Microbial transformation of oxandrolone with Macrophomina phaseolina and Cunninghamella blakesleeana

Smith, Colin A.; Wahab, Atia‐tul; Khan, Mahwish Shafi Ahmed; Ahmad, Malik Shoaib; Farran, Dina; Choudhary, M. Iqbal; Baydoun, Elias

doi:10.1016/j.steroids.2015.06.008

Cited by 17 publications

(5 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“… Werner et al (1997) revealed that several endophytes from the roots of Aphelandra plant could well-metabolize aphelandrine, a macrocylic polyamine alkaloid isolated in the roots of different species of the genus Aphelandra , which was the first report on the biotransformation of endophytic fungi. After that, similar findings that endophytic fungi were capable of transforming some natural products and metabolizing drugs have been reported continuously ( Gniłka et al, 2015 ; Smith et al, 2015 ). Specifically, compared to traditional method, the microbial transformation of raw herb powder has been reported to produce a higher yield of active components ( Liu et al, 2010 ; Zhu et al, 2010 ; Ding et al, 2014 ).…”

Section: Introductionsupporting

confidence: 63%

“…Recently, an alternative approach to study the influence of an endophytic fungus on the host–plant metabolic profiles has been achieved by the analysis of the fungal impacts on the compositions of the host–plant secondary metabolites and their feedback effects on the fungal growth ( Tian et al, 2014 ). Additionally, many studies on microbial transformation have demonstrated that endophytes play an important role in producing novel compounds and modifying their structures and bioactivities ( Zeng et al, 2013 ; Gniłka et al, 2015 ; Smith et al, 2015 ). In this paper, in order to obtain highly oxygenated schitriterpenoids/schinortriterpenoids and assess the impact of SWUKD3.1410 on the secondary metabolites of host–plant K. angustifolia , U. dimorpha SWUKD3.1410 was respectively grown on dead K. angustifolia plant materials and wheat bran, and their corresponding fermented products were analyzed.…”

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Effects of an Endophytic Fungus Umbelopsis dimorpha on the Secondary Metabolites of Host–Plant Kadsura angustifolia

et al. 2018

View full text Add to dashboard Cite

Fungal endophytes live widely inside plant tissues and some have been revealed to provide benefits to their host and ecological environment. Considering the fact that endophytes are engaged in remarkably stable long-term interactions with the host for their whole life cycle, it’s conceivable that both partners have substantial influence on each other’s metabolic processes. Here, we investigated the fermented products of an endophytic fungus Umbelopsis dimorpha SWUKD3.1410 grown on host–plant Kadsura angustifolia and wheat bran, respectively, to assess the impact of SWUKD3.1410 on the secondary metabolites of K. angustifolia. Twenty compounds (1–20) were isolated and identified as 11 schitriterpenoids (1–9, 17–18), two lignans (10, 20), two sesquiterpenoids (11–12), one trinorsesquiterpenoid (13), one monoterpene (14), one sterol (19), and two simple aromatic compounds (15–16) by the extensive 1D-, 2D-NMR and HR-ESI-MS data analysis. Except for nigranoic acid (1), compounds 2–19 have been firstly found from K. angustifolia. Of them, metabolites 2, 11, and 14 were identified to be new. Obtained results indicated that U. dimorpha SWUKD3.1410 could not only produce the same/similar components as its host does, and modify the host–plant components, but also enhance the production of these highly oxygenated schitriterpenoids/schinortriterpenoids in plants. This study suggested an interesting prospective for setting up alternative processing techniques to improve the quality of crude drugs derived from K. angustifolia and increase their values.

show abstract

Section: Introductionsupporting

confidence: 63%

Section: Discussionmentioning

confidence: 99%

Effects of an Endophytic Fungus Umbelopsis dimorpha on the Secondary Metabolites of Host–Plant Kadsura angustifolia

et al. 2018

View full text Add to dashboard Cite

show abstract

“…At present, biotransformation techniques are successfully used in various fields, such as medicines, agriculture, polymer, and food industry, etc. due to selective nature of biological catalysts (enzymes) [9][10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

Cunninghamella blakesleeana-mediated biotransformation of a contraceptive drug, desogestrel, and anti-MDR-Staphylococcus aureus activity of its metabolites

