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

Journal of Natural Products
Francisco Cen-PachecoAntonio Hernández Daranas

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.

References

Jul 11, 2000·Natural Product Reports·J J FernándezM Norte
Dec 21, 2002·The Journal of Organic Chemistry·Yujiro HayashiMitsuru Shoji
May 9, 2009·Chemical Reviews·Gordon M CraggDavid J Newman
May 23, 2009·The Journal of Organic Chemistry·Steven G Smith, Jonathan M Goodman
May 19, 2010·Marine Drugs·Francisco Cen-PachecoAntonio Hernández Daranas
Aug 28, 2010·Journal of the American Chemical Society·Steven G Smith, Jonathan M Goodman
Mar 29, 2011·Journal of the American Chemical Society·Giacomo SaielliAlessandro Bagno
May 7, 2011·Chemistry : a European Journal·José G NapolitanoAntonio Hernández Daranas
May 28, 2011·European Journal of Medicinal Chemistry·Francisco Cen-PachecoJosé J Fernández
Dec 14, 2011·Marine Drugs·Francisco Cen PachecoAntonio Hernández Daranas
Jun 28, 2012·The Journal of Organic Chemistry·Abil E AlievStephen Caddick
May 8, 2013·Chemistry : a European Journal·Francisco Cen-PachecoAntonio Hernández Daranas
Jan 7, 2014·Natural Product Reports·John W BluntMichèle R Prinsep
Feb 7, 2014·Journal of Natural Products·Gordon M CraggDavid J Newman

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Citations

Apr 6, 2016·Organic & Biomolecular Chemistry·Kristaps ErmanisJonathan M Goodman
Aug 29, 2017·Marine Drugs·Hans Uwe Dahms, Sergey Dobretsov
Dec 30, 2017·Marine Drugs·Adrián Morales-AmadorManuel Norte
Jul 10, 2019·Magnetic Resonance in Chemistry : MRC·Leonid B Krivdin
Feb 15, 2020·Natural Product Reports·Robert A Hill, Joseph D Connolly
Jun 15, 2018·Journal of Applied Phycology·Mahasweta SahaPunyasloke Bhadury
Jul 25, 2019·Marine Drugs·Jacob Lorenzo-MoralesJosé J Fernández
Mar 16, 2017·Natural Product Reports·John W BluntMichèle R Prinsep
Dec 29, 2020·The Journal of Organic Chemistry·Francisco Cen-PachecoAntonio Hernández Daranas

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