Microbial hydroxylation and glycosidation of oleanolic acid by <i>Circinella muscae</i> and their anti-inflammatory activities

Yan, Sensen; Lin, Haijun; Huang, Huilian; Yang, Min; Xu, Bohui; Chen, Guangtong

doi:10.1080/14786419.2018.1477150

Cited by 16 publications

(11 citation statements)

References 13 publications

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“…Xu et al (2020) have recently used the tandem biotransformation of oleanane-type pentacyclic triterpenoids using the fungal strain Rhizopus chinensis CICC 40335 and bacterial strains Bacillus subtilis ATCC 6633 and Streptomyces griseus ATCC 13273 [34]. The primary transformation of OA (0.2 g/L) using R. chinensis CICC 40335 occurred within 4 days by the formation of 7β,21β-dihydroxy-OA (54, 53.75%) previously obtained using the fungal strains Mucor rouxii NRRL 1894 [131] and Circinella muscae AS 3.2695 [15]. Further 4-day biotransformation of the obtained compound (54) led to the formation of 7β,21β-dihydroxy-olean-12-en-28-oic acid 3-O-β-D-glucopyranoside (108, 46.5%) using B. subtilis ATCC 6633 cells and a mixture of 7β,21β,29-trihydroxy-OA (109, 26.0%) and 3β,7β,21βtrihydroxy-olean-12-ene-28,29-dioic acid (110, 15.0%) using S. griseus ATCC 13273 cells [34].…”

Section: Bacterial Transformationmentioning

confidence: 92%

“…Furthermore, microbial conversion ensures specific modifications of triterpenic molecule sites that are either not modified or poorly modified by synthetic transformations [12]. Note that, among the known microbial biocatalysts, members of mycelial fungi are the most studied [13][14][15] whereas bacterial catalysts are only represented by a few gram-positive species [16][17][18][19][20]. The first papers on microbial transformation of triterpenoids were published in the 1960s [21].…”

Section: Distribution In Naturementioning

confidence: 99%

“…Substitutions of CYP88D6 (C11 oxidase) for Unigene25647 (97% similarity) and ATR1 (A. thaliana) for GuCPR1 (G. uralensis) were performed, and a combination of GuCPR1 and two Unigene25647 cassettes was inserted into the genome of S. cerevisiae SGib. These manipulations resulted in the formation of 18.9 ± 2.0 mg/L GA and about 80.0 mg/L 11-oxo-β-amyrin (15) after 144 h of the fed-batch fermentation with ethanol (30 mL every 24 h) compared with the previously obtained 20.4 ± 7.7 µg/L GA and 0.5 ± 0.1 mg/L 11-oxo-β-amyrin (15) and β-amyrin (6) and trace amounts of 11α-hydroxy-β-amyrin (16), 30-hydroxy-11-oxo-β-amyrin (17), and glycyrrhetaldehyde (18) [62]. In strain S. cerevisiae BY-OA, substitution of CYP716C49 (C. pinnatifida) for the homologue (47.9% similarity) CaCYP716C49 (C. asiatica) allowed for obtaining 384.3 mg/L maslinic acid (19, 2α-hydroxy-OA) after 96-h incubation in a 5-L fermenter with glucose (5 g/L).…”

Section: Biosynthesis Of Pentacyclic Triterpenic Acids Using Microorgmentioning

confidence: 99%

“…AS 3.4486 was shown to catalyze the C15 hydroxylation of OA to form 15αhydroxy-OA(50) [113]. In turn, ascomycete Trichothecium roseum (M 95.56)[114] and mucoromycete Circinella muscae AS 3.2695[15] catalyzed the oxidation of OA (0.08 g/L and 0.02 g/L, respectively) to form 7β,15α-dihydroxy-3-oxo-olean-12-en-28-oic acid (51) on day 6 (7.5%) and day 7 (6.1%), respectively. At the same time, an intermediate (6.25%) of the dihydroxylation process-15αhydroxy-3-oxo-olean-12-en-28-oic acid (52)-was also isolated from the culture medium of T. roseum (M 95.56)[114].…”

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confidence: 99%

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Biotransformation of Oleanane and Ursane Triterpenic Acids

2020

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Oleanane and ursane pentacyclic triterpenoids are secondary metabolites of plants found in various climatic zones and regions. This group of compounds is highly attractive due to their diverse biological properties and possible use as intermediates in the synthesis of new pharmacologically promising substances. By now, their antiviral, anti-inflammatory, antimicrobial, antitumor, and other activities have been confirmed. In the last decade, methods of microbial synthesis of these compounds and their further biotransformation using microorganisms are gaining much popularity. The present review provides clear evidence that industrial microbiology can be a promising way to obtain valuable pharmacologically active compounds in environmentally friendly conditions without processing huge amounts of plant biomass and using hazardous and expensive chemicals. This review summarizes data on distribution, microbial synthesis, and biological activities of native oleanane and ursane triterpenoids. Much emphasis is put on the processes of microbial transformation of selected oleanane and ursane pentacyclic triterpenoids and on the bioactivity assessment of the obtained derivatives.

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Section: Bacterial Transformationmentioning

confidence: 92%

Section: Distribution In Naturementioning

confidence: 99%

Section: Biosynthesis Of Pentacyclic Triterpenic Acids Using Microorgmentioning

confidence: 99%

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confidence: 99%

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Biotransformation of Oleanane and Ursane Triterpenic Acids

2020

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“…In addition, the selective glycosylation at C-28 was another main reaction type. It was also observed that the 3β-OH group was selectively dehydrogenated into carbonyl group [42].…”

Section: Microorganism Products Action Referencementioning

confidence: 99%

Microorganisms as Biocatalysts and Enzyme Sources

Cano-Flores¹,

Gómez²,

Escalona-Torres³

et al. 2020

Microorganisms

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Microbial-catalyzed biotransformations have considerable potential for the generation of an enormous variety of structurally diversified organic compounds, especially natural products with complex structures like triterpenoids, flavonoids, steroids, steroidal saponins, and sesquiterpenoids. They offer efficient and economical ways to produce semisynthetic analogues and novel lead molecules. Microorganisms such as bacteria and fungi could catalyze chemo-, regio-, and stereospecific hydroxylations of diverse substrates that are extremely difficult to produce by chemical routes. During recent years, considerable research has been performed on the microbial transformation of bioactive compounds, in order to obtain biologically active molecules with diverse structural features. In green chemistry, biotransformations are an important chemical methodology toward more sustainable industrial processes.

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Oleanolic acid 28-O-β-D-glucopyranoside: A novel therapeutic agent against ulcerative colitis via anti-inflammatory, barrier-preservation, and gut microbiota-modulation

Wang,

Liu,

et al. 2024

Biomedicine & Pharmacotherapy

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Microbial hydroxylation and glycosidation of oleanolic acid by Circinella muscae and their anti-inflammatory activities

Cited by 16 publications

References 13 publications

Biotransformation of Oleanane and Ursane Triterpenic Acids

Biotransformation of Oleanane and Ursane Triterpenic Acids

Microorganisms as Biocatalysts and Enzyme Sources

Oleanolic acid 28-O-β-D-glucopyranoside: A novel therapeutic agent against ulcerative colitis via anti-inflammatory, barrier-preservation, and gut microbiota-modulation

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