Microbial Conversion of 18β-Glycyrrhetinic Acid and 22α-Hydroxy-18β-glycyrrhetinic Acid byChainia antibiotic

Sakano, Katsu-ichi; Ohshima, Masayuki

doi:10.1080/00021369.1986.10867532

Cited by 6 publications

(5 citation statements)

References 2 publications

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“…Full structural elucidation of the new glycyrrhetinic acid derivatives was achieved using nuclear magnetic resonance (NMR), mass spectrometry (MS) and elemental analysis. The analytical data obtained for the known compounds 1 – 5 and 8 – 10 were in agreement with those reported in the literature [39,41,42,43].…”

Section: Resultssupporting

confidence: 89%

Synthesis and Antiproliferative Activity of Novel A-Ring Cleaved Glycyrrhetinic Acid Derivatives

et al. 2019

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A series of new glycyrrhetinic acid derivatives was synthesized via the opening of its ring A along with the coupling of an amino acid. The antiproliferative activity of the derivatives was evaluated against a panel of nine human cancer cell lines. Compound 17 was the most active compound, with an IC50 of 6.1 µM on Jurkat cells, which is 17-fold more potent than that of glycyrrhetinic acid, and was up to 10 times more selective toward that cancer cell line. Further biological investigation in Jurkat cells showed that the antiproliferative activity of compound 17 was due to cell cycle arrest at the S phase and induction of apoptosis.

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Section: Resultssupporting

confidence: 89%

Synthesis and Antiproliferative Activity of Novel A-Ring Cleaved Glycyrrhetinic Acid Derivatives

et al. 2019

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“…The authors found that this culture converted GA into 22-α-hydroxy-18 β-GA (as a major product) and two minor hydrolyxlated derivatives of that later major product. In addition, the same authors Sakano & Ohshima (1986b) found that Chainia antibiotica IFO 12, 246 converted GA and 22αhydroxy GA into three kinds of 3,4-seco-oleanane-type conversion products. Studies were made by El-Menoufy (1988) on 102 different microbial cultures and found that Saccharomycoposis lipolytica was the most active organism, it catalyses the conversion of crude GL to GA in a yield of 49.6%.…”

Section: Introductionmentioning

confidence: 92%

“…Medium IV (%, w/v): GL, 1; CSL, 0.8; pH 5.7. Medium V (%, w/v): Glucose, 2; peptone, 0.5; meat extract, 0.3 ; dry yeast, 0.3; NaCl, 0.5; CaCO3, 0.3; pH 7 (Sakano & Ohshima 1986b). Medium VI (%, w/v): Glycerol, 1; peptone, 0.5; meat extract, 0.3; yeast extract, 0.3; K2HPO4, 0.5; pH 7.4 (Sakano & Ohshima 1986a).…”

Section: Types Of Mediamentioning

confidence: 99%

Physiological and Chemical Studies on the Bioconversion of Glycyrrhizin by Aspergillus niger NRRL595

El-Refai¹,

Sallam²,

Menoufy³

et al. 2012

MJM

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Glycyrrhizin (GL), the well-known sweet saponin of licorice, has been used as a food-additive and as a medicine. Its aglycone, glycyrrhetic acid (GA) showed antiinflamatory, antiulcer and antiviral properties. GA is now produced form GL by acid hydrolysis. However, it is difficult to obtain GA in a good yield by using this method, because many by-products are also produced. Screening of different microorganisms (13 bacteria, 2 yeasts and 23 fungi) for production of GA from GL revealed that Aspergillus niger NRRL 595 produced the highest yield of GA. The bioconversion of GL by A. niger NRRL 595 for 96 h, followed by isolation and purification of the transformation products led to the separation of two conversion products, namely: GA and 3-oxo-GA. Confirmation of the identity of these products was established by determination of their Rf values, m.p., and IR, UV, MS and NMR spectra. The conditions for cultivation of this fungus with the maximum hydrolytic activity for the maximum yield of GA were investigated. Based on the results, A. niger NRRL 595 was cultivated with a medium composed of 1.75 % GL, 0.5 % glucose, 0.8 % corn steep liquor at pH 6.5 at 32 °C for 96 h. The cultivation of fungal cells under the latter conditions afforded GA and 3-oxo-GA in a yield of 65 % and 22 %, respectively.

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“…The data on bacterial transformation of oleanane triterpenoids by Streptomyces sp. G-20 and Chainia antibiotica IFO 12,246 were reported in the second half of the 1980s [ 26 , 27 ]. As for microbial transformations of ursane pentacyclic triterpenoids by both fungal ( Mucor plumbeus ATCC 4740 [ 28 ]) and bacterial ( Nocardia sp.…”

Section: Introductionmentioning

confidence: 99%

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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Microbial Conversion of 18β-Glycyrrhetinic Acid and 22α-Hydroxy-18β-glycyrrhetinic Acid byChainia antibiotic

Cited by 6 publications

References 2 publications

Synthesis and Antiproliferative Activity of Novel A-Ring Cleaved Glycyrrhetinic Acid Derivatives

Synthesis and Antiproliferative Activity of Novel A-Ring Cleaved Glycyrrhetinic Acid Derivatives

Physiological and Chemical Studies on the Bioconversion of Glycyrrhizin by Aspergillus niger NRRL595

Biotransformation of Oleanane and Ursane Triterpenic Acids

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