larvicidal activities against Aedes aegypti of essential oils from Piper marginatum Jacq. (Piperaceae). Bioresour. Technol. 2009, 100, 2284–2288. [Google Scholar] [CrossRef] [PubMed]
  61. Aguiar, J.C.D.; Santiago, G.M.P.; Lavor, P.L.; Veras, H.N.H.; Ferreira, Y.S.; Lima, M.A.A.; Arriaga, A.M.C.; Lemos, T.L.G.; Lima, J.Q.; de Jesus, H.C.R.; et al. Chemical constituents and larvicidal activity of Hymenaea courbaril fruit peel. Nat. Prod. Commun. 2010, 5, 1977–1980. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  62. Dai, D.N.; Chung, N.T.; Huong, L.T.; Hung, N.H.; Chau, D.T.M.; Yen, N.T.; Setzer, W.N. Chemical compositions, mosquito larvicidal and antimicrobial activities of essential oils from five species of Cinnamomum growing wild in north central Vietnam. Molecules 2020, 25, 1303. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  63. Finney, D. Probit Analysis, Reissue ed.; Cambridge University Press: Cambridge, UK, 2009; ISBN 978-0521135900. [Google Scholar]
Table 1. Premna species examined in this study.
Table 1. Premna species examined in this study.
Premna SpeciesNative RangeEthnobotanical Use in Vietnam
Premna cambodiana Dop (Vietnamese name Cách cam bốt)Laos, Cambodia and Vietnam (Kon Tum, Gia Lai, and Đắk Nông provinces) [38,39,40].Used to treat spermatorrhea and gynecological diseases [40].
Premna chevalieri Dop (syn. Premna acuminatissima Merr.) (Vietnamese name Cách vàng)Thailand, Laos, Vietnam, China (Hainan, Yunnan) [41]. In Vietnam, the plant has been recorded in Thái Nguyên, Phú Thọ, Bắc Giang, Hà Nội, Hòa Bình, Ninh Bình, Nghệ An, Hà Tĩnh, and Quảng Nam provinces [39,40].The plant is used to treat polio, jaundice [40].
Premna corymbosa Rottler & Willd. (syn. Premna serratifolia L., Cornutia corymbosa Burm. f., Premna integrifolia L., Gumira corymbosa (Rottler & Willd.) Kuntze) (Vietnamese name Vọng cách, Cách biển)Ranges from Madagascar, through tropical and subtropical Asia, to Australia and Pacific islands [38]. In Vietnam, P. corymbosa has been found in Quảng Ninh, Hà Nội, Hải Phòng, Hà Nam, Ninh Bình, Thanh Hóa, Thừa Thiên Huế, Đà Nẵng, Quảng Nam, Khánh Hòa, Kon Tum, Đắk Nông, Đồng Nai, Hồ Chí Minh, Bà Rịa-Vũng Tàu, Long An, and Kiên Giang provinces [39,40].The plant used to treat skin diseases. Additionally, the leaves are used as culinary additives [40].
Premna flavescens Buch.-Ham. ex C.B. Clarke (syn. Premna lucidula Miq.)Southern China (Guangdong, Guangxi, and southern Yunnan), India, Indonesia, Malaysia, and Vietnam [41]. In Vietnam, P. flavescens has been recorded in Vĩnh Phúc, Nghệ An, Quảng Nam, Kon Tum, Gia Lai, Đắk Nông, and Đồng Nai provinces [39,40]. A species commonly grown in Vietnam; a decoction of the leaves is taken daily as a tonic [40].
Premna maclurei Merr. (Vietnamese name Cách maclura)China (Hainan) [41] as well as the provinces of Nghệ An and Quảng Nam, Vietnam [39,40].
Premna mekongensis W.W. Sm. (Vietnamese name Cách mê công)China (northwestern and western Yunnan province) [41] and in Vietnam (Hà Giang and Quảng Nam Provinces) [39,40].
Premna puberula Pamp. (syn. Premna martini H.Lév.) (Vietnamese name Cách lún phún)China (Fujian, Gansu, Guangdong, Guangxi, Guizhou, Hubei, Hunan, southern Shanxi, Sichuan, and Yunnan) [41] as well as Vietnam (Hà Giang, Bắc Giang, and Nghệ An) [39,40].Used in traditional medicine [40].
