Cytotoxic 5-Hydroxyindole Alkaloids from the Marine Sponge Scalarispongia sp.

被引:22
作者
Lee, Yeon-Ju [1 ]
Lee, Dong-Geun [1 ]
Rho, Hyun Soo [1 ]
Krasokhin, Vladimir B. [2 ]
Shin, Hee Jae [1 ]
Lee, Jong Seok [1 ]
Lee, Hyi-Seung [1 ]
机构
[1] Korea Ocean Res & Dev Inst, Ansan 426744, South Korea
[2] RAS, Pacific Inst Bioorgan Chem, Vladivostok 690022, Russia
关键词
ANNELATED INDOLE SERIES; NATURAL-PRODUCTS; DRUG LEADS; BISINDOLE ALKALOIDS; SPONGOSORITES SP; A-C; INHIBITORS; HYRTIOS; BIS; DERIVATIVES;
D O I
10.1002/jhet.1599
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Three new 5-hydroxyindole alkaloids (1, 2, 3) along with seven known analogs (4, 5, 6, 7, 8, 9, 10) were isolated from a Dokdo marine sponge Scalarispongia sp. The elucidation of the structures of the new compounds by spectroscopic analyses indicated that these compounds were an indole glyoxylate (1), a mono-indole analog of hyrtinadine A (2), and a symmetrical bis-indole with pyridine linker (3). The comparison of IC50 values for obtained compounds against a human leukemia cell line revealed that the bis-indole structure is a requirement for cytotoxicity.
引用
收藏
页码:1400 / 1404
页数:5
相关论文
共 32 条
[1]  
ALVAREZ M, 1991, HETEROCYCLES, V32, P1391
[2]   Chemistry and biology of new marine alkaloids from the indole and annelated indole series [J].
Aygün, A ;
Pindur, U .
CURRENT MEDICINAL CHEMISTRY, 2003, 10 (13) :1113-1127
[3]  
Bao B, 2007, MAR DRUGS, V5, P31, DOI 10.3390/md502031
[4]   Cytotoxic bisindole alkaloids from a marine sponge Spongosorites sp. [J].
Bao, BQ ;
Sun, QS ;
Yao, XS ;
Hong, JK ;
Lee, CO ;
Sim, CJ ;
Im, KS ;
Jung, JH .
JOURNAL OF NATURAL PRODUCTS, 2005, 68 (05) :711-715
[5]   Birnbaumin A and B:: Two unusual 1-hydroxyindole pigments from the "flower pot parasol" Leucocoprinus birnbaumii [J].
Bartsch, A ;
Bross, M ;
Spiteller, P ;
Spiteller, M ;
Steglich, W .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (19) :2957-2959
[6]  
Berridge M.V., 1996, Biochemica, P14, DOI DOI 10.1155/2013/420601
[7]   Marine natural products [J].
Blunt, JW ;
Copp, BR ;
Munro, MHG ;
Northcote, PT ;
Prinsep, MR .
NATURAL PRODUCT REPORTS, 2006, 23 (01) :26-78
[8]   Coscinamides A, B and C, three new bis indole alkaloids from the marine sponge Coscinoderma sp. [J].
Bokesch, HR ;
Pannell, LK ;
McKee, TC ;
Boyd, MR .
TETRAHEDRON LETTERS, 2000, 41 (33) :6305-6308
[9]   PSAMMOPEMMINS (A-C), NOVEL BROMINATED 4-HYDROXYINDOLE ALKALOIDS FROM AN ANTARCTIC SPONGE, PSAMMOPEMMA SP [J].
BUTLER, MS ;
CAPON, RJ ;
LU, CC .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1992, 45 (11) :1871-1877
[10]   Leptoclinidamines A-C, Indole Alkaloids from the Australian Ascidian Leptoclinides durus [J].
Carroll, Anthony R. ;
Avery, Vicky M. .
JOURNAL OF NATURAL PRODUCTS, 2009, 72 (04) :696-699