Biotransformation of sesquiterpenoids from liverworts by fungi and mammals

Natural Product Communications

Volumn 5, Issue 5, 2010, Pages 695-707

  Asakawa, Yoshinori ^a   Hashimoto, Toshihiro ^a   Noma, Yoshiaki ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

Aspergillus cellulosae; Aspergillus niger; Biotransformation; Cytochrome P450; Sesquiterpenoids

Indexed keywords

ALCOHOL; CYCLOPENTANE; CYCLOPROPANE; CYTOCHROME P450; EPOXIDE; HYDROXYL GROUP; METHYL GROUP; OXYGEN; SESQUITERPENOID;

ARTICLE; ATOM; BIOTRANSFORMATION; FUNGUS; HYDROLYSIS; LIVERWORT; MAMMAL; NONHUMAN; OXIDATION;

ASPERGILLUS CELLULOSAE; ASPERGILLUS NIGER; EMBRYOPHYTA; FUNGI; MAMMALIA; MARCHANTIOPHYTA;

EID: 77954128316     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x1000500506     Document Type: Article

References (48)

1. Asakawa Y. (1982) Chemical constituents of the Hepaticae. In Progress in the Chemistry of Organic Natural Products. Herz W, Grisebach H, Kirby GW (Eds). Springer, Vienna, Austria, 42, 1-285.
2. Asakawa Y. (1995) Chemical constituents of the bryophytes. In Progress in the Chemistry of Organic Natural Products. Herz W, Kirby GW, Moore RE, Steglich W, Tamm Ch (Eds). Springer, Vienna, Austria, 65, 1-618.
3. Asakawa Y. (1990) Terpenoids and aromatic compounds with pharmaceutical activity from bryophytes. In Bryophytes: Their Chemistry and Chemical Taxonomy, Zinsmeister DH, Mues R (Eds). Clarendon Press, Oxford, UK, 369-410.
4. Asakawa Y. (1999) Phytochemistry of bryophytes. In Phytochemicals in Human Health Protection, Nutrition, and Plant Defense. Romeo J (Ed). Kluwer Academic, Plenum Publishers, New York, 33, 319-342.
5. Asakawa Y. (2007) Biologically active compounds from bryophytes. Pure and Applied Chemistry, 75, 557-580.
6. Asakawa Y. (2008) Recent advances of biologically active substances from the Marchantiophyta. Natural Product Communications, 3, 77-92.
7. Asakawa Y, Ludwiczuk A. (2008) Bryophytes-chemical diversity, bioactivity and chemosystematics. Part 1. Chemical diversity and bioactivity. Medicinal Plants in Poland and in the World, 14, 33-53.
8. rd Symposium on the Chemistry of Terpenes, Essential Oils, and Aromatics, Oita, Japan, 208-210.
9. th Symposium on the Chemistry of Terpenes, Essential Oils, and Aromatics, Saga, Japan, 108-110.
10. Furusawa M, Hashimoto T, Noma Y, Asakawa Y. (2006) Biotransformation of aristolene- and 2,3-secoaromadendrane-type sesquiterpenoids having a 1,1-dimethylcyclopropane ring by Chlorella fusca var. vacuolata, Mucor species, and Aspergillus niger. Chemical and Pharmaceutical Bulletin, 54, 861-868.
11. th Symposium on the Chemistry of Terpenes, Essential Oils, and Aromatics, Tokyo, Japan, 139-141.
12. th Symposium on the Chemistry of Terpenes, Essential Oils, and Aromatics, Sapporo, Japan, 151-13.
13. Ishida T, Asakawa Y, Takemoto T, Aratani T. (1981) Terpenoid biotransformation in mammals. III. Biotransformation of α-pinene, β-pinene, pinane, 3-carene, carane, myrcene and p-cymene in rabbits. Journal of Pharmaceutical Sciences, 70, 406-415.
14. Ishida T. (2005) Biotransformation of terpenoids by mammals, microorganisms, and plant-cultured cells. Chemistry and. Biodiversity, 2, 569-590.
15. th Symposium on the Chemistry of Terpenes, Essential Oils, and Aromatics, Saga, Japan, 95-97.
16. Kumar N, Ravindkanath B, Seshadri TR. (1974) Terpenoids of Pterocarpus santalinus Heartwood. Phytochemistry, 13, 633-636.
17. st Symposium on the Chemistry of Terpenes, Essential Oils, and Aromatics, Iwate, Japan, 224-226.
18. rd Symposium on the Chemistry of Terpenes, Essential Oils, and Aromatics, Oita, Japan, 205-207.
19. Hashimoto T, Noma Y, Asakawa Y. (2001) Biotransformation of terpenoids from the crude drugs and animal origin by microorganisms. Heterocycles, 54, 529-559. (Pubitemid 32162761)
20. th Symposium on the Chemistry of Terpenes, Essential Oils, and Aromatics, Fukui, Japan, 387-389.
21. Clark AM, Hufford CD. (1979) Microbial transformation of the sesquiterpene lactone costunolide. Journal of the Chemical Society, Perkin Transactions 1, 3022-3028.
22. Barrero AF, Oltra J E, Raslan DS, Sade DA. (1999) Microbial transformation of sesquiterpene lactones by the fungi Cunninghamella echinulata and Rhizopus oryzae. Journal of Natural Products, 62, 726-729.
