Isolation and structure of five lyngbyabellin derivatives from a Papua New Guinea collection of the marine cyanobacterium Lyngbya majuscula

被引:70
作者
Han, BN
McPhail, KL
Gross, H
Goeger, DE
Mooberry, SL
Gerwick, WH [1 ]
机构
[1] Oregon State Univ, Coll Pharm, Corvallis, OR 97331 USA
[2] SW Fdn Biomed Res, Dept Physiol & Med, San Antonio, TX 78245 USA
基金
美国国家卫生研究院;
关键词
Lyngbya majuscula; dolabellin; lyngbyabellin; lipopeptide; cytotoxin; actin-disruption;
D O I
10.1016/j.tet.2005.09.036
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
Five new lyngbyabellin analogs along with a known compound, dolabellin, have been isolated from the marine cyanobacterium Lyngbya majuscula collected from Papua New Guinea. The structures of lyngbyabellins E-I were elucidated through extensive spectroscopic analysis, including HR-FABMS and I D and 2D NMR experiments. The absolute configurations of lyngbyabellin E and H were ascertained by chiral HPLC and GUMS analysis of degradation products, in combination with NMR experiments. All five lynabyabellins showed cytotoxicity to NCI-H460 human lung tumor and neuro-2a mouse neuroblastoma cell lines with LC50 values between 0.2 and 4.8 mu M. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:11723 / 11729
页数:7
相关论文
共 19 条
[1]
ALLEY MC, 1988, CANCER RES, V48, P589
[2]
Microbial symbionts of the Australian Great Barrier Reef sponge, Candidaspongia flabellata [J].
Burja, AM ;
Hill, RT .
HYDROBIOLOGIA, 2001, 461 (1-3) :41-47
[3]
Gerwick WH, 2001, ALKALOIDS, V57, P75, DOI 10.1016/S0099-9598(01)57003-0
[4]
Symplostatin 1:: A dolastatin 10 analogue from the marine cyanobacterium Symploca hydnoides [J].
Harrigan, GG ;
Luesch, H ;
Yoshida, WY ;
Moore, RE ;
Nagle, DG ;
Paul, VJ ;
Mooberry, SL ;
Corbett, TH ;
Valeriote, FA .
JOURNAL OF NATURAL PRODUCTS, 1998, 61 (09) :1075-1077
[5]
Structurally diverse new alkaloids from Palauan collections of the apratoxin-producing marine cyanobacterium Lyngbya sp. [J].
Luesch, H ;
Toshida, WY ;
Moore, RE ;
Paul, VJ .
TETRAHEDRON, 2002, 58 (39) :7959-7966
[6]
Isolation and structure of the cytotoxin lyngbyabellin B and absolute configuration of lyngbyapeptin A from the marine cyanobacterium Lyngbya majuscula [J].
Luesch, H ;
Yoshida, WY ;
Moore, RE ;
Paul, VJ .
JOURNAL OF NATURAL PRODUCTS, 2000, 63 (10) :1437-1439
[7]
Isolation, structure determination, and biological activity of lyngbyabellin A from the marine cyanobacterium Lyngbya majuscula [J].
Luesch, H ;
Yoshida, WY ;
Moore, RE ;
Paul, VJ ;
Mooberry, SL .
JOURNAL OF NATURAL PRODUCTS, 2000, 63 (05) :611-615
[8]
MANGER RL, 1995, J AOAC INT, V78, P521
[9]
Structure and absolute stereochemistry of hectochlorin, a potent stimulator of actin assembly [J].
Marquez, BL ;
Watts, KS ;
Yokochi, A ;
Roberts, MA ;
Verdier-Pinard, P ;
Jimenez, JI ;
Hamel, E ;
Scheuer, PJ ;
Gerwick, WH .
JOURNAL OF NATURAL PRODUCTS, 2002, 65 (06) :866-871
[10]
Stereochemical determination of acyclic structures based on carbon-proton spin-coupling constants. A method of configuration analysis for natural products [J].
Matsumori, N ;
Kaneno, D ;
Murata, M ;
Nakamura, H ;
Tachibana, K .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :866-876