Advertisement

Planta

, Volume 250, Issue 1, pp 59–68 | Cite as

Phytochemical composition and larvicidal activity of essential oils from herbal plants

  • Hsiang-Ting Huang
  • Chien-Chung Lin
  • Tai-Chih Kuo
  • Shiang-Jiuun Chen
  • Rong-Nan HuangEmail author
Original Article

Abstract

Main conclusion

The essential oils (EOs) of Plectranthus amboinicus showed the highest larvicidal activity among four herbal plants studied and β-caryophyllene might be the major component responsible for its differential toxicity to the larvae of Culex quinquefasciatus and Aedes Aegypti.

Mosquitoes act as vectors for many life-threatening diseases, including malaria, dengue fever, and Zika virus infection. Management of mosquitoes mainly relies on synthetic insecticides, which usually result in the rapid development of resistance; therefore, alternative mosquito control strategies are urgently needed. This study characterized the major component of essential oils (EOs) derived from the vegetative parts of four herbal plants and their larvicidal activity toward important mosquito vectors. The EOs were extracted by hydro-distillation and subjected to gas chromatography–mass spectrometry (GC–MS) analysis and a larvicidal activity assay toward Aedes aegypti, Ae. albopictus and Culex quinquefasciatus. In total, 14, 11, 11 and 9 compounds were identified from the EOs of Plectranthus amboinicus, Mentha requienii, Vitex rotundifolia and Crossostephium chinense, respectively. The EOs derived from four herbal plants exhibited remarkable larvicidal activity against the three mosquito species. In particular, the EOs of P. amboinicus showed the highest larvicidal activity, and the larvae of Cx. quinquefasciatus were more sensitive to the P. amboinicus EOs than that of Ae. Aegypti. Although carvacrol (61.53%) was the predominant constituent of the P. amboinicus EOs, its precursors, γ-terpinene (8.51%) and p-cymene (9.42%), exhibited the most larvicidal activity toward Ae. aegypti and Cx. quinquefasciatus. However, β-caryophyllene (12.79%) might be the major component responsible for the differential toxicity of the P. amboinicus EOs, as indicated by the significant differences in its LC50 values toward both mosquitoes. Information from these studies will benefit the incorporation of EOs into integrated vector management.

Keywords

Vector control Essential oils Larvicide β-Caryophyllene 

Notes

Acknowledgements

We would like to thanks American Journal Experts for helping on the grammar editing of this manuscript. Funding for this research was provided by the Ministry of Science and Technology (MOST 106-2321-B-002-037), The Executive Yuan, Taiwan, R.O.C. are kindly acknowledged.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no competing interests.

