title: Oxasqualenoids from Laurencia viridis: Combined Spectroscopic-Computational Analysis and Antifouling Potential.
abstract: The chemical study of the red alga Laurencia viridis has led to the isolation of four new polyether triterpenoids: 28-hydroxysaiyacenol B (2), saiyacenol C (3), 15,16-epoxythyrsiferol A (4), and 15,16-epoxythyrsiferol B (5). The structures of 2 and 3 were established mainly by NMR data analysis and comparison with the well-known metabolite dehydrothyrsiferol (1). However, due to the existence of a nonprotonated carbon within the epoxide functionality, stereochemical assignments in 4 and 5 required an in-depth structural study that included NOESY data, J-based configuration analysis, comparison with synthetic models, and DFT calculations. The biological activities of the new metabolites and other related oxasqualenoids were evaluated for the first time against a panel of relevant biofouling marine organisms, and structure-activity conclusions were obtained.
authors.affiliation: ‡Faculty of Bioanalysis, Campus-Veracruz, Universidad Veracruzana, 91700, Veracruz, México.
authors.forename: Francisco
authors.initials: F
authors.lastname: Cen-Pacheco
authors.forename: Adrián J
authors.initials: AJ
authors.lastname: Santiago-Benítez
authors.forename: Celina
authors.initials: C
authors.lastname: García
authors.forename: Sergio J
authors.initials: SJ
authors.lastname: Álvarez-Méndez
authors.affiliation: ⊥Oceanic Platform of the Canary Islands (PLOCAN), Carretera de Taliarte s/n, 35214, Telde, Gran Canaria, Spain.
authors.forename: Alberto J
authors.initials: AJ
authors.lastname: Martín-Rodríguez
authors.forename: Manuel
authors.initials: M
authors.lastname: Norte
authors.forename: Victor S
authors.initials: VS
authors.lastname: Martín
authors.forename: José A
authors.initials: JA
authors.lastname: Gavín
authors.forename: José J
authors.initials: JJ
authors.lastname: Fernández
authors.forename: Antonio Hernández
authors.initials: AH
authors.lastname: Daranas
mesh_terms: D057219:Biofouling / Q000517:prevention & control*; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D044722:Laurencia / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011714:Pyrans / Q000737:chemistry / Q000302:isolation & purification; D013030:Spain; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D011714:Pyrans; D014315:Triterpenes; C114056:dehydrothyrsiferol