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Current IssueEditorial BoardOnline First ArticlesArchive

Research Article

volume 54 issue 5 (october 2020) : 571-577,   Doi: 10.18805/IJARe.A-5408

Isolation and Identification of Insect Antifeedant Compound from Ethanol Extract of Hemidesmus indicus Root

M
Maya G. Pillai
S
Susha Dayanandan
B
Beena Joy
1Centre for Innovation in Science and Social Action (CISSA), Thiruvananthapuram-695 010, Kerala, India.
Cite article:- Pillai G. Maya, Dayanandan Susha, Joy Beena (2020). Isolation and Identification of Insect Antifeedant Compound from Ethanol Extract of Hemidesmus indicus Root. Indian Journal of Agricultural Research. 54(5): 571-577. doi: 10.18805/IJARe.A-5408.

ABSTRACT

Phytochemicals with insect antifeedant potential can be used as a safer alternative to harmful chemicals that are used as grain protectants. The insect antifeedant effect of the extracts and fractions of Hemidesmus indicus root were tested against the stored grain insect pest Corcyra cephalonica Stainton. Bioactivity-guided study of ethanol extract of Hemidesmus indicus root led to isolation and identification of a triterpenoid, Lupeol with insect antifeedant potential. Although Lupeol showed insect antifeedant potential the ethanol extract was found to be more effective as an antifeedant. This implies that the synergistic action of compounds present in the ethanol extract of H. indicus root is responsible for the higher antifeedant potential.

