Biosynthesis of hyperforin in Hypericum perforatum

被引:110
作者
Adam, P
Arigoni, D
Bacher, A
Eisenreich, W
机构
[1] Tech Univ Munich, Lehrstuhl Organ Chem & Biochem, D-85747 Garching, Germany
[2] Swiss Fed Inst Technol, Organ Chem Lab, HCI, CH-8093 Zurich, Switzerland
关键词
D O I
10.1021/jm0209782
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Cut sprouts of Hypericum perforatum were proffered solutions containing [1-C-13]glucose or [U-C-13(6)]glucose. Hyperforin was isolated and analyzed by quantitative NMR spectroscopy. The labeling patterns show that the biosynthesis of hyperforin involves five isoprenoid moieties, which are derived entirely or predominantly (> 98%) via the deoxyxylulose phosphate pathway. The phloroglucinol moiety is generated via a polyketide type mechanism.
引用
收藏
页码:4786 / 4793
页数:8
相关论文
共 30 条
  • [1] BACHER A, 1999, FEMS MICROBIOL REV, P22567
  • [2] AN NMR TECHNIQUE FOR TRACING OUT THE CARBON SKELETON OF AN ORGANIC-MOLECULE
    BAX, A
    FREEMAN, R
    FRENKIEL, TA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) : 2102 - 2104
  • [3] Analysis of plant complex matrices by use of nuclear magnetic resonance spectroscopy: St. John's wort extract
    Bilia, AR
    Bergonzi, MC
    Mazzi, G
    Vincieri, FF
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2001, 49 (05) : 2115 - 2124
  • [4] THE RELATIVE STEREOCHEMISTRY OF HYPERFORIN - AN ANTIBIOTIC FROM HYPERICUM-PERFORATUM L
    BRONDZ, I
    GREIBROKK, T
    GROTH, PA
    AASEN, AJ
    [J]. TETRAHEDRON LETTERS, 1982, 23 (12) : 1299 - 1300
  • [5] THE ABSOLUTE-CONFIGURATION OF HYPERFORIN, AN ANTIBIOTIC FROM HYPERICUM-PERFORATUM-L, BASED ON THE CRYSTAL-STRUCTURE DETERMINATION OF ITS PARA-BROMOBENZOATE ESTER
    BRONDZ, I
    GREIBROKK, T
    GROTH, P
    AASEN, AJ
    [J]. ACTA CHEMICA SCANDINAVICA SERIES A-PHYSICAL AND INORGANIC CHEMISTRY, 1983, 37 (03): : 263 - 265
  • [6] BYSTROV N S, 1975, Tetrahedron Letters, V32, P2791
  • [7] Hyperforin as a possible antidepressant component of hypericum extracts
    Chatterjee, SS
    Bhattacharya, SK
    Wonnemann, M
    Singer, A
    Müller, WE
    [J]. LIFE SCIENCES, 1998, 63 (06) : 499 - 510
  • [8] STEREOCHEMISTRY OF VALINE BIOSYNTHESIS - CONFIGURATION OF THE PRODUCT OF REARRANGEMENT OF ALPHA-ACETOLACTATE
    CROUT, DHG
    HEDGECOCK, CJR
    LIPSCOMB, EL
    ARMSTRONG, FB
    [J]. EUROPEAN JOURNAL OF BIOCHEMISTRY, 1980, 110 (02): : 439 - 444
  • [9] St John's wort: Prozac from the plant kingdom
    Di Carlo, G
    Borrelli, F
    Ernst, E
    Izzo, AA
    [J]. TRENDS IN PHARMACOLOGICAL SCIENCES, 2001, 22 (06) : 292 - 297
  • [10] Analysis of metabolic pathways via quantitative prediction of isotope labeling patterns:: a retrobiosynthetic 13C NMR study on the monoterpene loganin
    Eichinger, D
    Bacher, A
    Zenk, MH
    Eisenreich, W
    [J]. PHYTOCHEMISTRY, 1999, 51 (02) : 223 - 236