Granuloside, A Unique Linear Homosesterterpene from the Antarctic Nudibranch Charcotia granulosa

J Nat Prod. 2015 Jul 24;78(7):1761-4. doi: 10.1021/acs.jnatprod.5b00378. Epub 2015 Jul 15.

Abstract

A new homosesterterpene with a unique linear skeleton, named granuloside (1), has been fully characterized from the Antarctic nudibranch Charcotia granulosa Vayssière, 1906 (Mollusca: Gastropoda). The planar structure of 1 was determined by extensive spectroscopic techniques on the methyl derivatives (1a and 1b), and the R absolute configuration at C-4 is suggested by comparison of experimental and calculated ECD spectra of 1b. Granuloside (1) is the first linear homosesterterpene skeleton ever reported and, despite the low molecular complexity, its chemical structure poses many questions about its biogenesis and origin in the nudibranch.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antarctic Regions
  • Gastropoda / chemistry*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Sesterterpenes / chemistry*
  • Sesterterpenes / isolation & purification*
  • Transcription Factors

Substances

  • Sesterterpenes
  • Transcription Factors
  • granulosa cell high-mobility group-box protein-1, rat
  • granuloside