REFERENCES

  1. Abdel-Rahman, H. R. and Al-Mozini, R. N. (2007). Antifeedant and toxic activity of some plant extracts against larvae of cotton leafworm Spodoptera littoralis (Lepidoptera: Noctuidae). Pakistan Journal of Biological Sciences, 10 (24): 4467–4472. http://www.docsdrive.com/pdfs/ansinet/ pjbs/2007/4467-4472.pdf.
  2. AlJabr, A.M., Hussain, A., Rizwan-ul-Haq, M. and Al-Ayedh, H. (2017). Toxicity of plant secondary metabolites modulating detoxification genes expression for natural red Palm Weevil Pesticide development. Molecules. 22(1).
  3. Atanasov, A.G. (2015, December). Discovery and resupply of pharmacologically active plant-derived natural products: A review 33: 1582–1614).https://doi.org/10.1016/j.biotechadv.2015.08.001.
  4. Caballero, C., Castaera, P., Ortego, F., Fontana, G., Pierro, P., Savona, G. and Rodríguez, B. (2001). Effects of ajugarins and related neoclerodane diterpenoids on feeding behaviour of Leptinotarsa decemlineata and Spodoptera exigua larvae. Phytochemistry. 58(2): 249–256. https://    doi.org/10.1016/S0031-9422(01)00253-9.
  5. Castellano, J.M., Guinda, A., Delgado, T., Rada, M. and Cayuela, J.A. (2013). Biochemical basis of the antidiabetic activity of oleanolic acid and related pentacyclic Triterpenes. Diabetes. 62(6): 1791 LP – 1799. Retrieved from http://diabetes.diabetesjournals.org/content/62/6/1791.abstract.
  6. Chen, C.-C., Wu, J.-H., Yang, N.-S., Chang, J.-Y., Kuo, C.-C., Wang, S.-Y. and Kuo, Y.-H. (2010). Cytotoxic C(35) terpenoid cryptotrione from the bark of Cryptomeria japonica. Organic Letters. 12(12): 2786–2789. https://doi.org/10. 1021/ol1009027.
  7. Danelli, M.G.M., Soares, D.C., Abreu, H.S., Pe??anha, L.M.T. and Saraiva, E.M. (2009). Leishmanicidal effect of LLD-3 (1), a nor-triterpene isolated from Lophanthera lactescens. Phytochemistry. 70(5): 608–614. https://doi.org/10.1016/j.phytochem.2009.03.009.
  8. de Andrade, S.F., Comunello, E., Noldin, V.F., Monache, F.D., Cechinel Filho, V. and Niero, R. (2008). Antiulcerogenic activity of fractions and 3,15-dioxo-21alpha-hydroxy friedelane isolated from Maytenus robusta (Celastraceae). Archives of Pharmacal Research. 31(1): 41–46.
  9. Dzubak, P., Hajduch, M., Vydra, D., Hustova, A., Kvasnica, M., Biedermann, D., … Sarek, J. (2005). Pharmacological activities of natural triterpenoids and their therapeutic implications. Nat. Prod. Rep. 2: 1990–2005. https: //doi. org/10.1039/b515312n.
  10. Dzubak, P., Hajduch, M., Vydra, D., Hustova, A., Kvasnica, M., Biedermann, D., … Sarek, J. (2006a). Pharmacological activities of natural triterpenoids and their therapeutic implications. Natural Product Reports. 23(3): 394–411. https://doi.org/10.1039/b515312n.
  11. Fiorentino, A., D’Abrosca, B., Pacifico, S., Mastellone, C., Piccolella, S. and Monaco, P. (2007). isolation, structure elucidation and antioxidant evaluation of cydonioside A, an unusual terpenoid from the fruits of Cydonia vulgaris. Chemistry and Biodiversity. 4(5): 973–979. https://doi.org/10.1002/cbdv.200790088.
  12. Gordaliza, M. (2010). Cytotoxic terpene quinones from marine sponges. Marine Drugs. 8(12): 2849–2870.https://doi.org/10.3390/md8122849.
  13. Ho, S. H., Wang, J., Sim, K. Y., Ee, G. C. L., Imiyabir, Z., Yap, K. F., … Goh, S. H. (2003). Meliternatin: A feeding deterrent and larvicidal polyoxygenated flavone from Melicope subunifoliolata. Phytochemistry. 62(7): 1121–1124. https: //doi.org/10.1016/S00319422(02)00632-5.
  14. Isman, M. (2002). Insect antifeedants. Pesticide Outlook. 13(4): 152–157. https://doi.org/10.1039/b206507j.
  15. Isman, M.B. (2006). Botanical insecticides, deterrents and repellents in modern agriculture and an increasingly regulated world. Annual Review of Entomology. 51(1): 45–66. https: //doi. org/10.1146/annurev.ento.51.110104.151146.
  16. Isman, M. B., Koul, O., Luczynski, A. and Kaminski, J. (1990). Insecticidal and antifeedant bioactivities of neem oils and their relationship to azadirachtin content. Journal of Agricultural and Food Chemistry. 38(6): 1406–1411. https: //doi.org/10.1021/jf00096a024.
  17. Koneri, R.B., Samaddar, S., Simi, S.M. and Rao, S.T. (2014). Neuroprotective effect of a triterpenoid saponin isolated from Momordica cymbalaria Fenzl in diabetic peripheral neuropathy. Indian Journal of Pharmacology. 46(1): 76-81.https://doi.org/10.4103/02537613.125179.
