Spectanoids A−H: Eight undescribed sesterterpenoids from Aspergillus spectabilis

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Nine new ergosteroids (1–9) and seven known ones (10–16) were isolated from Talaromyces adpressus. Their structures and absolute configurations were determined by the interpretation of NMR spectroscopic data, HRESIMS, ECD calculations, and single-crystal X-ray diffraction analyses. Structurally, compound 1 was an ergosteroid with two epoxy and a 3α-OH group at ring A, while compounds 8 and 9 had a contracted ring A with a peroxy bridge between C-3 and C-9, which were reported for the first time. Compounds 2–6, 9, 11, and 15 displayed cytotoxic activities with IC50 values ranging from 0.4 to 32 μM, and compound 7 exhibited an immunosuppressive effect against LPS-induced B lymphocyte proliferation with an IC50 value of 8.6 μM. The structure–activity relationships of these compounds are briefly discussed.

Section: Methodsmentioning

confidence: 99%

Cytotoxic Ergosteroids from a Strain of the Fungus Talaromyces adpressus

Zheng,

Xiao,

et al. 2023

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“…Aspergillus sp. are recognized for their biosynthetic capacities and produce secondary metabolites such as polyketides, alkaloids, terpenoids, steroids, and anthraquinone. − In a previous study on Aspergillus spectabilis, we isolated and characterized a series of sesterterpenoids . As a continuation of this work, five aromatic ergosterols, spectasterols A–E ( 1 – 5 ), were isolated, which have carbon skeletons that were possibly derived via additional cyclization ( 1 and 2 ) or pinacol rearrangements ( 3 , 4 , and 5 ).…”

mentioning

confidence: 86%

“…9−14 In a previous study on Aspergillus spectabilis, we isolated and characterized a series of sesterterpenoids. 15 As a continuation of this work, five aromatic ergosterols, spectasterols A−E (1− 5), were isolated, which have carbon skeletons that were possibly derived via additional cyclization (1 and 2) or pinacol rearrangements (3, 4, and 5). Herein are described details of their isolation, structure elucidation, and bioactivity, and a biosynthetic pathway is proposed.…”

mentioning

confidence: 87%

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

Wei

Huang

et al. 2023

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Spectasterols A−E (1−5), aromatic ergosterols with unique ring systems, were isolated from Aspergillus spectabilis. Compounds 1 and 2 possess a 6/6/6/5/5 ring system with an additional cyclopentene, while 3 and 4 have an uncommon 6/6/6/6 ring system generated by the D-ring expansion via 1,2-alkyl shifts. Compound 3 exhibited cytotoxic activity (IC 50 6.9 μM) and induced cell cycle arrest and apoptosis in HL60 cells. Compound 3 was antiinflammatory; it decreased COX-2 levels at the transcription and protein levels and inhibited the nuclear translocation of NF-κB p65.

“…In recent years, multiple lovastatin analogs have been derived from Aspergillus sp., such as A. terreus and A. sclerotiorum . As part of our continuing research on bioactive compounds derived from the genus Aspergillus , , the present study was focused on the chemical investigation of the extract derived from the strain Aspergillus aculeatus . Notably, we successfully isolated 10 lovastatin derivatives, including seven undescribed ones, aculeanoids A–G ( 1 – 7 ), and three known compounds, viz., peniciversiol C ( 8 ), versiol ( 9 ), and decumbenone B ( 10 ) .…”

mentioning

confidence: 99%

Aculeatiols A–G: Lovastatin Derivatives Extracted from Aspergillus aculeatus

Liu,

Qiao,

et al. 2024

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In this study, we isolated lovastatin derivatives, including aculeatiols A−G (1−7) and three known compounds (8−10), from Aspergillus aculeatus. Their structures and absolute configurations were experimentally determined by high-resolution electrospray ionization mass spectrometry, nuclear magnetic resonance spectroscopy, and X-ray diffraction analyses, and the results were corroborated by quantumchemical calculations. As members of the lovastatin derivatives, aculeatiols A−C (1−3) possess a γ-lactone functional group in the side chain. Compound 6 represents the first example that features an undescribed aromatized heterotetracyclic 6/6/6/6 ring system. Biologically, the lipid-lowering effects of all of these compounds were evaluated by analyzing the free fatty acid-induced intracellular lipid accumulation. In addition, compound 5, which regulated the transcription of genes associated with lipid uptake and synthesis, inhibited the accumulation of lipids.