Strong Larvicidal and Molluscicidal Activities of the (E)-β-caryophyllene-rich Chemotype of Callicarpa macrophylla Vah Leaf Essential Oil Growing Wild in Vietnam

References

• Soejima, A., Tagane, S., Van, N.N., Duy, C.N., Huong, N.T.T. and Yahara, T. (2016). Callicarpa bachmaensis Soejima & Tagane (Lamiaceae), a new species from Bach Ma National Park in Thua Thien Hue Province, Central Vietnam. PhytoKeys. 62: 33-39.
   Google Scholar
• Phuông, V.X. (2007). Flora of Vietnam. Vol. 6-Verbenaceae. Hanoi, Vietnam: Science & Technics Publishing House.
   Google Scholar
• Leeratiwond, C., Chantaranothai, P. and Paton, A.J. (2009). A synopsis of the genus Callicarpa L.(Lamiaceae) in Thailand. Thai For. Bull. (Bot.). 37: 36-58.
   Google Scholar
• Lam, D.T., Le, V.T.T., Quan, P.M., Minh, P.T.H., Thuy, T.T.T., Anh, N.T.N. and Kiem, P.V. (2021). Two new terpenoids from the leaves of Callicarpa macrophylla. Nat. Prod. Res. 35(7): 1107-1114.
   PubMed Web of Science ®Google Scholar
• Wang, Z.H., Niu, C., Zhou, D.J., Kong, J.C. and Zhang, W.K. (2017). Three new abietane-type diterpenoids from Callicarpa macrophylla Vahl. Molecules 22(5): 842.
   Web of Science ®Google Scholar
• Verma, V.K., Siddiqui, N.U. and Aslam, M. (2011). Isolation of 3β,16α,17-trihydroxy-phyllocladane from the leaves of Callicarpa macrophylla Vahl. Nat. Proda. Med. Preliminary 1–3.
   Google Scholar
• Chatterjee, A., Desmukh, S.K. and Chandrasekharan, S. (1972). Diterpenoid constituents of Callicarpa macrophylla vahl: The sturctures and stereochemistry of calliterpenone and calliterpenone monoacetate. Tetrahedron. 28(16): 4319-4323.
   Web of Science ®Google Scholar
• Verma, V.K., Siddiqui, N.U. and Aslam, M. (2012). A new kaurane diterpene from the leaves of Callicarpa macrophylla vahl. Biomed. Pharmacol. J. 5(1): 189-191.
   Google Scholar
• Chandra, M., Prakash, O., Kumar, R., Bachheti, R.K., Bhushan, B., Kumar, M. and Pant, A.K. (2017). β-Selinene-rich essential oils from the parts of Callicarpa macrophylla and their antioxidant and pharmacological activities. Medicines. 4(3): 52.
   Google Scholar
• Ban, N.T. (2003). Checklist of plant species of Vietnam. Vol III. Agriculture Publishing House.
   Google Scholar
• Chi, V.V. (2012). Dictionary of Vietnamese medical plants. Hanoi: Medicine Publishing House. Medicine Publishing House.
   Google Scholar
• Yadav, V., Jayalakshmi, S., Singla, R.K. and Patra, A. (2012). Ex vivo screening of stem extracts of Callicarpa macrophylla Vahl. for antifungal activity. Indo-Glob. Res. J. Pharm. Sci. 2(2): 103-107.
   Google Scholar
• Soni, R.K., Dixit, V., Irchhaiya, R. and Alok, S. (2014). Callicarpa macrophylla: a review update on its botany, ethnobotany, phytochemistry and pharmacology. Int. J. Pharmacogn. 1(2): 87-94.
   Google Scholar
• Yadav, V., Jayalakshmi, S., Singla, R.K., Patra, A. and Khan, S. (2011). Preliminary assessment of anti-inflammatory activity of Callicarpa macrophylla Vahl. leaves extracts. Indo Global J. Pharm. Sci. 1(3): 219-222.
   Google Scholar
• Patel, R. and Jawaid, T. (2014). Hepatoprotective activity of aerial parts of plant extract of Callicarpa macrophylla in rats. J. Pharm. Pharmacol. 2(1): 1-8.