  18. Koul, O. (2008). Phytochemicals and insect control: An antifeedant approach. Critical Reviews in Plant Sciences. 27(1): 1-    24. https://doi.org/10.1080/07352680802053908.
  19. Kuo, R.-Y., Qian, K., Morris-Natschke, S. L. and Lee, K.-H. (2009, October). Plant-derived triterpenoids and analogues as antitumor and anti-HIV agents. Natural Product Reports. 26: 1321–1344. https://doi.org/10.1039/b810774m.
  20. Li, Z.-W., Kuang, Y., Tang, S.-N., Li, K., Huang, Y., Qiao, X., … Ye, M. (2017). Hepatoprotective activities of Antrodia camphorata and its triterpenoid compounds against CCl4-    induced liver injury in mice. Journal of Ethnopharmacology. 206: 31-39. https://doi.org/10.1016/j.jep.2017.05.020.
  21. Mahato, S.B., Nandy, A.K. and Roy, G. (1992). Triterpenoids. Phytochemistry. 31: 2199–2249. https://doi.org/10. 1016/0031-9422(92)83257-Y.
  22. Miresmailli, S. and Isman, M. B. (2014). Botanical insecticides inspired by plant-herbivore chemical interactions. Trends in Plant Science. 19. https://doi.org/10.1016/j.tplants. 2013.10.002.
  23. Nawaz, M., Cai, W., Jing, Z., Zhou, X., Mabubu, J. I. and Hua, H. (2017). Toxicity and sublethal effects of chlorantraniliprole on the development and fecundity of a non-specific predator, the multicolored Asian lady beetle, Harmonia axyridis (Pallas). Chemosphere. 178: 496-503. https://doi.org/10.1016/j.chemosphere.2017.03.082.
  24. Nazaruk, J. and Borzym-Kluczyk, M. (2015). The role of triterpenes in the management of diabetes mellitus and its complications. Phytochemistry Reviews. 14: 675–690. https://doi.org/10.1007/s11101-014-9369-x.
  25. Nieto, F.R., Cobos, E.J., Entrena, J. M., Parra, A., Garcia-Granados, A. and Baeyens, J. M. (2013). Antiallodynic and analgesic effects of maslinic acid, a pentacyclic triterpenoid from Olea europaea. Journal of Natural Products. 76(4): 737–    740. https://doi.org/10.1021/np300783a.
  26. Patil, R., Patil, R., Ahirwar, B. and Ahirwar, D. (2011). Isolation and characterization of anti-diabetic component (bioactivity-guided fractionation) from Ocimum sanctum L. (Lamiaceae) aerial part. Asian Pacific Journal of Tropical Medicine. 4(4): 278–282. https://doi.org/https://doi.org/10.1016/    S1995-7645(11)60086-2.
  27. Pavela, R. (2010). Antifeedant activity of plant extracts on Leptinotarsa decemlineata Say. and Spodoptera littoralis Bois. larvae. Industrial Crops and Products. 32(3): 213–219. https:// doi.org/10.1016/j.indcrop.2010.04.010.
  28. Shanmugam, M.K., Nguyen, A.H., Kumar, A.P., Tan, B.K.H. and Sethi, G. (2012). Targeted inhibition of tumor proliferation, survival and metastasis by pentacyclic triterpenoids: Potential role in prevention and therapy of cancer. Cancer Letters. 320: 158–170. https://doi.org/10.1016/j.canlet.2012.02.037.
  29. Thoison, O., Sévenet, T., Niemeyer, H. M. and Russell, G. B. (2004). Insect antifeedant compounds from Nothofagus dombeyi and N. pumilio. Phytochemistry. 65(14): 2173–2176. https://doi.org/10.1016/j.phytochem.2004.04.002.
  30. Wu, C.R., Hseu, Y.C., Lien, J.C., Lin, L.W., Lin, Y.T. and Ching, H. (2010). Triterpenoid contents and anti-in fl ammatory properties of the methanol extracts of ligustrum species leaves. Molecules (Basel, Switzerland). 16(1): 1–15. https://doi.org/10.3390/molecules16010001.
  31. Wu, H., Tang, S., Huang, Z., Zhou, Q., Zhang, P. and Chen, Z. (2016). Hepatoprotective Effects and Mechanisms of Action of Triterpenoids from Lingzhi or Reishi Medicinal Mushroom Ganoderma lucidum (Agaricomycetes) on alpha-Amanitin-Induced Liver Injury in Mice. International Journal of Medicinal Mushrooms. 18(9): 841–850. https://doi.org/10.1615/IntJMedMushrooms.v18.i9.80.
  32. Yuan, W.H., Yi, Y., Tang, H.F., Liu, B.-S., Wang, Z.L., Sun, G.Q., … Sun, P. (2009). Antifungal Triterpene Glycosides from the Sea Cucumber Bohadschia marmorata. Planta Med. 75 (02): 168–173. https://doi.org/10. 1055/s-0028-1088348.
  33. Zhou, M., Zhang, R. H., Wang, M., Xu, G. B. and Liao, S. G. (2017). Prodrugs of triterpenoids and their derivatives. European Journal of Medicinal Chemistry. 131: 222–236. https://doi.org/10.1016/j.ejmech.2017.03.005.
  34. Zhu, J., Zhang, Y., Ghosh, A., Cuevas, R.A., Forero, A., Dhar, J., Sarkar, S.N. (2014). Antiviral activity of human OASL protein is mediated by enhancing signaling of the RIG-I RNA sensor. Immunity. 40(6): 936–948. https://doi.org/10.1016/j.immuni.2014.05.007.
     
