Novel cyclopropyl diketones and 14-membered macrolides from the soil fungus Hamigera avellanea BCC 17816

Isaka, Masahiko; Chinthanom, Panida; Veeranondha, Sukitaya; Supothina, Sumalee; Luangsa‐ard, J. Jennifer

doi:10.1016/j.tet.2008.09.077

Cited by 34 publications

(39 citation statements)

References 17 publications

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“…36 It can be speculated that the bilains function as signaling compounds, as do the related benzylidene-diketopiperazines. 37 Hamavellone C (14), an unusual cyclopropyl diketone, 38 was obtained as an amorphous, colorless solid, for which the molecular formula was determined as C 10 H 16 O 3 by ESI-HRMS, indicating 3 DBEs. The IR spectrum exhibited a broad absorption band centered at 3427 cm −1 and a sharp band at 1697 cm −1 , indicating hydroxy and carbonyl functionalities, respectively.…”

Section: Journal Of Agricultural and Food Chemistrymentioning

confidence: 99%

Macrocyclic Trichothecenes from Myrothecium roridum Strain M10 with Motility Inhibitory and Zoosporicidal Activities against Phytophthora nicotianae

Mondol

Surovy

Islam

et al. 2015

J. Agric. Food Chem.

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The cytotoxicity of the extract obtained from Myrothecium roridum M10 and a characteristic (1)H signal at δH ∼8 led to the assumption that verrucarin/roridin-type compounds were present. Upscaling on rice medium led to the isolation of four new metabolites: verrucarins Y (1) and Z (6) (macrocyclic trichothecenes), bilain D (12) (a diketopiperazine derivative), and hamavellone C (14) (an unusual cyclopropyl diketone). In addition, nine known trichothecenes [verrucarin A (3), 16-hydroxyverrucarin A (5), verrucarin B (7), 16-hydroxyverrucarin B (8), verrucarin J (2), verrucarin X (4), roridin A (9), roridin L-2 (10), and trichoverritone (11)] and a bicyclic lactone [myrotheciumone A (15)] were identified. Their structures and configurations were determined by spectroscopic methods, published data, Mosher's method, and considering biosyntheses. Some trichothecenes showed motility inhibition followed by lysis of the zoospores against devastating Phytophthora nicotianae within 5 min. Compounds 2, 3, 7, and 9 also exhibited potent activities against Candida albicans and Mucor miehei.

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Section: Journal Of Agricultural and Food Chemistrymentioning

confidence: 99%

Macrocyclic Trichothecenes from Myrothecium roridum Strain M10 with Motility Inhibitory and Zoosporicidal Activities against Phytophthora nicotianae

Mondol

Surovy

Islam

et al. 2015

J. Agric. Food Chem.

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“…citrinum OUCMDZ4136 in the SWS medium containing 0.5% NaF. By comparison of NMR and specific rotation data with those reported, their structures were identified as 2,4-dihydroxy-3,5,6-trimethylbenzoic acid ( 1 )1314, citreorosein ( 2 )1516, pinselin ( 3 )17, citrinin ( 4 )181920, dihydrocitrinone ( 5 )2122, pennicitrinone A ( 6 )2324 and quinolactacin A1 ( 7 )25, respectively (Fig. 9).…”

Section: Resultsmentioning

confidence: 94%

Diversity and function of the Antarctic krill microorganisms from Euphausia superba

Cui

Zhu

Liu

et al. 2016

Sci Rep

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The diversity and ecological function of microorganisms associated with Euphausia superba, still remain unknown. This study identified 75 microbial isolates from E. superba, that is 42 fungi and 33 bacteria including eight actinobacteria. And all the isolates showed NaF tolerance in conformity with the nature of the fluoride krill. The maximum concentration was 10%, 3% and 0.5% NaF for actinobacteria, bacteria and fungi, respectively. The results demonstrated that 82.4% bacteria, 81.3% actinobacteria and 12.3% fungi produced antibacterial metabolites against pathogenic bacteria without NaF; the MIC value reached to 3.9 μg/mL. In addition, more than 60% fungi produced cytotoxic metabolites against A549, MCF-7 or K562 cell lines. The presence of NaF led to a reduction in the producing antimicrobial compounds, but stimulated the production of cytotoxic compounds. Furthermore, seven cytotoxic compounds were identified from the metabolites of Penicillium citrinum OUCMDZ4136 under 0.5% NaF, with the IC50 values of 3.6–13.1 μM for MCF-7, 2.2–19.8 μM for A549 and 5.4–15.4 μM for K562, respectively. These results indicated that the krill microbes exert their chemical defense by producing cytotoxic compounds to the mammalians and antibacterial compounds to inhibiting the pathogenic bacteria.

