title: Granuloside, A Unique Linear Homosesterterpene from the Antarctic Nudibranch Charcotia granulosa.
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.
authors.affiliation: †Bio-Organic Chemistry Lab, Istituto di Chimica Biomolecolare, Consiglio Nazionale delle Ricerche, Via Campi Flegrei 34, 80078 Pozzuoli, Napoli, Italy.
authors.forename: Adele
authors.initials: A
authors.lastname: Cutignano
authors.affiliation: ‡Department of Animal Biology (Invertebrates) and Biodiversity Research Institute (IrBIO), University of Barcelona, Av. Diagonal 643, 08028 Barcelona, Catalonia, Spain.
authors.forename: Juan
authors.initials: J
authors.lastname: Moles
authors.affiliation: ‡Department of Animal Biology (Invertebrates) and Biodiversity Research Institute (IrBIO), University of Barcelona, Av. Diagonal 643, 08028 Barcelona, Catalonia, Spain.
authors.forename: Conxita
authors.initials: C
authors.lastname: Avila
authors.affiliation: †Bio-Organic Chemistry Lab, Istituto di Chimica Biomolecolare, Consiglio Nazionale delle Ricerche, Via Campi Flegrei 34, 80078 Pozzuoli, Napoli, Italy.
authors.forename: Angelo
authors.initials: A
authors.lastname: Fontana
mesh_terms: D000818:Animals; D000864:Antarctic Regions; D049851:Gastropoda / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D054830:Sesterterpenes / Q000737:chemistry* / Q000302:isolation & purification*; D014157:Transcription Factors
chemical_list: D054830:Sesterterpenes; D014157:Transcription Factors; C484903:granulosa cell high-mobility group-box protein-1, rat; C000602069:granuloside