Aromatic glycosides from the whole plants of Iris japonica

Abstract

Phytochemical investigation on the whole plants of Iris japonica led to the isolation of four new aromatic glycosides. Their structures including the absolute configurations were determined by spectroscopic and chemical methods as (−)-4-hydroxy-3-methoxy acetophenone 4-O-β-d-{6-O-[4-O-(7R,8S)-(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (1), (−)-4-hydroxy-3-methoxy acetophenone 4-O-β-d-{6-O-[4-O-(7S,8R)-(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (2), (−)-4-hydroxy-3-methoxy acetophenone 4-O-β-d-{6-O-[4-O-(7R,8R)-(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (3), (−)-4-hydroxy-3-methoxy acetophenone 4-O-β-d-{6-O-[4-O-(7S,8S)-(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (4), respectively.

Graphical abstract

Keywords:

• Iris japonica
• aromatic glycosides
• chiral resolution
• erythro-threo isomer
• CD difference spectrum

Acknowledgments

The authors gratefully acknowledge grants from the National Natural Science Foundation (No. 21472245) and the State Key Laboratory of Bioactive Substance and Function of Natural Medicines (No. GTZC201101), Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College.