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DOI: 10.1055/s-2005-873198
© Georg Thieme Verlag KG Stuttgart · New York
Microbial Transformation of Glycyrrhetinic Acid by Mucor polymorphosporus
Publication History
Received: May 19, 2005
Accepted: June 24, 2005
Publication Date:
05 January 2006 (online)
Abstract
Glycyrrhetinic acid (GA; 1) is one of the major constituents of a traditional Chinese medicine, the roots of Glycyrrhiza uralensis, called Gancao in Chinese. In the present paper, the biotransformation of GA by Mucor polymorphosporus (AS 3.3443) was investigated and eight metabolites were obtained. Based on their chemical and spectral data, the structures of the derivatives were respectively elucidated as 24-hydroxyglycyrrhetinic acid (2), 6β-hydroxyglycyrrhetinic acid (3), 7α-hydroxyglycyrrhetinic acid (4), 7β-hydroxyglycyrrhetinic acid (5), 3-O-acetyl-7β-hydroxyglycyrrhetinic acid (6), 3-oxo-7β-hydroxyglycyrrhetinic acid (7), 15α-hydroxyglycyrrhetinic acid (8), 3-oxo-15α-hydroxyglycyrrhetinic acid (9), among which metabolites 3, 4, 6, 7 and 9 are new compounds.
Abbreviations
GA:glycyrrhetinic acid
TFA:trifluoroacetic acid
RP-HPLC:reversed-phase HPLC
Key words
Microbial transformation - glycyrrhetinic acid - Mucor polymorphosporus - structural identification
References
- 1 Goldberg G S, Moreno A P, Bechberger J F, Hearn S S, Shivers R R, Macphee D J. et al . Evidence that disruption of connexon particle arrangements in gap junction plaques is associated with inhibition of gap junctional communication by a glycyrrhetinic acid derivative. Exp Cell. Res1996; 222 48-53
- 2 Salvi M, Fiore C, Armanini D, Toninello A. Glycyrrhetinic acid-induced permeability transition in rat liver mitochondria. Biochem Pharmacol. 2003; 66 2375-9
- 3 Salari M H, Eshraghi S, Noroozi M. Antibacterial effect of glycyrrhetinic acid on 55 hospital strains of Staphylococcus aureus and 32 Actinobacillus actinomycetemcomitans . J Faculty Pharm, Tehran University of Medical Sciences. 2001; 9 37-9
- 4 Lin Z J, Qiu S X, Wufuer A, Shum L. Simultaneous determination of glycyrrhizin, a marker component in radix Glycyrrhizae, and its major metabolite glycyrrhetic acid in human plasma by LC-MS/MS. J Chromatogr B Biomed Appl. 2005; 814 201-7
- 5 Srisilam K, Veeresham C. Biotransformation of drugs by microbial cultures for predicting mammalian drug metabolism. Biotechnol Adv. 2003; 21 3-39
- 6 Zhan J X, Zhang Y X, Guo H Z, Han J, Ning L L, Guo D A. Microbial metabolism of artemisinin by Mucor polymorphosporus and Aspergillus niger . J Nat Prod. 2002; 65 1693-5
- 7 Canonica L, Jommi G, Pagnoni U M, Pelizzoni F, Ranzi B M, Scolastico C. Microbiological oxidation of triterpenoids. I. 7β-Hydroxyglycyrrhetic acid. Gazz Chim Ital. 1966; 96 820-31
- 8 Canonica L, Ferrari M, Jommi G, Pagnoni U M, Pelizzoni F, Ranzi B M. et al . Microbiological oxidation of triterpenoids. II. 15α-Hydroxyglycyrrhetic and 7β,15α-hydroxyglycyrrhetic acids. Gazz Chim Ital. 1967; 97 1032-51
- 9 Akao T, Aoyama M, Akao T, Hattori M, Imai Y, Namba T. et al . Metabolism of glycyrrhetic acid by rat liver microsomes. II. 22α-and 24-hydroxylation. Biochem Pharmacol. 1990; 40 291-6
- 10 Komoda Y. Nuclear magnetic resonance spectra of 18β-glycyrrhetinic acid and its related compounds. Iyo Kizai Kenkyusho Hokoku (Tokyo Ika Shika Daigaku). 1984; 18 39-44
- 11 Abourashed E A, Clark A M, Hufford C D. Microbial models of mammalian metabolism of xenobiotics: an updated review. Curr Med Chem. 1999; 6 359-74
Prof. Dean Guo
The State Key Laboratory of Natural and Biomimetic Drugs
School of Pharmaceutical Sciences
Peking University
Xueyuan Road 38
Beijing 100083
People’s Republic of China
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Email: gda@bjmu.edu.cn