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Title

Oxasqualenoids from Laurencia viridis: Combined Spectroscopic–Computational Analysis and Antifouling Potential

AuthorsCen-Pacheco, Francisco; Santiago-Benítez, Adrián J.; García, Celina; Álvarez-Méndez, Sergio J.; Martín-Rodríguez, Alberto J.; Norte, Manuel; Martín, Víctor S.; Gavín, José A.; Fernández, José J.; Hernández Daranas, Antonio
KeywordsMetabolism
Carbon
Ethers
Quantum mechanics
Alkyls
Issue Date17-Mar-2015
PublisherAmerican Society of Pharmacognosy
American Chemical Society
CitationJournal of Natural Products 78(4): 712–721 (2015)
AbstractThe 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.
Publisher version (URL)https://doi.org/10.1021/np5008922
URIhttp://hdl.handle.net/10261/213200
DOIhttp://dx.doi.org/10.1021/np5008922
ISSN0163-3864
E-ISSN1520-6025
Appears in Collections:(IPNA) Artículos
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