Biotransformation of Monoterpenoids by the Larvae of Common Cutworm (Spodoptera litura)

Natural Product Communications

Volumn 2, Issue 4, 2007, Pages

  Miyazawa, Mitsuo ^a   Takechi, Hiromune ^a  

^a KINKI UNIVERSITY   (Japan)

Author keywords

biotransformation; Common cutworm; monoterpenes; Spodoptera litura

Indexed keywords

EID: 69949137506     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578X0700200415     Document Type: Article

References (75)

1. Passeriter CM, Wilson J, Andersen R, Isman MB. (2004) Metabolism of thymol and trans-anethole in larvae of Spodoptera litura and Trichoplusia ni (Lepidptera: Noctuidae). Journal of Agricultural and Food Chemistry, 52, 2549–2551.
2. Miyazawa M, Murata T. (2000) Biotransformation of β-myrcene by the larvae of common cutworm (Spodoptera litura), Journal of Agricultural and Food Chemistry, 48, 123–125.
3. Ishida T, Asakawa Y, Takemoto T, Aratani T. (1981) Biotransformation of α-pinane, β-pinane, pinane, 3-caren, caren, myrcene, and p-cymen in rabbits. Journal of Pharmaceutical Sciences, 70, 406–415.
4. Yamazaki Y, Hayashi Y, Hori N, Mikami Y. (1988) Microbial conversion of β-myrcene by Aspergillus niger. Agricultural and Biological Chemistry, 52, 2921–2922.
5. Miyazawa M, Murata T. (2001) Biotransformation of (-)-dihydromyrcenol and (-)-dihydromyrcenyl acetate by the larvae of common cutworm (Spodoptera litura). Journal of Oleo Science, 50, 921–925.
6. Miyazawa M, Akazawa S, Sakai H, Nankai H. (2000) Biotransformation of (-)-dihydromyrcenyl acetate using the plant parasitic fungus Glomerella cingulata as a biocatalyst. Journal of Agricultural and Food Chemistry, 48, 4826–4829.
7. Takechi H, Miyazawa M. (2006) Biotransformation of geraniol by the larvae of common cutworm (Spodoptera litura). Journal of Oleo Science, 55, 143–149.
8. Hamada H, Yasumune H, Fuchikami Y, Hirata T, Sattler I, Howard JW, Scott AI. (1997) Biotransformation of geraniol, nerol and (+)- and (-)-carvone by suspension cultured cells of Catharanthus roseus. Phytochemistry, 44, 615–621.
9. Figueiredo AC, Almendra MJ, Barroso JG, Scheffer JJC. (1996) Biotransformaion of monoterpenes and sesquiterpenes by cell suspension cultures of Achillea millefolium L. ssp. millefolium. Biotechnology Letters, 18, 863–868.
10. Corbier B, Ehret C. (1988) Biotransformation of monoterpenoids by cultured cells of Rosa centifolia. Developments in Food Science, 18, 731–741.
11. Itokawa H, Takeya K, Mihashi S. (1977) Biotransformation of cannabinoid precursors and related alcohols by suspension cultures of callus induced from Cannabis sativa L. Chemical and Pharmaceutical Bulletin, 25, 1941–1946.
12. Takeya K, Itokawa H. (1977) Stereochemistry in oxidation of allylic alcohols by cell-free system of callus induced from Cannabis sativa L. Chemical and Pharmaceutical Bulletin, 25, 1947–1951.
13. Carriere F, Gil G, Chagrardieff P. (1989) Biotransformation of geraniol by photoautotrophic, photomixotrophic and heterotrophic plant cell suspensions. Phytochemistry, 28, 1087–1090.
14. Gbolade AA, Lockwood GB. (1989) Selective biotransformation of monoterpenoids by cell suspensions of Petroselinum crispum. Zeitschrift fuer Naturforschung, C: Journal of Biosciences, 44, 1066–1068.
15. Zhu W, Asghari G, Lockwood GB. (2000) Factors affecting volatile terpene and non-terpene biotransformation products in plant cell cultures. Fitoterapia, 71, 501–506.
16. Everitt ZM, Lockwood GB. (1992) Biotransformation of geraniol by agitating and immobilized cultures of Anethum graveolens. Fitoterapia, 63, 534–536.
