Minor Withanolides from Physalis philadelphica: Structures, Quinone Reductase Induction Activities, and Liquid Chromatography (LC)-MS-MS Investigation as Artifacts

Jian-Qiao Gu; Wenkui Li; Young-Hwa Kang; Bao-Ning Su; Harry H. S. Fong; Richard B. van Breemen; John M. Pezzuto; A. Douglas Kinghorn

doi:10.1248/cpb.51.530

Regular Articles

Minor Withanolides from Physalis philadelphica: Structures, Quinone Reductase Induction Activities, and Liquid Chromatography (LC)-MS-MS Investigation as Artifacts

Jian-Qiao Gu, Wenkui Li, Young-Hwa Kang, Bao-Ning Su, Harry H. S. Fong, Richard B. van Breemen, John M. Pezzuto, A. Douglas Kinghorn

Author information

Jian-Qiao Gu
Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago
Wenkui Li
Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago
Young-Hwa Kang
Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago
Bao-Ning Su
Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago
Harry H. S. Fong
Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago
Richard B. van Breemen
Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago
John M. Pezzuto
Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago
A. Douglas Kinghorn
Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago

Keywords: Physalis philadelphica, withanolide, ixocarpalactone A, quinone reductase induction, artifact, liquid chromatography (LC)-MS-MS

JOURNAL FREE ACCESS

2003 Volume 51 Issue 5 Pages 530-539

DOI https://doi.org/10.1248/cpb.51.530

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Abstract

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-3β-methoxyixocarpalactone A (1), 2,3-dihydro-3β-methoxyixocarpalactone B (2), 2,3-dihydroixocarpalactone B (3), and 4β,7β,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.

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