23. Kumari GNK, Masilamani S, Ganesh R, Aravind S. (2003) Microbial biotransformation of zaluzanin D. Phytochemistry, 62, 1101-1104.
24. Aranda G, Facon I, Lallemand J-Y, Leclaire M. (1992) Microbiological hydroxylation in the drimane series. Tetrahedron Letters, 33, 7845-7848.
25. th Symposium on the Chemistry of Terpenes, Essential Oils, and Aromatics, Fukui, Japan, 380-381.
26. Ayer WA, Craw PA. (1989) Metabolites of fairy ring fungus, Marasmius oreades. Part 2. Norsesquiterpenes, further sesquiterpenes and argocybin. Canadian Journal of Chemistry, 67, 1371-1380.
27. th Symposium on the Chemistry of Terpenes, Essential Oils, and Aromatics, Yokohama, Japan, 406-408.
28. th Symposium on the Chemistry of Terpenes, Essential Oils, and Aromatics, Yokohama, Japan, 263-265.
29. th Symposium on the Chemistry of Terpenes, Essential Oils, and Aromatics, Tokyo, Japan, 142-144.
30. Harinantenaina, L, Quang DN, Nishizawa T, Hashimoto T, Kochi C, Soma, G-I, Asakawa Y. (2007) Bioactive compounds from liverworts: Inhibition of lipopolysaccharide-induced inducible NOS mRNA in RAW 264.7 cells by herbertenoids and cuparenoids. Phytomedicine, 14, 486-491.
31. Harinantenaina L, Noma Y, Asakawa Y. (2005) Penicillium sclerotiorum catalyzes the conversion of herbertenediol into its dimers: mastigophorenes A and B. Chemical and Pharmaceutical Bulletin, 53, 256-257.
32. Hashimoto T, Noma Y, Goto Y, Tanaka M, Takaoka S, Asakawa Y. (2004) Biotransformation of (-)-maalioxide by Aspergillus niger and Aspergillus cellulosae. Heterocycles, 62, 655-666.
33. Wang Y, Tan T -K, Tan GK, Connolly JD, Harrison LJ. (2006) Microbial transformation of the sesquiterpenoid (-)-maalioxide by Mucor plumbeus. Phytochemistry, 67, 58-61.
34. Tori M, Sono M, Asakawa Y. (1990) The reaction of three sesquiterpene ethers with m-chloroperbenzoic acid. Bulletin of Chemical Society of Japan, 63, 1770-1776.
35. th Symposium on the Chemistry of Terpenes, Essential Oils, and Aromatics, Fukui, Japan, 235-237.
36. Furusawa M, Hashimoto T, Noma Y, Asakawa Y. (2006) Isolation and structures of new cyclomyltaylane and ent-chamigrane-type sesquiterpenoids from the liverwort Reboulia hemisphaerica. Chemical and Pharmaceutical Bulletin, 54, 996-1003.
37. Lahlou EL, Noma Y, Hashimoto T, Asakawa Y. (2000) Microbiotransformation of dehydropinguisenol by Aspergillus sp. Phytochemistry, 54, 455-460.
38. Lamare V, Furstoss R. (1990) Bioconversion of sesquiterpenes. Tetrahedron, 46, 4109-4132.
39. Devi JR. (1979) Microbiological transformation of terpenes: Part XXVI. Microbial transformation of caryophyllene. Indian Journal of Biochemistry and Biophysics, 16, 76-79.
40. Abraham WR, Ernst L, Stumpf B. (1990) Biotransformation of caryophyllene by Diplodia gossypina. Phytochemistry, 29, 115-120.
41. Choudhary MI, Siddiqui ZA, Nawaz SA, Atta-ur-Rahman. (2006) Microbial transformation and butyrylcholinesterase inhibitory activity of (-)-caryophyllene oxide and its derivatives. Journal Natural Products, 69, 1429-1434.
42. Duran R, Corrales E, Hernandez-Galan R, Collado G. (1999) Biotransformation of caryophyllene oxide by Botrytis cinerea. Journal of Natural Products, 62, 41-44.
43. Asakawa Y, Taira Z, Takemoto T, Ishida T, Kido M, Ichikawa Y. (1981) X-ray crystal structure analysis of 14-hydroxycaryophyllene oxide, a new metabolite of (-)-caryophyllene in rabbits. Journal of Pharmaceutical Sciences, 70, 710-711.
44. Daniewski WM, Grieco PA, Huffman J, Rymkiewicz A, Wawrzun A. (1981) Isolation of 12-hydroxycaryophyllene-4,5-oxide, a sesquiterpene from Lactarius camphorates. Phytochemistry, 20, 2733-2734.
45. Asakawa Y, Ishida T, Toyota M, Takemoto T. (1986) Terpenoid biotransformation in mammals IV. Biotransformation of (+)-longifolene, (-)-caryophyllene, (-)-caryophyllene oxide, (-)-cyclocolorenone, (+)-nootkatone, (-)-elemol, (-)-abietic acid and (+)-dehydroabietic acid in rabbits. Xenobiotica, 6, 753-767. (Pubitemid 16044823)
46. Asakawa Y. (unpublished results).
47. Furusawa M, Hashimoto T, Noma Y, Asakawa Y. (2005) Highly efficient production of nootkatone, the grapefruit aroma from valencene, by biotransformation. Chemical and Pharmaceutical Bulletin, 53, 1513-1514.
48. Furusawa M, Hashimoto T, Noma Y, Asakawa Y. (2005) Biotransformation of Citrus aromatics nootkatone and valencene by microorganisms. Chemical and Pharmaceutical Bulletin, 53, 1423-1429.