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Imidazolone and Imidazolidinone Artifacts of a Pivotal Imidazolthione, Zyzzin, from the poecilosclerid sponge Zyzza massalis from the coral sea. The first thermochromic systems of marine origin
Author(s) -
Mancini Ines,
Guella Graziano,
Pietra Francesco,
Debitus Cécile,
Duhet Daniel
Publication year - 1994
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.19940770719
Subject(s) - chemistry , sponge , acetone , coral , antifungal , stereochemistry , organic chemistry , botany , microbiology and biotechnology , ecology , biology
Dry acetone extracts of the freeze‐dried, deep‐red powder of the poecilosclerid sponge Zyzza massalis (D ENDY ) from the Coral Sea gave the orange alkaloid zyzzin (= 4‐(1 H ‐indol‐3‐yl)‐1,5‐dihydro‐5‐thioxo‐1 H ‐imidazol‐2‐one 14 ), which underwent exchange of the 5‐thioxo for the 5‐oxo group during aqueous chromatographic workup, giving yellow 13 . Both 13 and 14 added hydroxylic solvents at C(4)=N giving colourless, racemic products, 3 and 8 , respectively, by incorporation of MeOH and 10 and 11 , respectively, by incorporation of H 2 O. On warming 3 or 10 in DMSO, 13 was recovered, thus furnishing a novel thermochromic system. Optically active (+)‐ 12 , which may be viewed to derive from enzymatic reduction of 14 at C(4)=N followed by S→O exchange, was also isolated from this sponge, along with the linear amides 16 and 19 . Compound 3 proved to have antibacterial and antifungal activities.