Atia-tul-Wahab

Siddiqui

Ibrahim

et al. 2018

Bioorganic Chemistry

Self Cite

View full text Add to dashboard Cite

Staphylococcus aureus is one of the most infectious agents among staphylococcal bacteria. Currently many strains of S. aureus have developed resistance against available antibiotics. Therefore, the treatment of infections caused by them is a major challenge. During current study, desogestrel (1), a contraceptive drug, was found to be a potent growth inhibitor of drug resistant strains of S. aureus. Therefore, in search of new and effective agents against multi-drug resistant S. aureus strains, whole-cell bio-catalytic conversion of desogestrel (1) by Cunninghamella blakesleeana ATCC 8688A at pH 7.0 and 25 °C was carried out, yielding three new metabolites, 13-ethyl-11-methylene-18,19-dinor-17α-pregn-4-en-20-yn-6β,15β,17β-triol (2), 13-ethyl-11-methylene-18,19-dinor-17α-pregn-4-en-20-yn-3β,6β,17β-triol (3), and 13-ethyl-11-methylene-18,19-dinor-17α-pregn-20-yn-3α,5α,6β,17β-tetraol (4), along with a known metabolite, 13-ethyl-11-methylene-18,19-dinor-17α-pregn-4-en-20-yn-6β,17β-dihydroxy-3-one (5). Among them, compounds 1-2 showed a potent activity against S. aureus EMRSA-17, S. aureus NCTC 13277 (MRSA-252), and S. aureus NCTC 13143, and clinically isolated Pakistani strain of S. aureus in an in vitro Microplate Alamar Blue Assay (MABA). Vancomycin was used as the standard drug in this assay. In addition, compound 1 also showed a significant activity against vancomycin-resistant S. aureus (VRSA) ATCC 700699. Compounds 1-5 were also evaluated against 3T3 normal cell line (mouse fibroblast) where they all were identified as non-cytotoxic. The present study thus provides new leads for the development of anti-bacterial drugs against MDR S. aureus.

show abstract

“…Biotransformation has been widely employed in the structural modification of organic compounds to find more promising lead compounds in the development of new drugs. The whole cell, dead microorganism or enzymes all could act as catalyst, which catalyze kinds of chemical reactions, such as oxidation, reduction and hydroxylation (Smith et al 2015 ). In addition, compared with traditional chemical modification, microbial transformation has numerous superiorities, such as higher stereo- and regioselectivity, higher efficiency, lower pollution, and less cost (Dong et al 2016 ).…”

Section: Introductionmentioning

confidence: 99%

A new terpene coumarin microbial transformed by Mucor polymorphosporus induces apoptosis of human gastric cancer cell line MGC-803

Wang

et al. 2018

Arch. Pharm. Res.

View full text Add to dashboard Cite

2′-Z auraptene (1) is a synthesized monoterpene coumarin with anticancer activity against human gastric cancer cells. In order to find new potential anticancer agent, Mucor polymorphosporus was used to transform cis-auraptene. Four new terpene coumarins with notable changes in the skeletal backbone, 2′-Z auraptene A-D (2–5), were obtained and evaluated for their antiproliferative effects against human normal gastric epithelium cells and human gastric cancer cells. These new compounds showed selective cytotoxic activity against MGC-803 cells with IC50 values from 0.78 ± 0.13 to 10.78 ± 1.83 μM and the therapeutic index could also be significantly improved (TI = 59.0) compared with that of 1 (TI = 5.5). The structures of these metabolites were elucidated through extensive spectroscopic methods, and the possible biotransformation pathway of 1 by Mucor polymorphosporus was also proposed. Furthermore, the mechanism of the antiproliferative effects against MGC-803 cells of the most potent compound, 2′-Z auraptene A (2), was characterized. Annexin V/PI staining and abnormal expression of apoptosis-related protein suggested that compound 2 induces apoptosis in gastric cancer MGC-803 cells. Therefore, it is possible that compound 2 has the potential to be applied in gastric cancer therapy.Electronic supplementary materialThe online version of this article (10.1007/s12272-018-1028-0) contains supplementary material, which is available to authorized users.

show abstract

Microbial transformation of oxandrolone with Macrophomina phaseolina and Cunninghamella blakesleeana

Cited by 17 publications

References 20 publications

Effects of an Endophytic Fungus Umbelopsis dimorpha on the Secondary Metabolites of Host–Plant Kadsura angustifolia

Effects of an Endophytic Fungus Umbelopsis dimorpha on the Secondary Metabolites of Host–Plant Kadsura angustifolia

Cunninghamella blakesleeana-mediated biotransformation of a contraceptive drug, desogestrel, and anti-MDR-Staphylococcus aureus activity of its metabolites

A new terpene coumarin microbial transformed by Mucor polymorphosporus induces apoptosis of human gastric cancer cell line MGC-803

Contact Info

Product

Resources

About