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.
Gu
Jian-Qiao
JQ
Program for Collaborative Research in the Pharmaceutical Sciences, College of Pharmacy, University of Illinois at Chicago, 60612, USA.
Li
Wenkui
W
Kang
Young-Hwa
YH
Su
Bao-Ning
BN
Fong
Harry H S
HH
van Breemen
Richard B
RB
Pezzuto
John M
JM
Kinghorn
A Douglas
AD
D000818:Animals; D016477:Artifacts; D045744:Cell Line, Tumor; D002853:Chromatography, Liquid; D018360:Crystallography, X-Ray; D004790:Enzyme Induction / Q000187:drug effects; D004875:Ergosterol / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000494:pharmacology*; D005638:Fruit / Q000737:chemistry; D007783:Lactones / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D008114:Liver Neoplasms, Experimental / Q000201:enzymology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051379:Mice; D016660:NAD(P)H Dehydrogenase (Quinone) / Q000096:biosynthesis*; D032321:Physalis / Q000737:chemistry*; D018515:Plant Leaves / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D013329:Structure-Activity Relationship
D007783:Lactones; D016660:NAD(P)H Dehydrogenase (Quinone); D004875:Ergosterol