17. Guardiola J, Canovas M, Iborra JL. (1996) Modelling of the biotransformation from geraniol to nerol by freely suspended and immobilized grape (Vitis vinifera) cells. Progress in Biotechnology, 11, 349–354.
18. Guardiola J, Icorra JL, Rodenas L, Canovas M. (1996) Biotransformation from geraniol and nerol by immobilized grapevine cells (V. vinifera). Applied Biochemistry and Biotechnology, 56, 169–180.
19. Chatterjee T. (2004) Biotransformation of geraniol by Rhodococcus sp. Strain GR3. Biotechnology and Applied Biochemistry, 39, 303–306.
20. Seubert W, Remberger U. (1963) Studies on the bacterial degradation of isoprenoid compounds. II. The role of carbon dioxide. Biochemische Zeitschrift, 338, 245–246.
21. Madyastha KM. (1984) Microbial transformations of acyclic monoterpenes. Proceedings - Indian Academy of Sciences, Chemical Sciences, 93, 677–686.
22. Cantwell SG, Lau EP, Watt DS, Fall RR. (1978) Biodegradation of acyclic isoprenoids by Pseudomonas species. Journal of Bacteriology, 135, 324–333.
23. Madyastha KM, Bhattacharyyav PK, Vaidyanathan CS. (1977) Metabolism of a monoterpene alcohol, linalool, by a soil pseudomonad. Canadian Journal of Microbiology, 23, 230–239.
24. Chadha A, Madyastha KM. (1984) Metabolism of geraniol and linalool in the rat and effects on liver and lung microsomal enzymes. Xenobiotica, 14, 365–374.
25. Abraham WR, Kieslich K, Reng H, Stumpf B. (1984) Formation and production of 1,2-trans-glycols from various monoterpenes with 1-menthane skeletons by microbial transformation with Diplodia gossypina. European Congress for Biotechnology. 1, 245–248.
26. Miyazawa M, Wada T, Kameoka H. (1998) Biotransformation of (+)-and (-)-limonene by the larvae of common cutworm (Spodoptera litura). Journal of Agricultural and Food Chemistry, 46, 300–303.
27. Carman RM, Greenfield KL, Robinson WT. (1986) Halogenated terpenoids. XXII Uroterpenol. The C8 stereochemistry, Australian Journal of Chemistry, 39, 21–30.
28. Dhavalikar RS, Bhattacharyya PK. (1966) Microbiological transformation of terpenes. VIII. Fermentation of limonene by a soil pseudomonad. Indian Journal of Biochemistry, 3, 144–157.
29. Dhavalikar RS, Rangachari PN. (1966) Microbiological transformations of terpenes. IX. Pathways of degradation of limonene in a soil pseudomonad. Indian Journal of Biochemistry, 3, 158–164.
30. Dhere SG, Dhavalikar RS. (1970) Microbial transformations of terpenoids: limonene. Science and Culture, 36, 292.
31. Mukherjee BB, Kraidman G, Mill ID. (1973) Synthesis of glycols by microbial transformation of some monocyclic terpenes. Applied Microbiology, 25, 447–453.
32. Bowen ER. (1976) Potential by-products from microbial transformation of d-limonene. Proceedings of the Florida State Horticultural Society, 88, 304–308.
33. Devi JR, Bhattacharyya PK. (1977) Microbiological transformations of terpenes. Part XXIV. Pathways of degradation of linalool, geraniol, nerol and limonene by Pseudomonas incognita (linalool strain). Indian Journal of Biochemistry & Biophysics, 14, 288–291.
34. Abraham WR, Kieslich K, Reng H, Stumpf B. (1984) Formation and production of 1,2-trans-glycols from various monoterpenes with 1-menthene skeletons by microbial transformation with Diplodia gossypina. European Congress for Biotechnology 3rd, 1, 245–248.
35. Abraham WR, Stumpf B, Kieslich K. (1986) Microbial transformations of terpenoids with 1-p-menthene skeleton. Applied Microbiology and Biotechnology, 24, 24–30.
