Photooxidation of nimbin and salannin, tetranortriterpenoids from the neem tree (Azadirachta indica)

Journal of Chemical Ecology

Volumn 23, Issue 12, 1997, Pages 2841-2860

  Jarvis, Andrew P ^a   Johnson, Shaun ^a   David Morgan, E ^a   Simmonds, Monique S J ^b   Blaney, Wally M ^c  

^a KEELE UNIVERSITY   (United Kingdom)

^b JODRELL LABORATORY   (United Kingdom)

^c UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

Antifeedant; Azadirachta indica; Azadirachtin; Growth inhibition; Locusta migratoria; Nimbin; Photoisomerization; Photooxidation; Salannin; Schistocerca gregaria; Spodoptera littoralis

Indexed keywords

AZADIRACHTA INDICA;

EID: 0031460543     PISSN: 00980331     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1022523329255     Document Type: Article

References (28)

1. ARA, I., SIDDIQUI, B. S., FAIZI, S., and SIDDIQUI, S. 1988. Terpenoids from the stem bark of Azadirachta indica. Phytochemistry 27:1801-1804.
2. BARNBY, M. A., YAMASAKI, R. B., and KLOCKE, J. A. 1989. Biological activity of azadirachtin, three derivatives, and their ultraviolet radiation degradation products against tobacco budworm (Lepidoptera: Noctuidae) larvae. J. Econ. Entomol. 82:58-63.
3. BLANEY, W. M., SIMMONDS, M. S. J., LEY, S. V., ANDERSON, J. C., and TOOGOOD, P. L. 1990. Antifeedant effects of azadirachtin and structurally related compounds on lepidopterous larvae. Entomol. Exp. Appl. 55:149-160.
4. BOKEL, M., CRAMER, R., GUTZEIT, H., REEB, S., and KRAUS, W. 1990. Tetranortriterpenoids related to nimbin and nimbolide from Azadirachta indica A. Juss (Meliaceae). Tetrahedron 46:775-782.
5. BUTTERWORTH, J. H., and MORGAN, E. D. 1968. Isolation of a substance that suppresses feeding in locusts. J. Chem. Soc. Chem. Commun. 1968:23.
6. CONNOLLY, J. D., HANDA, K. L., and MCCRINDLE, R. 1968. Further constituents of neem oil: The constitution of meldenin. Tetrahedron Lett. 4:437-440.
7. ERMEL, K., PAHLICH, E., and SCHMUTTERER, H. 1987. Azadirachtin content of neem kernels from different geographical locations, and its dependence on temperature, relative humidity, and light, pp. 171-184, in H. Schmutterer and K. R. S. Ascher (eds.). Natural pesticides from the neem tree and other tropical plants. GTZ, Eschborn.
8. FOOTE, C. S., WUESTHOFF, M. T., WEXLER, S., BURSTAIN, I. G., DENNY, R., SCHENCK, G. O., and SCHULTE-ELTE, K-H. 1967. Photosensitized oxygenation of alkyl substituted furans. Tetrahedron 23:2583-2599.
9. GARG, H. S., and BHAKUNI, D. S. 1984. Salannolide, a meliacin from Azadirachta indica. Phytochemistry 23:2383-2385.
10. HUANG, H.-P., and MORGAN, E. D. 1991. Analysis of azadirachtin by supercritical fluid chromatography. J. Chromatogr. 519:137-143.
11. JOHNSON, S. 1995. The development, isolation and degradation of insect antifeedants from the seeds of Azadirachta indica. PhD dissertation. Keele University, Keele, UK, p. 50.
12. JOHNSON, S., MORGAN, E. D., WILSON, I. D., SPRAUL, M., and HOFMANN, M. 1994. Photoisomerization of azadirachtin studied by high performance liquid chromatography coupled to high field proton NMR spectroscopy. J. Chem. Soc. Perkin Trans. 1, 1994:1499-1502.
