Peniphenones A–D from the Mangrove Fungus <i>Penicillium dipodomyicola</i> HN4-3A as Inhibitors of <i>Mycobacterium tuberculosis</i> Phosphatase MptpB

Li, Hanxiang; Jiang, Jin; Zhao-ming, Liu; Lin, Shao'e; Xia, Guoping; Xia, Xuekui; Ding, Bo; He, Lei; Lü, Yongjun; She, Zhigang

doi:10.1021/np400880w

Cited by 73 publications

(52 citation statements)

References 32 publications

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“…The negative circular dichroism at 265 nm (Fig. 5) suggested R configuration at C-3, by comparison with data for isocoumarin derivatives described in the literature [13]. Thus, asperisocoumarin E ( 5 ) was elucidated as ( R )-1-(8-hydroxy-3-methyl-1-oxoisochroman-7-yl)-3-methylbutane-1,2-dione.…”

Section: Resultssupporting

confidence: 61%

“…The molecular formula of 6 was deduced as C 22 H 22 O 9 from HRESIMS analysis ( m / z 429.1186 [M − H] − ), implying 12 degrees of unsaturation. Its 1 H NMR spectrum resembled that of stellatin [13], except the absence of a hydroxy proton at δ H 2.24. In the 13 C NMR spectrum, the chemical shift value of the oxygenated methylene at C-9 was 3.9 ppm higher than that of stellatin [19].…”

Section: Resultsmentioning

confidence: 99%

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New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242

Xiao¹,

Chen²,

Cai³

et al. 2016

Beilstein J. Org. Chem.

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SummaryThe chemical investigation of the mangrove endophytic fungus Aspergillus sp. 085242 afforded eight isocoumarin derivatives 1–8 and one isoquinoline 9. Asperisocoumarins A and B (1 and 2) were new furoisocoumarins, and asperisocoumarins E and F (5 and 6) were new isocoumarins. Their structures were established by analysis of their spectroscopic data and the absolute configuration of compound 2 was unambiguously determined by X-ray structure analysis and ECD calculation. Moreover, the absolute configurations of compounds 3–5 were assigned by comparison of their ECD spectra with isocoumarins described in the literature. Asperisocoumarins C and D (3 and 4) were fully characterized spectroscopically and isolated from a natural source for the first time. Asperisocoumarins A–D (1–4) related to the class of furo[3,2-h]isocoumarins are rarely occurring in natural sources. Compounds 2, 5, and 6 showed moderate α-glucosidase inhibitory activity with IC50 of 87.8, 52.3, and 95.6 μM, respectively. In addition, compounds 1 and 3 exhibited weak radical scavenging activity with EC50 values of 125 and 138 μM, respectively.

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Section: Resultssupporting

confidence: 61%

Section: Resultsmentioning

confidence: 99%

New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242

Xiao¹,

Chen²,

Cai³

et al. 2016

Beilstein J. Org. Chem.

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“…The few limited reports of soft coral-associated fungi provide a clue that they would be a promising source for structurally diverse and biologically active secondary metabolites [18,19,20,21,22]. Recently, in our ongoing search for new and potent natural products from marine fungi in the South China Sea [23,24,25,26,27], we initiated investigations of those fungi associated with corals. In the course of this study, a soft coral-derived fungus, Eurotium rubrum SH-823, attracted our attention because the EtOAc extract of the fungal fermentation on rice exhibited significant α-glucosidase inhibitory activity.…”

Section: Introductionmentioning

confidence: 99%

Eurothiocin A and B, Sulfur-Containing Benzofurans from a Soft Coral-Derived Fungus Eurotium rubrum SH-823

et al. 2014

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Two new sulfur-containing benzofuran derivatives, eurothiocin A and B (1 and 2), along with five known compounds, zinniol (3), butyrolactone I (4), aspernolide D (5), vermistatin (6), and methoxyvermistatin (7), were isolated from the cultures of Eurotium rubrum SH-823, a fungus obtained from a Sarcophyton sp. soft coral collected from the South China Sea. The new compounds (1 and 2) share a methyl thiolester moiety, which is quite rare among natural secondary metabolites. The structures of these metabolites were assigned on the basis of detailed spectroscopic analysis. The absolute configurations of 1 and 2 were determined by comparison of the experimental and calculated electronic circular dichroism (ECD) data. Compounds 1 and 2 exhibited more potent inhibitory effects against α-glucosidase activity than the clinical α-glucosidase inhibitor acarbose. Further mechanistic analysis showed that both of them exhibited competitive inhibition characteristics.

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“…is a prolific producer of secondary metabolites with anticancer and antibacterial potential (Gao et al 2010;Xu et al 2015;Jouda et al 2016). Several compounds isolated from P. dipodomyicola have been reported as anticancer/antibacterial drugs including Speradine B, griseofulvin, epigriseofulvin and isogriseofulvin and Peniphenones A-D (Porsani et al 2013;Li et al 2014;Wang et al 2015).…”

Section: Discussionmentioning

confidence: 99%

Bioprospecting potential and secondary metabolite profile of a novel sediment-derived fungus Penicillium sp. ArCSPf from continental slope of Eastern Arabian Sea

Farha

Hatha

2019

Mycology

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Marine fungi, one of the major decomposers of marine environment, is found to produce potential enzymes and novel biomolecules. The present study explored bioprospecting potentials such as antimicrobial, anticancer and enzymatic activities of marine sediment-derived fungi isolated from continental slope of Eastern Arabian Sea. Morphology and ITS sequencing identified the fungus as Penicillium sp. ArCSPf. The fungal strain exhibited amylase, gelatinase, phytase, lipase and pectinase activity. The active fraction obtained from the ethyl acetate extract column fractionation (F2) of fungus showed antibacterial activity against both methicillin-resistant Staphylococcus aureus (MRSA) and Bacillus cereus. Minimum inhibitory concentrations of F2 were 125 μg/mL for MRSA and 62.5 μg/mL for B. cereus. The active fraction showed a significant anticancer activity (IC 50 = 22.79 µg/mL) against MCF-7 breast cancer cells. The secondary metabolite (Z)-Octadec-9-enamide (oleamide, m/z 282.27 (M + H +)] was identified in the LC-MS/MS analysis of active fraction F2 in positive ionisation mode. To the best of our knowledge, this is the first report on exploring the bioprospecting potential of a sediment-derived fungus from continental slope of eastern Arabian Sea for the production of therapeutically active compounds.

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Peniphenones A–D from the Mangrove Fungus Penicillium dipodomyicola HN4-3A as Inhibitors of Mycobacterium tuberculosis Phosphatase MptpB

Cited by 73 publications

References 32 publications

New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242

New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242

Eurothiocin A and B, Sulfur-Containing Benzofurans from a Soft Coral-Derived Fungus Eurotium rubrum SH-823

Bioprospecting potential and secondary metabolite profile of a novel sediment-derived fungus Penicillium sp. ArCSPf from continental slope of Eastern Arabian Sea

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