References

  1. Adams RP (2017) Identification of essential oil components by gas chromatography/mass spectrometry, 5th edn. Texensis Publishing, GruverGoogle Scholar
  2. Aguiar JJS, Sousa CPB, Araruna MKA, Silva MKN, Portelo AC, Lopes JC, Carvalho VRA, Figueredo FG, Bitu VCN, Coutinho HDM, Miranda TAS, Matias EFF (2015) Antibacterial and modifying-antibiotic activities of the essential oils of Ocimum gratissimum L. and Plectranthus amboinicus L. Eur J Integr Med 7(2):151–156.  https://doi.org/10.1016/j.eujim.2014.10.005 CrossRefGoogle Scholar
  3. Arumugam G, Swamy MK, Sinniah UR (2016) Plectranthus amboinicus (Lour.) Spreng: botanical, phytochemical, pharmacological and nutritional significance. Molecules 21(4):369.  https://doi.org/10.3390/molecules21040369 CrossRefPubMedPubMedCentralGoogle Scholar
  4. Bae H, Kim Y, Lee E, Park S, Jung KH, Gu MJ, Hong SP, Kim J (2013) Vitex rotundifolia L. prevented airway eosinophilic inflammation and airway remodeling in an ovalbumin-induced asthma mouse model. Int Immunol 25(3):197–205.  https://doi.org/10.1093/intimm/dxs102 CrossRefPubMedGoogle Scholar
  5. Benelli G, Govindarajan M, Rajeswary M, Senthilmurugan S, Vijayan P, Alharbi NS, Kadaikunnan S, Khaled JM (2017) Larvicidal activity of Blumea eriantha essential oil and its components against six mosquito species, including Zika virus vectors: the promising potential of (4E,6Z)-allo-ocimene, carvotanacetone and dodecyl acetate. Parasitol Res 116(4):1175–1188.  https://doi.org/10.1007/s00436-017-5395-0 CrossRefPubMedGoogle Scholar
  6. Chao LK, Hua KF, Hsu HY, Cheng SS, Liu JY, Chang ST (2005) Study on the antiinflammatory activity of essential oil from leaves of Cinnamomum osmophloeum. J Agric Food Chem 53(18):7274–7278CrossRefGoogle Scholar
  7. Chen YS, Yu HM, Shie JJ, Cheng TJ, Wu CY, Fang JM, Wong CH (2014) Chemical constituents of Plectranthus amboinicus and the synthetic analogs possessing anti-inflammatory activity. Bioorg Med Chem 22(5):1766–1772.  https://doi.org/10.1016/j.bmc.2014.01.009 CrossRefPubMedGoogle Scholar
  8. Chessa M, Sias A, Piana A, Mangano GS, Petretto GL, Masia MD, Tirillini B, Pintore G (2013) Chemical composition and antibacterial activity of the essential oil from Mentha requienii Bentham. Nat Prod Res 27(2):93–99CrossRefGoogle Scholar
  9. da Costa JGM, Pereira CKB, Rodrigues FFG, de Lima SG (2010) Chemical composition, antibacterial and fungicidal activities of leaf oil of Plectranthus amboinicus (Lour.) Spreng. J Essent Oil Res 22(2):183–185.  https://doi.org/10.1080/10412905.2010.9700298 CrossRefGoogle Scholar
  10. Gerberg EJ (1979) Manual for mosquito rearing and experimental techniques (bulletin No 5). American Mosquito Control Association, Selma, pp 7–26Google Scholar
  11. Golden G, Quinn E, Shaaya E, Kostyukovsky M, Poverenov E (2018) Coarse and nano emulsions for effective delivery of natural pest control agent pulegone for stored grain protection. Pest Manag Sci 74(4):820–827CrossRefGoogle Scholar
  12. Govindarajan M, Benelli G (2016) alpha-Humulene and beta-elemene from Syzygium zeylanicum (Myrtaceae) essential oil: highly effective and eco-friendly larvicides against Anopheles subpictus, Aedes albopictus, and Culex tritaeniorhynchus (Diptera: Culicidae). Parasitol Res 115(7):2771–2778.  https://doi.org/10.1007/s00436-016-5025-2 CrossRefPubMedGoogle Scholar
  13. Govindarajan M, Sivakumar R, Rajeswary M, Yogalakshmi K (2013) Chemical composition and larvicidal activity of essential oil from Ocimum basilicum (L.) against Culex tritaeniorhynchus, Aedes albopictus and Anopheles subpictus (Diptera: Culicidae). Exp Parasitol 134(1):7–11.  https://doi.org/10.1016/j.exppara.2013.01.018 CrossRefPubMedGoogle Scholar
