Roridin A and verrucarin A, inhibitors of pollen development in Arabidopsis thaliana, produced by Cylindrocarpon sp.

Shimada, Atsumi; Takeuchi, Sumiyo; Kusano, Miyako; Fujioka, Shozo; Kimura, Yasuo

doi:10.1016/j.plantsci.2004.01.009

Cited by 13 publications

(10 citation statements)

References 16 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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“…Large‐scale fermentation and bioassay‐guided fractionation of the crude extract led to the isolation of two new ( 1 , 2 ) and six known macrocyclic trichothecenes ( 3–8 ). The structures of 3–8 were identified as 8 α ‐acetoxy roridin H ( 3 ), isororidin K ( 4 ), verrucarin A ( 5 ), verrucarin J ( 6 ), verrucarin L ( 7 ), and 8 α ‐acetoxy verrucarin L ( 8 ) by comparing their 1 H and 13 C NMR data with those in the literature. The structures of 1 and 2 were established by comprehensive spectroscopic analyses.…”

Section: Introductionmentioning

confidence: 99%

Structure determination of two new trichothecenes from a halotolerant fungus Myrothecium sp. GS‐17 by NMR spectroscopy

Zhang

Guan

et al. 2012

Magnetic Reson in Chemistry

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Two new trichothecenes, named 8α-hydroxyroridin H and myrothecin A, along with six known compounds, 8α-acetoxy roridin H, isororidin K, verrucarin A, verrucarin J, verrucarin L and 8α-acetoxy verrucarin L, were isolated from the fermentation broth of a halotolerant fungus Myrothecium sp. GS-17, which was separated from the soil sample of a salina. Structure elucidation and NMR signal assignments were achieved on the basis of spectroscopy. In addition, compounds 1 and 2 were active against plant pathogenic fungi Rhizoctonia solani and Fusarium oxysporum.

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“…1). Compounds 6-8 and 13-19 were identified as dehydrobotrydienol (6) [12], 12-hydroxydehydrobotrydienol (7) [12], hypocriol F (8) [13], 2,8-dihydroxy-3-methyl-9-oxoxanthene-1-carboxylic acid methyl ester (13) [14], preussochromone A (14) [15], preussochromone E (15) [15], roridin A (16) [16], roridin D (17) [17], roridin E (18) [18], and trichodermadienediol B (19) [19], respectively, by comparing their NMR, MS, and optical rotation data with literature values. The structure of 10 was identified as roseotoxin Z [20] by X-ray crystallographic analysis.…”

Section: Resultsmentioning

confidence: 99%

“…Trichothecenes (16)(17)(18)(19) have been recorded as important food mycotoxins that can cause serious harm to skin and mucosa [36]. Considering the high content of trichothecenes produced by this fungus, T. oligosporum should be seen as a potential mycotoxigenic fungus in food or feed.…”

Section: Resultsmentioning

confidence: 99%

“…During our ongoing search for cytotoxic secondary metabolites from fungi [10], the EtOAc extract prepared from the solidsubstrate fermentation of Trichoderma oligosporum Z. X. Zhu & W. Y. Zhuang (Hypocreaceae) [11] was found to exhibit significant cytotoxicity against K562 cells (IC 50 150 µg/mL). Chemical investigation on the EtOAc extract of T. oligosporum led to the isolation of 19 secondary metabolites including botryanes (1)(2)(3)(4)(5)(6)(7)(8), cyclopetadepsipeptides (9-10), xanthones (11)(12)(13)(14)(15), and trichothecenes (16)(17)(18)(19). The isolation, structure elucidation, and cytotoxic activity of these metabolites are reported herein.…”

Section: Introductionmentioning

confidence: 96%

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Botryane Sesquiterpenoids, Cyclopentadepsipeptides, Xanthones, and Trichothecenes from Trichoderma oligosporum

Chen

Liu

et al. 2018

Planta Med

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Five new botryane sesquiterpenes (1: -5: ), one new cyclopentadepsipeptide (9: ), and two new xanthones (11: - 12: ), together with 11 known compounds, were isolated from . The structures of the new compounds were identified by comprehensive spectroscopic methods including nuclear magnetic resonance and mass spectrometry. The cytotoxicity of 1: -19: was evaluated against K562, A549, and ASPC cell lines. Compounds 5, 8, 11, 17: , and 18: showed cytotoxicity against the K562 cell line with more than 50% inhibition at 12.5 µM. As to A549 cell line, compound 8: showed the strongest cytotoxicity with approximately 50% inhibition at 25.0 µM. No compounds showed cytotoxicity against the ASPC cell line.

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Roridin A and verrucarin A, inhibitors of pollen development in Arabidopsis thaliana, produced by Cylindrocarpon sp.

Cited by 13 publications

References 16 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

Structure determination of two new trichothecenes from a halotolerant fungus Myrothecium sp. GS‐17 by NMR spectroscopy

Botryane Sesquiterpenoids, Cyclopentadepsipeptides, Xanthones, and Trichothecenes from Trichoderma oligosporum

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