13. JONES, P. S., LEY, S. V., MORGAN, E. D., and SANTAFIANOS, D. 1988. The chemistry of the neem tree, pp. 19-45, in M. Jacobson (ed.). The Neem Tree. CRC Press, Boca Raton, Florida.
14. KEARNS, D. R. 1971. Physical and chemical properties of singlet molecular oxygen. Chem. Rev. 1971:395-427.
15. KRAUS, W. 1995. Biologically active ingredients, pp. 35-88, in H. Schmutterer (ed.). The Neem Tree. VCH, Weinheim.
16. KRAUS, W., KLENK, A., BOKEL, M., and VOGLER, B. Tetranortriterpenoid-Lactame mit Insektenfrasshemmender Wirkung aus Azadirachta indica A. Juss (Meliaceae). Liebigs Ann. Chem. 1987:337-340.
17. PURUSHOTHAMAN, K. K., DURAISWAMY, K., and CONNOLLY, J. D. 1984. Tetranortriterpenoids from Melia dubia. Phytochemistry 23:135-137.
18. RUSCOE, C. N. E. 1972. Growth disruption effects of an insect antifeedant. Nature (London) New Biol. 236:159-160.
19. SCHMUTTERER, H. 1988. Potential of azadirachtin containing pesticides for integrated pest control in developing and industrialized countries. J. Insect. Physiol. 34:713-719.
20. SIDDIQUI, S., FAIZI, S., MAHMOOD, T., and SIDDIQUI, B. S. 1986a. Two new insect growth regulator meliacins from Azadirachta indica A. Juss (Meliaceae). J. Chem. Soc. Perkin Trans. 1 1986:1021-1025.
21. SIDDIQUI, S., FAIZI, S., MAHMOOD, T., and SIDDIQUI, B. S. 1986b. Margosinolide and isomargosinolide, two new tetranortriterpenoids from Azadirachta indica A. Juss (Meliaceae). Tetrahedron 42:4849-4856.
22. SIMMONDS, M. S. J., BLANEY, W. M., LEY, S. V., ANDERSON, J. C., and TOOGOOD, P. L. 1990. Azadirachtin: structural requirements for reducing growth and increasing mortality in lepidopterous larvae. Entomol. Exp. Appl. 55:169-181.
23. SIMMONDS, M. S. J., BLANEY, W. M., LEY, S. V., ANDERSON, J. C., BANTELI, R., DENHOLM, A. A., GREEN, P. C. W., GROSSMAN, R. B., GUTTERIDGE, C., JENNENS, L., SMITH, S. C., TOOGOOD, P. L., and WOOD, A. 1995. Behavioural and neurophysiological responses of Spodoptera littoralis to azadirachtin and a range of synthetic analogues. Entomol. Exp. Appl. 77:69-80.
24. STOKES, J. B., and REDFERN, R. E. 1982. Effect of sunlight on azadirachtin: Antifeeding potency. J. Environ. Sci. Health A 17:57-65.
25. SUNDARAM, K. M. S., and CURRY, J. 1996. Effect of some UV light absorbers on the photostabilization of azadirachtin, a neem-based biopesticide. Chemosphere 32:649-659.
26. TAKESHITA, H., KANAMORI, H., and HATSUI, T. 1973. Sensitized photooxidation of spiro[2,4]hepta-4,6-diene. Tetrahedron Lett. 34:3139-3140.
27. THIELE, S. 1991. Isolierung und Strukturaufklärung neuer Tetranortriterpenoide aus Azadirachta indica A. Juss (neem tree, Meliaceae) und Untersuchung der nematiziden Wirkung von Neem-Extracten. PhD dissertation. University of Hohenheim, Hohenheim, Germany.
28. VAN BEEK, T. A., and DE GROOT, A. 1986. Terpenoid antifeedants, part I. An overview of terpenoid antifeedants of natural origin. Recl. Trav. Chim. Pays-Bos 105:513-527.