Microbial transformation of diosgenin by Syncephalastrum racemosum (Cohn) Schroeter

Zhao, Ying; Sun, Lei; Wang, Xiao Ning; Shen, Tao; Ji, Mei; Li, Xia; Lou, Hong

doi:10.1016/j.cclet.2009.08.015

Cited by 8 publications

(2 citation statements)

References 13 publications

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“…With the development of biotechnology, biotransformation has become a powerful tool to generate derivatives of natural compounds. The hydroxylation reactions of DSG by several fungi and bacteria, such as Syncephalastrum racemosum [ 10 ], Cunninghamella echinulata [ 11 ], Bacillus megaterium [ 12 ], Coriolus versicolor [ 13 ], Cunninghamella blakesleeana [ 14 ], and Streptomyces virginiae IBL-14 [ 15 ], occur at the C-9, C-11, C-12, C-15, C-18, and C-25 positions. Streptomyces virginiae IBL-14 can also transform DSG to 6-methoxy-6-dehydronuatigenone and 6-dimethoxy-7α-hydroxyldiosgenone [ 16 ].…”

Section: Introductionmentioning

confidence: 99%

Characterization and Biological Activities of Four Biotransformation Products of Diosgenin from Rhodococcus erythropolis

Zhang

Kong

et al. 2023

Molecules

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Diosgenin (DSG), a steroidal sapogenin derived from the tuberous roots of yam, possesses multiple biological properties. DSG has been widely used as a starting material for the industrial production of steroid drugs. Despite its significant pharmacological activities, moderate potency and low solubility hinder the medicinal application of DSG. Biotransformation is an efficient method to produce valuable derivatives of natural products. In this work, we performed the biotransformation of DSG using five Rhodococcus strains. Compounds 1–4 were isolated and identified from Rhodococcus erythropolis. Compounds 1 and 2 showed potent cytotoxicity against the A549, MCF-7, and HepG2 cell lines. Compounds 3 and 4 are novel entities, and each possesses a terminal carboxyl group attached to the spiroacetal ring. Remarkably, 4 exhibited significant cell protective effects for kidney, liver, and vascular endothelial cells, suggesting the therapeutic potential of this compound in chronic renal diseases, atherosclerosis, and hypertension. We further optimized the fermentation conditions aiming to increase the titer of compound 4. Finally, the yield of compound 4 was improved by 2.9-fold and reached 32.4 mg/L in the optimized conditions. Our study lays the foundation for further developing compound 4 as a cell protective agent.

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Section: Introductionmentioning

confidence: 99%

Characterization and Biological Activities of Four Biotransformation Products of Diosgenin from Rhodococcus erythropolis

Zhang

Kong

et al. 2023

Molecules

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“…18β-glycyrrhetinic acid(48) is the active form of glycyrrhizin which is the major pentacyclic triterpene found in licorice (Glycyrrhiza glabra L.). Glycyrrhetinic acid has been shown to possess several pharmacological activities, such as antiulcerative, anti-inflammatory, immunomodulating, antitumor, antiviral, antihepatitis effects, and anticancer.…”

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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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Biocatalysis of Cycloastragenol by Syncephalastrum racemosum and Alternaria alternata to Discover Anti‐Aging Derivatives

Feng

Qiao

et al. 2015

Adv Synth Catal

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Cycloastragenol is ac ycloartane-type triterpenoid with significant telomerase-activating activities.Inthis paper, the biocatalysisofc ycloastragenol by two strains of filamentous fungi, namely Syncephalastrum racemosum AS 3.264 and Alternaria alternata AS 3.4578, was investigated. Scaled-up biotransformation reactions yielded 27 metabolites. Their structures were established on the basis of extensiveN MR and HR-ESI-MS data analyses,a nd 18 of them are new compounds.T he twof ungal strains exhibited distinct biocatalytic features. S. racemosum could catalyzer ing expansion ande poxidation reactions to form 3b,10b-epoxy-o r6 a ,19a-epoxy-9,10-seco-cycloartane structures,w hereas A. alternata preferredt oc atalyzea cetylation reactions,e specially at 3-OH, 6-OH and1 9-OH. These regio-ands tereoselective reactions are difficult to achieve by chemical means,b ut could be realized under mild conditions by biocatalysis.F urthermore,w ef ound that some acetylated derivatives at 50 mMc ould significantly extend the lifespan of Caenorhabditise legans from 16.93 AE 0.70 do ft he control group to 20.01 AE 0.75 d (P < 0.01), versus 18.54 AE 0.67 df or cycloastragenol. These biotransformed derivatives of cycloastragenol could be potential anti-aginga gents.

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Microbial transformation of diosgenin by Syncephalastrum racemosum (Cohn) Schroeter

Cited by 8 publications

References 13 publications

Characterization and Biological Activities of Four Biotransformation Products of Diosgenin from Rhodococcus erythropolis

Characterization and Biological Activities of Four Biotransformation Products of Diosgenin from Rhodococcus erythropolis

Microorganisms as Biocatalysts and Enzyme Sources

Biocatalysis of Cycloastragenol by Syncephalastrum racemosum and Alternaria alternata to Discover Anti‐Aging Derivatives

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