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

Bedir, Erdal; Kula, Ceyda; Öner, Özlem; Altaş, Melis; Tag̀, Özgür; Öngen, Gaye

doi:10.1016/j.molcatb.2015.01.013

Cited by 16 publications

(13 citation statements)

References 25 publications

(31 reference statements)

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“…The 1D NMR spectra of 11 and 13 were identical to those reported for 20( R ),24( S )-epoxy-3β,6α,12β,16β,25-pentahydroxylanost-9(11)-ene and 20( R ),24( S )-epoxy-3β,6α,12α,16β,25-pentahydroxylanost-9(11)-ene, respectively.…”

Section: Results and Discussionsupporting

confidence: 68%

“…Compounds 15 and 16 , the 3,4- seco derivatives of astragenol, were isolated previously from the biotransformation of this compound with Glomerella fusarioides . Metabolite 17 was also identified as 20( R ),24( S )-epoxy-6α,16β,25-trihydroxylanost-9(11)-en-3-one by comparing its NMR data with those previously reported in the literature…”

Section: Results and Discussionmentioning

confidence: 76%

“…In the 13 C NMR spectrum, the olefinic carbon signals of C-11 and C-9 were replaced with two resonances at δ C 57.9 and 67.5. A proton resonating at δ H 3.22, which correlated with a resonance at δ C 57.9 in the HSQC spectrum, showed a cross-peak with H-12a (δ H 1.81) in the COSY spectrum, suggesting a modification on the ring C. In addition, the carbon and proton chemical shifts of H-11 were significant for the oxidation of the C-9(11) double bond, affording a C-9(11) epoxide . The HMBC correlations of H-11 with C-12 and C-13, of H 3 -18 with C-12, and of H-8 with C-30 were supportive of the proposed structure.…”

Section: Results and Discussionmentioning

confidence: 92%

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Microbial Transformation of Cycloastragenol and Astragenol by Endophytic Fungi Isolated from Astragalus Species

et al. 2019

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Biotransformation of Astragalus sapogenins (cycloastragenol (1) and astragenol (2)) by Astragalus species originated endophytic fungi resulted in the production of five new metabolites (3,7,10, 12,14) together with 10 known compounds. The structures of the new compounds were established by NMR spectroscopic and HRMS analysis. Oxygenation, oxidation, epoxidation, dehydrogenation, and ring cleavage reactions were observed on the cycloartane (9,19-cyclolanostane) nucleus. The ability of the compounds to increase telomerase activity in neonatal cells was also evaluated. After prescreening studies to define potent telomerase activators, four compounds were selected for subsequent bioassays. These were performed using very low doses ranging from 0.1 to 30 nM compared to the control cells treated with DMSO. The positive control cycloastragenol and 8 were found to be the most active compounds, with 5.2-(2 nM) and 5.1-(0.5 nM) fold activations versus DMSO, respectively. At the lowest dose of 0.1 nM, compounds 4 and 13 provided 3.5and 3.8-fold activations, respectively, while cycloastragenol showed a limited activation (1.5-fold).

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Section: Results and Discussionsupporting

confidence: 68%

Section: Results and Discussionmentioning

confidence: 76%

Section: Results and Discussionmentioning

confidence: 92%

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Microbial Transformation of Cycloastragenol and Astragenol by Endophytic Fungi Isolated from Astragalus Species

et al. 2019

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“…Our previous studies revealed the biotransformation capacity of the filamentous fungi, viz. Cunninghamella blakesleeana and Glomerella fusarioides , toward triterpenoids. − In this study, we demonstrated the potential of an endophytic fungus ( A. eureka ) as biocatalyst to transform the steroidal sapogenin neoruscogenin. As a result, 14 new metabolites were obtained, and their structures were elucidated.…”

Section: Resultsmentioning

confidence: 79%

Biotransformation of Neoruscogenin by the Endophytic Fungus Alternaria eureka

Özçınar

Tag̀²,

Yusufoğlu

et al. 2018

J. Nat. Prod.

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Biotransformation of neoruscogenin (NR, 1, spirosta-5,25(27)-diene-1β,3β-diol), the major bioactive sapogenin of Ruscus preparations, was carried out with the endophytic fungus Alternaria eureka. Fourteen new biotransformation products (2-15) were isolated, and their structures were elucidated by NMR and HRESIMS data analyses. A. eureka affected mainly oxygenation, oxidation, and epoxidation reactions on the B and C rings of the sapogenin to afford compounds 8-15. In addition to these, cleavage of the spiroketal system as in compounds 2-7 and subsequent transformations provided unusual metabolites. This is the first study reporting conversion of the spirostanol skeleton to cholestane-type metabolites 2-5. Additionally, the cleavage of the C-22/C-26 oxygen bridge yielding a furostanol-type steroidal framework and subsequent formation of the epoxy bridge between C-18 and C-22 in 7 was encountered for the first time in steroid chemistry.

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

Cited by 16 publications

References 25 publications

Microbial Transformation of Cycloastragenol and Astragenol by Endophytic Fungi Isolated from Astragalus Species

Microbial Transformation of Cycloastragenol and Astragenol by Endophytic Fungi Isolated from Astragalus Species

Biotransformation of Neoruscogenin by the Endophytic Fungus Alternaria eureka

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

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