Synthesis and Characterization of Puerarin Derivatives and the Mechanism of Derivation Reaction

Chem. J. Chinese Universities

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Synthesis and Characterization of Puerarin Derivatives and the Mechanism of Derivation Reaction

HAN Rui-Min¹, TIAN Yu-Xi¹, WANG Peng¹, XIANG Jun-Feng², AI Xi-Cheng¹, ZHANG Jian-Ping¹

1. State Key Laboratory for Structural Chemistry of Unstable and Stable Species,
2. Center for Physiochemical Analysis & Measurement, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100080, China

Received:2005-10-21 Revised:1900-01-01 Online:2006-09-10 Published:2006-09-10
Contact: ZHANG Jian-Ping

Abstract

Abstract: 7,4'-Dipropyl(Ⅰ), 7-propyl(Ⅱ) and 4'-propyl(Ⅲ) derivatives of puerarin were synthesized and characterized by using ¹H NMR, NOESY and HRMS. Among the derivatives, Ⅱ is a new-type substituted compound of puerarin. ¹H NMR spectroscopic analysis of aromatic protons combined with theoretical analysis of molecular structures proved the existence of two rotational isomers at 300 K, as well as a rapid interconversion equilibrium at 330 K for both compounds Ⅰ and Ⅱ. However, only one conformer exists for compound Ⅲ and puerarin containing 7-phenolic hydroxyl instead of propyl in A-ring as the case of compounds Ⅰ and Ⅱ. Based on UV-Visible absorption data of neutral and basic solutions, and on the density function calculations, the 7-phenolic hydroxyl group in A-ring was found to be more acidic than the 4'-phenolic hydroxyl group in B-ring. The mechanism of derivation reaction and the structure-reactivity relationship of puerarin as an antioxidant were further discussed.

Key words: Puerarin, Derivative, 1H NMR, Antioxidation

CLC Number:

O641

TrendMD:

HAN Rui-Min¹, TIAN Yu-Xi¹, WANG Peng¹, XIANG Jun-Feng², AI Xi-Cheng¹, ZHANG Jian-Ping¹. Synthesis and Characterization of Puerarin Derivatives and the Mechanism of Derivation Reaction[J]. Chem. J. Chinese Universities, doi: .

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Synthesis and Characterization of Puerarin Derivatives and the Mechanism of Derivation Reaction

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