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DOI: 10.1039/A902326G (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1999, 2367-2370

New insect-growth-regulator meliacin butenolides from the leaves of Azadirachta indica A. Juss

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Bina Shaheen Siddiqui, Farhana Afshan, Farhana Afshan, Ghiasuddin , Shaheen Faizi, Syed Naeem-ul-Hassan Naqvi, Rajput Mohammad Tariq , Shaheen Faizi, Syed Naeem-ul-Hassan Naqvi and Rajput Mohammad Tariq

Abstract

Two new triterpenoids, 23-O-methylnimocinolide [7α-acetoxy-6α-hydroxy-23ξ-methoxy-3-oxo-24,25,26,27-tetranorapotirucalla(apoeupha)-1,14,20(22)-trieno-21,23-lactone] 1, 7-O-deacetyl-23-O-methyl-7α-O-senecioylnimocinolide [6α-hydroxy-23ξ-methoxy-3-oxo-7α-senecioyloxy-24,25,26,27-tetranorapotirucalla(apoeupha)-1,14,20(22)-trieno-21,23-lactone] 2 have been isolated from the methanolic extract of the fresh leaves of Azadirachta indica (neem). Their structures were elucidated through spectral studies, including 2D NMR (NOESY, COSY-45, HMQC and HMBC). Compounds 1 and 2 show insect-growth-regulating effect on mosquitoes (Aedes aegypti) with LC50 53 ppm and 2.14 ppm, respectively. The senecioyloxy substituent at C-7 in 2 results in a significant increase of activity.

References

  1. W. Dymock, C. J. H. Warden and D. Hooper, Pharmacographia Indica 1890, The Institute of Health and Tibbi Research, New Delhi, India, republished under the auspices of the Hamdard National Foundation, Karachi, Pakistan, 1977, vol. 1, p. 89 Search PubMed.
  2. R. N. Chopra, S. L. Nayar and I. C. Chopra, Glossary of Indian Medicinal Plants, Council of Scientific and Industrial Research, New Delhi, India, 1956, p. 31 Search PubMed.
  3. T. Fujiwara, T. Takeda, Y. Ogihara, M. Shimizu, T. Nomura and Y. Tomita, Chem. Pharm. Bull., 1982, 30, 4025 CAS.
  4. S. N. Okpanyi and G. C. Ezeukwu, Planta Med., 1981, 41, 34 CAS.
  5. W. Kraus, in Neem Tree, Azadirachta Indica A. Juss and Other Meliaceous Plants, ed. H. Schmutterer, VCH Weinheim, Germany, 1995, pp. 35–74, 76–88 Search PubMed.
  6. S. Siddiqui, B. S. Siddiqui, S. Faizi and T. Mahmood, J. Nat. Prod., 1988, 51, 30 CrossRef CAS.
  7. C. Y. Ragasa, Z. D. Nacpil, G. M. Natividfad and M. Tada, Phytochemistry, 1997, 46, 555 CrossRef CAS and the references cited therein.
  8. D. Lavie, E. C. Levy and M. K. Jain, Tetrahedron, 1971, 27, 3927 CrossRef CAS.
  9. S. Siddiqui, B. S. Siddiqui, S. Faizi and T. Mahmood, Phytochemistry, 1984, 23, 2899 CrossRef CAS.
  10. S. Siddiqui, S. Faizi, T. Mahmood and B. S. Siddiqui, J. Chem. Soc., Perkin Trans. 1, 1986, 1021 RSC.
  11. W. Kraus and R. Cramer, Liebigs Ann. Chem., 1981, 181 Search PubMed.
  12. B. S. Siddiqui, Ghiasuddin and S. Faizi, Phytochemistry, 1998, 47, 1631 CrossRef CAS.
  13. W. S. Abbot, J. Econ. Ent., 1925, 18, 265 Search PubMed.
  14. M. Raymond, G. Proto and D. Ratsira, PROBIT Analysis of Mortality Assays Displaying Quantal Response, version 3.3 Licence L 93019, Praxeme, 34680 St. Georges d'Orques, France, 1993.
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