Umwandlung von Krötengiften (Bufadienoliden) durch Mikroorganismen. II. 12β‐Hydroxyresibufogenin . 12. Mitteilung über Reaktionen mit Mikroorganismen | Zendy

Schüpbach M. | Zendy; Tamm Ch. | Zendy

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Umwandlung von Krötengiften (Bufadienoliden) durch Mikroorganismen. II. 12β‐Hydroxyresibufogenin . 12. Mitteilung über Reaktionen mit Mikroorganismen

Author(s) -

Schüpbach M.,

Tamm Ch.

Publication year - 1964

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19640470815

Subject(s) - chemistry , digoxigenin , incubation , derivative (finance) , medicinal chemistry , stereochemistry , biochemistry , in situ hybridization , gene expression , financial economics , economics , gene

Incubation of resibufogenin ( 1 ) with cultures of Fusarium lini (B OLLEY ) yielded the unknown 12β‐hydroxyresibufogenin ( 4 ). The structure of 4 was proved by the degradation of its diacetyl derivative 5 to methyl 3β,12β‐diacetoxy‐l4β, 15β‐epoxy‐5β, 14β, 17αH‐etianate ( 9 ) which was identical with the degradation product obtained from 14β,15β‐epoxy‐14‐anhydro‐digoxigenin diacetate ( 7 ). The latter was prepared from di‐O‐acetyl digoxigenin ( 8 ). Incubation of 14β, 15β‐epoxy‐14‐anhydro‐digitoxigenin ( 2 ) with F. lini led to the 12β‐hydroxy derivative 6 , its diacetate being identical with 7 . LiAlH 4 ‐reduction of both the epoxyester 9 and the hydroxyester 12 derived from digoxigenin gave the same tetrol 10 .

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