Premna tomentosa Willd. (syn. Premna cordata Blanco) (Vietnamese name Cách lông tơ)Ranges from China (Guangdong), through tropical Asia, to North Queensland, Australia [38]. In Vietnam, the plant has been recorded in Nghệ An province and South Vietnam [39,40].Leaves, roots as medicine [40].
Table 2. Collection details and yields for Premna leaf essential oils from central Vietnam.
Table 2. Collection details and yields for Premna leaf essential oils from central Vietnam.
Premna SpeciesCollection SiteVoucher NumbersEssential Oil Yield (% v/w)
Premna cambodianaChu Mom Ray National Park
14°25′33.5″ N, 107°43′15.6″ E, 672 m elevation
DND 880.14
Premna chevalieriTay Giang District, Quang Nam Province
15°49′59″ N 107°21′10″ E, 962 m elevation
DND 1010.10
Premna corymbosaNậm Giải Commune, Quế Phong district, Pu Hoat Nature Reserve, Nghe An province
19°41′40″ N, 104°49′29″ E, 670 m elevation
DND 7880.22
Son Tra Peninsula, Da Nang province
16°05′57″ N 108°15′59″ E, 6 m elevation
DND 490.25
Premna flavescensNậm Giải Commune, Quế Phong district, Pu Hoat Nature Reserve, Nghe An province
19°41′40″ N, 104°49′29″ E, 670 m elevation
DND 7870.11
Đồng Văn Commune, Quế Phong District, Pu Hoat Nature Reserve, Nghe An province
19°50′45″ N, 105°06′09″ E, 511 m elevation
DND 7110.12
Premna maclureiNậm Giải Commune, Quế Phong district, Pu Hoat Nature Reserve, Nghe An province
19°41′40″ N, 104°49′29″ E, 670 m elevation
DND 7470.12
Premna mekongensisNgoc Linh Nature Reserve, Quang Nam Province
15°50′16.0″ N, 107°22′54.7″ E, 1341 m elevation
DND 1020.19
Chu Mom Ray National Park
14°25′33.5″ N, 107°43′15.6″ E, 672 elevation
DND 840.21
Premna puberulaĐồng Văn Commune, Quế Phong District, Pu Hoat Nature Reserve, Nghe An province
19°50ʹ45″ N, 105°06′09″ E, 511 m elevation
DND 7100.11
Premna tomentosaNghia Dan District, Nghe An province
19°20′23″ N 105°25′18″ E, 49 elevation
DND 230.12
Table 3. Chemical compositions of leaf essential oils of Premna species from central Vietnam.
Table 3. Chemical compositions of leaf essential oils of Premna species from central Vietnam.
RIcalc aRIdb bCompound cP. cambodianaP. chevalierP. corymbosa (Nghe An)P. corymbosa
(Da Nang)
P. flavescens (Nậm Giải)P. flavescens (Đồng Văn)P. maclureiP. mekongensis (Ngoc Linh)P. mekongensis (Chu Mom Ray)P. puberulaP. tomentosa
922923Tricyclene---tr d------------------tr------
925927α-Thujene---0.10.1---------------tr---0.1
931933α-Pinene1.912.20.50.50.20.10.466.91.51.33.0
947948α-Fenchene---tr---------------------------
949953Camphene---0.1------trtr---0.21.5---tr
952953Thuja-2,4(10)-diene---tr---------------0.1---------
971971Sabinene---tr0.8tr---trtr0.90.1---2.0
976978β-Pinene1.716.80.60.10.10.10.20.50.70.10.7
9789781-Octen-3-ol---------------0.3---0.2------tr
9789866-Methylhept-5-en-2-one------------------tr------------
9839863-Octanone---0.1---------------------------
987991Myrcene---0.2---0.4---0.3tr1.63.1---0.1
9979993-Octanol---0.1------------------------tr
10011004p-Mentha-1(7),8-diene---------tr---------------------
10061007α-Phellandrene---------0.2---------0.31.6---tr
10081009δ-3-Carene---------------tr---------------
10171018α-Terpinene---tr------------------tr---0.1
10231025p-Cymenetr0.10.51.90.1trtr0.30.60.10.4
10271030Limonene0.21.00.21.70.10.10.11.11.70.30.2
10291031β-Phellandrene ---tr---0.6tr------0.41.3---tr
103110321,8-Cineole---tr0.1---0.1tr---0.9tr---tr
10341034(Z)-β-Ocimene---0.1---------------0.1tr---tr
10451045(E)-β-Ocimene---1.3---------tr---0.10.2---0.1
