Altereporenes A–E, five epoxy octa-hydronaphthalene polyketides produced by an endophytic fungus<i>Alternaria</i>sp. YUD20002

Xia, Dan-Dan; Duan, Hao-Jie; Xie, Fei; Xie, Tian-Peng; Zhang, Yan; Sun, Yanfang; Lu, Jian-Mei; Gao, Yu‐Hong; Zhou, Hao; Ding, Zhong‐Tao

doi:10.1039/d2ra03917f

Cited by 2 publications

(3 citation statements)

References 29 publications

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“…During the study of fungal secondary metabolites, we have isolated many natural products with different structures and biological activities [12–15] . Recently, a fungus Penicillium sp.…”

Section: Introductionmentioning

confidence: 99%

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Two Decarestrictine Analogs from the Soil‐Derived Fungus Penicillium sp. YUD18003 Associated with Gastrodia elata

Xie,

Xia,

Duan

et al. 2023

Chemistry & Biodiversity

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Two new decarestrictine analogs decarestrictine P and penicitone, together with eight known homologous compounds were isolated from the soil fungus from the rhizosphere of Penicillium sp. YUD18003 related to Gastrodia elata. Their different structures include a decanolides decartestridine P and a long‐chain polyhydroxyketone penicitone. The structures of new compounds were determined by nuclear magnetic resonance (NMR) spectroscopic analysis and high resolution electrospray ionization mass spectrometry (HR‐ESI‐MS), while their absolute configurations were determined by spectroscopic methods, DP4+ probability analysis, modified Snatzke's method and electron circular dichroism (ECD) calculations. All compounds were evaluated for antimicrobial activities.

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“…During the study of fungal secondary metabolites, we have isolated many natural products with different structures and biological activities [12–15] . Recently, a fungus Penicillium sp.…”

Section: Introductionmentioning

confidence: 99%

“…[11] During the study of fungal secondary metabolites, we have isolated many natural products with different structures and biological activities. [12][13][14][15] Recently, a fungus Penicillium sp. YUD18003 was isolated from rhizospheric soil associated with Gastrodia elata.…”

Section: Introductionmentioning

confidence: 99%

Two Decarestrictine Analogs from the Soil‐Derived Fungus Penicillium sp. YUD18003 Associated with Gastrodia elata

Xie,

Xia,

Duan

et al. 2023

Chemistry & Biodiversity

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“…For example, chemical investigation of Alternaria sp. YUD20002, an endophytic fungus derived from the tubers of Solanum tuberosum , yielded five previously undescribed epoxy octa-hydronaphthalene polyketides altereporenes A-E ( Xia et al, 2022 ). Acrocalysterols A and B, two new steroids were isolated from an endophytic fungus Acrocalymma sp.…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic secondary metabolites isolated from Penicillium sp. YT2019-3321, an endophytic fungus derived from Lonicera Japonica

et al. 2022

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IntroductionEndophytic fungi associated with medicinal plants have proven to possess a high potential to produce structurally diverse metabolites, some of which are valuable for medicinal applications. In this study, Penicillium sp. YT2019-3321, an endophytic fungus derived from traditional Chinese medicine Lonicera japonica, was chemically studied.MethodsThe chemical structures of the isolated compounds were established by a correlative interpretation of HRESIMS and NMR spectroscopic data. The optical resolution of (±)-1 by chiral HPLC yielded individual enantiomers (+)-1 and (–)-1, and their stereochemistry were solved by X-ray diffraction crystallography, respectively.Results and discussionEight structurally diversified secondary metabolites, including two previously unreported polyketides, named (±)-chrysoalide B (1) and penicidone E (2), were isolated and identified from Penicillium sp. YT2019-3321. Compound 2 possessed the γ-pyridone nucleus, which is rarely found in natural products. Cytotoxic assay revealed that the new compound 2 demonstrated a dose-dependent cytotoxicity against the human pancreatic tumor cells PATU8988T with the IC50 value of 11.4 μM. Further studies indicated that 2 significantly induced apoptosis of PATU8988T cell lines, characterized by the morphologies abnormity, the reduction of cell number, the upregulation of proportion of apoptotic cells, and the ratio of Bcl-2 to Bax. Our study demonstrates that fungal secondary metabolites may have important significance in the discovery of drug leads.

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Altereporenes A–E, five epoxy octa-hydronaphthalene polyketides produced by an endophytic fungusAlternariasp. YUD20002

Abstract: Five previously undescribed epoxy octa-hydronaphthalene polyketides, altereporenes A–E (1–5) were isolated from rice culture of the endophytic fungus Alternaria sp. YUD20002 derived from the tubers of Solanum tuberosum.

Cited by 2 publications

References 29 publications

Two Decarestrictine Analogs from the Soil‐Derived Fungus Penicillium sp. YUD18003 Associated with Gastrodia elata

Two Decarestrictine Analogs from the Soil‐Derived Fungus Penicillium sp. YUD18003 Associated with Gastrodia elata

Cytotoxic secondary metabolites isolated from Penicillium sp. YT2019-3321, an endophytic fungus derived from Lonicera Japonica

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