Abstract
The effects of the oxygenase inhibitors, 1-aminobenzotriazole (ABT), ketoconazole, metyrapone and proadifen, on the metabolism of 18β-glycyrrhetinic acid (18β-GRA) in Sphingomonas paucimobilis strain G5 were investigated. Strain G5 transformed 18β-GRA into a major new metabolite (M-D) in the presence of 1 mM ABT or metyrapone. M-D was purified and identified as 3β-hydroxy-11-oxo-olean-12-en-24,30-dioic acid by NMR and MS. Based on the structure of M-D, we propose the metabolic pathway of 18β-GRA in strain G5.
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Baran JS,Langford DD,Liang CD,Pitzele BS (1974) Synthesis and biological activities of substituted glycyrrhetic acids. J. Med. Chem. 17: 184-191.
Bezalel L,Hadar Y,Fu PP,Freeman JP,Cerniglia CE (1996) Metabolism of phenanthrene by the white rot fungus Pleurotus ostreatus. Appl. Environ. Microbiol. 62: 2547-2553.
Budzikiewicz H,Wilson JM,Djerassi C (1963) Mass spectrometry in structural and stereochemical problems. XXXII. Pentacyclic triterpenes. J. Am. Chem. Soc. 85: 3688-3699.
Canonica L,Ferrari M,Jommi G,Pagnoni UM,Pelizzoni F,Ranzi BM,Maroni S,Nencini G,Salvatori T (1967) Microbial oxidation of triterpenoids II. Gazz. Chim. Ital. 97: 1032-1051.
Sakano K,Ohshima M (1986a) Structures of conversion products formed from 18?-glycyrrhetinic acid by Streptomyces sp. G-20. Agric. Biol. Chem. 50: 763-766.
Sakano K,Ohshima M (1986b) Microbial conversion of 18?-glycyrrhetinic acid and 22?-hydroxy-18?-glycyrrhetinic acid by Chainia antibiotica. Agric. Biol. Chem. 50: 1239-1245.
Sashi BM,Sucharita S (1997) Advances in triterpenoid research, 1990-1994. Phytochemistry 44: 1185-1236.
Sashi BM,Ashoke KN,Gita R (1992) Triterpenoids. Phytochemistry 31: 2199-2249.
Shibata S (1994) Antitumor-promoting and anti-inflammatory activities of licorice principles and their modified compounds. ACS Symposium Series, Vol. 547. Washington, D.C.: American Chemical Society, pp. 308-321.
Wahlberg I,Karlsson K,Enzell CR (1971) A mass spectral fragmentation reaction characteristic of 11-oxo-?-amyrin and 11-oxo-?-amyrin derivatives. Acta Chem. Scand. 25: 3192-3193.
Yoshida K,Furihata K,Yamane H,Omori T (2001) Metabolism of 18?-glycyrrhetinic acid in Sphingomonas paucimobilis strain G5. Biotechnol. Lett. 23: 253-258.
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Yoshida, K., Furihata, K., Habe, H. et al. Microbial transformation of 18β-glycyrrhetinic acid by Sphingomonas paucimobilis strain G5. Biotechnology Letters 23, 1619–1624 (2001). https://doi.org/10.1023/A:1011976300594
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DOI: https://doi.org/10.1023/A:1011976300594