   Google Scholar
• Barkatullah, M.I., Nafees, M., Rauf, A. and Khan, H. (2015). Cytotoxic, acute toxicity and phytotoxic activity of Callicarpa macrophylla in various models. Am. J. Biomed. Life Sci. 3(2-1): 1-4.
   Google Scholar
• World Health Organization, WHO. (2022). Launch of the global arbovirus initiative. https://www.who.int/news-room/events/detail/2022/03/31/default-calendar/ global-arbovirus-initiative.
   Google Scholar
• Wilder-Smith, A., Ooi, E.E., Horstick, O. and Wills, B. (2019). Dengue. The Lancet. 393(10169): 350-363.
   PubMed Web of Science ®Google Scholar
• Sivaratnam, L., Wong, C.M., Selimin, D.S., Bakar, S.A., Ghazi, H. and Hassan, M.R. (2022). Impact of climate change on abundance, distribution, and survival of Aedes species: systematic review. Glob. J. Public Heal. Med. 4(1): 579-607.
   Google Scholar
• Bharati, M. and Saha, D. (2021). Insecticide resistance status and biochemical mechanisms involved in Aedes mosquitoes: A scoping review. Asian Pac. J. Trop. Med. 14(2): 52-63.
   Web of Science ®Google Scholar
• Miller, C.L., Kinsella, J.M., Garner, M.M., Evans, S., Gullett, P.A. and Schmidt, R.E. (2006). Endemic infections of Parastrongylus (=Angiostrongylus) costaricensis in two species of nonhuman primates, raccoons, and an opossum from Miami, Florida. J. Parasitol. 92(2): 406-408.
   PubMed Web of Science ®Google Scholar
• Komalamisra, C., Nuamtanong, S. and Dekumyoy, P. (2009). Pila ampullacea and Pomacea canaliculata, as new paratenic hosts of Gnathostoma spinigerum. Southeast Asian J. Trop. Med. Public Health. 40(2): 243-246.
   PubMed Web of Science ®Google Scholar
• Chobchuenchom, W. and Bhumiratana, A. (2003). Isolation and characterization of pathogens attacking Pomacea canaliculata. World J. Microbiol. Biotechnol. 19(9): 903-906.
   Web of Science ®Google Scholar
• Hortle, K.G. (2008). Liver and intestinal flukes: an underrated health risk in the Mekong Basin. Catch Cult. 14(2): 1-4.
   Google Scholar
• Toledo, R. and Esteban, J.G. (2016). An update on human echinostomiasis. Trans. R. Soc. Trop. Med. Hyg. 110(1): 37-45.
   PubMed Web of Science ®Google Scholar
• Yang, S., Zhong, J.R., Zhao, L.L., Wu, H., Du, Z.J., Liu, Q., Zhang, J.E., Yan, T.M. and Huang, X.L. (2018). The salinity tolerance of the invasive golden apple snail (Pomacea canaliculata). Molluscan Res. 38(2): 90-98.
   Web of Science ®Google Scholar
• Yang, T.B., Wu, Z.D. and Lun, Z.R. (2013). The apple snail Pomacea canaliculata, a novel vector of the rat lungworm, Angiostrongylus cantonensis: its introduction, spread, and control in China. Hawaii J. Med. Public Health. 72(6 Suppl 2): 23-25.
   PubMedGoogle Scholar
• Naylor, R. (1996). Invasions in agriculture: assessing the cost of the golden apple snail in Asia. Ambio. 25(7): 443-448.
   Web of Science ®Google Scholar
• Van Tu, D., Nha, N.P. and Joshi, R.C. (2018). Invasive apple snails (Pomacea spp.) in Vietnam: Short review. Aquaculture. 22(1): 3-8.
   Google Scholar
• Halwart, M. (1994). The golden apple snail Pomacea canaliculata in Asian rice farming systems: present impact and future threat. Int. J. Pest Manag. 40(2): 199-206.
   Web of Science ®Google Scholar
• Carlsson, N.O. and Lacoursiere, J.O. (2005). Herbivory on aquatic vascular plants by the introduced golden apple snail (Pomacea canaliculata) in Lao PDR. Biol. Invasions. 7(2): 233-241.
