NEW CYTOTOXIC ANNONACEOUS ACETOGENINS - BULLATANOCIN AND CIS-BULLATANOCINONE AND TRANS-BULLATANOCINONE, FROM ANNONA-BULLATA (ANNONACEAE)

被引：29

作者：

GU, ZM

FANG, XP

RIESER, MJ

HUI, YH

MIESBAUER, LR

SMITH, DL

WOOD, KV

MCLAUGHLIN, JL

机构：

[1] PURDUE UNIV,SCH PHARM & PHARMACAL SCI,DEPT MED CHEM & PHARMACOGNOY,W LAFAYETTE,IN 47907

[2] PURDUE UNIV,SCH SCI,DEPT CHEM,W LAFAYETTE,IN 47907

来源：

TETRAHEDRON | 1993年 / 49卷 / 04期

关键词：

D O I：

10.1016/S0040-4020(01)80320-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Further bioactivity-directed fractionation of the ethanol extract of the bark of Annona bullata Rich. (Annonaceae) has led to the isolation of the new nonadjacent bis-tetrahydrofuran acetogenins, bullatanocin (1), cis-bullatanocinone (2) and trans-bullatanocinone (3). A known adjacent bis-tetrahydrofuran acetogenin, desacetyluvaricin (4), which is new to this species, was also isolated. Brine shrimp lethality test (BST) data and cytotoxicities against human solid tumor cell lines of 1-4 were compared with those of the diastereoisomers, bullatalicin (5), cis- and trans-bullatalincinone (6 and 7) and 4-deoxyasimicin (8). 1 shows cytotoxic potencies 10,000 times those of adriamycin in the lung and colon cancer cell lines.

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页码：747 / 754

页数：8

相关论文

共 23 条

[1] ROLLINONE, A REVISION AND EXTENSION OF STRUCTURE [J].

ABREO, MJ ;

SNEDEN, AT .

JOURNAL OF NATURAL PRODUCTS, 1990, 53 (04) :983-985

[2] GIGANTECIN - A NOVEL ANTIMITOTIC AND CYTOTOXIC ACETOGENIN, WITH NONADJACENT TETRAHYDROFURAN RINGS, FROM GONIOTHALAMUS-GIGANTEUS (ANNONACEAE) [J].

ALKOFAHI, A ;

RUPPRECHT, JK ;

LIU, YM ;

CHANG, CJ ;

SMITH, DL ;

MCLAUGHLIN, JL .

EXPERIENTIA, 1990, 46 (05) :539-541

[3] THE RELATIVE CONFIGURATION OF ACETOGENINS ISOLATED FROM ANNONA-SQUAMOSA - ANNONIN-I (SQUAMOCIN) AND ANNONIN-VI [J].

BORN, L ;

LIEB, F ;

LORENTZEN, JP ;

MOESCHLER, H ;

NONFON, M ;

SOLLNER, R ;

WENDISCH, D .

PLANTA MEDICA, 1990, 56 (03) :312-316

[4]

FANG XP, 1992, HETEROCYCLES, V34, P1075

[5]

Fogh J., 1975, HUMAN TUMOR CELLS IN, P115

[6] IN-VITRO CULTIVATION OF HUMAN TUMORS - ESTABLISHMENT OF CELL LINES DERIVED FROM A SERIES OF SOLID TUMORS [J].

GIARD, DJ ;

AARONSON, SA ;

TODARO, GJ ;

ARNSTEIN, P ;

KERSEY, JH ;

DOSIK, H ;

PARKS, WP .

JOURNAL OF THE NATIONAL CANCER INSTITUTE, 1973, 51 (05) :1417-1423

[7] ACETOGENINS FROM ROOT BARK OF UVARIA-NARUM [J].

HISHAM, A ;

PIETERS, LAC ;

CLAEYS, M ;

VANDENHEUVEL, H ;

ESMANS, E ;

DOMMISSE, R ;

VLIETINCK, AJ .

PHYTOCHEMISTRY, 1991, 30 (07) :2373-2377

[8] SYNTHESIS OF (+)-(15,16,19,20,23,24)-HEXEPI-UVARICIN - A BIS(TETRAHYDROFURANYL) ANNONACEOUS ACETOGENIN ANALOG [J].

HOYE, TR ;

HANSON, PR ;

KOVELESKY, AC ;

OCAIN, TD ;

ZHUANG, ZP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) :9369-9371

[9] ASSIGNING THE RELATIVE STEREOCHEMISTRY BETWEEN C(2) AND C(4) OF THE 2-ACETONYL-4-ALKYLBUTYROLACTONE SUBSTRUCTURES OF THE APPROPRIATE ANNONACEOUS ACETOGENINS [J].

HOYE, TR ;

HANSON, PR .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (17) :5092-5095

[10] VALIDATION OF THE H-1-NMR CHEMICAL-SHIFT METHOD FOR DETERMINATION OF STEREOCHEMISTRY IN THE BIS(TETRAHYDROFURANYL) MOIETY OF UVARICIN-RELATED ACETOGENINS FROM ANNONACEAE - ROLLINIASTATIN-1 (AND ASIMICIN) [J].

HOYE, TR ;

ZHUANG, ZP .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) :5578-5580