36. Cadwallader KR, Braddock RJ, Parish ME, Higgins DP. (1989) Bioconversion of (+)-limonene by Pseudomonas gladioli. Journal of Food Science, 54, 1241–1245.
37. Devi JR, Bhattacharyya PK. (1977) Microbiological transformations of terpenes. Part XXIV. Pathways of degradation of linalool geraniol, nerol and limonene by Pseudomonas incognita (linalool strain). Indian Journal of Biochemistry & Biophysics, 14, 359–363.
38. Noma Y, Yamasaki S, Asakawa Y. (1992) Biotransformation of limonene and related compounds by Aspergillus cellulosae. Phytochemistry, 31, 2725–2727.
39. Igimi H, Nshimura M, Kodama R, Ide H. (1974) Metabolism of d-limonene (p-mentha-1,2-diene). I. Absorption, distribution, and excretion of d-limonene in rats. Xenobiotica, 4, 77–84.
40. Kodama R, Noda K, Ide H. (1974) Metabolism of d-limonene (p-mentha-1,8-diene). II. Metabolic fate of d-limonene in rabbits. Xenobiotica, 4, 85–95.
41. Kodama R, Yano T, Furukawa K, Noda K, Ide H. (1976) Studies on the metabolism of d-limonene (p-mentha-1,8-diene). IV. Isolation and characterization of new metabolites and species differences in metabolism. Xenobiotica, 6, 377–389.
42. Regan JW, Bjeldanes LF. (1976) Metabolism of (+)-limonene in rats. Journal of Agricultural and Food Chemistry, 24, 377–380.
43. Watabe T, Hiratsuka A, Isobe M, Ozawa N. (1980) Metabolism of d-limonene by hepatic microsomes to nonmutagenic epoxides toward Salmonella typhimurium. Biochemical Pharmacology, 29, 1068–1071.
44. Watabe T, Hiratsuka A, Ozawa N, Isobe M. (1981) A comparative study on the metabolism of d-limonene and 4-vinylcyclohex-1 ene by hepatic microsomes. Xenobiotica, 11, 333–344.
45. Miyazawa M, Wada T, Kameoka H. (1996) Biotransformation of a-terpinene in common cutworm larvae (Spodoptera litura Fabricius). J. Journal of Agricultural and Food Chemistry, 44, 2889–2893.
46. Abraham WR, Stumpf B, Kieslish K. (1986) Microbial transformation of terpenoids with 1-p-menthene skeleton. Applied Biochemistry and Biotechnology, 24, 24–30.
47. Miyazawa M, Wada T. (2000) Biotransformation of γ-terpinene and (-)-α-phellandrene by the larvae of common cutworm (Spodoptera litura). Journal of Agricultural and Food Chemistry, 48, 2893–2895.
48. Pierce HD Jr, Com JE, Oehlschlager AC, Borden JH. (1987) Monoterpene metabolism in female mountain pine beetles, Dendroctonus ponderosae Hopkins, attacking ponderosa pine. Journal of Chemical Ecology, 13, 1455–1480.
49. Miyazawa M, Ohsawa M. (2002) Biotransformation of α-terpineol by the larvae of common cutworm (Spodoptera litura). Journal of Agricultural and Food Chemistry, 50, 4916–4918.
50. Suga T, Aoki T, Hirata T, Ym Sook Lee, Nishimura O, Utsumi M. (1980) Biotransformation of foreign substrates with callus tissues. Transformation of terpineols with tobacco suspension cells. Chemistry Letters, 229–230.
51. Madyastha KM, Sriratsar V. (1985) Biotransformation of α-terpineol in rat: Its effects on the liver microsomal cytochrome P-450 system. Bulletin of Environmental Contamination and Toxicology, 15, 165–170.
52. Draczynska-Lusiak B, Siewinski A. (1989) Enantioselectivity of the metabolism of some monoterpenic components of coniferous tree resin by Armillariella mellea (honey fungus). Journal of Basic Microbiology, 29, 269–275.
53. Miyazawa M, Kumagae S, Kameoka H. (1999) Biotransformation of (+)- and (-)-menthol by the larvae of common cutworm (Spodoptera litura). Journal of Agricultural and Food Chemistry, 47, 3938–3940.
54. Suga T, Hamada H, Hirata T, Izumi S. (1987) Stereoselectivity in oxidative and reductive transformations of p-menthane derivatives with the cultured cells of Nicotiana tabacum. Chemistry Letters, 5, 903–906.