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    Research Article

    volume 54 issue 5 (october 2020) : 571-577,   Doi: 10.18805/IJARe.A-5408

    Isolation and Identification of Insect Antifeedant Compound from Ethanol Extract of Hemidesmus indicus Root

    M
    Maya G. Pillai
    S
    Susha Dayanandan
    B
    Beena Joy
    1Centre for Innovation in Science and Social Action (CISSA), Thiruvananthapuram-695 010, Kerala, India.
    Cite article:- Pillai G. Maya, Dayanandan Susha, Joy Beena (2020). Isolation and Identification of Insect Antifeedant Compound from Ethanol Extract of Hemidesmus indicus Root. Indian Journal of Agricultural Research. 54(5): 571-577. doi: 10.18805/IJARe.A-5408.

    ABSTRACT

    Phytochemicals with insect antifeedant potential can be used as a safer alternative to harmful chemicals that are used as grain protectants. The insect antifeedant effect of the extracts and fractions of Hemidesmus indicus root were tested against the stored grain insect pest Corcyra cephalonica Stainton. Bioactivity-guided study of ethanol extract of Hemidesmus indicus root led to isolation and identification of a triterpenoid, Lupeol with insect antifeedant potential. Although Lupeol showed insect antifeedant potential the ethanol extract was found to be more effective as an antifeedant. This implies that the synergistic action of compounds present in the ethanol extract of H. indicus root is responsible for the higher antifeedant potential.