   Web of Science ®Google Scholar
• Calumpang, S.M.F., Medina, M.J.B., Tejada, A.W. and Medina, J.R. (1995). Environmental impact of two molluscicides: niclosamide and metaldehyde in a rice paddy ecosystem. Bull. Environ. Contam. Toxicol. 55(4): 494-501.
   PubMed Web of Science ®Google Scholar
• Castle, G.D., Mills, G.A., Gravell, A., Jones, L., Townsend, I., Cameron, D.G. and Fones, G.R. (2017). Review of the molluscicide metaldehyde in the environment. Environ. Sci. Water Res. Technol. 3(3): 415-428.
   Google Scholar
• Radwan, M.A. and Gad, A.F. (2021). Essential oils and their components as promising approach for gastropod mollusc control: a review. J. Plant Dis. Prot. 128(4): 923-949.
   Web of Science ®Google Scholar
• Djeddour, D., Pratt, C., Makale, F., Rwomushana, I. and Day, R. (2021). The apple snail, Pomacea canaliculata: an evidence note on invasiveness and potential economic impacts for East Africa. CABI Working Paper. 21: 77.
   Google Scholar
• Joshi, R.C., Desamito, M.S., Martin, A.R., Sebastian, L.S. and Coupland, J.B. (2004). Detrimental effects of niclosamide 250EC at preseeding in direct-seeded rice culture. Int. Rice Res. Notes. 29(2): 36-37.
   Google Scholar
• World Health Organization, WHO. (2014). Aglobal brief on vector-borne diseases. http://apps.who.int/iris/bitstream/10665/111008/1/WHO_DCO_WHD_2014.1_eng.pdf.
   Google Scholar
• Pavela, R. (2015). Essential oils for the development of eco-friendly mosquito larvicides: a review. Ind. Crops Prod. 76: 174-187.
   Web of Science ®Google Scholar
• Begum, T., Gogoi, R., Sarma, N., Pandey, S.K. and Lal, M. (2022). Direct sunlight and partial shading alter the quality, quantity, biochemical activities of Kaempferia parviflora Wall., ex Baker rhizome essential oil: A high industrially important species. Ind. Crops Prod. 180: 114765.
   Web of Science ®Google Scholar
• Dutta, P., Sarma, N., Saikia, S., Gogoi, R., Begum. T. and Lal, M. (2021). Pharmacological activity of Trachyspermum ammi L. seeds essential oil grown from Northeast India. J. Essent. Oil Bear. Plants. 24(6): 1373-1388.
   Web of Science ®Google Scholar
• Sarma, N., Begum. T., Pandey, S.K., Gogoi, R., Munda, S., Lal, M. (2020). Chemical Composition of Syzygium cumini (L.) Skeels leaf essential oil with respect to its uses from North East Region of India. J. Essent. Oil Bear. Plants. 23(3): 601-607.
   Web of Science ®Google Scholar
• Pandey, S.K., Sarma, N., Begum, T. and Lal, M. (2020). Standardization of different drying methods of fresh patchouli (Pogostemon cablin) leaves for high essential oil yield and quality. J. Essent. Oil Bear. Plants. 23(3): 484-492.
   Web of Science ®Google Scholar
• Hung, N.H., Huong, L.T., Chung, N.T., Thuong, N.T.H., Satyal, P., Dung, N.A., Tai, T.A. and Setzer, W.N. (2020). Callicarpa species from central Vietnam: Essential oil compositions and mosquito larvicidal activities. Plants. 9(1): 113.
   Google Scholar
• Huy Hung, N., Ngoc Dai, D., Satyal, P., Thi Huong, L., Thi Chinh, B., Quang Hung, D., Anh Tai, T. and Setzer, W.N. (2021). Lantana camara essential oils from Vietnam: Chemical composition, molluscicidal, and mosquito larvicidal activity. Chem. Biodivers. 18(5): e2100145.
   PubMed Web of Science ®Google Scholar
• Ellman, G.L., Courtney, K.D., Andres Jr, V. and Featherstone, R.M. (1961). A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 7(2): 88-95.
   PubMed Web of Science ®Google Scholar
• Finney, D. (2009). Probit Analysis. Cambridge University Press, Cambridge, UK.
