Microbial Transformation of Sesquiterpene Lactones by the Fungi Cunninghamella echinulata and Rhizopus oryzae

Incubations of the fungi Cunninghamella echinulata and Rhizopus oryzae with the sesquiterpene lactones (+)-costunolide (1), (+)-cnicin (2), (+)-salonitenolide (3), (−)-dehydrocostuslactone (4), (−)-lychnopholide (5), and (−)-eremantholide C (6) were perfomed. Incubation of 1 with C. echinulata affor...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 1999-05, Vol.62 (5), p.726-729
Main Authors: Barrero, Alejandro F, Oltra, J. Enrique, Raslan, Délio S, Saúde, Dênia A
Format: Article
Language:English
Subjects:
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
chemical composition
chemical structure
cnicin
costunolide
Cunninghamella
Cunninghamella echinulata
dehydrocostuslactone
derivatives
Fundamental and applied biological sciences. Psychology
lychnopholide
metabolism
Methods. Procedures. Technologies
Rhizopus oryzae
salonitenolide
sesquiterpene lactones
sesquiterpenoid lactones
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Summary:Incubations of the fungi Cunninghamella echinulata and Rhizopus oryzae with the sesquiterpene lactones (+)-costunolide (1), (+)-cnicin (2), (+)-salonitenolide (3), (−)-dehydrocostuslactone (4), (−)-lychnopholide (5), and (−)-eremantholide C (6) were perfomed. Incubation of 1 with C. echinulata afforded Δ11(13)-dihydrogenation and Δ1(10)-epoxidation products (7−10). C. echinulata also hydrolyzed the side chain of 2, and transformed 4 into (+)-11α,13-dihydrodehydrocostuslactone (12), a new natural product. R. oryzae converted 4 into both Δ11(13)-dihydrogenation and Δ10(14)-epoxidation products (16 and 17). Both fungi transformed 5 into (−)-16-(1-methyl-1-propenyl)eremantholanolide (13), providing experimental evidence for the biosynthesis of the eremantholide hemiketal unit. Compounds 3 and 6 were not metabolized by either fungus under the test conditions.
ISSN:0163-3864
1520-6025
DOI:10.1021/np980520w