Biotransformation of Industrially Important Steroid Drug Precursors

Pendharkar, Girish B.; Banerjee, Tushar; Patil, Sandeep; Dalal, Kiran S.; Chaudhari, Bhushan L.

doi:10.1007/978-981-16-5214-1_12

Cited by 3 publications

(3 citation statements)

References 117 publications

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“…Several interesting biotransformations of small molecules using different fruits and vegetables have reported in literature [ 7 – 10 ] but no such method is reported for the steroidal compounds. Steroidal compounds have large assortment in clinical applications with diversified functions—they are second biggest class of present-day drugs [ 11 ]. Steroidal compounds are captivating substrates for biotransformations because of their inactivated carbons and immense biological activities that make chemical alterations complex.…”

Section: Introductionmentioning

confidence: 99%

Betamethasone Dipropionate Derivatization, Biotransformation, Molecular Docking, and ADME Analysis as Glucocorticoid Receptor

Rashid

Anjum

Ahmad

et al. 2022

BioMed Research International

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Betamethasone is an important glucocorticoids (GCs), frequently used to cure allergies (such as asthma and angioedema), Crohn’s disease, skin diseases (such as dermatitis and psoriasis), systemic lupus erythematosus, rheumatic disorders, and leukemia. Present investigation deals to find potential agonist of glucocorticoid receptors after biotransformation of betamethasone dipropionate (1) and to carry out the molecular docking and ADME analyses. Biotransformation of 1 was carried out with Launaea capitata (dandy) roots and Musa acuminate (banana) leaves. M. acuminate furnished low-cost value-added products such as Sananone dipropionate (2) in 5% yields. Further, biocatalysis of Sananone dipropionate (2) with M. acuminate gave Sananone propionate (3) and Sananone (4) in 12% and 7% yields, respectively. However, Sananone (4) was obtained in 37% yields from Launaea capitata. Compound 5 was obtained in 11% yield after β-elimination of propionic acid at C-17 during oxidation of compound 1. The structure elucidation of new compounds 2-5 was accomplished through combined use of X-ray diffraction and NMR (1D and 2D) studies. In addition to this, molecular docking and ADME analyses of all transformed products of 1 were also done. Compounds 1-5 showed -12.53 to -10.11 kcal/mol potential binding affinity with glucocorticoid receptor (GR) and good ADME profile. Moreover, all the compounds showed good oral bioavailability with the octanol/water partition coefficient in the range of 2.23 to 3.65, which indicated that compounds 1-5 were in significant agreement with the given criteria to be considered as drug-like.

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Section: Introductionmentioning

confidence: 99%

Betamethasone Dipropionate Derivatization, Biotransformation, Molecular Docking, and ADME Analysis as Glucocorticoid Receptor

Rashid

Anjum

Ahmad

et al. 2022

BioMed Research International

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“…A growing need for efficient microbial transforming systems currently exists in the pharmaceutical industry for the commercial production of steroids. The production of many valuable steroids is based mainly on bioconversion of plant sterols—phytosterols 1 . A significant number of modern technologies for the combined chemical–microbial synthesis of steroid hormones are known, which include specific bioconversion of phytosterol and key steroid intermediates 2 .…”