    REFERENCES

    1. Abdel-Rahman, H. R. and Al-Mozini, R. N. (2007). Antifeedant and toxic activity of some plant extracts against larvae of cotton leafworm Spodoptera littoralis (Lepidoptera: Noctuidae). Pakistan Journal of Biological Sciences, 10 (24): 4467–4472. http://www.docsdrive.com/pdfs/ansinet/ pjbs/2007/4467-4472.pdf.
    2. AlJabr, A.M., Hussain, A., Rizwan-ul-Haq, M. and Al-Ayedh, H. (2017). Toxicity of plant secondary metabolites modulating detoxification genes expression for natural red Palm Weevil Pesticide development. Molecules. 22(1).
    3. Atanasov, A.G. (2015, December). Discovery and resupply of pharmacologically active plant-derived natural products: A review 33: 1582–1614).https://doi.org/10.1016/j.biotechadv.2015.08.001.
    4. Caballero, C., Castaera, P., Ortego, F., Fontana, G., Pierro, P., Savona, G. and Rodríguez, B. (2001). Effects of ajugarins and related neoclerodane diterpenoids on feeding behaviour of Leptinotarsa decemlineata and Spodoptera exigua larvae. Phytochemistry. 58(2): 249–256. https://    doi.org/10.1016/S0031-9422(01)00253-9.
    5. Castellano, J.M., Guinda, A., Delgado, T., Rada, M. and Cayuela, J.A. (2013). Biochemical basis of the antidiabetic activity of oleanolic acid and related pentacyclic Triterpenes. Diabetes. 62(6): 1791 LP – 1799. Retrieved from http://diabetes.diabetesjournals.org/content/62/6/1791.abstract.
    6. Chen, C.-C., Wu, J.-H., Yang, N.-S., Chang, J.-Y., Kuo, C.-C., Wang, S.-Y. and Kuo, Y.-H. (2010). Cytotoxic C(35) terpenoid cryptotrione from the bark of Cryptomeria japonica. Organic Letters. 12(12): 2786–2789. https://doi.org/10. 1021/ol1009027.
    7. Danelli, M.G.M., Soares, D.C., Abreu, H.S., Pe??anha, L.M.T. and Saraiva, E.M. (2009). Leishmanicidal effect of LLD-3 (1), a nor-triterpene isolated from Lophanthera lactescens. Phytochemistry. 70(5): 608–614. https://doi.org/10.1016/j.phytochem.2009.03.009.
    8. de Andrade, S.F., Comunello, E., Noldin, V.F., Monache, F.D., Cechinel Filho, V. and Niero, R. (2008). Antiulcerogenic activity of fractions and 3,15-dioxo-21alpha-hydroxy friedelane isolated from Maytenus robusta (Celastraceae). Archives of Pharmacal Research. 31(1): 41–46.
    9. Dzubak, P., Hajduch, M., Vydra, D., Hustova, A., Kvasnica, M., Biedermann, D., … Sarek, J. (2005). Pharmacological activities of natural triterpenoids and their therapeutic implications. Nat. Prod. Rep. 2: 1990–2005. https: //doi. org/10.1039/b515312n.
    10. Dzubak, P., Hajduch, M., Vydra, D., Hustova, A., Kvasnica, M., Biedermann, D., … Sarek, J. (2006a). Pharmacological activities of natural triterpenoids and their therapeutic implications. Natural Product Reports. 23(3): 394–411. https://doi.org/10.1039/b515312n.
    11. Fiorentino, A., D’Abrosca, B., Pacifico, S., Mastellone, C., Piccolella, S. and Monaco, P. (2007). isolation, structure elucidation and antioxidant evaluation of cydonioside A, an unusual terpenoid from the fruits of Cydonia vulgaris. Chemistry and Biodiversity. 4(5): 973–979. https://doi.org/10.1002/cbdv.200790088.
    12. Gordaliza, M. (2010). Cytotoxic terpene quinones from marine sponges. Marine Drugs. 8(12): 2849–2870.https://doi.org/10.3390/md8122849.
    13. Ho, S. H., Wang, J., Sim, K. Y., Ee, G. C. L., Imiyabir, Z., Yap, K. F., … Goh, S. H. (2003). Meliternatin: A feeding deterrent and larvicidal polyoxygenated flavone from Melicope subunifoliolata. Phytochemistry. 62(7): 1121–1124. https: //doi.org/10.1016/S00319422(02)00632-5.
    14. Isman, M. (2002). Insect antifeedants. Pesticide Outlook. 13(4): 152–157. https://doi.org/10.1039/b206507j.
    15. Isman, M.B. (2006). Botanical insecticides, deterrents and repellents in modern agriculture and an increasingly regulated world. Annual Review of Entomology. 51(1): 45–66. https: //doi. org/10.1146/annurev.ento.51.110104.151146.
    16. Isman, M. B., Koul, O., Luczynski, A. and Kaminski, J. (1990). Insecticidal and antifeedant bioactivities of neem oils and their relationship to azadirachtin content. Journal of Agricultural and Food Chemistry. 38(6): 1406–1411. https: //doi.org/10.1021/jf00096a024.
    17. Koneri, R.B., Samaddar, S., Simi, S.M. and Rao, S.T. (2014). Neuroprotective effect of a triterpenoid saponin isolated from Momordica cymbalaria Fenzl in diabetic peripheral neuropathy. Indian Journal of Pharmacology. 46(1): 76-81.https://doi.org/10.4103/02537613.125179.
