Biotransformation of α-Terpinene in Common Cutworm Larvae (Spodoptera litura Fabricius)

Journal of Agricultural and Food Chemistry

Volumn 44, Issue 9, 1996, Pages 2889-2893

  Miyazawa, Mitsuo ^a   Wada, Takashi ^a   Kameoka, Hiromu ^a  

^a KINKI UNIVERSITY   (Japan)

Author keywords

4 isopropyl 1,3 cyclohexadienemethanol; 4 isopropyl 1,3 cyclohexadienoic acid; Allylic oxidation; Biotransformation; Common cutworm; Cumic acid; Cumic alcohol; Intestinal bacteria; Larvae; p cymene; Spodoptera litura Fabricius; terpinene

Indexed keywords

FABRICIUS; SPODOPTERA LITURA;

EID: 0001302074     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf9502966     Document Type: Article

References (46)

1. Abraham, W. R.; Stumpf, B.; Kieslich, K. Microbial transformation of terpenoids with 1-p-menthene skeleton. Appl. Microbiol. Biotechnol. 1986, 24, 24-30.
2. Asakawa, Y.; Ishida, T.; Toyota, M.; Takemoto, T. Presented at the 26th Symposium on the Chemistry of Terpens, Essential Oils and Aromatics of Japan, Yamagata, 1982; pp 153-155.
3. Byers, J. A. Bark beetle conversion of a plant compound to a sex specific inhibitor of pheromone attraction. Science 1983, 220, 624-626.
4. De Smet, M-J.; Friedman, M. B.; Gunsalus, I. C. Plasmid control of the Pseudomonas aeruginosa and Pseudomonas putida phenotypes and of linalool and p-cymene oxidation. J. Bacteriol. 1989, 171, 5155-5161.
5. Fish, R. H.; Browne, L. E.; Wood, D. L.; Hendry, L. B. Pheromone biosynthetic pathways: Conversion of deuterium labelled ispsdienol with sexual and enantioselectivity in Ips paraconfusus Lanier. Tetrahedron Lett. 1979, 1465-1468.
6. Francke, W.; Vite, J. P. Oxygenated terpenes in pheromone systems of bark beetles. Z. Angew. Entomol. 1983, 96, 146-156.
7. Fujii, Y.; Yasuda, T. Biologically active substances in relation to plant interactions. Bunseki 1987, 148, 231-237.
8. Fujii Y. Prospective view of biological control by allelochemicals. Nippon Dojo Hiryogaku Zasshi 1989, 60, 240-245.
9. Hughes, P. R. Dendroctonus: Production of pheromones and related compounds in response to host monoterpenes. Z. Angew. Entomol. 1973, 73, 294-312.
10. Ishida, T.; Asakawa, Y.; Takemoto, T.; Aratani, T. Terpenoids biotransformation in mammals. III Biotransformation of α-pinene, β-pinene, pinane, 3-carene, carane, myrcene, and p-cymene in rabbits. J. Pharm. Sci. 1981, 70, 406-415.
11. Klimetzek, D.; Francke, W. Relationship between the enantiomeric composition of α-pinene in host trees and the production of verbenols in Ips species. Experientia 1980, 36, 1343-1344.
12. Madhyastha, K. M.; Bhattacharyya, P. K. Microbiological transformations of terpenes. XII Fermentation of p-cymene by a soil pseudomonad (PL-strain). Indian J. Biochem. 1968, 5, 102-111.
13. Matsumoto, T.; Ishida, T.; Yoshida, T.; Terao, H.; Takeda, Y.; Asakawa, Y. The enantioselective metabolism of p-cymene in rabbits. Chem. Pharm. Bull. 1992, 40, 1721-1726.
