Antimicrobial secondary metabolites from an endophytic fungus Aspergillus polyporicola

Liu, Sisi; Huang, Rong; Zhang, Shou-Peng; Xu, Tang-Chang; Hu, Kun; Wu, Shaohua

doi:10.1016/j.fitote.2022.105297

Cited by 7 publications

(8 citation statements)

References 30 publications

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“…product, still shows a good inhibitory effect on B. cinerea, which is stronger than several recently reported natural products, such as 2H-pyran-2-one, 5,6-dihydro-6-pentyl from Macrophomina phaseolina (OSHL-2.1) with an IC 50 of 17.86 mM19 and 11α-hydroxycurvularin from Aspergillus polyporicola R2 with a minimal inhibitory concentration (MIC) of 1.66 mM 20. In…”

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confidence: 75%

Discovery of a Natural Hybrid Polyketide Produced by Endophytic Cladosporium sphaerospermum for Biocontrol of Phytopathogenic Fungus Botrytis cinerea

Pan

Yang

Zhu

et al. 2023

J. Agric. Food Chem.

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The endophytic fungus Cladosporium sphaerospermum WBS017 exhibits broad-spectrum activity against plant pathogens, with particular effectiveness against Botrytis cinerea. Subsequently, a compound is isolated from strain WBS017 as the main active ingredient against B. cinerea using activity-guided separation and identified as hybrid polyketide (namely cladodionen, CLD) using UV, MS, NMR, etc. In vitro and in vivo antifungal activity tests demonstrate that CLD effectively inhibits the mycelial growth and spore germination, with an IC 50 value of 1.13 and 0.095 mM, respectively, and exerts antifungal and fresh-keeping effects on both strawberry and tomato. Microscopy analysis reveals that the inhibitory effects of CLD on hyphae and spore germination are attributed to a decrease in structural stability of mycelia cells as well as the accumulation of reactive oxygen species (ROS). Furthermore, transcriptome analysis further indicates that spore germination is inhibited by suppressing the transcription levels of membrane or membrane-related genes, disturbing the balance of ROS metabolism, altering the primary metabolic pathways, genetic information processing, and cellular processes. Importantly, CLD demonstrates no significant toxicity on zebrafish embryos even at a concentration of 0.226 mM, indicating its potential as a safe biological-control agent. In summary, CLD would be a novel potential biological-control agent and can be considered as a promising fungicide to control B. cinerea.

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confidence: 75%

Discovery of a Natural Hybrid Polyketide Produced by Endophytic Cladosporium sphaerospermum for Biocontrol of Phytopathogenic Fungus Botrytis cinerea

Pan

Yang

Zhu

et al. 2023

J. Agric. Food Chem.

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“…For this discussion, we applied the numbering used for 1 – 4 throughout this report to 5 – 9 as well as other structural analogs described below for convenience. The physical data involving specific rotation ([α] 20 D −153.9 ( c 0.28, CHCl 3 ), lit: [α] 20 D −106.0 ( c 0.15, MeOH)) and the ECD spectral profile (Figure S46) of 5 agreed well with those reported in the literature . Its absolute configuration has been established by ECD spectral analysis, and our independent calculations lead to the same conclusion.…”

Section: Resultsmentioning

confidence: 95%

“…Paraphaeosphaeria sp. KT4192 also produces several known compounds, including arthropsadiol D ( 5 ), massariphenone ( 6 ) and its positional isomer ( 7 ), massarilactone E ( 8 ), and massarilactone G ( 9 ) . For this discussion, we applied the numbering used for 1 – 4 throughout this report to 5 – 9 as well as other structural analogs described below for convenience.…”