  14. Govindarajan M, Rajeswary M, Hoti SL, Bhattacharyya A, Benelli G (2016) Eugenol, alpha-pinene and beta-caryophyllene from Plectranthus barbatus essential oil as eco-friendly larvicides against malaria, dengue and Japanese encephalitis mosquito vectors. Parasitol Res 115(2):807–815.  https://doi.org/10.1007/s00436-015-4809-0 CrossRefPubMedGoogle Scholar
  15. Gurgel AP, da Silva JG, Grangeiro AR, Oliveira DC, Lima CM, da Silva AC, Oliveira RA, Souza IA (2009) In vivo study of the anti-inflammatory and antitumor activities of leaves from Plectranthus amboinicus (Lour.) Spreng (Lamiaceae). J Ethnopharmacol 125(2):361–363.  https://doi.org/10.1016/j.jep.2009.07.006 CrossRefPubMedGoogle Scholar
  16. Hu Y, Hou TT, Zhang QY, Xin HL, Zheng HC, Rahman K, Qin LP (2007a) Evaluation of the estrogenic activity of the constituents in the fruits of Vitex rotundifolia L. for the potential treatment of premenstrual syndrome. J Pharm Pharmacol 59(9):1307–1312CrossRefGoogle Scholar
  17. Hu Y, Zhang QY, Xin HL, Qin LP, Lu BR, Rahman K, Zheng HC (2007b) Association between chemical and genetic variation of Vitex rotundifolia populations from different locations in China: its implication for quality control of medicinal plants. Biomed Chromatogr 21(9):967–975.  https://doi.org/10.1002/bmc.841 CrossRefPubMedGoogle Scholar
  18. Hu Y, Zhu Y, Zhang QY, Xin HL, Qin LP, Lu BR, Rahman K, Zheng HC (2008) Population genetic structure of the medicinal plant Vitex rotundifolia in China: implications for its use and conservation. J Integr Plant Biol 50(9):1118–1129.  https://doi.org/10.1111/j.1744-7909.2008.00635.x CrossRefPubMedGoogle Scholar
  19. Jayaraman M, Senthilkumar A, Venkatesalu V (2015) Evaluation of some aromatic plant extracts for mosquito larvicidal potential against Culex quinquefasciatus, Aedes aegypti, and Anopheles stephensi. Parasitol Res 114(4):1511–1518.  https://doi.org/10.1007/s00436-015-4335-0 CrossRefPubMedGoogle Scholar
  20. Kim YA, Kim H, Seo Y (2013) Antiproliferative effect of flavonoids from the halophyte Vitex rotundifolia on human cancer cells. Nat Prod Commun 8(10):1405–1408PubMedGoogle Scholar
  21. Kumar P, Mishra S, Malik A, Satya S (2013) Housefly (Musca domestica L.) control potential of Cymbopogon citratus Stapf. (Poales: Poaceae) essential oil and monoterpenes (citral and 1,8-cineole). Parasitol Res 112(1):69–76CrossRefGoogle Scholar
  22. Kumaran A, Karunakaran RJ (2006) Antioxidant and free radical scavenging activity of an aqueous extract of Coleus aromaticus. Food Chem 97(1):109–114.  https://doi.org/10.1016/j.foodchem.2005.03.032 CrossRefGoogle Scholar
  23. Lee SM, Lee YJ, Kim YC, Kim JS, Kang DG, Lee HS (2012) Vascular protective role of vitexicarpin isolated from Vitex rotundifolia in human umbilical vein endothelial cells. Inflammation 35(2):584–593.  https://doi.org/10.1007/s10753-011-9349-x CrossRefPubMedGoogle Scholar
  24. Lee C, Lee JW, Jin Q, Lee HJ, Lee SJ, Lee D, Lee MK, Lee CK, Hong JT, Lee MK, Hwang BY (2013) Anti-inflammatory constituents from the fruits of Vitex rotundifolia. Bioorg Med Chem Lett 23(21):6010–6014.  https://doi.org/10.1016/j.bmcl.2013.08.004 CrossRefPubMedGoogle Scholar
  25. Lessler J, Chaisson LH, Kucirka LM, Bi Q, Grantz K, Salje H, Carcelen AC, Ott CT, Sheffield JS, Ferguson NM, Cummings DA, Metcalf CJ, Rodriguez-Barraquer I (2016) Assessing the global threat from Zika virus. Science 353(6300):aaf8160.  https://doi.org/10.1126/science.aaf8160 CrossRefPubMedPubMedCentralGoogle Scholar
  26. Liu K, Rossi PG, Ferrari B, Berti L, Casanova J, Tomi F (2007) Composition, irregular terpenoids, chemical variability and antibacterial activity of the essential oil from Santolina corsica Jordan et Fourr. Phytochemistry 68(12):1698–1705CrossRefGoogle Scholar
