Identification de stérols à chaînes latérales courtes dans l′éponge Damiriana hawaiiana

Abstract

Identification of short side chain sterols in the sponge Damiriana hawaiianaThe steroidal composition of the sponge Damiriana hawaiiana is examined. Twenty‐seven components are identified. In addition to the C26‐C29, Δ5‐mono and diunsaturated sterols, the sponge contains sterols without side‐chain: androsta‐5, 16‐dien‐3β‐ol(1), androst‐5‐en‐3β‐ol(2); sterols with a non‐functionalized side‐chain consisting of two, three, four, five and six carbon atoms: pregna‐5, 20‐dien‐3β‐ol(5), pregn‐5‐en‐3β‐ol(6), 23, 24‐bisnor‐chola‐5, 20‐dien‐3β‐ol(7), 23, 24‐bisnor‐chol‐5‐en‐3β‐ol(8), 24‐nor‐chol‐5‐en‐3β‐ol(10), chol‐5‐en‐3β‐ol(11), 26, 27‐bisnor‐cholest‐5‐en‐3β‐ol(12), and sterols possessing a short oxygenated side‐chain such as 3β‐hydroxy‐androst‐5‐en‐17‐one(3), androst‐5‐en‐3β, 17β‐diol(4) and 3β‐hydroxy‐26, 27‐bisnor‐22‐trans‐cholesta‐5, 22‐dien‐24‐one(14). The probable biological or dietary origin rather than artifact production of these hitherto undescribed components from marine sources is supported by their relatively high concentration and their relative proportions, both very different from those expected for autoxidation.