Azaphilones isolated from an alga-derived fungus Penicillium sp. ZJ-27

Zhang, Liuhong; Yi, Long; Lei, Xiaofei; Xu, Jun; Huang, Zhijian; She, Zhigang; Lin, Yongcheng; Li, Jing; Liu, Lan

doi:10.1016/j.phytol.2016.10.010

Cited by 15 publications

(8 citation statements)

References 20 publications

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“…Five molecules, i.e., geumsanol A-C and G ( 14–17) and eupeniazaphilone C ( 18 ), were therefore annotated in cluster C, where hypocrellone ( 7 ) was first dereplicated [ 25 , 26 , 27 ]. Two molecules, i.e., isochromophilone IX ( 6 ) or penazaphilone F ( 19 ) and penazaphilone D ( 20 ), were also annotated in cluster B, including compounds 2 and 5 [ 28 , 29 ]. Isochromophilone IV ( 21 ) and sclerketide B isomer ( 22 ) completed the annotation of cluster A, including sclerotiorin ( 1 ) [ 30 , 31 ].…”

Section: Resultsmentioning

confidence: 99%

“…The 3,5-dimethyl-1,3-heptadienyl unit, the azaphilone scaffold and their connection were identified as described for 63 . The lactone ring was established with the HMBC correlation of H-5″ with C-4″, C-3″ and C-2″ and by comparison with its analog described in the literature [ 28 , 32 ] ( Figures S103–S108, S117, Tables S1 and S2 ). Compound 74 was named peniazaphilone E.…”

Section: Resultsmentioning

confidence: 99%

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Dereplication, Annotation, and Characterization of 74 Potential Antimicrobial Metabolites from Penicillium Sclerotiorum Using t-SNE Molecular Networks

et al. 2021

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Microorganisms associated with termites are an original resource for identifying new chemical scaffolds or active metabolites. A molecular network was generated from a collection of strain extracts analyzed by liquid chromatography coupled to tandem high-resolution mass spectrometry, a molecular network was generated, and activities against the human pathogens methicillin-resistant Staphylococcus aureus, Candida albicans and Trichophyton rubrum were mapped, leading to the selection of a single active extract of Penicillium sclerotiorum SNB-CN111. This fungal species is known to produce azaphilones, a colorful family of polyketides with a wide range of biological activities and economic interests in the food industry. By exploring the molecular network data, it was shown that the chemical diversity related to the P. sclerotiorum metabolome largely exceeded the data already reported in the literature. According to the described fragmentation pathways of protonated azaphilones, the annotation of 74 azaphilones was proposed, including 49 never isolated or synthesized thus far. Our hypothesis was validated by the isolation and characterization of eight azaphilones, among which three new azaphilones were chlorogeumasnol (63), peniazaphilone E (74) and 7-deacetylisochromophilone VI (80).

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Dereplication, Annotation, and Characterization of 74 Potential Antimicrobial Metabolites from Penicillium Sclerotiorum Using t-SNE Molecular Networks

et al. 2021

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“…The extracts were subjected to stepwise chromatographic procedures, which afforded isolation of 14 compounds ( 1 – 14 ). Compounds 7 and 11 – 14 were determined to be dechloroisochromophilone III ( 7 ), isochromophilone V ( 11 ), penazaphilone E ( 12 ), isochromophilone VI ( 13 ), , and peniazaphilone D ( 14 ), respectively, comparing their spectroscopic data with those provided in the references, while 1 – 6 and 8 – 10 were determined to be new azaphilones.…”

Section: Results and Discussionmentioning

confidence: 98%

“…The known compounds ( 7 , 11 – 14 ) were identified by analysis of 1D and 2D NMR spectra along with comparison of MS, UV, and optical rotation data to the literature. − …”

Section: Results and Discussionmentioning

confidence: 99%

Azaphilones from an Endophytic Penicillium sp. Prevent Neuronal Cell Death via Inhibition of MAPKs and Reduction of Bax/Bcl-2 Ratio

et al. 2021

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Fourteen azaphilone-type polyketides (1–14), including nine new ones (1–6 and 8–10), were isolated from cultures of Vitex rotundifolia-associated Penicillium sp. JVF17, and their structures were determined by spectroscopic analysis together with computational methods and chemical reactions. Neuroprotective effects of the isolated compounds were evaluated against glutamate-induced neurotoxicity. Treatment with compounds 3, 6, 7, and 11–14 increased cell viabilities of hippocampal neuronal cells damaged by glutamate, with compound 12 being the most potent. Compound 12 markedly decreased intracellular Ca2+ and nuclear condensation levels. Mechanistically, molecular markers of apoptosis induced by treatment with glutamate, i.e., phosphorylation of MAPKs and elevated Bax/Bcl-2 expression ratio, were significantly lowered by compound 12. The azaphilones with an isoquinoline core structure were more active than those with pyranoquinones, but N-substitution decreased the activity. This study, including the structure–activity relationship, indicates that the azaphilone scaffold is a promising lead toward the development of novel neuroprotective agents.

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“…65 Varioloid A (75), a new indolyl-6,10b-dihydro-5aH- [1]benzofuro [2,3-b]indole derivative, and another similar compound varioloid B (76), was characterized from the endophytic fungus Paecilomyces variotii EN-291 derived from an unidentified marine alga. 66 (Table 4, Figure 3)…”

Section: Quinolines and Quinazoline Derivativesmentioning

confidence: 99%

Cytotoxic Compounds Derived from Marine Algicolous and Spongicolous Endophytic Fungi: A Review

Ahmed

Noor

Rahman

et al. 2021

Dhaka Univ. J. Pharm. Sci

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Endophytes have gained particular interest in the search of potential pharmaceutical candidates for a long time due to their diversity, species richness and bioprospecting nature. They generally produce the essential metabolites for their expansion inside the plant which is involved in various biotransformation processes of utilizing host nutrients and cell components to continue microbial growth, sustenance, and reproduction. In above processes, they produce a huge amount of both structurally and functionally diverse secondary metabolites for maintaining an effective symbiosis with hosts. These compounds are proven to have significant bioactive properties like antibacterial, antifungal, antiviral, anti-inflammatory, antioxidants, antitumor activities. Despite the proven significance, a little is exploited so far about endophytes. Particularly marine fungal endophytes which are the centre of attention in this review have gained much less importance. Due to unique environmental feature, fungal endophytes derived from marine environment offer vast diversity in different bioactive secondary metabolites. This review has focused on algicolous endophytes and bioactive secondary metabolites discovered during the last two decades. Particular importance has been given to cytotoxic and antimicrobial metabolites. Due to intensive studies during last several years, an extensive number of publications are now available on cytotoxic compounds derived from endophytic fungi of marine algicolous and spongicolous origin that have been summarized in this review. Dhaka Univ. J. Pharm. Sci. 20(2): 247-265, 2021 (December)

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Azaphilones isolated from an alga-derived fungus Penicillium sp. ZJ-27

Cited by 15 publications

References 20 publications

Dereplication, Annotation, and Characterization of 74 Potential Antimicrobial Metabolites from Penicillium Sclerotiorum Using t-SNE Molecular Networks

Dereplication, Annotation, and Characterization of 74 Potential Antimicrobial Metabolites from Penicillium Sclerotiorum Using t-SNE Molecular Networks

Azaphilones from an Endophytic Penicillium sp. Prevent Neuronal Cell Death via Inhibition of MAPKs and Reduction of Bax/Bcl-2 Ratio

Cytotoxic Compounds Derived from Marine Algicolous and Spongicolous Endophytic Fungi: A Review

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