Section: Introductionmentioning

confidence: 99%

Novel approach for downstream processing of phytosterol bioconversion

Хомутов

Шутов

Averin

et al. 2023

J of Chemical Tech & Biotech

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BACKGROUNDDownstream processing is an important part of industrial steroid biotechnology. The traditional recovery methods require significant amounts of the organic solvents which are associated with environmental risks. There is a need for environmentally friendly downstream processing which also may open the prospects for regeneration and repeated use of the costly materials.RESULTSMicrobial conversion of phytosterol to C17‐ketosteroids in methylated cyclodextrin (mCD) solutions was studied as a model bioprocess. Quantitative aspects of competitive complexation of mCD and natural β‐CD (β‐CD) with steroids were studied under different temperature modes and CD concentrations. The method of steroid recovery based on precipitation of insoluble β‐CD complexes ensured the complete isolation of androst‐4‐ene‐3,17‐dione, androsta‐1,4‐diene‐3,17‐dione, 9α‐hydroxyandrost‐4‐ene‐3,17‐dione, 20‐hydroxymethyl‐pregna‐1,4‐dien‐3‐one and 3β‐hydroxyandrost‐5‐en‐17‐one from aqueous media. Analysis of the 1H nuclear magnetic resonance (NMR) spectra showed a constant molar ratio of β‐CD to steroid equal to 2 in the obtained steroid β‐CD complexes. The extraction of the steroid from the β‐CD complex by small volumes of organic solvent provided a quantitative yield. The method developed ensures regeneration and repeated use of the mCDs without decrease of the basic bioconversion outputs, as was demonstrated in a series of phytosterol to androsta‐1,4‐diene‐3,17‐dione bioconversions by Mycolicibacterium neoaurum VKM Ac‐1816D.CONCLUSIONSDownstream processing based on manipulation of steroid solubility in aqueous cyclodextrin solutions is a promising alternative to traditional steroid extraction with organic solvents. This environmentally friendly approach ensures re‐use of materials without decrease in bioconversion outputs. © 2023 Society of Chemical Industry (SCI).

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“…Solasodine is a steroidal alkaloid, found in nature mainly in plants of the genus Solanum , being widely studied for its pharmacological applications in view of the presence of steroidal sapogenins that have pharmaceutical and industrial importance [ 11 , 13 , 14 ]. Thus, the interest in promoting this work is due to the activities already described in previous studies, in which solasodine demonstrates anticonvulsant [ 15 ], anti-inflammatory [ 16 ], antioxidant [ 17 ], antiviral [ 18 ], antifungal [ 19 , 20 ], anticancer [ 21 , 22 , 23 ], and antibacterial activity [ 24 , 25 , 26 ].…”

Section: Introductionmentioning

confidence: 99%

Potentiation of Antibiotic Action and Efflux Pump Inhibitory Effect on Staphylococcus aureus Strains by Solasodine

et al. 2022

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A worrisome fact is the increase in microbial resistance, which has as its main cause the indiscriminate use of antibiotics. Scientific studies have investigated bioactive compounds such as steroidal sapogenins, in the perspective of new beneficial alternatives for the control of bacterial resistance. Therefore, the objective of this work was to verify the antibacterial activity as well as the modifying action of antibiotics associated with solasodine and its ability to inhibit the efflux pump mechanism in strains of Staphylococcus aureus. Tests were performed to verify the minimum inhibitory concentration (MIC). In addition, the action-modifying potential of antibiotics and the inhibitory capacity of the efflux pump NorA and MepA through synergistic effects on the antibiotic and ethidium bromide were evaluated. Solasodine showed significant results for the standard bacteria with an MIC of 512 μg/mL, and when associated with the antibiotics gentamicin and nofloxacin for the multidrug-resistant bacteria S. aureus 10, Escherichia coli 06, and Pseudomonas aeruginosa 24, it showed a 50% reduction in MIC. The association of solasodine with the antibiotic ciprofloxacin against S. aureus K2068 (MepA) showed synergism, with a reduction in the MIC of the antibiotic from 64 μg/mL to 40 μg/mL, and also a reduction in the MIC when the antibiotic was used in conjunction with the efflux pump inhibitors. Solasodine may be acting on the mechanism of action of the antibiotic, as it has shown a potentiating effect when associated with antibiotics, inducing a reduction in the MIC against Gram-positive and Gram-negative bacteria. Therefore, this study demonstrated significant results for the potentiating action of solasodine when associated with antibiotics of clinical importance.

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Biotransformation of Industrially Important Steroid Drug Precursors

Cited by 3 publications

References 117 publications

Betamethasone Dipropionate Derivatization, Biotransformation, Molecular Docking, and ADME Analysis as Glucocorticoid Receptor

Betamethasone Dipropionate Derivatization, Biotransformation, Molecular Docking, and ADME Analysis as Glucocorticoid Receptor

Novel approach for downstream processing of phytosterol bioconversion

Potentiation of Antibiotic Action and Efflux Pump Inhibitory Effect on Staphylococcus aureus Strains by Solasodine

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