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[Two new phenolic acids from Drynariae rhizoma]
Yong-hong Liang1, Min Ye, Ling-zhi Zhang
1The State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China.
Yao Xue Xue Bao = Acta Pharmaceutica Sinica
|October 12, 2010
Summary
Researchers identified nine phenolic acids from Drynariae Rhizoma, including two novel compounds. Three known compounds were isolated from this plant source for the first time, expanding knowledge of its chemical constituents.
Area of Science:
- Phytochemistry
- Natural Product Chemistry
- Organic Chemistry
Context:
- Drynariae Rhizoma is a traditional medicinal herb.
- Understanding its chemical composition is crucial for pharmacological research.
- Previous studies have not fully characterized its phenolic acid profile.
Purpose:
- To isolate and identify phenolic acids from Drynariae Rhizoma.
- To characterize novel compounds and report new findings for known compounds.
Summary:
- Nine phenolic acids were isolated from a 70% ethanol extract of Drynariae Rhizoma using chromatography (silica gel, ODS, Sephadex LH-20) and semi-preparative HPLC.
- Compounds were identified using spectroscopic methods (1H NMR, 13C NMR, 2D NMR, HR-ESI-MS).
- Identified compounds include 4,4'-dihydroxy-3,3'-imino-di-benzoic acid (1) and 23(S)-12-O-caffeoyl-12-hydroxyllauric acid glycerol ester (9), which are new. Gallic acid (3), p-hydroxybenzoic acid (4), and ethyl trans-3,4-dihydroxycinnamate (6) were isolated from Drynaria for the first time.
Impact:
- This study expands the known phytochemical profile of Drynariae Rhizoma.
- The identification of new compounds may lead to further investigation of their biological activities.
- Reporting previously undiscovered constituents contributes to the chemotaxonomic understanding of the Drynaria genus.
Related Concept Videos
Acidity and Basicity of Alcohols and Phenols
Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
Preparation of Diols and Pinacol Rearrangement
Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
