Preparation of Glycyrrhetinic Acid Monoglucuronide by Selective Hydrolysis of Glycyrrhizic Acid via Biotransformation

LU Li; ZHAO Yang; YU He-shui; HUANG Hong-zhi; KANG Li-ping; CAO Man; CUI Jiang-ming; YU Li-yan; SONG Xin-bo; MA Bai-ping; LU Li; ZHAO Yang; YU He-shui; HUANG Hong-zhi; KANG Li-ping; CAO Man; CUI Jiang-ming; YU Li-yan; SONG Xin-bo; MA Bai-ping

Archive > Volume 4 Issue 4 > 2012,4(4):325-329. DOI:10.3969/j.issn.1674-6348.2012.04.010 Prev Next

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Preparation of Glycyrrhetinic Acid Monoglucuronide by Selective Hydrolysis of Glycyrrhizic Acid via Biotransformation

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摘要:

Abstract:

Objective To search for the microorganisms which have the high selectivity of hydrolyzing glycyrrhizic acid (GL) into 18β-glycyrrhetinic acid-3-O-β-D-glucuronide (GAMG) without glycyrrhetinic acid (GA) byproduct. Methods GL was biotransformed by Aspergillus sp., the products were separated by chromatography on reverse phase C18 column and semi-preparative HPLC, and their structures were elucidated on the basis of HR-ESI-MS, 1D NMR (1H-NMR, 13C-NMR, and NOESY) and 2D NMR (1H-1H COSY, HSQC, and HMBC) spectral analyses. Results Aspergillus sp. could partially hydrolyze GL into GAMG (3), along with two minor byproducts, 3-O-β-D-glucurono- pyranosyl-18β-liquiritic acid (1) and 3-O-β-D-glucuronopyranosyl-24-hydroxy-18β-glycyrrhetinic acid (2). Conclusion Aspergillus sp. has the high selectivity of hydrolyzing GL into GAMG without GA byproduct and the yield of GAMG is about 60%. The complete assignments of 1H-NMR and 13C-NMR data for compounds 1 and 2 are reported for the first time.

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National Science & Technology Pillar Program (2011BAI07B02-5)

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