Exserolides A–F, new isocoumarin derivatives from the plant endophytic fungus Exserohilum sp.

Li, Ruxin; Chen, Shenxi; Niu, Shubin; Guo, Liang‐Dong; Yin, Jun; Che, Yongsheng

doi:10.1016/j.fitote.2014.04.013

Cited by 38 publications

(35 citation statements)

References 24 publications

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“…Comparison of the NMR data of compounds 4 and 5 suggested that they differed only in the substituents on C-3. The absolute configuration of C-10 and C-12 of compound 4 was determined as 10 R , 12 S by applying Mosher’s methods to the 1, 3-anti-diol model as reported [ 20 , 21 , 22 ]. The procedure started with esterification of 4 with the two enantiomers of ( R )- or ( S )-MTPA chloride ( 4a = R or 4b = S ) [ 23 ], and then the differences in chemical shift values (Δδ = δ S − δ R ) for 4b and 4a were calculated to assign the configuration of C-10 and C-12 ( Figure 3 ).…”

Section: Resultsmentioning

confidence: 99%

Polyketides from the Mangrove-Derived Endophytic Fungus Nectria sp. HN001 and Their α-Glucosidase Inhibitory Activity

et al. 2016

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Four new polyketides: nectriacids A–C (1–3) and 12-epicitreoisocoumarinol (4), together with three known compounds: citreoisocoumarinol (5), citreoisocoumarin (6), and macrocarpon C (7) were isolated from the culture of the endophytic fungus Nectria sp. HN001, which was isolated from a fresh branch of the mangrove plant Sonneratia ovata collected from the South China Sea. Their structures were determined by the detailed analysis of NMR and mass spectroscopic data. The absolute configuration of the stereogenic carbons for compound 4 was further assigned by Mosher’s ester method. All of the isolated compounds were tested for their α-glucosidase inhibitory activity by UV absorbance at 405 nm, and new compounds 2 and 3 exhibited potent inhibitory activity with IC50 values of 23.5 and 42.3 μM, respectively, which were more potent than positive control (acarbose, IC50, 815.3 μM).

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Section: Resultsmentioning

confidence: 99%

Polyketides from the Mangrove-Derived Endophytic Fungus Nectria sp. HN001 and Their α-Glucosidase Inhibitory Activity

et al. 2016

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“…Arunpanichlert et al reported that 213 had a mild antifungal effect against Cryptococcus neoformans and C. albicans with equal MICs of 200 µg/mL, while 212 was inactive (Conc. 200 mg/mL)[60]. Furthermore, 212 and 213 had a weak antibacterial effect against B. subtilis and S. aureus (Conc.…”

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confidence: 98%

Naturally Occurring Isocoumarins Derivatives from Endophytic Fungi: Sources, Isolation, Structural Characterization, Biosynthesis, and Biological Activities

et al. 2020

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Recently, the metabolites separated from endophytes have attracted significant attention, as many of them have a unique structure and appealing pharmacological and biological potentials. Isocoumarins represent one of the most interesting classes of metabolites, which are coumarins isomers with a reversed lactone moiety. They are produced by plants, microbes, marine organisms, bacteria, insects, liverworts, and fungi and possessed a wide array of bioactivities. This review gives an overview of isocoumarins derivatives from endophytic fungi and their source, isolation, structural characterization, biosynthesis, and bioactivities, concentrating on the period from 2000 to 2019. Overall, 307 metabolites and more than 120 references are conferred. This is the first review on these multi-facetted metabolites from endophytic fungi.

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“…The whole culture broth of A. oryzae was extracted with ethyl acetate. The extract was subjected repeatedly to column chromatography on silica gel, MCI, RP-18, preparative high-performance liquid chromatography (HPLC), and semipreparative HPLC to afford compounds 1-9, including four new isocoumarin derivatives, oryzaeins A-D (1-4), along with five known ones (5-9), tabaisocoumarin A (5) [7], caudacoumarin C (6) [8], versicolol B (7) [9], exserolide D (8) [10], and exserolide F (9) [10]. The structures of compounds 1-9 are shown in l " Fig.…”

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confidence: 99%

“…The 13 C NMR and distortionless enhancement by polarization transfer (DEPT) data exhibited fifteen carbon signals, consisting of one methyl, four methylenes (of which one was oxygenated), one olefinic and two aromatic methines, and seven quaternary carbons (including two oxygenated ones and two carbonyls). The initial analysis of these 1D NMR data indicated that compound 1 had an isocoumarin skeleton [7][8][9][10] with a hydroxyl group, a 2-oxopropyl group, and a 3-hydroxypropyl group, which were further established by the heteronuclear multiple-bond correlation (HMBC) and 1 H-1 H correlation spectroscopy (COSY) spectra analysis. Firstly, the isocoumarin skeleton was assigned by the key HMBC correlations from H-4 to C-1 ( 4 J CH ), C-3, C-4a, C-5, and C-8a, from H-6 to C-4a, C-5, C-7, and C-8, and from H-8 to C-4a, C-6, C-7, and C-8a.…”

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confidence: 99%

Antiviral and Cytotoxic Isocoumarin Derivatives from an Endophytic Fungus Aspergillus oryzae

Zhou

et al. 2016

Planta Med

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Oryzaeins A-D (1-4), four new isocoumarin derivatives, along with five known ones (5-9) were isolated from solid cultures of an endophytic fungus Aspergillus oryzae. Their structures were elucidated by detailed spectroscopic analysis and by comparison with reported data of related derivatives. Among them, compounds 1 and 2 represent the first examples of isocoumarins possessing an unusual 2-oxopropyl group and a rare 3-hydroxypropyl group. Compounds 1 and 2 displayed moderate anti-tobacco mosaic virus activities with inhibition rates of 28.4% and 30.6%, respectively, at the concentration of 20 µM. The new compounds showed moderate inhibitory activities against several human tumor cell lines with IC50 values in the range of 2.8-8.8 µM. Supporting information available online at http://www.thieme-connect.de/products.

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Exserolides A–F, new isocoumarin derivatives from the plant endophytic fungus Exserohilum sp.

Cited by 38 publications

References 24 publications

Polyketides from the Mangrove-Derived Endophytic Fungus Nectria sp. HN001 and Their α-Glucosidase Inhibitory Activity

Polyketides from the Mangrove-Derived Endophytic Fungus Nectria sp. HN001 and Their α-Glucosidase Inhibitory Activity

Naturally Occurring Isocoumarins Derivatives from Endophytic Fungi: Sources, Isolation, Structural Characterization, Biosynthesis, and Biological Activities

Antiviral and Cytotoxic Isocoumarin Derivatives from an Endophytic Fungus Aspergillus oryzae

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