Unusual bioactive annonaceous acetogenins from Goniothalamus giganteus

被引:69
作者
Alali, FQ [1 ]
Rogers, L [1 ]
Zhang, Y [1 ]
McLaughlin, JL [1 ]
机构
[1] Purdue Univ, Sch Pharm & Pharmacal Sci, Dept Med Chem & Mol Pharmacol, W Lafayette, IN 47907 USA
关键词
D O I
10.1016/S0040-4020(98)00286-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pyranicin (1) and pyragonicin (2) are the first mono-tetrahydropyran annonaceous acetogenins, and goniotrionin (3) possesses an unusual hydroxylated-allylic moiety. 1-3 were isolated from the bark of Goniothalamus giganteus using activity-directed fractionation with the brine shrimp lethality test. Both 1 and 2 are selectively cytotoxic against the pancreatic cell line (PACA-2) in a panel of six human solid tumor cell lines with 1 showing ten times the potency of adriamycin, while 3 showed more potent selectivity against the breast cell line (MCF-7). (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5833 / 5844
页数:12
相关论文
共 27 条
  • [1] MODE OF ACTION OF BULLATACIN - A POTENT ANTITUMOR AND PESTICIDAL ANNONACEOUS ACETOGENIN
    AHAMMADSAHIB, KI
    HOLLINGWORTH, RM
    MCGOVREN, JP
    HUI, YH
    MCLAUGHLIN, JL
    [J]. LIFE SCIENCES, 1993, 53 (14) : 1113 - 1120
  • [2] 4-deoxyannomontacin and (2,4-cis and trans)-annomontacinone, new bioactive mono-tetrahydrofuran annonaceous acetogenins from Goniothalamus giganteus
    Alali, F
    Zeng, L
    Zhang, Y
    Ye, Q
    Hopp, DC
    Schwedler, JT
    McLaughlin, JL
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 1997, 5 (03) : 549 - 555
  • [3] ALALI FQ, UNPUB J EC ENTOMOL
  • [4] THE RELATIVE CONFIGURATION OF ACETOGENINS ISOLATED FROM ANNONA-SQUAMOSA - ANNONIN-I (SQUAMOCIN) AND ANNONIN-VI
    BORN, L
    LIEB, F
    LORENTZEN, JP
    MOESCHLER, H
    NONFON, M
    SOLLNER, R
    WENDISCH, D
    [J]. PLANTA MEDICA, 1990, 56 (03) : 312 - 316
  • [5] FUJIMOTO Y, 1994, CHEM PHARM BULL, V42, P1175, DOI 10.1248/cpb.42.1175
  • [6] GU ZM, 1995, RECENT ADV PHYTOCHEM, V29, P249
  • [7] STEREOSTRUCTURAL STUDIES ON THE 4-HYDROXYLATED ANNONACEOUS ACETOGENINS - A NOVEL USE OF MOSHER ESTER DATA FOR DETERMINING RELATIVE CONFIGURATION [BETWEEN C(4) AND C(36)]
    HOYE, TR
    HANSON, PR
    HASENWINKEL, LE
    RAMIREZ, EA
    ZHUANG, ZP
    [J]. TETRAHEDRON LETTERS, 1994, 35 (46) : 8529 - 8532
  • [8] Mclaughlin JL, 1991, METHODS PLANT BIOCH, V6, P1
  • [9] BRINE SHRIMP - A CONVENIENT GENERAL BIOASSAY FOR ACTIVE-PLANT CONSTITUENTS
    MEYER, BN
    FERRIGNI, NR
    PUTNAM, JE
    JACOBSEN, LB
    NICHOLS, DE
    MCLAUGHLIN, JL
    [J]. PLANTA MEDICA, 1982, 45 (01) : 31 - 34
  • [10] Morre D. James, 1995, Life Sciences, V56, P343