Microbial transformation of cycloastragenol

Kuban, Melis; Öngen, Gaye; Khan, Ikhlas A.; Bedir, Erdal

doi:10.1016/j.phytochem.2012.12.007

Cited by 22 publications

(22 citation statements)

References 26 publications

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“…The exact transformation product was observed with the leading compound CA in our preceding study [10]. Resemblance of the spectral data of 7, deduced from 1D-and 2D NMR spectra, with those of previously reported compound was evident for the characteristic 3,4-seco structures with a carboxyl group at C-3 and hydroxyl functionality at C-4 establishing the structure of 7.…”

Section: Resultssupporting

confidence: 68%

“…With these findings, a hydroxylation at C-12 was suggested. Comparing the chemical shifts and coupling constants with the previously obtained data, the hydroxyl group was proposed to be in ␤ configuration [10]. Furthermore, in the 1D-NOESY spectrum of 3, irradiation of alpha oriented CH 3 -30 (ı 0.92) resulted in NOE increments for H-17 (ı 2.61) and H-12 (ı 4.49) protons confirming their cofacial arrangement.…”

Section: Resultssupporting

confidence: 67%

“…Our findings and literatures showed that G. fusarioides catalyzed Baeyer-Villiger-type oxidation in an extremely effective way by using P450 systems [10,[12][13][14][15][16][17][18].…”

Section: Resultsmentioning

confidence: 56%

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Microbial transformation of Astragalus sapogenins using Cunninghamella blakesleeana NRRL 1369 and Glomerella fusarioides ATCC 9552

Bedir

Kula

Öner

et al. 2015

Journal of Molecular Catalysis B: Enzymatic

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a b s t r a c tThe microbial transformation of Astragalus sp. derived sapogenins, namely cycloastragenol, astragenol and cyclocanthogenol, by Cunninghamella blakesleeana NRRL 1369 and Glomerella fusarioides ATCC 9552 were investigated. The unique enzyme system of both fungi resulted hydroxylation, cyclization, dehydrogenation and oxidation reactions. Structures of the new metabolites were elucidated by 1-D ( 1 H, 13 C, NOESY), 2-D NMR (DQF-COSY, HMBC, HMQC, NOESY) and HR-MS analyses.

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Section: Resultssupporting

confidence: 68%

Section: Resultssupporting

confidence: 67%

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Microbial transformation of Astragalus sapogenins using Cunninghamella blakesleeana NRRL 1369 and Glomerella fusarioides ATCC 9552

Bedir

Kula

Öner

et al. 2015

Journal of Molecular Catalysis B: Enzymatic

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“…Astragalus species are the richest source of cycloartanes; the unique triterpenoids have a characteristic 9,19-cyclopropane ring, and cycloastragenol, a key intermediate in the biosynthesis of different phytosterols [33][34][35]. In Kuban's study, a rearrangement to provides a novel triterpene framework via a ring cleavage (cycloastragenol) followed by a methyl migration, demonstrating once more the potential of the microbial systems and Cunninghamella blakesleeana for the transformation of bioactive molecules [36].…”

Section: Effect Of Concentrations Of Astragalus Water Extractsmentioning

confidence: 99%

“…bacteria. The two fungi mainly provided hydroxylated metabolites together with products formed by dehydrogenation, cyclization and oxidation of Baeyer-Villiger, leading to a ring cracking [35,37]. It is an important reason why the addition of Astragalus water extract achieved the highest crude triterpenoid content.…”

Section: Effect Of Concentrations Of Astragalus Water Extractsmentioning

confidence: 99%

Effect of Chinese Herb Extract on the Formation of Triterpenoids in Shake-Flask Cultures of Antrodia cinnamomea

Wei¹,

Yang²,

Yang³

2017

J Bioprocess Biotech

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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 cycloastragenol

Cited by 22 publications

References 26 publications

Microbial transformation of Astragalus sapogenins using Cunninghamella blakesleeana NRRL 1369 and Glomerella fusarioides ATCC 9552

Microbial transformation of Astragalus sapogenins using Cunninghamella blakesleeana NRRL 1369 and Glomerella fusarioides ATCC 9552

Effect of Chinese Herb Extract on the Formation of Triterpenoids in Shake-Flask Cultures of Antrodia cinnamomea

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

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