14. Miyazawa, M.; Kameoka, H. 10-Hydroxyfenchone: A new metabolite of (+)-fenchone in rabbits. Chem. Express 1987, 2, 547-550.
15. Miyazawa, M.; Kameoka, H. 9-Hydroxyfenchone: A new metabolite of (+)-fenchone in rabbits. Chem. Express 1988, 3, 231-234.
16. Miyazawa, M.; Kameoka, H.; Morinaga, K.; Negoro, K.; Mura, N. Hydroxycineole: Four new metabolites of 1,8-cineole in rabbits. J. Agric. Food Chem. 1989, 37, 222-226.
17. Miyazawa, M.; Yamamoto, K.; Noma, Y.; Kameoka, H. Bioconversion of (+)-fenchone to (+)-6-endo-hydroxyfenchone by Aspergillus niger. Chem. Express 1990a, 5, 237-240.
18. Miyazawa, M.; Yamamoto, K.; Noma, Y.; Kameoka, H. Bioconversion of (+)-fenchone to (+)-5-endo-hydroxyfenchone by Aspergillus niger. Chem. Express 1990b, 5, 407-410.
19. Miyazawa, M.; Funatsu, Y.; Kameoka, H. Biotransformation of (-)-α-bisabolol to (-)-α-bisabololoxid B by Aspergillus niger. Chem. Express 1990c, 5, 589-592.
20. Miyazawa, M.; Huruno, H.; Kameoka, H. Biotransformation of (+)-pulegone to (-)-1R-8-hydroxy-4-p-menthen-3-one by Botrytis allii. Chem. Express 1991a, 6, 479-482.
21. Miyazawa, M.; Nakaoka, H.; Hyakumachi, M.; Kameoka, H. Biotransformation of 1,8-cineole to (+)-2-endo-hydroxy-1,8-cineole by Glomerella cingulata. Chem. Express 1991b, 6, 667-670.
22. Miyazawa, M.; Noma, Y.; Yamamoto, K.; Kameoka, H. Biotransformation of 1,4-cineole to 2-endo-hydroxy-1,4-cineole by Aspergillus niger. Chem. Express 1991c, 6, 771-774.
23. Miyazawa, M.; Huruno, H.; Kameoka, H. Biotransformation of (+)-pulegone to piperitenone by Botrytis allii. Chem. Express 1991d, 6, 873-874.
24. Miyazawa, M.; Noma, Y.; Yamamoto, K.; Kameoka, H. Biotransformation of 1,4-cineole to 3-endo-hydroxy-1,4-cineole by Aspergillus niger. Chem. Express 1992a, 7, 125-128.
25. Miyazawa, M.; Funatsu, Y.; Kameoka, H. Biotransformation of (-)-α-bisabolol to (-)-α-tetrahydrobisabolen-2,5,6-triol by Aspergillus niger. Chem. Express 1992b, 7, 217-220.
26. Miyazawa, M.; Noma, Y.; Yamamoto, K.; Kameoka, H. Biohydroxylation of 1,4-cineole to 9-hydroxy-1,4-cineole by Aspergillus niger. Chem. Express 1992c, 7, 305-308.
27. Miyazawa, M.; Funatsu, Y.; Kameoka, H. Biotransformation of (-)-α-bisabolol to 6-methyl-2-(4′-methylcyclohexan-1′-yl)-2,5-epoxyheptane-3′, 4′,6-triol by Aspergillus niger. Chem. Express 1992d, 7, 573-576.
28. Miyazawa, M.; Noma, Y.; Yamamoto, K.; Kameoka, H. Biohydroxylation of 1,4-cineole to 8-hydroxy-1,4-cineole by Aspergillus niger. Chem. Express 1992e, 7, 721-724.
29. Miyazawa, M.; Kakita, H.; Hyakumachi, M.; Kameoka, H. Enantioselective hydroxylation of (±)-piperitone to (-)-(4R, 6S)-6-hydroxy-piperitone by Rhizoctonia solani. Chem. Express 1993a, 8, 61-64.
30. Miyazawa, M.; Nankai, H.; Kameoka, H. Biotransformation of (-)-α-bisabolol to (2S, 5S, 1′S, 3′R, 4′R)-6-methyl-2-(4′-methylcyclohexane-1′-yl)-2,5-epoxyheptane- 3′,4′,6-triol by Glomerella cingulata. Chem. Express 1993b, 8, 149-152.
