A phytotoxic bicyclic lactone and other compounds from endophyte <i>Xylaria curta</i>

Tchoukoua, Abdou; Ota, Takuma; Akanuma, Rima; Ju, Yu‐Ming; Supratman, Unang; Murayama, Tetsuya; Koseki, Takuya; Shiono, Yoshihito

doi:10.1080/14786419.2016.1277352

Cited by 14 publications

(13 citation statements)

References 17 publications

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“…(3aS,6aR)-4,5-Dimethyl-3,3a,6,6a-tetrhydro-2H-cyclopenta [b]furan-2-one (125) and myrotheciumone A (126) were isolated from fermentation broth of endophytic fungus Xylaria curta 92092022. Both compounds inhibited hypocotyl and root growth of lettuce seedlings [109].…”

Section: Simple Furan and Furanone Analoguesmentioning

confidence: 95%

Phytotoxic Secondary Metabolites from Fungi

Xue

Shen

et al. 2021

Toxins

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Fungal phytotoxic secondary metabolites are poisonous substances to plants produced by fungi through naturally occurring biochemical reactions. These metabolites exhibit a high level of diversity in their properties, such as structures, phytotoxic activities, and modes of toxicity. They are mainly isolated from phytopathogenic fungal species in the genera of Alternaria, Botrytis, Colletotrichum, Fusarium, Helminthosporium, and Phoma. Phytotoxins are either host specific or non-host specific phytotoxins. Up to now, at least 545 fungal phytotoxic secondary metabolites, including 207 polyketides, 46 phenols and phenolic acids, 135 terpenoids, 146 nitrogen-containing metabolites, and 11 others, have been reported. Among them, aromatic polyketides and sesquiterpenoids are the main phytotoxic compounds. This review summarizes their chemical structures, sources, and phytotoxic activities. We also discuss their phytotoxic mechanisms and structure–activity relationships to lay the foundation for the future development and application of these promising metabolites as herbicides.

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Section: Simple Furan and Furanone Analoguesmentioning

confidence: 95%

Phytotoxic Secondary Metabolites from Fungi

Xue

Shen

et al. 2021

Toxins

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“…The AcOEt extract from the culture filtrate, without cells, of Colletotrichum dematium showed phytotoxic action against Parthenium hysterophorus L. (22) . And the substances (3aS, 6aR) -4,5-dimethyl-3,3a,6,6a-tetrahydro-2Hcyclopenta[b] furan-2-one and myrothe-ciumone A, isolated from the ethyl acetate extract of Xylaria curta broth, presented inhibitory effects against Lactuca sativa, both of growth and germination, in concentrations below 200 μg/mL, these substances being considered phytotoxic (23) .…”

Section: Discussionmentioning

confidence: 99%

Evaluation of the phytotoxic effect of extracts from endophytic fungi Colletotrichum dianesei and Xylaria sp. isolated from Palicourea corymbifera (Rubiaceae)

2020

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The allelopathic action can be verified by the presence of phytotoxic substances, molecules that are directed to the agribusiness sector. The objective of this study was to evaluate the chemical composition of the methanolic extracts from Colletotrichum dianesei and Xylaria sp., and phytotoxic potential on Lactuca sativa. The fungi were grown in Sabouraud liquid medium supplemented with 0.2% yeast extract, under stirring. The mycelia were subjected to solvent extraction in order of increasing polarity, but methanol extracts were used in this investigation. The allelopathic activity was evaluated at a concentration of 1000 µg/mL in quadruplicate, evaluating: percentage and speed of germination, and growth of lettuce seedlings under laboratory conditions. C. dianesei extract reduced germination percentage by 36% and delayed germination speed by 63.8%, while Xylaria sp. didn't interfere with the germination percentage, it only delayed the germination rate by 43.9%. Root growth was negatively affected in 30.5% and 51.1% under the influence of extracts from Xylaria sp. and C. dianesei, there was also a reduction of 33.1 and 31.8% in the aerial part length, respectively. The thin layer chromatography showed the presence of aromatic substances and terpenes in both extracts, and alkaloids only in C. dianesei extract. The 1H nmr spectra showed signals between 6 and 8.5 ppm (aromatic substances), being relatively more intense for Xylaria sp., signals between 3 and 4 ppm (sugars, showing anomers only for Xylaria sp.) and methyl groups between 0.7 and 1.3 ppm, suggesting terpenes. The results suggest that the fungal species evaluated have phytotoxic potential, and produce terpenes and aromatic substances.

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“…Compound 246 inhibited root growth by 50% at a concentration of 25 µg/mL. In addition, the highest concentration of 246 (200 µg/mL) strongly exerted an inhibitory effect on seed germination (90% inhibition) [81].…”

Section: Other Activitiesmentioning

confidence: 98%

“…245 is epimeric at C-7 relative to compound 244 [80]. A new phytotoxic bicyclic lactone (3aS,6aR)-4,5-dimethyl-3,3a,6,6a-tetrahydro-2H-cyclopenta [b]furan-2-one 246 (Figure 9), was isolated from the ethyl acetate extract of fermentation broth of Xylaria curta 92092022 [81]. Three new lactones de-O-methyllasiodiplodins, (3R, 7R)-7-hydroxy-de-O-methyllasiodiplodin 247 (Figure 9) and (3R)-5-oxo-deOmethyllasiodiplodin 248 (Figure 9), together with (3R)-7-oxo-de-O-methyllasiodiplodin 249 (Figure 9) were isolated from the co-cultivation of mangrove endophytic fungus Trichoderma sp.…”

Section: Lactonesmentioning

confidence: 99%

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Biological Activities of Some New Secondary Metabolites Isolated from Endophytic Fungi: A Review Study

Zheng

Zhang

et al. 2021

IJMS

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Secondary metabolites isolated from plant endophytic fungi have been getting more and more attention. Some secondary metabolites exhibit high biological activities, hence, they have potential to be used for promising lead compounds in drug discovery. In this review, a total of 134 journal articles (from 2017 to 2019) were reviewed and the chemical structures of 449 new metabolites, including polyketides, terpenoids, steroids and so on, were summarized. Besides, various biological activities and structure-activity relationship of some compounds were aslo described.

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A phytotoxic bicyclic lactone and other compounds from endophyte Xylaria curta

Cited by 14 publications

References 17 publications

Phytotoxic Secondary Metabolites from Fungi

Phytotoxic Secondary Metabolites from Fungi

Evaluation of the phytotoxic effect of extracts from endophytic fungi Colletotrichum dianesei and Xylaria sp. isolated from Palicourea corymbifera (Rubiaceae)

Biological Activities of Some New Secondary Metabolites Isolated from Endophytic Fungi: A Review Study

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