<sup>1</sup>H and <sup>13</sup>C NMR assignments of three nitrogen containing compounds from the mangrove endophytic fungus (ZZF08)

Tao, Yiwen; Zeng, Xianjian; Mou, Chengbo; Li, Jun; Cai, Xueli; She, Zhigang; Zhou, Shining; Lin, Yongcheng

doi:10.1002/mrc.2194

Cited by 20 publications

(13 citation statements)

References 8 publications

(6 reference statements)

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“…Column chromatography and preparative HPLC were used to isolate the six known compounds: cytochalasin J ( 1 ), cytochalasin H ( 2 ) [10,11,12], 5'-epialtenuene ( 3 ) [13,14], alternariol monomethyl ether (AME) ( 4 ) alternariol (AOH) ( 5 ) [15,16,17], cytosporone C ( 6 ) [18,19], and the new natural product 2-hydroxyalternariol ( 7 ).…”

Section: Resultsmentioning

confidence: 99%

Bioactive Secondary Metabolites from Phomopsis sp., an Endophytic Fungus from Senna spectabilis

et al. 2014

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Chemical investigation of an acetonitrile fraction from the endophytic fungus Phomopsis sp. led to the isolation of the new natural product 2-hydroxy-alternariol (7) together with the known compounds cytochalasins J (1) and H (2), 5'-epialtenuene (3) and the mycotoxins alternariol monomethyl ether (AME, 4), alternariol (AOH, 5) and cytosporone C (6). The structure of the new compound was elucidated by using 1-D and 2-D NMR (nuclear magnetic resonance) and high resolution mass spectrometry. The cytochalasins J (1) and H (2) and AOH (5) exhibited potent inhibition of the total ROS (reactive oxygen species) produced by stimulated human neutrophils and acted as potent potential anti-inflammatory agents. Moreover, cytochalasin H (2) demonstrated antifungal and acetylcholinesterase enzyme (AChE) inhibition in vitro.

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Section: Resultsmentioning

confidence: 99%

Bioactive Secondary Metabolites from Phomopsis sp., an Endophytic Fungus from Senna spectabilis

et al. 2014

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“…Further known cytochalasans were isolated from other species of Sordariomycetes and identified by comparing the 1 H and 13 C chemical shifts and the HRMS data to those reported previously ([25] for 6 ; [26] for 7 , [27] for 8 ; [28] for 1 0 , [21] for 11 – 13 , [27] for 15 – 18 ). However, upon comparison of our NMR data with those published previously [26,27] for l -696,474 ( 7 ) and 21- O -deacetyl- l -696,474 ( 8 ), respectively, it was found that 1 H and 13 C assignments for methyl groups CH 3 -22 and CH 3 -23 were different to those in the literature.…”

Section: Resultsmentioning

confidence: 99%

Cytochalasans Act as Inhibitors of Biofilm Formation of Staphylococcus aureus

et al. 2018

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During the course of our ongoing work to discover new inhibitors of biofilm formation of Staphylococcus aureus from fungal sources, we observed biofilm inhibition by cytochalasans isolated from cultures of the ascomycete Hypoxylon fragiforme for the first time. Two new compounds were purified by a bioassay-guided fractionation procedure; their structures were elucidated subsequently by nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HR-MS). This unexpected finding prompted us to test further cytochalasans from other fungi and from commercial sources for comparison. Out of 21 cytochalasans, 13 showed significant inhibition of Staphylococcus aureus biofilm formation at subtoxic levels. These findings indicate the potential of cytochalasans as biofilm inhibitors for the first time, also because the minimum inhibitory concentrations (MIC) are independent of the anti-biofilm activities. However, cytochalasans are known to be inhibitors of actin, making some of them very toxic for eukaryotic cells. Since the chemical structures of the tested compounds were rather diverse, the inclusion of additional derivatives, as well as the evaluation of their selectivity against mammalian cells vs. the bacterium, will be necessary as next step in order to develop structure-activity relationships and identify the optimal candidates for development of an anti-biofilm agent.

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“…Compounds isolated from active extracts included eight well‐known cytochalasins ( 1–8 ) (Fig. ), which were identified from several endophytic fungi and some terrestrial filamentous fungi.…”

Section: Resultsmentioning

confidence: 99%

Miniaturized Cultivation of Microbiota for Antimalarial Drug Discovery

Waterman

Calcul

Beau

et al. 2014

Medicinal Research Reviews

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The ongoing search for effective antiplasmodial agents remains essential in the fight against malaria worldwide. Emerging parasitic drug resistance places an urgent need to explore chemotherapies with novel structures and mechanisms of action. Natural products have historically provided effective antimalarial drug scaffolds. In an effort to search nature's chemical potential for antiplasmodial agents, unconventionally sourced organisms coupled with innovative cultivation techniques were utilized. Approximately 60,000 niche microbes from various habitats (slow-growing terrestrial fungi, Antarctic microbes, and mangrove endophytes) were cultivated on a small-scale, extracted, and used in high-throughput screening to determine antimalarial activity. About 1% of crude extracts were considered active and 6% partially active (≥ 67% inhibition at 5 and 50 μg/mL, respectively). Active extracts (685) were cultivated on a large-scale, fractionated, and screened for both antimalarial activity and cytotoxicity. High interest fractions (397) with an IC50 < 1.11 μg/mL were identified and subjected to chromatographic separation for compound characterization and dereplication. Identifying active compounds with nanomolar antimalarial activity coupled with a selectivity index tenfold higher was accomplished with two of the 52 compounds isolated. This microscale, high-throughput screening project for antiplasmodial agents is discussed in the context of current natural product drug discovery efforts.

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¹H and ¹³C NMR assignments of three nitrogen containing compounds from the mangrove endophytic fungus (ZZF08)

Cited by 20 publications

References 8 publications

Bioactive Secondary Metabolites from Phomopsis sp., an Endophytic Fungus from Senna spectabilis

Bioactive Secondary Metabolites from Phomopsis sp., an Endophytic Fungus from Senna spectabilis

Cytochalasans Act as Inhibitors of Biofilm Formation of Staphylococcus aureus

Miniaturized Cultivation of Microbiota for Antimalarial Drug Discovery

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1H and 13C NMR assignments of three nitrogen containing compounds from the mangrove endophytic fungus (ZZF08)

Cited by 20 publications

References 8 publications

Bioactive Secondary Metabolites from Phomopsis sp., an Endophytic Fungus from Senna spectabilis

Bioactive Secondary Metabolites from Phomopsis sp., an Endophytic Fungus from Senna spectabilis

Cytochalasans Act as Inhibitors of Biofilm Formation of Staphylococcus aureus

Miniaturized Cultivation of Microbiota for Antimalarial Drug Discovery

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¹H and ¹³C NMR assignments of three nitrogen containing compounds from the mangrove endophytic fungus (ZZF08)