Section: Resultsmentioning

confidence: 99%

“…colorless prisms (EtOAc/hexane); mp 105–106 °C; [α] 20 D −153.9 ( c 0.28, CHCl 3 ) (lit . [α] 20 D −106.0 ( c 0.15, MeOH)); UV (CH 3 CN) λ max (log ε ) 224 (3.81), 195 (3.79) nm; ECD (0.12 mM in CH 3 CN) λ (Δ ε ) 280 (−1.8), 220 (−4.5) nm (Figure S46); IR (film) ν max 3394, 2904, 2843, 1714, 1699, 1238, 1120, 1082, 910, 791 cm –1 ; 1 H NMR (CDCl 3 ) δ 1.01 (3H, d, J = 7.3 Hz, H 3 -1), 2.27 (1H, ddd, J = 1.4, 9.8, 12.3 Hz, H-7), 2.30 (3H, s, H 3 -10), 3.02 (1H, m, H-2), 3.82 (1H, d, J = 4.6 Hz, 8-OH), 3.86 (1H, brs, 6-OH), 4.30 (1H, brd, J = 12.3 Hz, H-6), 4.64 (1H, brd, J = 4.6 Hz, H-8), 6.07 (1H, dd, J = 3.0, 10.1 Hz, H-4), 6.73 (1H, dd, J = 2.2, 10.1 Hz, H-3); 13 C NMR (CDCl 3 ) δ 19.1 (C-1), 25.8 (C-10), 31.4 (C-2), 53.1 (C-7), 72.6 (C-6), 75.5 (C-8), 124.6 (C-4), 157.4 (C-3), 199.6 (C-5), 211.4 (C-9); ESI-TOFMS m / z 419.1684 [2 M + Na] + (calcd for C 20 H 28 O 8 Na + , 419.1676), 221.0798 [M + Na] + (calcd for C 10 H 14 O 4 Na + , 221.0784), 181.0869 [M + H – H 2 O] + (calcd for C 10 H 13 O 3 + , 181.0859), 163.0763 [M + H – 2H 2 O] + (calcd for C 10 H 11 O 2 + , 163.0754).…”

Section: Methodsmentioning

confidence: 99%

“…D −153.9 (c 0.28, CHCl 3 ), lit: [α] 20 D −106.0 (c 0.15, MeOH)) and the ECD spectral profile (Figure S46) of 5 agreed well with those reported in the literature. 8 Its absolute configuration has been established by ECD spectral analysis, and our independent calculations lead to the same conclusion. The 1 H and 13 C NMR data of 6 were also identical with those in the literature.…”

Section: The Physical Data Involving Specific Rotation ([α] 20mentioning

confidence: 99%

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Pseudo-Enantiomeric Paraphaeolactones and Their Biosynthetic Derivatives from Paraphaeosphaeria sp. KT4192: A Proposition of a Favorskii Rearrangement for Their Biosynthesis

Kanehara,

Oinuma,

Maeda

et al. 2023

J. Nat. Prod.

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Paraphaeolactones A1, A2, B1, and B2 (1–4, respectively), known arthropsadiol D (5), massariphenone (6) and its positional isomer 7, and massarilactones E (8) and G (9) were isolated from the culture broth of Paraphaeosphaeria sp. KT4192. Although the structural resemblance between 1 and 2 implies that these comprised a diastereomeric pair at the C-2 stereogenic center, electronic circular dichroism (ECD) spectral analyses revealed that they were pseudo-enantiomers possessing the common (2R)-configuration. Paraphaeolactones B1 and B2 (3 and 4) were the derivatives of 2, which equipped the 3-(1-hydroxy-2-oxopropyl)-4-methylcatechol moiety via an acetal bond at C-10. The relative configurations of their acetal carbons were elucidated by NOE experiments, and those of C-8′ were deduced independently by ECD spectral analysis. The present study disclosed that 1–5, 8, and 9 contain a methylcyclohexene substructure with the same absolute configuration. This prompted us to reinvestigate the absolute configurations of known structurally related fungal metabolites, allowing us to conclude that the methylcyclohexene moieties of these natural products have the same absolute configuration despite the variety of configurations of other stereogenic centers. The plausible biosynthetic routes for 1–9 are discussed on the basis of the above conclusion. We propose a Favorskii rearrangement as the key transformation for biosyntheses of 1–4.

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Aromatic polyketide aspergillones A-D from the endophytic fungus Aspergillus sclerotiorum

Zheng

Zhou

et al. 2023

Phytochemistry Letters

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Antimicrobial secondary metabolites from an endophytic fungus Aspergillus polyporicola

Cited by 7 publications

References 30 publications

Discovery of a Natural Hybrid Polyketide Produced by Endophytic Cladosporium sphaerospermum for Biocontrol of Phytopathogenic Fungus Botrytis cinerea

Discovery of a Natural Hybrid Polyketide Produced by Endophytic Cladosporium sphaerospermum for Biocontrol of Phytopathogenic Fungus Botrytis cinerea

Pseudo-Enantiomeric Paraphaeolactones and Their Biosynthetic Derivatives from Paraphaeosphaeria sp. KT4192: A Proposition of a Favorskii Rearrangement for Their Biosynthesis

Aromatic polyketide aspergillones A-D from the endophytic fungus Aspergillus sclerotiorum

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