5α-24-Norcholestan-3β-ol and (24Z)-Stigmasta-5,7,24(28)-trien-3β-ol, Two New Marine Sterols from the Pacific Sponges Terpios zeteki and Dysidea herbacea

✍ Scribed by Claude Delseth; Luhata Tolela; Carl Djerassi; Paul J. Scheuer; Robert J. Wells

• Publisher: John Wiley and Sons
• Year: 1979
• Tongue: German
• Weight: 607 KB
• Volume: 62
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19790620115

✦ Synopsis

Abstract

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.