10571057γ-Terpinene---tr---------------0.1tr---0.2
10851086Terpinolene---tr---------------tr0.1---0.1
10981101Linalooltr0.80.80.20.10.40.21.40.30.10.2
110211042-Methylbutyl 2-methylbutanoate------------------------tr------
11031104Nonanaltr0.1---trtr---tr0.1---------
11071108p-Mentha-2,8-dien-1-ol---------------------------0.4---
11111113(3E)-4,8-Dimethyl-1,3,7-nonatriene---1.1------------tr---------tr
11251126α-Campholenal---------------------------0.1---
11361138Benzeneacetonitrile---------------tr---------0.1---
11391141trans-Pinocarveoltr0.1---------------------0.2---
11431145trans-Verbenol---------------------0.1---0.3---
11461153p-Vinylanisole------------------0.1---------0.2
11611164Pinocarvone---tr---------------------------
11701173Borneol------------------------tr------
11791180Terpinen-4-ol------0.1---------tr---tr---0.3
11821187(3Z)-Hexenyl butyrate---------tr---0.1---------------
11821188Naphthalene---------------0.1---------------
11841187Cryptone---------tr------------tr------
11851188p-Cymen-8-ol---------------------------0.1---
11891193Butyl hexanoate------------------------0.6------
11891192Methyl salicylate---0.1---tr------tr---------tr
11921196Myrtenaltr---------------tr------0.1---
11931195α-Terpineol---0.1---tr------tr0.1tr---tr
12001202cis-Sabinol---------0.1------------tr------
12041208Decanaltr------------------------------
12051208Verbenone---------------------------0.1---
12061207(3E)-Octenyl acetate ---0.1---------------------------
12271229Thymol methyl ether------------------------0.1------
12471257p-Anisaldehyde------------------tr------------
12481250Linalyl acetate------------------------tr------
12511252Isopentyl hexanoate------------------------0.3------
12821282Bornyl acetate---tr------tr---------3.9------
12861287Dihydroedulan IA---tr------0.8---tr---0.2---tr
12911294Dihydroedulan IIA---0.1---------tr0.4---------0.1
12971299Theaspirane A---tr---------------------------
13001300Tridecane------------tr------------------
13071306Isoascaridole------------------------------tr
1312-Unidentified e---------------1.2------3.4------
13131315Theaspirane B---tr---------------------------
131713183-Hydroxycineole------------------------tr------
13291328Bicycloelemene---------0.10.60.1------1.1---0.2
13321335δ-Elemene0.2---------0.1tr0.2---0.6---0.2
13451349α-Cubebene0.70.10.50.3---0.20.5---0.40.50.2
13451349α-Terpinyl acetate------------------tr---1.5------
13561361Neryl acetate------------------------tr------
13621367Decanoic acid---tr---------------------------
13651372Isoledene------------------tr------------
13671371α-Ylangene0.3---0.60.1------0.1---0.3---0.1
13681367Cyclosativenetr---------tr0.1------0.1------
13741378Geranyl acetate0.1------------------------------
13741375α-Copaene23.30.96.88.10.12.92.6---1.65.33.1
13761379(E)-β-Damascenone---0.1------------0.1---------tr
13781382(3Z)-Hexenyl hexanoate---tr---------------------------
13791383cis-β-Elemene0.2tr---tr0.50.50.1---0.1---0.3
13811382β-Bourbonenetrtr---tr---0.10.1---------tr
13841390Hexyl hexanoate------------------------2.1------
13861392β-Cubebene 1.10.21.80.9---0.61.6---0.31.50.7
13871390trans-β-Elemene3.50.31.51.09.98.71.80.51.31.95.0
14021405(Z)-Caryophyllene ---0.1------0.2------------------
140214039,10-Dehydroisolongifolene---------------------------0.8---
14021406Cyperene---------------1.1------0.1------
14051406α-Gurjunene 11.3---0.60.10.119.6------0.31.35.2
14121415β-Maaliene 0.2------------0.4------------2.8
14191417(E)-Caryophyllene 12.831.56.913.341.011.830.714.73.90.622.0
