Spectasterols, Aromatic Ergosterols with 6/6/6/5/5, 6/6/6/6, and 6/6/6/5 Ring Systems from <i>Aspergillus spectabilis</i>

Wei, Mengsha; Huang, Liping; Li, Qin; Qiao, Xinyi; Zhao, Ziming; Yin, Jie; Fu, Aimin; Guo, Jieru; Hao, Xiao‐Jiang; Gu, Lianghu; Wang, Jianping; Chen, Chunmei; Zhu, Hucheng; Zhang, Yonghui

doi:10.1021/acs.jnatprod.2c01034

Cited by 15 publications

(2 citation statements)

References 26 publications

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“…Mangrove endophytic fungi of the genus Aspergillus can produce structurally unique metabolites with diverse bioactivities [10][11][12][13][14][15][16][17][18][19]. In order to search for bioactive natural compounds with new structures, two new compounds, named rhizoaspergillin A (1) and rhizoaspergillinol A (2), were isolated from the mangrove endophytic fungus Aspergillus sp.…”

Section: Introductionmentioning

confidence: 99%

Aspergilins A–B, Including a Unique Orsellinic Acid–Ribose–Pyridazinone-N-Oxide Hybrid, from the Mangrove Endophytic Fungus Aspergillus sp. A1E3

Wu,

Xu,

Chen

et al. 2023

Preprint

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Two new compounds, named aspergilins A (1) and B (2), were isolated from the mangrove endophytic fungus Aspergillus sp. A1E3 associated with the fruit of Rhizophora mucronata, together with averufanin (3). The planar structures and absolute configurations of these compounds were unambiguously established by extensive NMR investigations, quantum-chemical electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction analysis. Most notably, the absolute configuration of aspergillin A (1) was determined by single-crystal X-ray diffraction analysis of its tri-pivaloyl derivative 4, conducted with Cu Kα radiation, whereas that of averufanin (3) was first clarified by quantum-chemical ECD calculations. Aspergilin A is the first orsellinic acid–ribose–pyridazinone-Noxide hybrid containing a unique β-oxo-2,3-dihydropyridazine 1-oxide moiety, whereas aspergilin B and averufanin are the sterigmatocystin and anthraquinone derivative, respectively. From the perspective of biosynthesis, aspergilin A could be originated from the combined assembly of three building blocks, viz., orsellinic acid, β-D-ribofuranose, and L-glutamine. It is an unprecedented alkaloid-Noxide involving biosynthetic pathways of polyketide, pentose, and amino acid. Aspergilin B (2) exhibited potent antiproliferative activity against four cancer cell lines. In addition, Aspergilin B (2) dose-dependently induced G2/M phase arrest in HepG2 cells.

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Section: Introductionmentioning

confidence: 99%

Aspergilins A–B, Including a Unique Orsellinic Acid–Ribose–Pyridazinone-N-Oxide Hybrid, from the Mangrove Endophytic Fungus Aspergillus sp. A1E3

Wu,

Xu,

Chen

et al. 2023

Preprint

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“…Steroids identified from fungi are highly functionalized and display diverse activities, − attracting considerable attention from natural product chemists. Ergone, an ergosterol derivative characterized by a highly conjugated system (a 4,6,8(14)-trien-3-one unit), is a major metabolite of several medicinal macrofungi ( Ganoderma lucidum , Polyporus umbellatus ) and has demonstrated to possess biological activities including antitumor, diuresis, immunosuppression, and antidiabetic properties. , As part of our ongoing efforts to discover cytotoxic molecules from deep-sea-derived fungi, − a Sephadex LH-20 fraction of the EtOAc extract of Aspergillus terreus YPGA10 showed inhibition of 68% toward the SW620 cell line, while showing negligible effects against four other tumor cell lines at a concentration of 100 μg/mL.…”

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confidence: 99%

Ergone Derivatives from the Deep-Sea-Derived Fungus Aspergillus terreus YPGA10 and 25,28-Dihydroxyergone-Induced Apoptosis in Human Colon Cancer SW620 Cells

Zhang,

Li,

Wang

et al. 2024

J. Nat. Prod.

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Polyaspers A and B, the First Ergosterol‐Polyether Adducts with Unprecedented 6/6/6/5/5/6/6/6/6 Nonacyclic Architecture from Aspergillus sp. TJ507

Hu,

Li,

Shi

et al. 2023

Chin. J. Chem.

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Comprehensive SummaryPsoriasis is a chronic immune‐mediated inflammatory skin disease and the TNF‐α is an important therapeutic target of this disease. In our continuous study of bioactive natural products from fungi, the first ergosterol‐polyether adducts, polyaspers A (1) and B (2), along with two known ergosterols, (3β,5α,6α,22E)‐5,6‐epoxy‐3‐hydroxyergosta‐8,22‐dien‐7‐one (3) and calvasterol B (4), were isolated from Aspergillus sp. TJ507. Structure elucidation was accomplished by extensive spectroscopic analysis and single‐crystal X‐ray diffraction tests. Polyaspers A and B possessing an unequalled 6/6/6/5/5/6/6/6/6 nonacyclic system, and their biosynthetic pathways were proposed to include intermolecular cyclization and Diels‐Alder reactions. Activity screen of these isolates showed that 1—3 could improve the cell viability in an actinomycin D/TNF‐α induced L929 cells death model, with the EC50 values of 49.85, 46.75 and 4.99 μmol/L, respectively, and the activity of 3 was even comparable with that of the positive control SPD304. Further bioactive investigations discovered 3 could suppress the inflammatory response simulated with TNF‐α in HaCaT cells. In an imiquimod‐induced psoriasis murine model, 3 significantly restrained the development of psoriasis symptoms and reduced the expression of IL‐17 and IL‐23, presenting an anti‐psoriatic effect. As such, those ergosterol derivatives, might serve as lead compounds for the development of novel TNF‐α inhibitory agents in the clinical treatment of psoriasis.

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Spectasterols, Aromatic Ergosterols with 6/6/6/5/5, 6/6/6/6, and 6/6/6/5 Ring Systems from Aspergillus spectabilis

Cited by 15 publications

References 26 publications

Aspergilins A–B, Including a Unique Orsellinic Acid–Ribose–Pyridazinone-N-Oxide Hybrid, from the Mangrove Endophytic Fungus Aspergillus sp. A1E3

Aspergilins A–B, Including a Unique Orsellinic Acid–Ribose–Pyridazinone-N-Oxide Hybrid, from the Mangrove Endophytic Fungus Aspergillus sp. A1E3

Ergone Derivatives from the Deep-Sea-Derived Fungus Aspergillus terreus YPGA10 and 25,28-Dihydroxyergone-Induced Apoptosis in Human Colon Cancer SW620 Cells

Polyaspers A and B, the First Ergosterol‐Polyether Adducts with Unprecedented 6/6/6/5/5/6/6/6/6 Nonacyclic Architecture from Aspergillus sp. TJ507

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