    18. Koul, O. (2008). Phytochemicals and insect control: An antifeedant approach. Critical Reviews in Plant Sciences. 27(1): 1-    24. https://doi.org/10.1080/07352680802053908.
    19. Kuo, R.-Y., Qian, K., Morris-Natschke, S. L. and Lee, K.-H. (2009, October). Plant-derived triterpenoids and analogues as antitumor and anti-HIV agents. Natural Product Reports. 26: 1321–1344. https://doi.org/10.1039/b810774m.
    20. Li, Z.-W., Kuang, Y., Tang, S.-N., Li, K., Huang, Y., Qiao, X., … Ye, M. (2017). Hepatoprotective activities of Antrodia camphorata and its triterpenoid compounds against CCl4-    induced liver injury in mice. Journal of Ethnopharmacology. 206: 31-39. https://doi.org/10.1016/j.jep.2017.05.020.
    21. Mahato, S.B., Nandy, A.K. and Roy, G. (1992). Triterpenoids. Phytochemistry. 31: 2199–2249. https://doi.org/10. 1016/0031-9422(92)83257-Y.
    22. Miresmailli, S. and Isman, M. B. (2014). Botanical insecticides inspired by plant-herbivore chemical interactions. Trends in Plant Science. 19. https://doi.org/10.1016/j.tplants. 2013.10.002.
    23. Nawaz, M., Cai, W., Jing, Z., Zhou, X., Mabubu, J. I. and Hua, H. (2017). Toxicity and sublethal effects of chlorantraniliprole on the development and fecundity of a non-specific predator, the multicolored Asian lady beetle, Harmonia axyridis (Pallas). Chemosphere. 178: 496-503. https://doi.org/10.1016/j.chemosphere.2017.03.082.
    24. Nazaruk, J. and Borzym-Kluczyk, M. (2015). The role of triterpenes in the management of diabetes mellitus and its complications. Phytochemistry Reviews. 14: 675–690. https://doi.org/10.1007/s11101-014-9369-x.
    25. Nieto, F.R., Cobos, E.J., Entrena, J. M., Parra, A., Garcia-Granados, A. and Baeyens, J. M. (2013). Antiallodynic and analgesic effects of maslinic acid, a pentacyclic triterpenoid from Olea europaea. Journal of Natural Products. 76(4): 737–    740. https://doi.org/10.1021/np300783a.
    26. Patil, R., Patil, R., Ahirwar, B. and Ahirwar, D. (2011). Isolation and characterization of anti-diabetic component (bioactivity-guided fractionation) from Ocimum sanctum L. (Lamiaceae) aerial part. Asian Pacific Journal of Tropical Medicine. 4(4): 278–282. https://doi.org/https://doi.org/10.1016/    S1995-7645(11)60086-2.
    27. Pavela, R. (2010). Antifeedant activity of plant extracts on Leptinotarsa decemlineata Say. and Spodoptera littoralis Bois. larvae. Industrial Crops and Products. 32(3): 213–219. https:// doi.org/10.1016/j.indcrop.2010.04.010.
    28. Shanmugam, M.K., Nguyen, A.H., Kumar, A.P., Tan, B.K.H. and Sethi, G. (2012). Targeted inhibition of tumor proliferation, survival and metastasis by pentacyclic triterpenoids: Potential role in prevention and therapy of cancer. Cancer Letters. 320: 158–170. https://doi.org/10.1016/j.canlet.2012.02.037.
    29. Thoison, O., Sévenet, T., Niemeyer, H. M. and Russell, G. B. (2004). Insect antifeedant compounds from Nothofagus dombeyi and N. pumilio. Phytochemistry. 65(14): 2173–2176. https://doi.org/10.1016/j.phytochem.2004.04.002.
    30. Wu, C.R., Hseu, Y.C., Lien, J.C., Lin, L.W., Lin, Y.T. and Ching, H. (2010). Triterpenoid contents and anti-in fl ammatory properties of the methanol extracts of ligustrum species leaves. Molecules (Basel, Switzerland). 16(1): 1–15. https://doi.org/10.3390/molecules16010001.
    31. Wu, H., Tang, S., Huang, Z., Zhou, Q., Zhang, P. and Chen, Z. (2016). Hepatoprotective Effects and Mechanisms of Action of Triterpenoids from Lingzhi or Reishi Medicinal Mushroom Ganoderma lucidum (Agaricomycetes) on alpha-Amanitin-Induced Liver Injury in Mice. International Journal of Medicinal Mushrooms. 18(9): 841–850. https://doi.org/10.1615/IntJMedMushrooms.v18.i9.80.
    32. Yuan, W.H., Yi, Y., Tang, H.F., Liu, B.-S., Wang, Z.L., Sun, G.Q., … Sun, P. (2009). Antifungal Triterpene Glycosides from the Sea Cucumber Bohadschia marmorata. Planta Med. 75 (02): 168–173. https://doi.org/10. 1055/s-0028-1088348.
    33. Zhou, M., Zhang, R. H., Wang, M., Xu, G. B. and Liao, S. G. (2017). Prodrugs of triterpenoids and their derivatives. European Journal of Medicinal Chemistry. 131: 222–236. https://doi.org/10.1016/j.ejmech.2017.03.005.
    34. Zhu, J., Zhang, Y., Ghosh, A., Cuevas, R.A., Forero, A., Dhar, J., Sarkar, S.N. (2014). Antiviral activity of human OASL protein is mediated by enhancing signaling of the RIG-I RNA sensor. Immunity. 40(6): 936–948. https://doi.org/10.1016/j.immuni.2014.05.007.
       
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