   Google Scholar
• Singh, A.K., Chanotiya, C.S., Yadav, A. and Kalra, A. (2010). Volatiles of Callicarpa macrophylla: a rich source of selinene isomers. Nat. Prod. Commun. 5(2): 1934578X1000500.
   Web of Science ®Google Scholar
• Adams, R.P. (2017). Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry. 4th Ed. Allured Publ. Co. Carol Stream, Illinois, USA.
   Google Scholar
• Mondello, L. (2016). FFNSC 3. Shimadzu Scientific Instruments. Columbia, Maryland, USA.
   Google Scholar
• NIST17 (2017). National Institute of Standards and Technology. Gaithersburg, Maryland, USA.
   Google Scholar
• Satyal, P. (2015). 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. ProQuest Diss Theses. Published online. http://210,48.222.80/proxy.pac/docview/1837119262?accountid=44024.
   Google Scholar
• Pavela, R. (2015). Acute toxicity and synergistic and antagonistic effects of the aromatic compounds of some essential oils against Culex quinquefasciatus Say larvae. Parasitol Res. 114(10): 3835-3853.
   PubMed Web of Science ®Google Scholar
• Sarma, R., Adhikari, K., Mahanta, S. and Khanikor, B. (2019). Combinations of plant essential oil based terpene compounds as larvicidal and adulticidal agent against Aedes aegypti (Diptera: Culicidae). Sci. Rep. 9(1): 9471.
   PubMedGoogle Scholar
• Sobrinho, A.C.N., de Morais, S.M., Marinho, M.M., de Souza, N.V. and Lima, D.M. (2021). Antiviral activity on the Zika virus and larvicidal activity on the Aedes spp. of Lippia alba essential oil and β-caryophyllene. Ind. Crops Prod. 162(July 2020): 113281.
   Web of Science ®Google Scholar
• 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. and Cavalcanti, S.C.H. (2008). Effects of essential oils on Aedes aegypti larvae: alternatives to environmentally safe insecticides. Bioresour. Technol. 99(8): 3251-3255.
   PubMed Web of Science ®Google Scholar
• Alı, A., Tabanca, N., Kurkcuoglu, M., Duran, A., Blythe, E.K., Khan, I.A. and Can Baser, K.H. (2014). Chemical composition, larvicidal, and biting deterrent activity of essential oils of two subspecies of Tanacetum argenteum (Asterales: Asteraceae) and individual constituents against Aedes aegypti (Diptera: Culicidae). J. Med. Entomol. 51(4): 824-830.
   PubMed Web of Science ®Google Scholar
• Cheng, S.S., Chang, H.T., Lin, C.Y., Chen, P.S., Huang, C.G., Chen, W.J. and Chang, S.T. (2009). Insecticidal activities of leaf and twig essential oils from Clausena excavata against Aedes aegypti and Aedes albopictus larvae. Pest Manag. Sci. 65(3): 339-343.
   PubMed Web of Science ®Google Scholar
• Hoi, T.M., Huong, L.T., Chinh, H.V., Hau, D.V., Satyal, P., Tai, T.A., Dai, D.N., Hung, N.H., Hien, V.T. and Setzer, W.N. (2020). Essential oil compositions of three invasive Conyza species collected in Vietnam and their larvicidal activities against Aedes aegypti, Aedes albopictus, and Culex quinquefasciatus. Molecules. 25(19): 4576.
   Web of Science ®Google Scholar
• Arriaga, A.M., Rodrigues, F.E., Lemos, T.L., de Oliveira, M.D.C., Lima, J.Q., Santiago, G.M., Braz-Filho, R. and Mafezoli, J. (2007). Composition and larvicidal activity of essential oil from Stemodia maritima L. Nat. Prod. Commun. 2(12): 1934578X0700201.
   Web of Science ®Google Scholar
• World Health Organization, WHO. UNDP/ World Bank/WHO Special programme for research and training in tropical diseases available online: https://apps.who.int/iris/ handle/10665/60086 (accessed on Mar 12, 2021).
   Google Scholar
• Pereira, L.P.L.A., Ribeiro, E.C.G., Brito, M.C.A., Silveira, D.P.B., Araruna, F.O.S., Araruna, F.B., Leite, J.A. C., Dias, A.A.S., Firmo, W.D.C.A., da Rocha Borges, M.O. and Borges, A.C.R. (2020). Essential oils as molluscicidal agents against schistosomiasis transmitting snails-A review. Acta Trop. 209: 105489.
