Dataset Information

Antiurolithic activity and biotransformation of galloylquinic acids by Aspergillus alliaceus ATCC10060, Aspergillus brasiliensis ATCC 16404, and Cunninghamella elegans ATCC 10028b.

ABSTRACT: Copaifera lucens n-butanolic fraction (BF) was used as a source of galloylquinic acids, and aerobically incubated with Aspergillus alliaceus ATCC10060, Aspergillus brasiliensis ATCC 16404, and Cunninghamella elegans ATCC 10028b cultures for 60 and 120 h. Out of the three studied filamentous fungi, A. alliaceus ATCC10060 was able to degrade galloylquinic acids into one major metabolite, 3-O-methylgallic acid (M1). The product was identified by 1H-NMR, UPLC-MS/MS and its potential effect on calcium oxalate monohydrate (COM) crystal binding to Madin-Darby canine kidney cells type I surface was studied. Renal cells pretreatment with BF and M1 for 3 h significantly decreased calcium oxalate monohydrate crystal-adherence at 50 ?g/mL and 5 ?M, respectively. Both M1 and BF significantly reduced surface expression of COM-binding proteins annexin A1 and heat shock protein 90, respectively as evidenced by Western blot analysis of membrane, cytosolic, and whole cell lysate fractions. The compounds also showed antioxidant activities in DPPH assay.

SUBMITTER: El-Salam MA

PROVIDER: S-EPMC6936763 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

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Antiurolithic activity and biotransformation of galloylquinic acids by Aspergillus alliaceus ATCC10060, Aspergillus brasiliensis ATCC 16404, and Cunninghamella elegans ATCC 10028b.

El-Salam Mohamed Abd MA Furtado Niege N Haskic Zejfa Z Lieske John J Bastos Jairo J

Biocatalysis and agricultural biotechnology 20190129

Copaifera lucens n-butanolic fraction (BF) was used as a source of galloylquinic acids, and aerobically incubated with Aspergillus alliaceus ATCC10060, Aspergillus brasiliensis ATCC 16404, and Cunninghamella elegans ATCC 10028b cultures for 60 and 120 h. Out of the three studied filamentous fungi, A. alliaceus ATCC10060 was able to degrade galloylquinic acids into one major metabolite, 3-O-methylgallic acid (M1). The product was identified by 1</sup ...[more]

PMID: 31890054

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Project description:Seven metabolites were obtained from the microbial transformation of anabolic-androgenic steroid mibolerone (1) with Cunninghamella blakesleeana, C. echinulata, and Macrophomina phaseolina. Their structures were determined as 10β,17β-dihydroxy-7α,17α-dimethylestr-4-en-3-one (2), 6β,17β-dihydroxy-7α,17α-dimethylestr-4-en-3-one (3), 6β,10β,17β-trihydroxy-7α,17α-dimethylestr-4-en-3-one (4), 11β,17β-dihydroxy-(20-hydroxymethyl)-7α,17α-dimethylestr-4-en-3-one (5), 1α,17β-dihydroxy-7α,17α-dimethylestr-4-en-3-one (6), 1α,11β,17β-trihydroxy-7α,17α-dimethylestr-4-en-3-one (7), and 11β,17β-dihydroxy-7α,17α-dimethylestr-4-en-3-one (8), on the basis of spectroscopic studies. All metabolites, except 8, were identified as new compounds. This study indicates that C. blakesleeana, and C. echinulata are able to catalyze hydroxylation at allylic positions, while M. phaseolina can catalyze hydroxylation of CH2 and CH3 groups of substrate 1. Mibolerone (1) was found to be a moderate inhibitor of β-glucuronidase enzyme (IC50 = 42.98 ± 1.24 μM) during random biological screening, while its metabolites 2-4, and 8 were found to be inactive. Mibolerone (1) was also found to be significantly active against Leishmania major promastigotes (IC50 = 29.64 ± 0.88 μM). Its transformed products 3 (IC50 = 79.09 ± 0.06 μM), and 8 (IC50 = 70.09 ± 0.05 μM) showed a weak leishmanicidal activity, while 2 and 4 were found to be inactive. In addition, substrate 1 (IC50 = 35.7 ± 4.46 μM), and its metabolite 8 (IC50 = 34.16 ± 5.3 μM) exhibited potent cytotoxicity against HeLa cancer cell line (human cervical carcinoma). Metabolite 2 (IC50 = 46.5 ± 5.4 μM) also showed a significant cytotoxicity, while 3 (IC50 = 107.8 ± 4.0 μM) and 4 (IC50 = 152.5 ± 2.15 μM) showed weak cytotoxicity against HeLa cancer cell line. Compound 1 (IC50 = 46.3 ± 11.7 μM), and its transformed products 2 (IC50 = 43.3 ± 7.7 μM), 3 (IC50 = 65.6 ± 2.5 μM), and 4 (IC50 = 89.4 ± 2.7 μM) were also found to be moderately toxic to 3T3 cell line (mouse fibroblast). Interestingly, metabolite 8 showed no cytotoxicity against 3T3 cell line. Compounds 1-4, and 8 were also evaluated for inhibition of tyrosinase, carbonic anhydrase, and α-glucosidase enzymes, and all were found to be inactive.

Dataset Information

Antiurolithic activity and biotransformation of galloylquinic acids by Aspergillus alliaceus ATCC10060, Aspergillus brasiliensis ATCC 16404, and Cunninghamella elegans ATCC 10028b.

Publications

Antiurolithic activity and biotransformation of galloylquinic acids by <i>Aspergillus alliaceus</i> ATCC10060, <i>Aspergillus brasiliensis</i> ATCC 16404, and <i>Cunninghamella elegans</i> ATCC 10028b.

Similar Datasets

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