  27. Luo YP (2014) A novel multiple membrane blood-feeding system for investigating and maintaining Aedes aegypti and Aedes albopictus mosquitoes. J Vector Ecol 39(2):271–277CrossRefGoogle Scholar
  28. Murthy PS, Ramalakshmi K, Srinivas P (2009) Fungitoxic activity of Indian borage (Plectranthus amboinicus) volatiles. Food Chem 114(3):1014–1018.  https://doi.org/10.1016/j.foodchem.2008.10.064 CrossRefGoogle Scholar
  29. Naqqash MN, Gokce A, Bakhsh A, Salim M (2016) Insecticide resistance and its molecular basis in urban insect pests. Parasitol Res 115(4):1363–1373.  https://doi.org/10.1007/s00436-015-4898-9 CrossRefPubMedGoogle Scholar
  30. Patel K, Patel DK (2017) Medicinal importance, pharmacological activities, and analytical aspects of hispidulin: a concise report. J Tradit Complement Med 7(3):360–366CrossRefGoogle Scholar
  31. Pavela R (2015) Essential oils for the development of eco-friendly mosquito larvicides: a review. Ind Crop Prod 76:174–187.  https://doi.org/10.1016/j.indcrop.2015.06.050 CrossRefGoogle Scholar
  32. Pavela R, Žabka M, Vrchotová N, Třískab J (2018) Effect of foliar nutrition on the essential oil yield of Thyme (Thymus vulgaris L.). Ind Crop Prod 112:762–765CrossRefGoogle Scholar
  33. Pinheiro PF, Costa AV, Alves Tde A, Galter IN, Pinheiro CA, Pereira AF, Oliveira CM, Fontes MM (2015) Phytotoxicity and cytotoxicity of essential oil from leaves of Plectranthus amboinicus, carvacrol, and thymol in plant bioassays. J Agric Food Chem 63(41):8981–8990CrossRefGoogle Scholar
  34. Regnault-Roger C, Vincent C, Arnason JT (2012) Essential oils in insect control: low-risk products in a high-stakes world. Annu Rev Entomol 57:405–424.  https://doi.org/10.1146/annurev-ento-120710-100554 CrossRefPubMedGoogle Scholar
  35. Riccobono L, Maggio A, Bruno M, Spadaro V, Raimondo FM (2017) Chemical composition and antimicrobial activity of the essential oils of some species of Anthemis sect. Anthemis (Asteraceae) from Sicily. Nat Prod Res 31(23):2759–2767CrossRefGoogle Scholar
  36. Sasaki S, Aoyagi S, Hsu HY (1965) The isolation of taraxerol, taraxeryl acetate, and taraxerone from Crossostephium chinense Makino (Compositae). Chem Pharm Bull (Tokyo) 13(1):87–88CrossRefGoogle Scholar
  37. Senthilkumar A, Venkatesalu V (2010) Chemical composition and larvicidal activity of the essential oil of Plectranthus amboinicus (Lour.) Spreng against Anopheles stephensi: a malarial vector mosquito. Parasitol Res 107(5):1275–1278.  https://doi.org/10.1007/s00436-010-1996-6 CrossRefPubMedGoogle Scholar
  38. Senthilkumar N, Varma P, Gurusubramanian G (2009) Larvicidal and adulticidal activities of some medicinal plants against the Malarial Vector, Anopheles stephensi (Liston). Parasitol Res 104(2):237–244.  https://doi.org/10.1007/s00436-008-1180-4 CrossRefPubMedGoogle Scholar
  39. Sohn SH, Ko E, Oh BG, Kim SH, Kim Y, Shin M, Hong M, Bae H (2009) Inhibition effects of Vitex rotundifolia on inflammatory gene expression in A549 human epithelial cells. Ann Allergy Asthma Immunol 103(2):152–159.  https://doi.org/10.1016/S1081-1206(10)60169-X CrossRefPubMedGoogle Scholar
  40. Tabari MA, Youssefi MR, Esfandiari A, Benelli G (2017) Toxicity of beta-citronellol, geraniol and linalool from Pelargonium roseum essential oil against the West Nile and filariasis vector Culex pipiens (Diptera: Culicidae). Res Vet Sci 114:36–40.  https://doi.org/10.1016/j.rvsc.2017.03.001 CrossRefPubMedGoogle Scholar
  41. Tawaha K, Hudaib M (2010) Volatile oil profiles of the aerial parts of Jordanian garland, Chrysanthemum coronarium. Pharm Biol 48(10):1108–1114CrossRefGoogle Scholar
  42. Tolle MA (2009) Mosquito-borne diseases. Curr Probl Pediatr Adolesc Health Care 39(4):97–140.  https://doi.org/10.1016/j.cppeds.2009.01.001 CrossRefPubMedGoogle Scholar
