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Dendryphiellin A, the First Fungal Trinor‐eremophilane. Isolation from the marine deuteromycete Dendryphiella salina (S UTHERLAND ) P UGH et N ICOT
Author(s) -
Guerriero Antonio,
D'Ambrosio Michele,
Pietra Francesco,
Cuomo Vincenzo,
Vanzanella Fortunato
Publication year - 1988
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.19880710107
Subject(s) - chemistry , moiety , stereochemistry , hydrolysis , metabolite , terpene , biochemistry
The novel metabolite dendryphiellin A ( = (+)‐(1 R ,2 S ,8a R )‐ 1,2,6,7,8,8a‐hexahydro‐7‐hydroxy‐1,8a‐dimethyl‐6‐oxonaphthalen‐2‐yl (6 R *, 2 E ,4 E )‐8‐hydroxy‐6‐methylocta‐2,4‐dienoate; (+)‐ 1 ) is isolated from cultures of the marine deuteromycete Dendryphiella salina . There is no precedent in fungi for trinor‐eremophilanes or for branched C 9 carboxylic acids, the two classes of compounds constituting (+)‐1. The structure is secured by NMR spectroscopy and hydrolysis of (+)‐1 to give the side‐chain moiety ((6 R *,2 E ,4 E )‐8‐hydroxy‐6‐methylocta‐2,4‐dienoic acid ( 2 )) intact, whilst the trinor‐ermophilane moiety is decomposed. The absolute configuration at the trinor‐eremophilane moiety is established from exciton coupling between the dienone and the diene‐ester functions.