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Hydrolytic Reaction of Plant Extracts to Generate Molecular Diversity: New Dammarane Glycosides from the Mild Acid Hydrolysate of Root Saponins of Panax notoginseng
Author(s) -
Teng RongWei,
Li HaiZhou,
Wang DeZu,
Yang ChongRen
Publication year - 2004
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200490116
Subject(s) - panax notoginseng , dammarane , chemistry , hydrolysate , glycoside , stereochemistry , acid hydrolysis , saponin , hydrolysis , ginsenoside , diol , triterpene , organic chemistry , ginseng , medicine , alternative medicine , pathology
Molecular diversity was generated by hydrolyzing the crude root saponins of Panax notoginseng ( Burk .) F. H. Chen under mild acidic condition (AcOH/EtOH 1 : 1). From the acid hydrolysate, five new dammarane glycosides, named notoginsenoside T 1 (=(3 β ,6 α ,12 β ,20 E ,23 RS )‐24,25‐epoxy‐6‐[( β ‐ D ‐glucopyranosyl)oxy]‐dammar‐20(22)‐ene‐3,12,23‐triol; 1 ), notoginsenoside T 2 (=(3 β ,6 α ,12 β ,20 E ,23 RS )‐24,25‐epoxy‐6‐[( β ‐ D ‐glucopyranosyl)oxy]‐23‐methoxydammar‐20(22)‐ene‐3,12‐diol; 2 ), notoginsenoside T 3 (=(3 β ,6 α ,12 β ,20 S )‐6‐[( β ‐ D ‐glucopyranosyl)oxy]‐20‐ethoxydammar‐24‐ene‐3,12‐diol; 3 ), notoginsenoside T 4 (=(3 β ,6 α ,12 β ,20 S ,22 E ,24 RS )‐6‐[( β ‐ D ‐glucopyranosyl)oxy]dammar‐22‐ene‐3,12,20,24,25‐pentol; 4 ), and notoginsenoside T 5 (=(3 β ,6 α ,12 β , 24 E )‐6‐[( β ‐ D ‐xylopyranosyl‐(1→2)‐ β ‐ D ‐glucopyranosyl)oxy]dammara‐20(21),24‐diene‐3,12‐diol; 5 ), were isolated, together with 15 known dammarane glycosides, and their structures were elucidated on the basis of spectroscopic evidence. Among the known compounds, ginsenosides Rg 3 and Rh 1 were isolated as major constituents, in addition to ginsenosides Rg 5 , Rh 4 , and a mixture of (20 R )‐ and (20 S )‐25‐hydroxyginsenoside Rh 1 , all of which were obtained from P. notoginseng for the first time.