   PubMed Web of Science ®Google Scholar
• Lahlou, M. and Berrada, R. (2001). Potential of essential oils in schistosomiasis control in Morocco. Int. J. Aromather. 11(2): 87-96.
   Google Scholar
• Rouquayrol, M.Z. (1984). Atividade moluscicida de plantas do Nordeste Brasileiro. Rev. Bras. Promoç. Saúde. 1(1): 24-26.
   Google Scholar
• Salleh, W.M.N.H.W. and Khamis, S. (2020). Chemical composition and anticholinesterase inhibitory activity of Pavetta graciliflora Wall. ex Ridl. essential oil. Z. Naturforsch., C, J. Biosci. 75(11-12): 467-471.
   Web of Science ®Google Scholar
• Ali, N.A.A., Crouch, R.A., Al-Fatimi, M.A., Arnold, N., Teichert, A., Setzer, W.N. and Wessjohann, L. (2012). Chemical composition, antimicrobial, antiradical and anticholinesterase activity of the essential oil of Pulicaria stephanocarpa from Soqotra. Nat. Prod. Commun. 7(1): 1934578X1200700.
   Web of Science ®Google Scholar
• Siebert, D.A., Tenfen, A., Yamanaka, C.N., de Cordova, C.M.M., Scharf, D.R., Simionatto, E.L. and Alberton, M.D. (2015). Evaluation of seasonal chemical composition, antibacterial, antioxidant and anticholinesterase activity of essential oil from Eugenia brasiliensis Lam. Nat. Prod. Res. 29(3): 289-292.
   PubMed Web of Science ®Google Scholar
• Karakaya, S., Yilmaz, S.V., Özdemir, Ö., Koca, M., Pınar, N.M., Demirci, B., Yıldırım, K., Sytar, O., Turkez, H. and Baser, K.H.C. (2020). A caryophyllene oxide and other potential anticholinesterase and anticancer agent in Salvia verticillata subsp. amasiaca (Freyn & Bornm.) Bornm. (Lamiaceae). J. Essent. Oil Res. 32(6): 512–525.
   Web of Science ®Google Scholar
• Kaufmann, D., Dogra, A.K. and Wink, M. (2011). Myrtenal inhibits acetylcholinesterase, a known Alzheimer target. J. Pharm. Pharmacol. 63(10): 1368-1371.
   PubMed Web of Science ®Google Scholar
• Bonesi, M., Menichini, F., Tundis, R., Loizzo, M.R., Conforti, F., Passalacqua, N.G., Statti, G.A. and Menichini, F. (2010). Acetylcholinesterase and butyrylcholinesterase inhibitory activity of Pinus species essential oils and their constituents. J. Enzyme Inhib. Med. Chem. 25(5): 622-628.
   PubMed Web of Science ®Google Scholar
• Savelev, S.U., Okello, E.J. and Perry, E.K. (2004). Butyryl- and acetyl-cholinesterase inhibitory activities in essential oils of Salvia species and their constituents. Phyther. Res. 18(4): 315-324.
   PubMed Web of Science ®Google Scholar
• Savelev, S., Okello, E., Perry, N.S.L., Wilkins, R.M. and Perry, E.K. (2003). Synergistic and antagonistic interactions of anticholinesterase terpenoids in Salvia lavandulaefolia essential oil. Pharmacol. Biochem. Behav. 75(3): 661-668.
   PubMed Web of Science ®Google Scholar
• Miyazawa, M. and Yamafuji, C. (2005). Inhibition of acetylcholinesterase activity by bicyclic monoterpenoids. J. Agric. Food Chem. 53(5): 1765-1768.
   PubMed Web of Science ®Google Scholar
• Wright, B.S., Bansal, A., Moriarity, D.M., Takaku, S. and Setzer, W.N. (2007). Cytotoxic leaf essential oils from Neotropical Lauraceae: Synergistic effects of essential oil components. Nat. Prod. Commun. 2(12): 1934578X0700201.
   Web of Science ®Google Scholar