BULLATACIN, BULLATACINONE, AND SQUAMONE, A NEW BIOACTIVE ACETOGENIN, FROM THE BARK OF ANNONA-SQUAMOSA

被引：44

作者：

LI, XH ^{[1
]}

HUI, YH ^{[1
]}

RUPPRECHT, JK ^{[1
]}

LIU, YM ^{[1
]}

WOOD, KV ^{[1
]}

SMITH, DL ^{[1
]}

CHANG, CJ ^{[1
]}

MCLAUGHLIN, JL ^{[1
]}

机构：

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

来源：

JOURNAL OF NATURAL PRODUCTS | 1990年 / 53卷 / 01期

关键词：

D O I：

10.1021/np50067a010

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

Activity-directed fractionation of the stem bark of Annona squamosa, monitoring with brine shrimp lethality, led to the isolation of the highly bioactive acetogenins bullatacin [1] and bullatacinone [2], thus demonstrating a new abundant plant source for these potent compounds. A new keto-monotetrahydrofuran acetogenin with a ketolactone terminus, as first seen in bullatacinone [2], was also isolated, characterized by spectral analyses, and named squamone [3]. The cytotoxicities of 3 were increased significantly by reduction of the two keto groups to hydroxyls, and the tetrahydrosquamone [7] and bullatacinone [2] both showed selective cytotoxicities to MCF-7 human breast carcinoma. Liriodenine and (–)-kaur-16-en-19-oic acid were also isolated. © 1990, American Chemical Society. All rights reserved.

引用

页码：81 / 86

页数：6

共 12 条

[1] GONIOTHALAMICIN AND ANNONACIN - BIOACTIVE ACETOGENINS FROM GONIOTHALAMUS-GIGANTEUS (ANNONACEAE) [J].

ALKOFAHI, A ;

RUPPRECHT, JK ;

SMITH, DL ;

CHANG, CJ ;

MCLAUGHLIN, JL .

EXPERIENTIA, 1988, 44 (01) :83-85

[2]

BORN L, 1989, IN PRESS PLANTA MED

[3]

FUJIMOTO Y, 1988, CHEM PHARM BULL, V36, P4802

[4] ON THE STEREOCHEMISTRY OF THE BISTETRAHYDROFURANYL MOIETY OF UVARICIN - PROTON CHEMICAL-SHIFTS CAN PLAY A CRUCIAL ROLE IN COMPLEX STRUCTURE DETERMINATION [J].

HOYE, TR ;

SUHADOLNIK, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (14) :4402-4403

[5] BULLATACIN AND BULLATACINONE - 2 HIGHLY POTENT BIOACTIVE ACETOGENINS FROM ANNONA-BULLATA [J].

HUI, YH ;

RUPPRECHT, JK ;

LIU, YM ;

ANDERSON, JE ;

SMITH, DL ;

CHANG, CJ ;

MCLAUGHLIN, JL .

JOURNAL OF NATURAL PRODUCTS, 1989, 52 (03) :463-477

[6] ANNONACIN, A NOVEL, BIOLOGICALLY-ACTIVE POLYKETIDE FROM ANNONA-DENSICOMA [J].

MCCLOUD, TG ;

SMITH, DL ;

CHANG, CJ ;

CASSADY, JM .

EXPERIENTIA, 1987, 43 (08) :947-949

[7] BRINE SHRIMP - A CONVENIENT GENERAL BIOASSAY FOR ACTIVE-PLANT CONSTITUENTS [J].

MEYER, BN ;

FERRIGNI, NR ;

PUTNAM, JE ;

JACOBSEN, LB ;

NICHOLS, DE ;

MCLAUGHLIN, JL .

PLANTA MEDICA, 1982, 45 (01) :31-34

[8]

MOESCHLER HF, 1984, Patent No. 3438763

[9]

Morton J. F., 1987, FRUITS WARM CLIMATE, P69

[10] ANTINEOPLASTIC AGENTS .132. ISOLATION AND STRUCTURE OF ROLLINIASTATIN-1 FROM THE SOUTH-AMERICAN TREE ROLLINIA-MUCOSA [J].

PETTIT, GR ;

CRAGG, GM ;

POLONSKY, J ;

HERALD, DL ;

GOSWAMI, A ;

SMITH, CR ;

MORETTI, C ;

SCHMIDT, JM ;

WEISLEDER, D .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (06) :1433-1435

← 1 2 →