Antimycobacterial dihydronaphthalenone from the endophytic fungus Nodulisporium sp. of Antidesma ghaesembilla

Prabpai, Samran; Wiyakrutta, Suthep; Sriubolmas, Nongluksna; Kongsaeree, Palangpon

doi:10.1016/j.phytol.2015.08.001

Cited by 25 publications

(19 citation statements)

References 20 publications

(20 reference statements)

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“…(3R)-5-methylmellein (4), (3R)-5-formylmellein (11) and (3R)-5-carboxymellein (12), were also synthesized, together with two undescribed dihydronaphthalenones and the known 2,6-dihydroxy-4methylacetophenone, by the endophytic fungus Nodulisporium sp., isolated from Antidesma ghaesembilla. No biological activities were reported for the mellein derivatives 4, 11 and 12 [66].…”

Section: Melleins From Fungimentioning

confidence: 99%

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Melleins—Intriguing Natural Compounds

Reveglia

Masi²,

Evidente³

2020

Biomolecules

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Melleins are 3,4-dihydroisocoumarins mainly produced by fungi, but also by plants, insects and bacteria. These specialized metabolites play important roles in the life cycles of the producers and they are involved in many biochemical and ecological processes. This review outlines the isolation and chemical and biological characterizations of natural-occurring melleins from the first report of (R)-mellein in 1933 to the most recent advances in their characterization in 2019. In addition, the pathways that could be involved in mellein biosynthesis are discussed, along with the enzymes and genes involved.

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Section: Melleins From Fungimentioning

confidence: 99%

“…fungal secondary metabolism [26] Nodulisporium sp. [66] Phomopsis oblonga larvicidal [27] Valsa ceratosperma phytotoxic [28] Xylariaceae CBS 120381 [43] Xylaria sp. PSU-G12 [60] Xylaria sp.…”

Section: Mellein Natural Source Biological Activity Referencesmentioning

confidence: 99%

Melleins—Intriguing Natural Compounds

Reveglia

Masi²,

Evidente³

2020

Biomolecules

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“…The glycosylated form of the ergosterol peroxide was annotated as 5α,8α-epidioxy-24(R)-methylcholesta-6,22-dien-3β-D-glucopyranoside [31]. The bioactive polyketide dihydroxymethylacetophenone was annotated to another singleton which was shared by both Cladosporium and Emericellopsis strains [33,60]. The low activity against the microbial pathogens may stem from the low concentration of the putative bioactive compounds in the crude extract.…”

Section: Discussionmentioning

confidence: 99%

“…We putatively annotated the steroid ergosterol peroxide [31], perylenequinone cladochrome D [32], polyketide dihydroxy methylacetophenone [33], meroterpenoid preaustinoid D [34], triterpenoid lucidenic acid D [35] and cyclic peptide icosalide [26] classes of compounds. In total, 88 parent ions were observed in the MN.…”

Section: Metabolomicsmentioning

confidence: 99%

Mining the Metabolome and the Agricultural and Pharmaceutical Potential of Sea Foam-Derived Fungi

et al. 2020

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Sea foam harbors a diverse range of fungal spores with biological and ecological relevance in marine environments. Fungi are known as the producers of secondary metabolites that are used in health and agricultural sectors, however the potentials of sea foam-derived fungi have remained unexplored. In this study, organic extracts of six foam-derived fungal isolates belonging to the genera Penicillium, Cladosporium, Emericellopsis and Plectosphaerella were investigated for their antimicrobial activity against plant and human pathogens and anticancer activity. In parallel, an untargeted metabolomics study using UPLC-QToF–MS/MS-based molecular networking (MN) was performed to unlock their chemical inventory. Penicillium strains were identified as the most prolific producers of compounds with an average of 165 parent ions per strain. In total, 49 known mycotoxins and functional metabolites were annotated to specific and ubiquitous parent ions, revealing considerable chemical diversity. This allowed the identification of putative new derivatives, such as a new analog of the antimicrobial tetrapeptide, fungisporin. Regarding bioactivity, the Penicillium sp. isolate 31.68F1B showed a strong and broad-spectrum activity against seven plant and human pathogens, with the phytopathogen Magnaporthe oryzae and the human pathogen Candida albicans being the most susceptible (IC50 values 2.2 and 6.3 µg/mL, respectively). This is the first study mining the metabolome of the sea foam-derived fungi by MS/MS-based molecular networking, and assessing their biological activities against phytopathogens.

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“…A large number of the new compounds from marine-derived fungi are discovered every year. Among these, naphthalenone derivatives are side products of the 1,8-dihydroxynaphthalene polyketide pathway [ 2 ], which are common in the secondary metabolites from fungi with diverse bioactivities, such as antimicrobial [ 3 ], antiviral [ 4 ], cytotoxic [ 5 ], and antimalarial activities [ 3 ]. Besides, naphthalenone derivatives have structural diversity not only in the planar structure but also in the absolute configuration.…”

Section: Introductionmentioning

confidence: 99%

Mono- and Dimeric Naphthalenones from the Marine-Derived Fungus Leptosphaerulina chartarum 3608

et al. 2018

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Five new naphthalenones, two enantiomers (−)-1 and (+)-1 leptothalenone A, (−)-4,8-dihydroxy-7-(2-hydroxy-ethyl)-6-methoxy-3,4-dihydro-2H-naphthalen-1-one ((−)-2), (4S, 10R, 4’S)-leptotha-lenone B (5), (4R, 10S, 4’S)-leptothalenone B (6), and a new isocoumarine, 6-hydroxy-5,8-dimethoxy-3-methyl-1H-isochromen-1-one (4), along with two known compounds (+)-4,8-dihydroxy-7-(2-hydroxy-ethyl)-6-methoxy-3,4-dihydro-2H-naphthalen-1-one ((+)-2) and (+)-10-norparvulenone (3) were isolated from the marine-derived fungus Leptosphaerulina chartarum 3608. The structures of new compounds were elucidated by HR-ESIMS, NMR, and ECD analysis. All compounds were evaluated for cytotoxicity and anti-inflammatory activity. Compound 6 showed moderate anti-inflammatory activity by inhibiting the production of nitric oxide (NO) in lipopolysaccharide-stimulated RAW264.7 cells, with an IC50 value of 44.5 μM.

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Antimycobacterial dihydronaphthalenone from the endophytic fungus Nodulisporium sp. of Antidesma ghaesembilla

Cited by 25 publications

References 20 publications

Melleins—Intriguing Natural Compounds

Melleins—Intriguing Natural Compounds

Mining the Metabolome and the Agricultural and Pharmaceutical Potential of Sea Foam-Derived Fungi

Mono- and Dimeric Naphthalenones from the Marine-Derived Fungus Leptosphaerulina chartarum 3608

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