14271427γ-Elemene0.7tr------------------------2.4
14271430γ-Maaliene------------------------0.1---0.3
14281433β-Copaene---tr0.20.2---0.10.4---1.2------
14291430trans-α-Bergamotene ---tr---0.10.7------------------
14301437β-Gurjunene (= Calarene) ---------------0.1---------------
14321436α-Guaiene 0.10.1---4.60.56.10.40.5---0.40.3
14331438α-Maaliene0.1---------------------0.1------
14371438Aromadendrene0.1tr0.50.10.40.10.3---1.0---3.4
14431444Guaia-6,9-diene0.1---------1.1tr------------0.1
14441445Selina-5,11-diene---0.1------------------0.1------
14451446Neryl acetone---tr---------------------------
14481453trans-Muurola-3,5-diene------------------------0.1------
14481445β-Barbatene---tr---------------------------
14501447iso-Germacrene D------------------------------tr
14501455Valerena-4,7(11)-diene0.1------0.4---0.3------0.1---0.1
14511452(E)-β-Farnesene ---0.1------0.1------------------
14541454α-Humulene3.77.52.63.72.43.15.32.52.00.43.9
14581457allo-Aromadendrene1.60.17.739.70.13.00.2---1.04.11.0
14581463cis-Cadina-1(6),4-diene 0.1------------------------------
14611459Rotundene---------------0.1---------------
14621466cis-Muurola-4(14),5-diene------------------------0.2---0.1
146914734,5-di-epi-Aristolochene---0.11.0------0.1---------------
14711472trans-Cadina-1(6),4-diene------------------------0.4------
14721478γ-Muurolene0.6---0.40.40.1---1.2---1.7---0.4
14731476γ-Gurjunene0.8------------0.4------0.3---0.3
14741475Selina-4,11-diene---2.0------0.20.1---0.5---------
14751477β-Chamigrene---------------1.30.1------------
14761481(E)-β-Ionone---tr---------------------------
14761479α-Amorphene0.3------0.2------------0.6------
14791480Germacrene D2.20.30.43.00.73.83.00.15.6---11.4
14791482γ-Himachalene0.1------------------------------
14801483trans-β-Bergamotene------------0.2------------------
14841491Eremophilene------------0.1------------------
14861488δ-Selinene------------------------0.2------
14871487β-Selinene 1.41.24.00.21.39.70.30.40.70.74.3
14911492trans-Muurola-4(14),5-diene ------------------------1.7------
14911492Valencene------0.2---------0.2------------
14911491Viridiflorene (= Ledene)0.1------0.30.11.8---------------
14911490γ-Amorphene0.2---------------------------0.3
14931493Curzerene------------------------1.2------
14931498epi-Cubebol ---------------------------0.9---
14951497α-Muurolene0.5---0.20.30.2---0.4---------0.2
14951497α-Selinene1.01.52.7------8.7---0.4------5.5
14961497Bicyclogermacrene---------1.17.8---1.9---11.9------
14971502ε-Amorphene---0.1---------------------------
14991505α-Bulnesene---0.1---4.10.25.40.30.1---0.60.1
15021503(E,E)-α-Farnesene---3.4------0.3------0.1------1.0
15031508β-Bisabolene ---------0.40.5------------------
15081511Germacrene A---------------0.2------------0.1
15111512γ-Cadinene0.4tr0.20.30.10.20.4---1.1---0.2
15131515Cubebol0.1---0.6---------0.2---0.30.6tr
15161518δ-Cadinene5.50.30.42.00.10.98.4---3.2---1.8
151815187-epi-α-Selinene------0.2------------------------
15181521α-Panasinsen---------------0.5---------------
15191519trans-Calamenene0.50.10.40.3------0.3---1.0---0.1
15221521Zonarene------------------------0.2------
15321538α-Cadinene0.2------0.1------0.1---0.3------
15341536trans-Cadina-1,4-diene------------------------0.2---0.1
15351529cis-Calamenene------------------0.2------------
15361540(E)-α-Bisabolene ------------0.3------------------
15381540Selina-4(15),7(11)-diene------------------------------0.1
15391546cis-Sesquisabinene hydrate ------------------------------0.1
