Pyrinodemins G-I, new bis-3-alkylpyridine alkaloids from a marine sponge Amphimedon sp.

被引：8

作者：

Kubota, Takaaki ^{[1
]}

Kura, Ken'ichi ^{[1
]}

Fromont, Jane ^{[2
]}

Kobayashi, Jun'ichi ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan

[2] Western Australian Museum, Welshpool Dc, WA 6986, Australia

来源：

TETRAHEDRON | 2013年 / 69卷 / 01期

关键词：

Marine sponge; Amphimedon sp; Bis-3-alkylpyridine alkaloid; Pyrinodemins G-I; Cytotoxicity; ANTINEOPLASTIC PYRIDINE ALKALOIDS; AMINO ACID MOIETY; CRIBROCHALINA-SP; NIPHATES SP; METHOXYLAMINE PYRIDINES; AZOXY MOIETY; A-D; METABOLITES;

D O I：

10.1016/j.tet.2012.10.062

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three new bis-3-alkylpyridine alkaloids, pyrinodemins G-I (1-3), were isolated from an Okinawan marine sponge Amphimedon sp. and the structures of 1-3 were elucidated on the basis of spectroscopic data. Pyrinodemins G-I (1-3) were novel bis-3-alkylpyridine alkaloids possessing an N-methoxy amide moiety, an alpha,beta-unsaturated 3,5-disubstituted gamma-lactone moiety, and a 2,3-di-substituted acrolein at a junction of two 3-alkylpyridines, respectively. Pyrinodemins G (1) and H (2) showed cytotoxicity against P388 murine leukemia cells. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：96 / 100

页数：5

共 22 条

[1] Marine natural products [J].

Blunt, John W. ;

Copp, Brent R. ;

Keyzers, Robert A. ;

Munro, Murray H. G. ;

Prinsep, Michele R. .

NATURAL PRODUCT REPORTS, 2012, 29 (02) :144-222

[2] 4 BETA-ALKYLPYRIDINES FROM A SPONGE [J].

CARROLL, AR ;

SCHEUER, PJ .

TETRAHEDRON, 1990, 46 (19) :6637-6644

[3] A NEW EGF-ACTIVE POLYMERIC PYRIDINIUM ALKALOID FROM THE SPONGE CALLYSPONGIA-FIBROSA [J].

DAVIESCOLEMAN, MT ;

FAULKNER, DJ ;

DUBOWCHIK, GM ;

ROTH, GP ;

POLSON, C ;

FAIRCHILD, C .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) :5925-5930

[4] BIOACTIVE MARINE METABOLITES .29. HALICLAMINE-A AND HALICLAMINE-B, CYTOTOXIC MACROCYCLIC ALKALOIDS FROM A SPONGE OF THE GENUS HALICLONA [J].

FUSETANI, N ;

YASUMURO, K ;

MATSUNAGA, S ;

HIROTA, H .

TETRAHEDRON LETTERS, 1989, 30 (49) :6891-6894

[5] Pyrinodemins B-D, potent cytotoxic bis-pyridine alkaloids from marine sponge Amphimedon sp. [J].

Hirano, K ;

Kubota, T ;

Tsuda, M ;

Mikami, Y ;

Kobayashi, J .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2000, 48 (07) :974-977

[6] Asymmetric synthesis of double bond isomers of the structure proposed for pyrinodemin A and indication of its structural revision [J].

Ishiyama, H ;

Tsuda, M ;

Endo, T ;

Kobayashi, J .

MOLECULES, 2005, 10 (01) :312-316

[7] Pyrinadine A, a novel pyridine alkaloid with an azoxy moiety from sponge Cribrochalina sp. [J].

Kariya, Y ;

Kubota, T ;

Fromont, J ;

Kobayashi, J .

TETRAHEDRON LETTERS, 2006, 47 (06) :997-998

[8] Pyrinadines B-G, new bis-pyridine alkaloids with an azoxy moiety from sponge Cribrochalina sp. [J].

Kariya, Yuuko ;

Kubota, Takaaki ;

Fromont, Jane ;

Kobayashi, Jun'ichi .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (24) :8415-8419

[9] NIPHATESINES E-H, NEW PYRIDINE ALKALOIDS FROM THE OKINAWAN MARINE SPONGE NIPHATES SP [J].

KOBAYASHI, J ;

ZENG, CM ;

ISHIBASHI, M ;

SHIGEMORI, H ;

SASAKI, T ;

MIKAMI, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (11) :1291-1294

[10] NIPHATESINES A-D, NEW ANTINEOPLASTIC PYRIDINE ALKALOIDS FROM THE OKINAWAN MARINE SPONGE NIPHATES SP [J].

KOBAYASHI, J ;

MURAYAMA, T ;

KOSUGE, S ;

KANDA, F ;

ISHIBASHI, M ;

KOBAYASHI, H ;

OHIZUMI, Y ;

OHTA, T ;

NOZOE, S ;

SASAKI, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (12) :3301-3303

← 1 2 3 →