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

A new homosesterterpene with a unique linear skeleton, named granuloside (1), has been fully characterized from the Antarctic nudibranch Charcotia granulosa Vayssiere, 1906 (Mollusca: Gastropoda). The planar structure of 1 was determined by extensive spectroscopic techniques on the methyl derivatives (la 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.