31. Miyazawa, M.; Nankai, H.; Kameoka, H. Biotransformation of (-)-α-bisabolol to (2S, 5S, 1′S, 3′S, 4′S)-6-methyl-2-(4′-methylcyclohexane-l'-yl)-2,5-epoxyheptane- 3′,4′,6-triol by Glomerella cingulata. Chem. Express 1993c, 8, 401-404.
32. Miyazawa, M.; Kakita, H.; Hyakumachi, M.; Kameoka, H. Preferential hydroxylation of (±)-piperitone to (-)-(4S, 6S)-6-hydroxypiperitone by Rhizoctonia solani. Chem. Express 1993d, 8, 569-572.
33. Miyazawa, M.; Nankai, H.; Kameoka, H. Microbial transformation of (+)-cedrol to 12-hydroxycedrol by Glomerella cingulata. Chem. Express 1993e, 8, 573-576.
34. Miyazawa, M.; Uemura, T.; Kameoka, H. Biotransformation of sesquiterpenoids, (-)-globulol and (+)-ledol by Glomerella cingulata. Phytochemistry 1994, 37, 1027-1030.
35. Ninnekar, H. Z.; Pujar, B. G. The metabolism of p-cymene by a Bacillus species. Microbios Lett. 1985, 28, 21-26.
36. Nishimura, H.; Nakamura, T.; Mizutani, J. Allelopathic substances, (±)-p-menthane-3,8-diols isolated from Eucalyptus citriodora Hook. Agric. Biol. Chem. 1982, 46, 319-320.
37. Renwick, J. A. A.; Hughes, P. R. Oxidation of unsaturated cyclic hydrocarbons by Dendroctonus frontalis. Insect Biochem. 1975, 5, 459-463.
38. Renwick, J. A. A.; Hughes, P. R.; Krull, I. S. Selective production of cis- and trans-verbenol from (-)- and (+)-α-pinene by a bark beetle. Science 1976, 191, 199-201.
39. Southwell, I. A.; Flynn, T. M.; Degabriele, R. Metabolism of α- and β-pinene, p-cymene, and 1,8-cineole in the brush tail possum, Trichosurus vulpecula. Xenobiotica 1980, 10, 17-23.
40. Tahara, S.; Yoshida, M.; Mizutani, J. Sex stimulant to the male American cockroach in Conpositae plants. Agric. Biol. Chem. 1975, 39, 1517-1518.
41. Tahara, S.; Hanawa, F.; Harada, Y.; Mizutani, J. A fungitoxin inducibly produced by dandelion leaves treated with cupric chloride. Agric. Biol. Chem. 1988, 52, 2947-2948.
42. Walde, A.; Ve, B.; Schelme, R. R.p-Cymene metabolism in rats and guinea pigs. Xenobiotica 1983, 13, 503-512.
43. White, R. A., Jr.; Agosin, R.; Franklin, R. T.; Webb, J. W. Bark beetle pheromones: Evidence for physiological synthesis mechanisms and the ecological implications. Z. Angew. Entomol. 1980, 90, 255-274.
44. Wigmore, G. J.; Ribbons, D. W. Selective enrichment of Pseudomonas spp. Defective in catabolism after exposure to halogenated substrates. J. Bacteriol. 1981, 146, 920-927.
45. Yamada, K.; Horiguchi, S.; Takahashi, J. Studies on the utilization of hydrocarbons by microorganisms part VI. Screening of aromatic hydrocarbon-assimilating microorganisms and cumic acid formation from p-cymene. Agric. Biol. Chem. 1965, 29, 943-948.
46. Yushima, K.; Kamano, S.; Tamaki, Y. Rearing Methods of Insects; Japan Plant Protection Association: Tokyo, Japan, 1991; pp 214-218.