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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
Author(s) -
Ziegler René,
Tamm Christoph
Publication year - 1976
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.19760590613
Subject(s) - chemistry , diene , stereochemistry , hydroxymethyl , ether , metabolite , chemical structure , epoxy , organic chemistry , biochemistry , natural rubber
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 ).