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5α‐24‐Norcholestan‐3β‐ol and (24 Z )‐Stigmasta‐5,7,24(28)‐trien‐3β‐ol, Two New Marine Sterols from the Pacific Sponges Terpios zeteki and Dysidea herbacea
Author(s) -
Delseth Claude,
Tolela Luhata,
Djerassi Carl,
Scheuer Paul J.,
Wells Robert J.
Publication year - 1979
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.19790620115
Subject(s) - sterol , chemistry , sponge , steroid , chromatography , stereochemistry , cholesterol , biochemistry , botany , biology , hormone
The steroidal components of 2 marine sponges, Terpios zeteki (from Hawaii) and Dysidea herbacea (from Australia) were fractionated through a combination of chromatographic methods, including reversed phase HPLC., and were analyzed by a combination of physical methods, including high resolution GC.‐MS. and 360 MHz 1 H‐NMR. T. zeteki contains 6 conventional 5α‐stanols which comprise 91% of the sterol mixture, and traces (0.5%) of a new C 26 sterol, 5α‐24‐norcholestan‐3β‐ol. Minor amounts of conventional Δ 5 ‐sterols (6.5%) and of a single Δ 4 ‐3‐ketosteroid (1.5%) were also present. In contrast, the Australian sponge (D. herbacea) contains 3 Δ 5,7 ‐sterols which comprise 1.5% of the sterol mixture, and one new C 29 sterol, (24 Z )‐stigmasta‐5,7,24(28)‐trien‐3β‐ol, as the major component (75%). In addition, minor amounts of conventional 5α‐stanols (0.5%), Δ 5 ‐sterols (5%) and 5α‐Δ 7 ‐sterols (18%) were present in this complex sterol mixture. The possible dietary or endosymbiotic origins of these sterols are discussed.