15391544α-Calacorene0.9---0.60.1------0.6---0.23.4---
15461546α-Elemol---0.1------------------0.2------
15471551(Z)-Caryophyllene oxide0.4------------0.10.6------1.5---
15501549cis-Muurol-5-en-4β-ol------------------------0.1------
15571557Germacrene B0.6---------0.1tr------0.5---3.5
15591560(E)-Nerolidol---0.2------0.3------0.17.5------
15601560β-Calacorene0.4---------------0.7------0.8---
156315581-Tetradecanol---0.3---------------------------
156515661,5-Epoxysalvial-4(14)-ene---------------------------1.1---
15681568Palustrol0.3------------0.66.8---1.71.9---
15691571Cedroxyde---------0.1---------------0.9---
15721568Dendrolasin---2.0---------------------------
15751578Furopelargone B------------0.2------------------
15751576Spathulenol0.80.617.31.41.81.0------2.87.70.8
15801587(E)-Caryophyllene oxide4.35.316.83.01.71.312.30.80.321.21.1
15841590Globulol0.50.11.70.30.30.20.3---1.22.00.7
15901596Cubeban-11-ol---------0.1---------------------
15931594Viridiflorol------1.80.30.20.1------5.60.7---
15951593Guaiol---1.2---------------------------
15981600Curzerenone------------------------0.3------
16021605Ledol0.2---0.30.3---0.3------1.20.66.1
16071613Humulene epoxide II0.81.03.40.40.10.21.00.1---4.70.1
16121615Rosifoliol---1.1------------------0.1------
161416161,10-di-epi-Cubenol------------------------0.2------
16221632Muurola-4,10(14)-dien-1β-ol0.1---------------0.2------------
162416271-epi-Cubenol0.4---0.40.2------0.1---1.0------
16291629iso-Spathulenol------1.00.10.4---0.5---------0.1
16331635Caryophylla-4(12),8(13)-dien-5β-ol0.1---------0.2---0.60.1---------
16331634cis-Cadin-4-en-7-ol 0.2---------------------0.9------
16371641allo-Aromadendrene epoxide0.6------0.3---0.1------0.1---0.2
16411643τ-Cadinol ------0.40.2---------------------
16421643Cubenol------------------------1.5------
16421643Hedycariol---0.1---------------------------
16431643α-Muurolol (= δ-Cadinol)0.3---0.30.10.1---------0.4---0.1
16431645τ-Murrolol0.2---0.40.2------------------0.1
16471649β-Eudesmol------------------0.1------------
16531652α-Cadinol0.60.31.90.30.30.10.3---1.60.60.3
16541663cis-Calamenen-10-ol0.4---------------0.9------0.8---
16541653Pogostol---0.30.3---------0.81.4---1.20.4
16571658Selin-11-en-4α-ol0.3---0.9---0.40.2------0.3------
16591664ar-Turmerone---------------------0.1---------
16621670trans-Calamenen-10-ol0.6---------------0.7------1.0---
16631664Bulnesol---0.4---------------------------
166416629-Methoxycalamenene------0.7tr---------------------
16681677Cadalene0.3------------------------------
1669166814-Hydroxy-9-epi-(E)-caryophyllene------0.5------------------------
16711681Mustakone------------------3.6------2.6---
16741677Apiole------1.6---0.6------------------
16821683Germacra-4(15),5,10(14)-trien-1α-ol------1.0------------------------
16851688α-Bisabolol---0.1---------------------------
1692170110-nor-Calamenen-10-one------------------0.4------------
16991704cis-Thujopsenol ---------0.1---------------1.8---
17001708δ-Dodecalactone---------------0.1---------------
17271729Zerumbone---------------0.4---------1.1---
17441746α-Cyperone ------0.6------------------------
17461748Geranyl hexanoate------------------------0.2------
17481763β-Costol---------0.4---------------------
17491757Cyclocolorenone1.1------------0.1---------2.0---
17581768Squamulosone---------------------------0.6---
1759-Unidentified f------------14.7------------------
1761-Unidentified g------------2.0------------------
18061813Nootkatone------0.50.3---------------1.4---
