Copyright (c) 2020 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Isolation, Semi-Synthesis and Antifeedant Activity of Constituents from Derris scandens Benth.
Corresponding Author(s) : K. Ramakrishna
Asian Journal of Chemistry,
Vol. 32 No. 10 (2020): Vol 32 Issue 10
Abstract
This work describes the semi-synthesis of derivatives from derris isoflavone-A (1), scandenin (2) and 6,8-diprenyl-4′,5,7-trihydroxy isoflavone (3) which are major constituents isolated from chloroform extract of Derris scandens Benth. All the semi-synthesized derivatives (4-11) were characterized by NMR and mass spectroscopic techniques. All these derivatives are evaluated for their antifeedant activity in castor semilooper and tobacco caterpillar using a no-choice laboratory bioassay. The results demonstrated that scandenin (2), compounds 5, 7 and 10 have shown potent insecticidal activity.
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- G.S. Dhaliwal, V. Jindal and B. Mohindru, Indian J. Entomol., 77, 165 (2015); https://doi.org/10.5958/0974-8172.2015.00033.4
- G.V.R. Rao, J.A. Wightman and D.V.R. Rao, Insect Sci. Appl., 14, 273 (1993); https://doi.org/10.1017/S1742758400014764
- C.A. Deutsch, J.J. Tewksbury, M. Tigchelaar, D.S. Battisti, S.C. Merrill, R.B. Huey and R.L. Naylor, Science, 361, 916 (2018); https://doi.org/10.1126/science.aat3466
- R. Brun, M. Niehues, T.J. Schmidt, S.A. Khalid, A.J. Romanha, T.M. Alves, M.W. Biavatti, R. Brun, F.B. Costa, S.L. Castro and V.F. Ferreira, Curr. Med. Chem., 19, 2128 (2012); https://doi.org/10.2174/092986712800229023
- T. Sreelatha, A. Hymavathi, V. Rama Subba Rao, P. Devanand, P. Usha Rani, J. Madhusudana Rao and K. Suresh Babu, Bioorg. Med. Chem. Lett., 20, 549 (2010); https://doi.org/10.1016/j.bmcl.2009.11.103
- P. Laupattarakasem, P.J. Houghton and J.R. Hoult, Planta Med., 70, 496 (2004); https://doi.org/10.1055/s-2004-827147
- B.N. Dhawan, G.K. Patnaik, R.P. Rastogi, K.K.S. Singh and J.S. Tandon, Indian J. Exp. Biol., 15, 208 (1977).
- W. Mahabusarakam, S. Deachathai, S. Phongpaichit, C. Jansakul and W.C. Taylor, Phytochemistry, 65, 1185 (2004); https://doi.org/10.1016/j.phytochem.2004.03.006
- A. Chuthaputti and P. Chavalittumrong, J. Pharm. Sci., 22, 137 (1998).
- C. Jansakul, A. Srichanbarn and A. Saelee, J. Sci. Soc. Thailand, 23, 323 (1997); https://doi.org/10.2306/scienceasia1513-1874.1997.23.323
- M. Chuankamnerdkarn, S. Sutthivaiyakit, S. Pisutjaroenpong and N. Thasana, Heterocycles, 57, 1901 (2002); https://doi.org/10.3987/COM-02-9544
- V. Rukachaisirikul, Y. Sukpondma, C. Jansakul and W.C. Taylor, Phytochemistry, 60, 827 (2002); https://doi.org/10.1016/S0031-9422(02)00163-2
- T. Sekine, M. Inagaki, F. Ikegami, Y. Fujii and N. Ruangrungsi, Phytochemistry, 52, 87 (1999); https://doi.org/10.1016/S0031-9422(99)00103-X
- L.I. Dianpeng, O. Mingan, C. Jansakul and Y. Chongren, Yao Xue Xue Bao, 34, 43 (1999).
