Regio- and stereoselective oxidation of (+)-δ3-carene by the larvae of common cutworm (spodoptera litura)

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 6, 2010, Pages 3855-3858

  Mitsuo, Miyazawa ^a   Haruki, Kano ^a  

^a KINKI UNIVERSITY   (Japan)

Author keywords

(+) 3 carene; Biotransformation; Epoxydatlon; Hydroxylatlon; Spodoptera litura

Indexed keywords

BICYCLO COMPOUND; DELTA(3) CARENE; DELTA(3)-CARENE;

ANIMAL; ARMYWORM; ARTICLE; BIOTRANSFORMATION; CHEMISTRY; LARVA; METABOLISM; OXIDATION REDUCTION REACTION; STEREOISOMERISM;

ANIMALS; BICYCLO COMPOUNDS; BIOTRANSFORMATION; LARVA; OXIDATION-REDUCTION; SPODOPTERA; STEREOISOMERISM;

SPODOPTERA LITURA;

EID: 77949846990     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf903301v     Document Type: Article

References (16)

1. Joshi, S; Chanotiya, C, S.; Agarwal, G; Prakash, O; Pant, A., K.; Matnela, C, S. Terpenoid compositions, and antioxidant and antimicrobial properties of the rhizome essential oils of different Hedychium species. Chem. Biodiversity 2008, 5 (2), 299-309.
2. Isida, T. Biotransformation of terpenoids by mammals, microorganisms and. plant-cultured cells. Chem. Biol. 2005, 2, 569-589.
3. Miyazawa, M; Suzuki, Y; Kameoka, H. Biotransformation of (-)cis-myrtanol and (+)-trans-myrtanol by plant pathogenic fungus Glomerella cingulata. Phvtochemistry 1997, 45 (5), 935-943.
4. Miyazawa, M.; Miyamoto, Y. Biotransformation of (1R)-(+)- and (1S)-(-)-camphor by the larvae of common cutworm (Spodoptera atura). J. Mol. Catal. B; Enzvm. 2004, 27, 83-89.
5. Miyazawa, M.; Miyamoto, Y. Biotransformation of (+)-(1R)- and (-)-(lS)-fenchone by the larvae of common cutworm (Spodoptera litura). J. Mol. Catai. B: Enzvm. 2005, 32, 123-130.
6. Miyazawa, M.; Miyamoto, Y. Biotransformation of (-)-(1R, 2S)fenchol by the larvae of common cutworm (Spodoptera litura). Tetrahedron 2004, 60 (13), 3091-3096.
7. Miyazawa, M.; Takechi, H. Biotransformation of monoterpenoids by the larvae of common cutworm (Spodoptera litura). Nat. Prod. Commun. 2007. 2 (4), 435-443.
8. Sandberg, R. Steric relations between homoterpenyl methyl ketone, terpenylic acid, and terebic acid. Ark. Kemi 1960, 16 (23), 255-265.
9. Pattekhan, H. H.; Varadaraj, C. M.; Keshava, N.; Divakar, S. Influence of β-cyclodextrin in bio-transformation of (+)-3-carene by cell suspension cultures of Acetobacter acetii. Biotechnol. Tech. 1997, 11 (6), 379-383.
10. Corbier, B.; Ehret, C. Biotransformation of monoterpenoids by cultured cells of Rosa centifolia. Flavor Fragrance, J. 1986, 18, 731-741.
11. Hirata, T.; Ikeda, Y.; Izumi, S.; Shimoda, K.; Hamada, H.; Kawamura, T. Introduction of oxygenated, functional groups into 3-carene and 2-pinene by cultured cells. Phytochemistry 1994, 37 (2), 401-403.
12. Ishida, T.; Asakawa, Y.; Okano, M.; Aratani, T. Biotransformation of terpenoids in mammal. I. Biotransformation of 3-carene and related compounds in rabbits. Tetrahedron Lett, 1977, 28, 2437-2440.
13. Ishida, T.; Asakawa, Y.; Takemoto, T.; Aratani, T. Biotransformation of terpenoids in mammals. Hiroshima Kogvo Daigaku Kenkvu Kivo 1980, 14, 9-14.
14. Ishida, T.; Asakawa, Y.; Takemoto, T.; Aratani, T. Terpenoids biotransformation in. mammals III: Biotransformation of alphapineiie, pinane, 3-carene, carane, myrcene, and p-cymene in rabbits. J. Pharm. Sci. 1981, 70 (4), 406-414.
15. Duisken, M.; Benz, D.; Peiffer, H. T.; Blomeke, B. Metabolism of Δ3-carene by human cytochrome P450 enzymes: Identification and characterization of two new metabolites. Curr. Drug Metab. 2005, 6, 593-601.
16. Crombie, L; Mary, W.; Crombie, L.; Jamieson, S. V.; Palmer, C. J. Acid catalyzed terpenylations of olivetol in the synthesis of cannabinoids. J. Chem. Soc. Perkin Trans. 1 1988, 5, 1243-1250