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Novel Trinor‐eremophilanes (Dendryphiellin B, C, and D), Eremophilanes (Dendryphiellin E, F, and G), and Branched C 9 ‐Carboxylic Acids (Dendryphiellic Acid A and B) from the Marine Deuteromycete Dendryphiella salina (S UTHERLAND ) P UGH et N ICOT
Author(s) -
Guerriero Antonio,
D'Ambrosio Michele,
Cuomo Vincenzo,
Vanzanella Fortunato,
Pietra Francesco
Publication year - 1989
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.19890720304
Subject(s) - chemistry , stereochemistry , hydroxymethyl , carboxylic acid , organic chemistry
Further investigation of global extracts from cultures of the marine deuteromycete Dendryphiella salina leads to the isolation of three novel trinor‐eremophilanes esterified by branched C 9 ‐carboxylic acids, dendryphiellin B (= (+)‐(1 R *,2 S *,7 R *,8a R *)‐1,2,6,7,8,8a‐hexahydro‐7‐hydroxy‐1,8a‐dimethyl‐6‐oxonaphthalen‐2‐yl (6 R *, 2 E , 4 E )‐6‐hydroxy‐6‐methylocta‐2,4‐dienoate; (+)‐ 2 ), dendryphiellin C (=(+)‐(1 R *, 2 S *, 7 R *, 8a R *)‐1,2,6,7,8,8a‐hexa‐hydro‐7‐hydroxy‐1,8a‐dimethyl‐6‐oxonaphthalen‐2‐yl (6 S , 2 E , 4 E )‐6‐methylocta‐2,4‐dienoate; (+)‐ 3 )), and dendryphiellin D (=(+)‐(1 R *, 2 S *, 7 R *, 8a R *)‐1,2,6,7(8,8a‐hexahydro‐7‐hydroxy‐1,8a‐dimethyl‐6‐oxonaphthalen‐2‐yl (6 R *,2 E ,4 E )‐6‐(hydroxymethyl)octa‐2,4‐dienoate; (+)‐ 4 ). An intact eremophilane, dendryphiellin E ( 5 ), and its ethanolysis product dendryphiellin F whose absolute configuration is represented by structural formula (+)‐ 6 are also isolated from the above extracts. Dendryphiellin E exists as an open form 5a in equilibrium with a closed form 5b . A similar equilibrium exists between the open form 8a and the closed form 8b of a non‐esterified eremophilane, dendryphiellin G ( 8 ), which is isolated too from the above extracts and proves structurally related to the cyclic portion of 5 . Finally, the free, branched C 9 ‐carboxylic acids dendryphiellic acid A ((+)‐ 9 ) and B ((+)‐ 10 ) which correspond to side chains of the above esterified terpenes are also isolated from the above extracts.