- M.N. Rao, G.L.D. Krupadanam and G. Srimannarayana, Phytochemistry, 37, 267 (1994); https://doi.org/10.1016/0031-9422(94)85038-0
- C.P. Falshaw, R.A. Harmer, W.D. Ollis, R.E. Wheeler, V.R. Lalitha and N.V.S. Rao, J. Chem. Soc. C. Org., 3, 374 (1969); https://doi.org/10.1039/j39690000374
- A.P. Johnson, A. Pelter and P.J. Stainton, Chem. Soc. C. Org., 2, 192 (1966); https://doi.org/10.1039/j39660000192
- A.P. Johnson and A. Pelter, J. Chem. Soc. C. Org., 6, 606 (1966); https://doi.org/10.1039/j39660000606
- J.H. Simons and H.J. Passino, J. Am. Chem. Soc., 62, 1624 (1940); https://doi.org/10.1021/ja01863a509
- F. Fringuelli, R. Germani, F. Pizzo and G. Savelli, Tetrahedron Lett., 30, 1427 (1989); https://doi.org/10.1016/S0040-4039(00)99483-8
- P.J. Choi, D.C.K. Rathwell and M.A. Brimble, Tetrahedron Lett., 50, 3245 (2009); https://doi.org/10.1016/j.tetlet.2009.02.030
- Y. Akhtar and M.B. Isman, Entomol. Exp. Appl., 111, 201 (2004); https://doi.org/10.1111/j.0013-8703.2004.00169.x
- M.S.A. Rao, G. Suresh, P.A. Yadav, K.R. Prasad, P.U. Rani, C.V. Rao and K.S. Babu, Tetrahedron, 71, 1431 (2015); https://doi.org/10.1016/j.tet.2015.01.011
References
G.S. Dhaliwal, V. Jindal and B. Mohindru, Indian J. Entomol., 77, 165 (2015); https://doi.org/10.5958/0974-8172.2015.00033.4
G.V.R. Rao, J.A. Wightman and D.V.R. Rao, Insect Sci. Appl., 14, 273 (1993); https://doi.org/10.1017/S1742758400014764
C.A. Deutsch, J.J. Tewksbury, M. Tigchelaar, D.S. Battisti, S.C. Merrill, R.B. Huey and R.L. Naylor, Science, 361, 916 (2018); https://doi.org/10.1126/science.aat3466
R. Brun, M. Niehues, T.J. Schmidt, S.A. Khalid, A.J. Romanha, T.M. Alves, M.W. Biavatti, R. Brun, F.B. Costa, S.L. Castro and V.F. Ferreira, Curr. Med. Chem., 19, 2128 (2012); https://doi.org/10.2174/092986712800229023
T. Sreelatha, A. Hymavathi, V. Rama Subba Rao, P. Devanand, P. Usha Rani, J. Madhusudana Rao and K. Suresh Babu, Bioorg. Med. Chem. Lett., 20, 549 (2010); https://doi.org/10.1016/j.bmcl.2009.11.103
P. Laupattarakasem, P.J. Houghton and J.R. Hoult, Planta Med., 70, 496 (2004); https://doi.org/10.1055/s-2004-827147
B.N. Dhawan, G.K. Patnaik, R.P. Rastogi, K.K.S. Singh and J.S. Tandon, Indian J. Exp. Biol., 15, 208 (1977).
W. Mahabusarakam, S. Deachathai, S. Phongpaichit, C. Jansakul and W.C. Taylor, Phytochemistry, 65, 1185 (2004); https://doi.org/10.1016/j.phytochem.2004.03.006
A. Chuthaputti and P. Chavalittumrong, J. Pharm. Sci., 22, 137 (1998).
C. Jansakul, A. Srichanbarn and A. Saelee, J. Sci. Soc. Thailand, 23, 323 (1997); https://doi.org/10.2306/scienceasia1513-1874.1997.23.323
M. Chuankamnerdkarn, S. Sutthivaiyakit, S. Pisutjaroenpong and N. Thasana, Heterocycles, 57, 1901 (2002); https://doi.org/10.3987/COM-02-9544
V. Rukachaisirikul, Y. Sukpondma, C. Jansakul and W.C. Taylor, Phytochemistry, 60, 827 (2002); https://doi.org/10.1016/S0031-9422(02)00163-2
T. Sekine, M. Inagaki, F. Ikegami, Y. Fujii and N. Ruangrungsi, Phytochemistry, 52, 87 (1999); https://doi.org/10.1016/S0031-9422(99)00103-X
L.I. Dianpeng, O. Mingan, C. Jansakul and Y. Chongren, Yao Xue Xue Bao, 34, 43 (1999).
M.N. Rao, G.L.D. Krupadanam and G. Srimannarayana, Phytochemistry, 37, 267 (1994); https://doi.org/10.1016/0031-9422(94)85038-0
C.P. Falshaw, R.A. Harmer, W.D. Ollis, R.E. Wheeler, V.R. Lalitha and N.V.S. Rao, J. Chem. Soc. C. Org., 3, 374 (1969); https://doi.org/10.1039/j39690000374
A.P. Johnson, A. Pelter and P.J. Stainton, Chem. Soc. C. Org., 2, 192 (1966); https://doi.org/10.1039/j39660000192
A.P. Johnson and A. Pelter, J. Chem. Soc. C. Org., 6, 606 (1966); https://doi.org/10.1039/j39660000606
J.H. Simons and H.J. Passino, J. Am. Chem. Soc., 62, 1624 (1940); https://doi.org/10.1021/ja01863a509
F. Fringuelli, R. Germani, F. Pizzo and G. Savelli, Tetrahedron Lett., 30, 1427 (1989); https://doi.org/10.1016/S0040-4039(00)99483-8
P.J. Choi, D.C.K. Rathwell and M.A. Brimble, Tetrahedron Lett., 50, 3245 (2009); https://doi.org/10.1016/j.tetlet.2009.02.030
Y. Akhtar and M.B. Isman, Entomol. Exp. Appl., 111, 201 (2004); https://doi.org/10.1111/j.0013-8703.2004.00169.x
M.S.A. Rao, G. Suresh, P.A. Yadav, K.R. Prasad, P.U. Rani, C.V. Rao and K.S. Babu, Tetrahedron, 71, 1431 (2015); https://doi.org/10.1016/j.tet.2015.01.011