  43. Uehara A, Kitajima J, Kokubugata G, Iwashina T (2014) Further characterization of foliar flavonoids in Crossostephium chinense and their geographic variation. Nat Prod Commun 9(2):163–164PubMedGoogle Scholar
  44. Vijayakumar S, Vinoj G, Malaikozhundan B, Shanthi S, Vaseeharan B (2015) Plectranthus amboinicus leaf extract mediated synthesis of zinc oxide nanoparticles and its control of methicillin resistant Staphylococcus aureus biofilm and blood sucking mosquito larvae. Spectrochim Acta A Mol Biomol Spectrosc 137:886–891.  https://doi.org/10.1016/j.saa.2014.08.064 CrossRefPubMedGoogle Scholar
  45. Waliwitiya R, Kennedy CJ, Lowenberger CA (2009) Larvicidal and oviposition-altering activity of monoterpenoids, trans-anithole and rosemary oil to the yellow fever mosquito Aedes aegypti (Diptera: Culicidae). Pest Manag Sci 65(3):241–248CrossRefGoogle Scholar
  46. Wang Y, Wu Q, Yang XW, Yang X, Wang K (2011) The membrane transport of flavonoids from Crossostephium chinense across the Caco-2 monolayer. Biopharm Drug Dispos 32(1):16–24CrossRefGoogle Scholar
  47. Watanabe K, Takada Y, Matsuo N, Nishimura H (1995) Rotundial, a new natural mosquito repellent from the leaves of Vitex rotundifolia. Biosci Biotechnol Biochem 59(10):1979–1980CrossRefGoogle Scholar
  48. Wu Q, Yang X, Zou L, Fu D (2009a) Bioactivity guided isolation of alpha-glucosidase inhibitor from whole herbs of Crossostephium chinense. Zhongguo Zhong Yao Za Zhi 34(17):2206–2211PubMedGoogle Scholar
  49. Wu Q, Zou L, Yang XW, Fu DX (2009b) Novel sesquiterpene and coumarin constituents from the whole herbs of Crossostephium chinense. J Asian Nat Prod Res 11(1):85–90CrossRefGoogle Scholar
  50. Yakob L, Dunning R, Yan GY (2011) Indoor residual spray and insecticide-treated bednets for malaria control: theoretical synergisms and antagonisms. J R Soc Interface 8(59):799–806.  https://doi.org/10.1098/rsif.2010.0537 CrossRefPubMedGoogle Scholar
  51. Ye Q, Zhang QY, Zheng CJ, Wang Y, Qin LP (2010) Casticin, a flavonoid isolated from Vitex rotundifolia, inhibits prolactin release in vivo and in vitro. Acta Pharmacol Sin 31(12):1564–1568CrossRefGoogle Scholar
  52. You KM, Son KH, Chang HW, Kang SS, Kim HP (1998) Vitexicarpin, a flavonoid from the fruits of Vitex rotundifolia, inhibits mouse lymphocyte proliferation and growth of cell lines in vitro. Planta Med 64(6):546–550CrossRefGoogle Scholar
  53. Zhang B, Liu L, Zhao S, Wang X, Liu L, Li S (2013) Vitexicarpin acts as a novel angiogenesis inhibitor and its target network. Evid Based Complement Altern Med 2013:278405Google Scholar
  54. Zhang Z, Xie Y, Wang Y, Lin Z, Wang L, Li G (2017) Toxicities of monoterpenes against housefly, Musca domestica L. (Diptera: Muscidae). Environ Sci Pollut Res Int 24(31):24708–24713CrossRefGoogle Scholar
  55. Zhao YY, Guo L, Cao LJ, Zhang J, Yin ZQ (2017) A new iridoid glycoside from the fruits of Vitex rotundifolia. Nat Prod Res 31(21):2491–2496CrossRefGoogle Scholar
  56. Zou L, Wu Q, Yang X, Fu D (2009) Effects of chemical constituents of Crossostephium chinense on insulin secretion in rat islets in vitro. Zhongguo Zhong Yao Za Zhi 34(11):1401–1405PubMedGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  • Hsiang-Ting Huang
    • 1
  • Chien-Chung Lin
    • 2
  • Tai-Chih Kuo
    • 3
  • Shiang-Jiuun Chen
    • 4
  • Rong-Nan Huang
    • 1
    Email author
  1. 1.Department of Entomology and Research Center for Plant Medicine, College of Bioresources and AgricultureNational Taiwan UniversityTaipeiTaiwan
  2. 2.Department of Orthopedic SurgeryTaipei City HospitalTaipeiTaiwan
  3. 3.Department of BiochemistryTaipei Medical UniversityTaipeiTaiwan
  4. 4.Department of Life Science, College of Life ScienceNational Taiwan UniversityTaipeiTaiwan

Personalised recommendations