The microbiological transformation of two 15B-hydroxy-ent-kaurene diterpenes by Gibberella fujikuroi
The incubation of 15B-hydroxy-3-oxo-ent-kaur-16-ene (1) with the fungus Gibberella fujikuroi afforded 11B-hydroxy-3,15-dioxo-ent-kaurane (6), 11B,15B-dihydroxy-3-oxo-ent-kaur-16-ene (8), 7B,11B,15B-trihydroxy-3-oxo-ent-kau-16-ene (9), 7a,11B-dihydroxy-3,15-dioxo-ent-kaurane (7), and 7a,11B,15B-trihidroxy-3-oxo-ent-kaur-16-ene (10). The incubation of 15B-hydroxy-ent-kaur-2,16-diene (3) with the same fungus yielded 7a,11B-dihydroxy-15-oxo-ent-kaur-3-ene (12), 7a,11B,15B-trihydroxy-ent-kaur-2,16-diene (13), 7B,-15B-dihydroxy-ent-kaur-2,16-dien-19,6-olide (14), 1B,7B,15B-trihydroxy-ent-kaur-2,16-dien-19-oic acid (15), 7a,11B,16a-trihydroxy-15-oxo-ent-kaur-2-ene (17), and 7a,15B,17-trihydroxy-11B,16B-epoxy-ent-kaur-2-ene (19). These results indicated that a 3-oxo group in ent-kaur-16-ene derivatives inhibits the oxidation at C-19, typical of the biosynthetic pathway of gibberellins and kaurenolides, while a 2,3-double bond or a 15B-OH does not. In both substrates a 15B-alcohol directs hydroxylations at C-11(B) and C-7(a), while in those with a 2,3-double bond the functionalization of C-1(B) is favored.
| Main Authors: | , , |
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| Format: | artículo biblioteca |
| Language: | English |
| Published: |
American Chemical Society
2004
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| Online Access: | http://hdl.handle.net/10261/21966 |
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