ISSN:
0075-4617
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Microbial Transformations of Δ4-Bufatrienolides, II. Structure Elucidation of the Products of Oxygenation of Scillarenin, 3-epi-Scillarenin, 5β-iso-Scillarenin, Scillarenone and Scillaridin by Rhizopus SpeciesBy chemical transformations (schemes 1-5) and interpretation of UV-, IR- and NMR-spectra the structure of the following oxygenated compounds (table 1), obtained by transformation from 3-epi-scillarenin (1), scillarenin (2), 5β-iso-scillarenin (3), scillaridin (4) and scillarenone (5) with the fungi Rhizopus arrhizus Fischer and Rhizopus nigricans Ehrenberg, have been established: 7β-hydroxy compounds 6-9, 6β-hydroxy compounds 16 and 17, 12β-hydroxy compounds 13 and 19 as well as Δ6-dehydroscillarenone (18). - Hereby the following new bufa-tri-, -tetra- and -pentaenolides (table 1) are obtained: 6α-hydroxyscillarenin (32), 6-oxoscillarenone (25), 6-acetoxy-6-dehydroscillarenone (26) and Δ6,8(14)-bisdehydro-scillarenone (30). - From 6, 12, 16 and 32 are obtained the diacetates 6a, 27, 23 and 33, from 8, 9, 17 and 19 the monoacetates 22, 21, 24 and 29 (table 1).
Notes:
Anhand chemischer Umsetzungen (Schemata 1-5) und Interpretation der UV-, IR- sowie NMR-Spektren wird die Struktur folgender, aus 3-epi-Scillarenin (1), Scillarenin (2), 5β-iso-Scillarenin (3), Scillaridin (4) und Scillarenon (5) mit den Pilzen Rhizopus arrhizus Fischer sowie Rhizopus nigricans Ehrenberg erhaltenen Oxygenierungsprodukte (Tab. 1) aufgeklärt: 7β-Hydroxy-Verbindungen 6-9, 6β-Hydroxy-Verbindungen 16 und 17, 12β-Hydroxy-Verbindungen 13 und 19 sowie Δ6-Dehydro-scillarenon (18). - Dabei werden als neue Bufa-tri-, -tetra- und -pentaenolide (Tab. 1) erhalten: 6α-Hydroxy-scillarenin (32), 6-Oxo-scillarenon (25), 6-Acetoxy-6-dehydro-scillarenon (26) und Δ6,8(14)-Bis-dehydro-scillarenon (30). - Aus 6, 12, 16 und 32 werden die Diacetate 6a, 27, 23 und 33, aus 8, 9, 17 und 19 die Monoacetate 22, 21, 24 und 29 hergestellt (Tab. 1).
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.19717530111
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