55. Furuya T, Orihara Y, Miyatake H. (1989) Biotransformation of (-)-menthol by Eucalyptus perriniana cultured cells. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry, 10, 1711–1719.
56. Asakawa Y, Takahashi H, Toyota M, Noma Y. (1991) Biotransformation of monoterpenoids, (+)-and (-)-menthols, terpinolene and carvotanacetone by Aspergillus species. Phytochemistry, 30, 3981–3987.
57. Madyastha KM, Srivatsan V. (1988) Studies on the metabolism of l-menthol in rats. Drug Metabolism and Disposition, 16, 765–772.
58. Miyazawa M, Kumagae S, Kameoka H. (2001) Biotransformation of (R)- and (S)-terpinen-4-ol by the larvae of common cutworm (Spodoptera litura). Journal of Agricultural and Food Chemistry, 49, 4312–4314.
59. Wolf-Rainar A, Stumpf B, Kieslish K. (1986) Microbial transformations of N-(4-chlorphenyl)benzoisothiazolone. AppliedMicrobiology and Biotechnology, 24, 24–30.
60. Miyazawa M, Miyamoto Y. (2004) Biotransformation of (1R)-(+)- and (1S)-(-)-camphor by the larvae of common cutworm (Spodoptera litura). Journal of Molecular Catalysis B: Enzymatic, 27, 83–89.
61. Tucker AO, Maciarello MJ. (1990) Essential oils of cultivars of Dalmatian sage (Salvia officinalis L.). Journal of Essential Oil Research, 2, 139–144.
62. Croteau R, Felton M, Karp F, Kjonaas R. (1981) Relationship of camphor biosynthesis to leaf development in sage (Salvia officinalis). Plant Physiology, 67, 820–824.
63. Harborne JB, Baxter H. Phytochemical Dictionary, A Handbook of Bioactive Compounds from Plants. Taylor and Francis, London, UK. 1993.
64. Asahina Y, Ishidate M. (1928) Camphorol. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen, 61, 533–536.
65. Leibman KC, Ortiz E. (1973) Mammalian metabolism of terpenoids. I. Reduction and hydroxylation of camphor and related compounds. Drug Metabolism and Disposition: the Biological Fate of Chemicals, 1, 543–551.
66. Robertson JS, Hussain M. (1969) Metabolism of camphors and related compounds. Biochemical Journal, 113, 57–65.
67. Ronald EW, Mary-Beth M, Karen DE, Stephen GS. (1984) Archives of Biochemistry and. Biophysics, 228, 493–495.
68. Bradshaw WH, Conrad HE, Corey EJ, Gunsalus IC, Lednicer D. (1959) Microbiological degradation of (+)-camphor. Journal of the American Chemical Society, 81, 5507–5560.
69. Miyazawa M, Miyamoto Y. (2004) Biotransformation of (1R)-(+)- and (1S)-(-)-camphor by the larvae of common cutworm (Spodoptera litura). Journal of Molecular Catalysis B: Enzymatic, 32, 83–89.
70. Chapman PJ, Meerman G, Gunsalus IC. (1965) The microbiological transformation of fenchone. Biochemical and Biophysical Research Communications, 20, 104–108.
71. Pfrunder B, Tamm C. (1969) Reactions with microorganisms. XVIII. Microbiological conversion of bicyclic monoterpenes by Absidia orchidis. 2. Hydroxylation of fenchone and isofenchone. Helvetica Chimica Acta, 52, 1643–1654.
72. Orihara Y, Furuya T. (1994) Biotransformation of (+)- and (-)-fenchone by cultured cells of Eucalyptus perriniana. Phytochemistry, 36, 55–59.
73. Miyazawa M, Yamamoto K, Noma Y, Kameoka H. (1990) Bioconversion of (+)-fenchone to 4-endo-hydroxfenchone by Aspergillus niger. Chemistry Express, 5, 407–410.
74. Miyazawa M., Kameoka H. (1988) Biotransformation and bioavailability of (+)-fenchone to hydroxyfenchone in rabbits. Chemistry Express, 3, 503–506.
75. Miyazawa M, Miyamoto Y. (2004) Biotransformation of (+)-(1R,2S)-fenchol by the larvae of common cutworm (Spodoptera litura). Tetrahedron, 60, 3091–3096.