Isodiplamine, cystodytin K and lissoclinidine:: novel bioactive alkaloids from the New Zealand ascidian Lissoclinum notti

被引：34

作者：

Appleton, DR

Pearce, AN

Lambert, G

Babcock, RC

Copp, BR

机构：

[1] Univ Auckland, Dept Chem, Auckland 1, New Zealand

[2] Calif State Univ Fullerton, Fullerton, CA 92634 USA

[3] Univ Auckland, Leigh Marine Lab, Auckland, New Zealand

来源：

TETRAHEDRON | 2002年 / 58卷 / 49期

关键词：

ascidian metabolites; lissoclinum; pyridoacridine; varacin;

D O I：

10.1016/S0040-4020(02)01296-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A study of the bioactive crude extract of the New Zealand ascidian Lissoclinum notti led to the isolation of the new pyridoacridine alkaloids isodiplamine (4), cystodytin K (5) and lissoclinidine (6), as well as the known pyridoacridine alkaloids diplamine (7) and cystodytin J (8) and the benzopentathiepin varacin (3) and related trithiane varacin A. The new alkaloids were characterised using standard spectroscopic techniques, including 2D H-1-N-15 NMR experiments. Pyridoacridine alkaloids 4-8 were assayed for a range of biological activities including antitumour and antibiotic properties. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：9779 / 9783

页数：5

相关论文

共 24 条

[1] CONSTITUENTS OF EUPOMATIA SPECIES .12. ISOLATION OF CONSTITUENTS OF THE TUBERS AND AERIAL PARTS OF EUPOMATIA-BENNETTII AND DETERMINATION OF THE STRUCTURES OF NEW ALKALOIDS FROM THE AERIAL PARTS OF E-BENNETTII AND MINOR ALKALOIDS OF E-LAURINA [J].

CARROLL, AR ;

TAYLOR, WC .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1991, 44 (11) :1615-1626

[2] DIPLAMINE, A CYTO-TOXIC POLYAROMATIC ALKALOID FROM THE TUNICATE DIPLOSOMA SP [J].

CHARYULU, GA ;

MCKEE, TC ;

IRELAND, CM .

TETRAHEDRON LETTERS, 1989, 30 (32) :4201-4202

[3] DNA cleavage by 7-methylbenzopentathiepin: A simple analog of the antitumor antibiotic varacin [J].

Chatterji, T ;

Gates, KS .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (05) :535-538

[4] PENTATHIEPINS AND TRITHIANES FROM 2 LISSOCLINUM SPECIES AND A EUDISTOMA SP - INHIBITORS OF PROTEIN-KINASE-C [J].

COMPAGNONE, RS ;

FAULKNER, DJ ;

CARTE, BK ;

CHAN, G ;

FREYER, A ;

HEMLING, ME ;

HOFMANN, GA ;

MATTERN, MR .

TETRAHEDRON, 1994, 50 (45) :12785-12792

[5] Styelsamines A-D:: New tetracyclic pyridoacridine alkaloids from the Indonesian ascidian Eusynstyela latericius [J].

Copp, BR ;

Jompa, J ;

Tahir, A ;

Ireland, CM .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :8024-8026

[6] Electrochemical properties of some biologically active quinone derivatives: Furanquinones, pyridoquinones, and diplamine, a cytotoxic pyridoacridine alkaloid [J].

Crawford, PW ;

Gross, J ;

Lawson, K ;

Cheng, CC ;

Dong, Q ;

Liu, DF ;

Luo, YL ;

Szczepankiewicz, BG ;

Heathcock, CH .

JOURNAL OF THE ELECTROCHEMICAL SOCIETY, 1997, 144 (11) :3710-3715

[7] VARACIN - A NOVEL BENZOPENTATHIEPIN FROM LISSOCLINUM-VAREAU THAT IS CYTOTOXIC TOWARD A HUMAN COLON-TUMOR [J].

DAVIDSON, BS ;

MOLINSKI, TF ;

BARROWS, LR ;

IRELAND, CM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (12) :4709-4710

[8] SYNTHESIS OF VARACIN, A CYTOTOXIC NATURALLY-OCCURRING BENZOPENTATHIEPIN ISOLATED FROM A MARINE ASCIDIAN [J].

FORD, PW ;

DAVIDSON, BS .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) :4522-4523

[9] NITRANIONS AND THEIR PRECURSORS - CHARGE-DENSITY REARRANGEMENTS AND N-15 NMR CHEMICAL-SHIFT CHANGES [J].

GATTI, C ;

PONTI, A ;

GAMBA, A ;

PAGANI, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (22) :8634-8644

[10] On the origin of cytotoxicity of the natural product varacin. A novel example of a pentathiepin reaction that provides evidence for a triatomic sulfur intermediate [J].

Greer, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (42) :10379-10386