tailieunhanh - Pinoresinol and 3,4’,5,7-tetrahydroxy-3’-methoxyflavanone from the fruits of silybum marianum (l.) gaertn

From the fruits of Silybum marianum (L.) Gaertn. cultivated in the North of Vietnam, (±)2,6- bis(4 -hydroxy-3 -methoxy-phenyl)-3,7-dioxabicyclo[]octane (pinoresinol) (1) and 3,4 ,5,7- tetrahydroxy-3 -methoxyflavanone (2) were isolated. Their structures were elucidated by analyses of the NMR and mass spectra in comparison with the reported data. This is the first report of both 1 and 2 from Silybum species. | Journal of Chemistry Vol. 45 2 P. 219 - 222 2007 PINORESINOL AND 3 4 5 7-TETRAHYDROXY-3 -METHOXYFLAVANONE FROM THE FRUITS OF SILYBUM MARIANUM L. GAERTN. Received 19 April 2006 TRINH THI DIEP1 PHAN VAN KIEM2 NGUYEN THUONG DONG1 NGUYEN HUU TUNG2 BUI THI BANG1 CHAU VAN MINH2 AND ALESSANDRA BRACA3 1National Institute of Medicinal Materials Ministry of Health institute of Natural Products Chemistry VAST Department of Bioorganic Chemistry and Biopharmaceutics University of Pisa Italia SUMMARY From the fruits of Silybum marianum L. Gaertn. cultivated in the North of Vietnam 2 6-bis 4 -hydroxy-3 -methoxy-phenyl -3 7-dioxabicyclo octane pinoresinol 1 and 3 4 5 7-tetrahydroxy-3 -methoxyflavanone 2 were isolated. Their structures were elucidated by analyses of the NMR and mass spectra in comparison with the reported data. This is the first report of both 1 and 2 from Silybum species. I - INTRODUCTION In previous papers we have reported the isolation and structural elucidation of flavonolignan and flavonoid compositions of the fruits of Silybum marianum L. Gaertn. Asteraceae cultivated the North of Vietnam and used in the folk medicines 1 - 3 . This paper deals with further investigation of the bioactive compositions from S. marianum. By various chromatography methods 2 6-bis 4 -hydroxy-3 -methoxy-phenyl -3 7- di oxabicyclo octane Pinoresinol 1 and 3 4 5 7-tetrahydroxy-3 -methoxyflavanone 2 were isolated from the methanolic extract of the fruits from this plant. The structures were elucidated by analyses of the NMR and ESI mass spectra in comparison with the reported data. This is the first report of both 1 and 2 from Silybum species. To the best of our knowledge no 13C-NMR data of 2 has been reported previously. II - EXPERIMENTAL 1. General experimental procedures The Electronspray Ionization ESI mass spectrum was obtained using a AGILENT 1100 LC-MSD Trap spectrometer. The 1H-NMR 500 MHz and 13C-NmR 125 MHz spectra were recorded on a Bruker AM500 FT-NMR .

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