Purification, identification and activity of phomodione, a furandione from an endophytic Phoma species

Hoffman, Angela; Mayer, Steven G.; Strobel, Gary A.; Hess, W. M.; Sovocool, G. Wayne; Grange, Andrew H.; Harper, James K.; Arif, Atta M.; Grant, David M.; Kelley-Swift, Elizabeth G.

doi:10.1016/j.phytochem.2007.10.031

Cited by 74 publications

(44 citation statements)

References 27 publications

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“…More than 200 species of endophytic fungi have been isolated and identified from mangrove plants and several reports on the isolation of antibiotic compounds from endophytic fungi have been reported. To mention a few griseofulvin, [7], chaetomugilin A and D [8], cytosporone B and C [9], 3-O-methylalaternin and altersolanol A [10], phomoenamide [11], phomodione [12], ambuic acid [13], isopestacin [14], munumbicin A, B, C, and D [15], pestalachlorides A and B, [16], brefeldin A [17], coronamycin, [18], pumilacidin [19], cytochalasin D [20], polyketide citrinin [21,22], fumigaclavine C, fumitremorgin C, physcion [23], and several others.…”

Section: Introductionmentioning

confidence: 99%

Isolation and Characterization of Antibacterial Compound from a Mangrove-Endophytic Fungus, Penicillium chrysogenum MTCC 5108

et al. 2012

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Microorganisms, especially endophytic fungi that reside in the tissue of living mangrove plants, seem to play a major role in meeting the general demand for new biologically active substances. During the course of screening for biologically active secondary metabolites from marine microorganisms, an antibiotic compound containing an indole and a diketopiperazine moiety was isolated from the culture medium of Penicillium chrysogenum, (MTCC 5108), an endophytic fungus on the mangrove plant Porteresia coarctata (Roxb.). The cell free culture medium of P. chrysogenum showed significant activity against Vibrio cholerae, (MCM B-322), a pathogen causing cholera in humans. Bioassay guided chemical characterization of the crude extract led to the isolation of a secondary metabolite possessing a molecular formula C 19 H 21 O 2 N 3 . Its antibacterial activity was comparable with standard antibiotic, streptomycin. This compound (1) was found to be (3,1 0 -didehydro-3[2 00 (3 000 ,3 000 -dimethyl-prop-2-enyl)-3 00 -indolylmethylene]-6-methyl pipera-zine-2,5-dione) on the basis of mass spectrometry, infrared spectroscopy and one and two-dimensional nuclear magnetic resonance analysis.

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Section: Introductionmentioning

confidence: 99%

Isolation and Characterization of Antibacterial Compound from a Mangrove-Endophytic Fungus, Penicillium chrysogenum MTCC 5108

et al. 2012

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“…NRRL 46751 has led to the identification of a new furandione in addition to several known fungal metabolites. 7 …”

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Phomapyrrolidones A–C, Antitubercular Alkaloids from the Endophytic Fungus Phoma sp. NRRL 46751

Wijeratne

Franzblau

et al. 2013

J. Nat. Prod.

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Three new alkaloids, phomapyrrolidones A–C (1–3), bearing a cyclopenta[b]fluorene ring system were isolated from the mycelium extract of the endophytic fungal strain, Phoma sp. NRRL 46751, inhabiting Saurauia scaberrinae. Methylation of 1 afforded its N-methyl derivative 4. The planar structures and relative configurations of 1–4 were elucidated by extensive spectroscopic analysis. Phomapyrrolidones B (2) and C (3) exhibited weak antitubercular activity at subcytotoxic concentrations.

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“…Fungal endophytes have been recognized as prolific producer of many chemical compounds having antibacterial, antifungal other biological potential [8,9]. Many endophytic fungi have been exploited for their active potential.…”

Section: Resultsmentioning

confidence: 99%

Isolation and Identification of Antibacterial Compounds Isolated from Endophytic Fungus Emericella qaudrilineata

Goutam¹

2016

Nat Prod Chem Res

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Present work is directed toward the isolation and identification of biological active (antimicrobial) compound from metabolite extracted from endophytic fungus Emericella qaudrilineata(RS-5) (Accession number KC662361). Crude extracted from endophytic fungus Emericella qaudrilineata possessing antibacterial activity was subjected to bioassay guided fractionation in which toluene fraction exhibited maximum antibacterial activity against Staphylococcus aureus (gram positive) and Aeromonas hydrophilla (gram negative) respectively. Sequentially compounds fractionated from ethyl acetate and hexane also shown feeble antibacterial activity. This reveals that toluene fraction contain active principle of antimicrobial interest. In continuation to above experiment, major active fractions were analyzed with the help of gas chromatography mass spectroscopy (GCMS). GCMS analysis of toluene fraction showed benzyl benzoate (27.3%), benzaldehyde dimethyl acetal (15.04%) and benzoic acid (17%), as the dominant compound present in fraction of toluene. In context to above details separation of compound was performed by silica gel column chromatography. Separated band showed its presence at 0.6 RF value in silica gel (TLC) plates. Separated compound also exhibited remarkable antibacterial activity. The optimized flow rate of column was 20 ml/min in ratio of hexane 20:80 toulene mobile phase. Prediction of C 13 NMR, H 1 NMR and FTIR data supported the dominating compound of GCMS profile of toulene fraction, and identified it as Benzyl benzoate. Medically benzyl benzoate is an active ingredient of Ascabiol that is generally used to treat scabies various skin diseases.

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Purification, identification and activity of phomodione, a furandione from an endophytic Phoma species

Cited by 74 publications

References 27 publications

Isolation and Characterization of Antibacterial Compound from a Mangrove-Endophytic Fungus, Penicillium chrysogenum MTCC 5108

Isolation and Characterization of Antibacterial Compound from a Mangrove-Endophytic Fungus, Penicillium chrysogenum MTCC 5108

Phomapyrrolidones A–C, Antitubercular Alkaloids from the Endophytic Fungus Phoma sp. NRRL 46751

Isolation and Identification of Antibacterial Compounds Isolated from Endophytic Fungus Emericella qaudrilineata

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