Isolation and Structure of Eucosterol and 16 β-Hydroxyeucosterol, Two Novel Spirocyclic Nortriterpenes, and of a New 24- Nor-5α-chola-8, 16-diene-23-oic Acid from Bulbs of Several Eucomis Species
✍ Scribed by René Ziegler; Christoph Tamm
- Publisher
- John Wiley and Sons
- Year
- 1976
- Tongue
- German
- Weight
- 883 KB
- Volume
- 59
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
Eucosterol and 16 β‐hydroxy‐eucosterol which have been isolated from several Eucomis species have been shown to be (23__S__)‐17,23‐epoxy‐3β,31‐dihydroxy‐27‐nor‐5α‐lanost‐8‐ene‐15,24‐dione (1) and (23 S)‐17,23‐epoxy‐3β,16β,31‐trihydroxy‐27‐nor‐5α‐lanost‐8‐ene‐15,24‐dione (2) by chemical transformations and spectral data. The spiro‐fused furanoic ether linkage of both metabolites represents a novel structural element for natural nortriterpenes. The structure of another metabolite (16), 3β‐hydroxy‐4β‐hydroxymethyl‐4,14α‐dimethyl‐15‐oxo‐24‐nor‐5α‐chola‐8,16‐diene‐23‐oic acid, from Eucomis autumnalis (Mill.) Chitt. was elucidated by chemical correlation of its methyl ester 17 with a degradation product of eucosterol (1).