18301836Neophytadiene------------0.1------------------
18371841Phytone0.2---------0.1---0.3------1.9---
18591860Platambin------------------0.8---------0.1
187318794-Phytadiene------------0.1------------------
18861884Corymbolone---------------------------1.1---
19391947iso-Phytol------------0.1------------------
19581958(Z,Z)-Geranyl linalool ---0.1---------------------------
19831995Manool oxide------------------0.4------------
20192022(E,E)-Geranyl linalool ---0.1---------------------------
21022102(E)-Phytol4.32.2---0.34.9---2.42.2------0.7
21312138Palmitaldehyde, diallyl acetal0.6---------------0.4------------
Monoterpene hydrocarbons3.831.82.75.30.50.60.772.512.51.87.0
Oxygenated monoterpenoids0.11.01.00.20.20.40.22.56.01.40.5
Sesquiterpene hydrocarbons76.149.940.285.469.992.262.519.646.922.481.0
Oxygenated sesquiterpenoids12.312.650.68.26.04.830.12.527.458.210.2
Diterpenoids4.52.40.00.35.20.03.12.20.01.90.7
Others0.62.01.6tr1.40.61.10.33.20.10.3
Total Identified97.499.896.199.683.398.697.799.696.085.799.8
a RIcalc = Retention indices determined with respect to a homologous series of n-alkanes on a ZB-5ms column. b RIdb = Retention indices from the databases [42,43,44,45]. c Tentative identification based on RI and MS fragmentation agreement. d tr = Trace (<0.05%). e MS: 162(42%), 147(54%), 133(24%), 120(24%), 119(36%), 105(100%), 91(79%), 79(37%), 77(26%), 65(14%), 55(23%), and 41(21%). f MS: 204(28%), 147(5%), 134(12%), 133(100%), 120(45%), 107(41%), 105(16%), 91(8%), 77(11%), 55(7%), and 41(6%). g MS: 206(10%), 107(100%), 77(6%), and 41(3%). Concentrations of major components are highlighted in bold.
Table 4. Twenty-four-hour mosquito larvicidal activities of Premna leaf essential oils.
Table 4. Twenty-four-hour mosquito larvicidal activities of Premna leaf essential oils.
Premna Species (Collection Site)LC50 (95% Limits), μg/mLLC90 (95% Limits), μg/mLχ2p
Aedes aegypti
P. cambodiana (Chu Mom Ray)16.79 (14.66–18.68)28.02 (25.18–32.82)0.006240.997
P. chevalieri (Quang Nam)31.72 (29.20–34.48)46.88 (43.14–52.00)2.540.281
P. corymbosa (Nghe An)37.96 (33.16–43.18)75.43 (66.72–88.43)4.530.104
P. corymbosa (Da Nang)61.78 (57.16–67.71)83.01 (75.71–93.93)5.750.056
P. flavescens (Đồng Văn)64.67 (58.99–71.10)106.1 (95.9–120.2)13.230.001
P. maclurei (Nghe An)43.66 (40.67–47.07)60.72 (56.03–67.58)1.2110.546
P. mekongensis (Ngoc Linh)17.98 (14.79–20.71)35.81 (31.76–42.26)4.140.126
P. mekongensis (Chu Mom Ray)41.63 (38.79–44.49)55.94 (52.45–60.49)35.00.000
P. puberula (Nghe An)50.88 (46.25–56.36)80.60 (72.74–91.86)12.70.002
P. tomentosa (Nghe An)34.21 (31.02–37.67)54.36 (49.42–61.35)0.2250.893
Permethrin (control)0.0094 (0.0082–0.0107)0.0211 (0.0185–0.0249)57.60.000
Aedes albopictus
P. corymbosa (Da Nang)45.89 (42.61–49.88)64.70 (59.15–73.12)1.550.460
P. flavescens (Đồng Văn)90.02 (80.92–99.87)165.4 (148.9–189.2)4.510.105
P. puberula (Nghe An)115.9 (108.2–124.1)176.7 (165.0–191.8)12.20.007
Permethrin (control)0.0024 (0.0021–0.0026)0.0042 (0.0038–0.0049)4.640.031
Culex quinquefasciatus
P. chevalieri (Quang Nam)75.68 (68.51–84.52)129.8 (115.9–150.0)6.940.031
P. mekongensis (Ngoc Linh)42.66 (38.71–47.43)69.35 (62.21–79.95)1.680.431
P. mekongensis (Chu Mom Ray)33.16 (30.30–36.25)52.01 (47.55–58.29)11.80.003
P. puberula (Nghe An)60.59 (55.77–66.33)87.68 (80.11–98.09)12.40.002
Permethrin (control)0.0188 (0.0173–0.0206)0.0294 (0.0270–0.0326)24.10.000
Table 5. Forty-eight-hour mosquito larvicidal activities of Premna leaf essential oils.
