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

被引：29

作者：

Cen-Pacheco, Francisco ^{[1
,4
]}

Santiago-Benitez, Adrian J. ^{[1
,2
]}

Garcia, Celina ^{[1
,2
]}

Alvarez-Mendez, Sergio J. ^{[1
,2
]}

Martin-Rodriguez, Alberto J. ^{[1
,5
]}

Norte, Manuel ^{[1
,2
]}

Martin, Victor S. ^{[1
,2
]}

Gavin, Jose A. ^{[1
,2
]}

Fernandez, Jose J. ^{[1
,2
]}

Hernandez Daranas, Antonio ^{[1
,3
]}

机构：

[1] Univ La Laguna, Inst Bioorgan Chem Antonio Gonzalez, Ctr Biomed Res Canary Isl CIBICAN, E-38206 Tenerife, Spain

[2] Univ La Laguna, Dept Organ Chem, E-38206 Tenerife, Spain

[3] Univ La Laguna, Dept Chem Engn & Pharmaceut Technol, Fac Hlth Sci, E-38206 Tenerife, Spain

[4] Univ Veracruzana, Fac Bioanal, Xalapa Enriquez 91700, Veracruz, Mexico

[5] Ocean Platform Canary Isl PLOCAN, Telde 35214, Gran Canaria, Spain

来源：

JOURNAL OF NATURAL PRODUCTS | 2015年 / 78卷 / 04期

关键词：

MARINE NATURAL-PRODUCTS; COUPLING-CONSTANTS; NMR-SPECTROSCOPY; CHEMICAL-SHIFTS; CONFIGURATION; STEREOCHEMISTRY; DIASTEREOISOMERS; MOLECULES;

D O I：

10.1021/np5008922

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

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 structureactivity conclusions were obtained.

引用

页码：712 / 721

页数：10

共 37 条

[1] Diastereomer Configurations from Joint Experimental-Computational Analysis [J].