Three New Aaptamines from the Marine Sponge Aaptos sp. and Their Proapoptotic Properties

被引：0

作者：

Shubina, Larisa K. ^{[1
]}

Makarieva, Tatyana N. ^{[1
]}

Dyshlovoy, Sergey A. ^{[1
]}

Fedorov, Sergey N. ^{[1
]}

Dmitrenok, Pavel S. ^{[1
]}

Stonik, Valentin A. ^{[1
]}

机构：

[1] Russian Acad Sci, Pacific Inst Bioorgan Chem, Lab Chem MaNaPro, Vladivostok 690022, Russia

来源：

NATURAL PRODUCT COMMUNICATIONS | 2010年 / 5卷 / 12期

关键词：

aaptamine; benzo[de][1,6]-naphthyridine alkaloids; marine sponge; apoptosis; NMR; ANTINEOPLASTIC AGENTS; ALKALOIDS; ISOAAPTAMINE;

D O I：

暂无

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Three new aaptamine-type alkaloids, 2,3-dihydro-2,3-dioxoaaptamine (1), 6-(N-morpholinyl)-4,5-dihydro-5-oxo-demethyl(oxy)aaptamine (2) and 3-(methylamino)demethyl(oxy)aaptamine (3), along with known aaptamines were isolated from the sponge Aaptos sp. Their structures were determined on the basis of detailed analysis of their 1D and 2D NMR spectroscopic and mass spectral data. The isolated compounds induced apoptosis in human leukemia THP-1 cells.

引用

页码：1881 / 1884

页数：4

共 18 条

[1] A SYNTHESIS OF AAPTAMINE FROM 6,7-DIMETHOXY-1-METHYLISOQUINOLINE [J].

BALCZEWSKI, P ;

MALLON, MKJ ;

STREET, JD ;

JOULE, JA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11) :3193-3198

[2] 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

[3] Novel alkaloids of the aaptamine class from an Indonesian marine sponge of the genus Xestopongia [J].

Calcul, L ;

Longeon, A ;

Al Mourabit, A ;

Guyot, M ;

Bourguet-Kondracki, ML .

TETRAHEDRON, 2003, 59 (34) :6539-6544

[4]

FEDOREYEV SA, 1988, KHIM FARM ZH+, V22, P943

[5] Marine Two-Headed Sphingolipid-Like Compound Rhizochalin Inhibits EGF-Induced Transformation of JB6 P+ Cl41 Cells [J].

Fedorov, Sergey N. ;

Makarieva, Tatyana N. ;

Guzii, Alla G. ;

Shubina, Larisa K. ;

Kwak, Jong Y. ;

Stonik, Valentin A. .

LIPIDS, 2009, 44 (09) :777-785

[6] Modification at the C9 position of the marine natural product isoaaptamine and the impact on HIV-1, mycobacterial, and tumor cell activity [J].

Gul, Waseem ;

Hammond, Nicholas L. ;

Yousaf, Muhammad ;

Bowling, John J. ;

Schinazi, Raymond F. ;

Wirtz, Susan S. ;

Andrews, Garcia de Castro ;

Cuevas, Carmen ;

Hamann, Mark T. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (24) :8495-8505

[7] Aaptamine and related products. Their isolation, chemical syntheses, and biological activity [J].

Larghi, Enrique L. ;

Bohn, Maria L. ;

Kaufman, Teodoro S. .

TETRAHEDRON, 2009, 65 (22) :4257-4282

[8] PHYSIOLOGICALLY ACTIVE MARINE NATURAL-PRODUCTS FROM PORIFERA .11. AAPTAMINES - NOVEL BENZO[DE][1,6]NAPHTHYRIDINES FROM THE OKINAWAN MARINE SPONGE AAPTOS-AAPTOS [J].

NAKAMURA, H ;

KOBAYASHI, J ;

OHIZUMI, Y ;

HIRATA, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (01) :173-176

[9] ISOLATION AND STRUCTURE OF AAPTAMINE A NOVEL HETEROAROMATIC SUBSTANCE POSSESSING ALPHA-BLOCKING ACTIVITY FROM THE SEA SPONGE AAPTOS-AAPTOS [J].

NAKAMURA, H ;

KOBAYASHI, J ;

OHIZUMI, Y .

TETRAHEDRON LETTERS, 1982, 23 (52) :5555-5558

[10] Antineoplastic agents 491. Synthetic conversion of aaptamine to isoaaptamine, 9-demethylaaptamine, and 4-methylaaptamine [J].

Pettit, GR ;

Hoffmann, H ;

Herald, DL ;

McNulty, J ;

Murphy, A ;

Higgs, KC ;

Hamel, E ;

Lewin, NE ;

Pearce, LV ;

Blumberg, PM ;

Pettit, RK ;

Knight, JC .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07) :2251-2256

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