Table 5. Forty-eight-hour mosquito larvicidal activities of Premna leaf essential oils.
Premna Species (Collection Site)LC50 (95% Limits), μg/mLLC90 (95% Limits), μg/mLχ2p
Aedes aegypti
P. cambodiana (Chu Mom Ray)13.68 (10.72–15.77)25.62 (22.82–30.59)0.003990.998
P. chevalieri (Quang Nam)30.23 (27.75–32.92)45.11 (41.41–50.23)4.590.101
P. corymbosa (Nghe An)33.59 (28.68–38.65)71.64 (62.98–84.86)2.980.225
P. corymbosa (Da Nang)60.43 (55.81–66.17)83.54 (76.24–94.13)8.070.018
P. flavescens (Đồng Văn)62.42 (56.58–69.12)105.9 (96.5–119.0)2.330.312
P. maclurei (Nghe An)41.63 (38.85–44.63)57.07 (53.07–62.68)0.9220.631
P. mekongensis (Ngoc Linh)17.62 (15.37–19.67)30.00 (26.76–35.65)0.03640.982
P. mekongensis (Chu Mom Ray)38.70 (36.18–41.21)49.94 (47.01–53.73)0.1300.937
P. puberula (Nghe An)45.71 (41.21–50.97)76.15 (68.30–87.56)3.400.182
P. tomentosa (Nghe An)31.4 (28.32–34.69)50.80 (46.13–57.36)0.08780.957
Permethrin (control)0.0087 (0.0074–0.0102)0.0204 (0.0181–0.0236)39.60.000
Aedes albopictus
P. corymbosa (Da Nang)35.13 (31.93–38.74)56.97 (51.54–64.86)0.1480.929
P. flavescens (Đồng Văn)74.14 (66.55–81.95)133.2 (121.1–149.9)9.870.007
P. puberula (Nghe An)98.1 (91.0–105.7)151.1 (140.3–165.0)37.20.000
Culex quinquefasciatus
P. chevalieri (Quang Nam)52.10 (44.16–60.92)121.1 (104.4–147.9)6.650.036
P. mekongensis (Ngoc Linh)38.72 (34.62–43.45)68.87 (61.30–80.21)0.5840.747
P. mekongensis (Chu Mom Ray)27.02 (23.51–30.51)51.55 (45.96–60.01)3.550.169
P. puberula (Nghe An)41.31 (37.07–46.27)72.04 (64.28–83.52)2.200.333

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Hung, N.H.; Huong, L.T.; Chung, N.T.; Truong, N.C.; Dai, D.N.; Satyal, P.; Tai, T.A.; Hien, V.T.; Setzer, W.N. Premna Species in Vietnam: Essential Oil Compositions and Mosquito Larvicidal Activities. Plants 2020, 9, 1130. https://doi.org/10.3390/plants9091130

AMA Style

Hung NH, Huong LT, Chung NT, Truong NC, Dai DN, Satyal P, Tai TA, Hien VT, Setzer WN. Premna Species in Vietnam: Essential Oil Compositions and Mosquito Larvicidal Activities. Plants. 2020; 9(9):1130. https://doi.org/10.3390/plants9091130

Chicago/Turabian Style

Hung, Nguyen Huy, Le Thi Huong, Nguyen Thanh Chung, Nguyen Cong Truong, Do Ngoc Dai, Prabodh Satyal, Thieu Anh Tai, Vu Thi Hien, and William N Setzer. 2020. "Premna Species in Vietnam: Essential Oil Compositions and Mosquito Larvicidal Activities" Plants 9, no. 9: 1130. https://doi.org/10.3390/plants9091130

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