Minor withanolides from Physalis philadelphica: structures, quinone reductase induction activities, and liquid chromatography (LC)-MS-MS investigation as artifacts.

As a result of a bioactivity-guided search for novel, plant-derived cancer chemopreventive agents, ixocarpalactone A (5) was isolated previously as a potent quinone reductase inducer from the leaves and stems of Physalis philadelphica. In the present study, this promising lead compound was reisolated in gram quantities for in vivo biological testing. During the course of this work, four additional minor new withanolides were also obtained and characterized, namely, 2,3-dihydro-3beta-methoxyixocarpalactone A (1), 2,3-dihydro-3beta-methoxyixocarpalactone B (2), 2,3-dihydroixocarpalactone B (3), and 4beta,7beta,20R-trihydroxy-1-oxowitha-2,5-dien-22,26-olide (4). However, compounds 1 and 2 were determined using liquid chromatography (LC)-MS-MS to be artifacts generated during the extraction and isolation procedure. Ixocarpalactone A was detected in the fresh fruits (tomatillos) of P. philadelphica by LC-MS-MS analysis at a concentration of 143+/-4.53 ppb.
AuthorsJian-Qiao Gu, Wenkui Li, Young-Hwa Kang, Bao-Ning Su, Harry H S Fong, Richard B van Breemen, John M Pezzuto, A Douglas Kinghorn
JournalChemical & pharmaceutical bulletin (Chem Pharm Bull (Tokyo)) Vol. 51 Issue 5 Pg. 530-9 (May 2003) ISSN: 0009-2363 [Print] Japan
PMID12736452 (Publication Type: Journal Article, Research Support, U.S. Gov't, P.H.S.)
Chemical References
  • Lactones
  • NAD(P)H Dehydrogenase (Quinone)
  • Ergosterol
  • Animals
  • Artifacts
  • Cell Line, Tumor
  • Chromatography, Liquid
  • Crystallography, X-Ray
  • Enzyme Induction (drug effects)
  • Ergosterol (analogs & derivatives, chemistry, pharmacology)
  • Fruit (chemistry)
  • Lactones (chemistry, isolation & purification, pharmacology)
  • Liver Neoplasms, Experimental (enzymology)
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Mice
  • NAD(P)H Dehydrogenase (Quinone) (biosynthesis)
  • Physalis (chemistry)
  • Plant Leaves (chemistry)
  • Plant Stems (chemistry)
  • Structure-Activity Relationship

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