Microbial Transformation of Dihydrosarsasapogenin with <i>Mycobacterium </i>sp.

Lee, Shoei‐Sheng; Yan, Jiann-Long; Lin, Gong-Yin; Wang, K. C.

doi:10.1021/np970392w

Cited by 4 publications

(1 citation statement)

References 11 publications

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“…However, yields have been poor or absent. Enzymatic transformations have also been attempted with structurally-similar molecules [22,23]. Obtaining diosgenone via Swern oxidation with subsequent double bond isomerization with oxalic acid in refluxing ethanol is reported here (84% overall yield).…”

Section: Chemical Transformationsmentioning

confidence: 99%

Diosgenone Synthesis, Anti-Malarial Activity and QSAR of Analogues of This Natural Product

et al. 2013

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Solanum nudum Dunal steroids have been reported as being antimalarial compounds; however, their concentration in plants is low, meaning that the species could be threatened by over-harvesting for this purpose. Swern oxidation was used for hemisynthesis of diosgenone (one of the most active steroidal sapogenin diosgenin compounds). Eighteen structural analogues were prepared; three of them were found to be more active than diosgenone (IC 50 27.9 μM vs. 10.1 μM, 2.9 μM and 11.3 μM). The presence of a 4-en-3-one grouping in the A-ring of the compounds seems to be indispensable for antiplasmodial activity; progesterone (having the same functional group in the steroid A-ring) has also displayed antiplasmodial activity. Quantitative correlations between molecular structure and bioactivity were thus explored in diosgenone and several derivatives using well-established 3D-QSAR techniques. The models showed that combining electrostatic (70%) and steric (30%) fields can explain most variance regarding OPEN ACCESSMolecules 2013, 18 3357 compound activity. Malarial parasitemia in mice became reduced by oral administration of two diosgenone derivatives.

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Section: Chemical Transformationsmentioning

confidence: 99%

Diosgenone Synthesis, Anti-Malarial Activity and QSAR of Analogues of This Natural Product

et al. 2013

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Selection of Mycobacterium sp. strains with capacity to biotransform high concentrations of β-sitosterol

Vidal

Becerra

Mondaca

et al. 2001

Applied Microbiology and Biotechnology

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In this work, phytosterol-biotransforming strains were selected from Mycobacterium sp., using a high concentration of beta-sitosterol. The selection was made by culturing the strains in a medium enriched with 14 g beta-sitosterol/l as the unique source of carbon. During 2 months, the bacterial cultures were transferred successively. The extraction of the biotransformation products was made with methanol and ethyl acetate. The qualitative and quantitative analysis was made by means of thin-layer chromatography, gas-liquid chromatography (GLC) and GLC-mass spectrometry. Under these conditions, it was observed that after seven transfers, the strains MYcobacterium sp. MB-3683 and the Mycobacterium fortuitum B-11045 increased their biotransformation capacity from 20% to 64% and from 34% to 55%, respectively. The products in the highest proportion identified for each trial were androstenedione and androstadienedione. The results suggest that the high substrate concentration could be a selective mechanism to obtain strains more efficient in the biotransformation of beta-sitosterol into steroidal bases.

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Microbial biotransformation of bioactive and clinically useful steroids and some salient features of steroids and biotransformation

Sultana

2018

Steroids

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Microbial Transformation of Dihydrosarsasapogenin with Mycobacterium sp.

Cited by 4 publications

References 11 publications

Diosgenone Synthesis, Anti-Malarial Activity and QSAR of Analogues of This Natural Product

Diosgenone Synthesis, Anti-Malarial Activity and QSAR of Analogues of This Natural Product

Selection of Mycobacterium sp. strains with capacity to biotransform high concentrations of β-sitosterol

Microbial biotransformation of bioactive and clinically useful steroids and some salient features of steroids and biotransformation

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