NATURAL PRODUCT RESEARCH AND DEVELOPMENT ›› 2016, Vol. 28 ›› Issue (7): 1045-1050. doi: 10.16333/j.1001-6880.2016.7.010

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Chemical Constituents from Valeriana jatamansi Jones and Spectral Characteristics of Diepoxide Lignans

YONG Yan,HUANG Qing,WANG Ru-jing,CHEN Yin,TAN Yu-zhu*,ZHANG Hai*   

  1. Pharmacy College,Chengdu University of Traditional Chinese Medicine;Ministry of Education Key Laboratory of Standardization of Chinese Herbal Medicine;State Key Laboratory Breeding Base of Systematic Research,Development and Utilization of Chinese Medicine Resources,Chengdu 611137,China
  • Online:2016-07-30 Published:2017-01-17

Abstract: Ten compounds were isolated from the root of Valeriana jatamansi Jones by ODS column,silica gel column and Sephadex LH-20 chromatography, etc. Their structures were elucidated by NMR,and were identified as double-tetrahydrofuran lignans-4-O-β-D-Glucopyranoside(1),4-hydroxybenzyl-β-D-glucopyranoside(2),methylarbutin(3),4-[(E)-3-ethoxyprop-1-enyl]-2-methoxyphenol(4),eugenyl-O-D-glunopyranoside(5),ethylconiferin(6),8-hydroxypinoresinol-4′-O-β-D-glucopyranoside(7), palmitic acid(8),protocatechuic acid(9),3-(4-β-D-Glucopyranosyloxy-3,5-dimethoxy)-phenyl-2E-propenol(10).Compounds 5、6 were isolated from Valerianaceae for the first time.The rule of hydroxylation and glycosidation shift effects on bisepoxy lignans were obtained by comparing the information of 13C NMR with known analogous.Glycosidation and hydroxylation 13C NMR chemical shift effects on double-tetrahydrofuran lignans were closely related to the number of hydroxyl-substitution.The rules for effects of glycosidation at C-1′and ortho-C-3′ downshift about △δ1.7 in no hydroxy or mono-hydroxy substitution,C-1′downshift about △δ2.4 in double-hydroxy substitution,while ortho-C-3′ only changes a little(△δ0.5).In hydroxylation,tertiary carbon downshift to quaternary carbon(△δ34.5-37.5) when hydroxy substitution at C-8 or C-8′.Besides,the C-1 upshift about △δ3.9-5.9 because of the effect of distance effect.C-8′ on mono-hydroxy substituted aromatic ring moves to low field(△δ6.0),while downshifts △δ34.5 for double-hydroxy substitution.The rules of displacement provided suggestion for the confirmation of double-tetrahydrofuran lignans,especially the position of hydroxylation and glycosylation.

Key words: Valeriana jatamansi Jones, chemical constituent, spectral characteristics

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