Cytotoxic Halogenated Metabolites from the Brazilian Red Alga Laurencia catarinensis

被引:47
作者
Lhullier, Cintia [1 ,2 ]
Falkenberg, Miriam [1 ,2 ]
Ioannou, Efstathia [1 ]
Quesada, Antonio [3 ]
Papazafiri, Panagiota [4 ]
Horta, Paulo Antunes [5 ]
Schenkel, Eloir Paulo [2 ]
Vagias, Constantinos [1 ]
Roussis, Vassilios [1 ]
机构
[1] Univ Athens, Dept Pharmacognosy & Chem Nat Prod, Sch Pharm, GR-15771 Athens, Greece
[2] Univ Fed Santa Catarina, Programa Posgrad Farm, BR-88040970 Florianopolis, SC, Brazil
[3] Univ Jaen, Dept Didact Sci, Jaen, Spain
[4] Univ Athens, Sch Sci, Dept Anim & Human Physiol, Athens 15784, Greece
[5] Univ Fed Santa Catarina, Programa Posgrad Biol Vegetal, BR-88040970 Florianopolis, SC, Brazil
来源
JOURNAL OF NATURAL PRODUCTS | 2010年 / 73卷 / 01期
关键词
MARINE NATURAL-PRODUCTS; HARE APLYSIA-DACTYLOMELA; BROMINATED DITERPENES; SESQUITERPENES; CAESPITOSA; OBTUSA;
D O I
10.1021/np900627r
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Seven new (1-7) and seven previously reported (8-14) halogenated metabolites were isolated from the organic extract of the Brazilian red alga Laurencia catarinensis. The structure elucidation and the assignment of the relative configurations of the new natural products were based oil detailed NMR and MS spectroscopic analyses, whereas the structure of metabolite 6 was confirmed by single-crystal X-ray diffraction analysis. The absolute configuration of metabolite I was determined using the modified Mosher's method. The in vitro cytotoxicity of compounds 1-14 was evaluated against HT29, MCF7, and A431 cell lines.
引用
收藏
页码:27 / 32
页数:6
相关论文
共 18 条
[1]   Marine natural products [J].
Blunt, John W. ;
Copp, Brent R. ;
Hu, Wan-Ping ;
Munro, Murray H. G. ;
Northcote, Peter T. ;
Prinsep, Michele R. .
NATURAL PRODUCT REPORTS, 2009, 26 (02) :170-244
[2]   Aplysiadiol from Aplysia dactylomela suggested a key intermediate for a unified biogenesis of regular and irregular marine algal bisabolene-type metabolites [J].
Brito, Inmaculada ;
Dias, Teresa ;
Diaz-Marrero, Ana R. ;
Darias, Jose ;
Cueto, Mercedes .
TETRAHEDRON, 2006, 62 (41) :9655-9660
[3]   REGULAR AND IRREGULAR SESQUITERPENES CONTAINING A HALOGENATED HYDROPYRAN FROM LAURENCIA-CAESPITOSA [J].
CHANG, M ;
VAZQUEZ, JT ;
NAKANISHI, K ;
CATALDO, F ;
ESTRADA, DM ;
FERNANDEZ, J ;
GALLARDO, A ;
MARTIN, JD ;
NORTE, M ;
PEREZ, R ;
RODRIGUEZ, ML .
PHYTOCHEMISTRY, 1989, 28 (05) :1417-1424
[4]   MARINE NATURAL-PRODUCTS FROM THE ATLANTIC ZONE .23. TOTAL SYNTHESIS OF 8-DESOXY-ISOCAESPITOL, A NEW POLYHALOGENATED SESQUITERPENE FROM LAURENCIA-CAESPITOSA [J].
GONZALEZ, AG ;
MARTIN, JD ;
PEREZ, C ;
RAMIREZ, MA ;
RAVELO, F .
TETRAHEDRON LETTERS, 1980, 21 (02) :187-188
[5]  
GONZALEZ AG, 1974, TETRAHEDRON LETT, V15, P1249
[6]  
GONZALEZ AG, 1973, TETRAHEDRON LETT, V14, P2381
[7]  
GONZALEZ AG, 1979, TETRAHEDRON LETT, V20, P2719
[8]   MARINE NATURAL-PRODUCTS - HALOGENATED ACETYLENIC ETHERS FROM THE SEA HARE APLYSIA-DACTYLOMELA [J].
GOPICHAND, Y ;
SCHMITZ, FJ ;
SHELLY, J ;
RAHMAN, A ;
VANDERHELM, D .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (25) :5192-5197
[9]   MARINE NATURAL-PRODUCTS - DEODACTOL, ANTI-NEOPLASTIC SESQUITERPENOID FROM THE SEA HARE APLYSIA DACTYLOMELA [J].
HOLLENBEAK, KH ;
SCHMITZ, FJ ;
HOSSAIN, MB ;
VANDERHELM, D .
TETRAHEDRON, 1979, 35 (04) :541-545
[10]   Novel cytotoxic brominated diterpenes from the red alga Laurencia obtusa [J].
Iliopoulou, D ;
Mihopoulos, N ;
Vagias, C ;
Papazafiri, P ;
Roussis, V .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (20) :7667-7674