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“…Alcohol 9 would be constructed by addition of the corresponding acetylide of known alkyne 11 [18] to chiral aldehyde 10. We envisioned that the synthesis of 5′ -hydroxyzearalenone (6) would be viable using the same strategy, starting from the enantiomer of 10 (epi-10).…”

Section: Resultsmentioning

confidence: 99%

“…We observed that both compounds inhibited the proliferation of all the cancer cell lines, with IC 50 values of 21.33-53.00 μM for compound 5, and 16.00-179.33 μM for compound 6; this was to a lesser extent than the standard drugs cisplatin and doxorubicin (Table 1). It should be noted that 5′-hydroxyzearalenone (5) showed more potent cytotoxic activity than its epimer, 5′ - hydroxyzearalenone (6), against most of the cancer cell lines. Of the seven cancer cell lines tested, the C33A was the most sensitive cell line to both compounds 5 and 6, with IC 50 values of 21.33 ± 6.43 μM and 16.00 ± 12.17 μM, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…[15] The absolute configuration of the alcohol stereogenic centre at the 5′-position of 5 and 6 was assigned based on Mosher ester analysis. Due to the paucity of natural material and also to the promising biological activities of this class of natural products, we became interested in synthesizing 5′-hydroxyzearalenone (5) and 5′ -hydroxyzearalenone (6) in order to confirm the absolute stereochemistry of the natural products, and also to provide material for further evaluation of their biological activity. In this paper, we describe efficient and convergent syntheses of both natural products, and the evaluation of their cytotoxic activity against seven human cancer cell lines.…”

Section: Introductionmentioning

confidence: 99%

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Total Synthesis and Cytotoxic Activity of 5′‐Hydroxyzearalenone and 5′β‐Hydroxyzearalenone

et al. 2017

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An efficient and convergent synthesis of 5′‐hydroxyzearalenone and 5′β‐hydroxyzearalenone, 14‐membered β‐resorcylic acid lactone (RAL) natural products, has been achieved in a longest linear sequence of 19 steps, and a total of 29 steps, starting from commercially available 5‐hexen‐1‐ol and methyl 2‐(3,5‐dimethoxyphenyl)acetate. The key features of our synthesis include a Jacobsen hydrolytic kinetic resolution, a Mitsunobu esterification and (an E)‐selective ring‐closing metathesis (RCM). Our synthesis also highlights the utility of the acetal protecting group for the resorcylate moiety, and its compatibility with RCM reactions for the synthesis of 14‐membered RALs. The cytotoxic activity of both synthetic compounds was evaluated against seven human cancer cell lines. 5′‐Hydroxyzearalenone shows more potent cytotoxic activity against most of the cancer cell lines tested than its epimer, 5′β‐hydroxyzearalenone. Both compounds show significant cytotoxic activity against the C33A cervical cancer cell line, with IC50 values of 21.33 ± 6.43 µm and 16.00 ± 12.17 µm, respectively.

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Novel cyclopropyl diketones and 14-membered macrolides from the soil fungus Hamigera avellanea BCC 17816

Cited by 34 publications

References 17 publications

Macrocyclic Trichothecenes from Myrothecium roridum Strain M10 with Motility Inhibitory and Zoosporicidal Activities against Phytophthora nicotianae

Macrocyclic Trichothecenes from Myrothecium roridum Strain M10 with Motility Inhibitory and Zoosporicidal Activities against Phytophthora nicotianae

Diversity and function of the Antarctic krill microorganisms from Euphausia superba

Total Synthesis and Cytotoxic Activity of 5′‐Hydroxyzearalenone and 5′β‐Hydroxyzearalenone

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