1. Ergosterols with rare peroxide, oxetane ring moiety, and a lactone ring from Aspergillus spectabilis and their immunosuppressive activities.
- Author
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Wei M, Liao H, Li Q, Deng X, Gao C, Ding N, Sun W, Zhu H, Guo J, Chen C, and Zhang Y
- Subjects
- Molecular Structure, Humans, Lactones chemistry, Lactones pharmacology, Lactones isolation & purification, Ergosterol chemistry, Ergosterol pharmacology, Ergosterol isolation & purification, Ergosterol analogs & derivatives, Cell Proliferation drug effects, Ethers, Cyclic chemistry, Ethers, Cyclic pharmacology, Ethers, Cyclic isolation & purification, Structure-Activity Relationship, Dose-Response Relationship, Drug, Mice, T-Lymphocytes drug effects, Aspergillus chemistry, Immunosuppressive Agents pharmacology, Immunosuppressive Agents chemistry, Immunosuppressive Agents isolation & purification, Peroxides chemistry, Peroxides pharmacology, Peroxides isolation & purification
- Abstract
Ten ergostane-type steroids, including seven undescribed ones named spectasteroids A-G, were obtained from Aspergillus spectabilis. Their structures and absolute configurations were determined based on HRESIMS, NMR, ECD calculations, and single-crystal X-ray diffraction analyses. Structurally, spectasteroid A was a unique example of aromatic ergostane-type steroid that featured a rare peroxide ring moiety; spectasteroid B contained a rare oxetane ring system formed between C-9 and C-14; and spectasteroid C was an unusual 3,4-seco-ergostane steroid with an extra lactone ring between C-3 and C-9. Spectasteroids F and G specifically showed inhibitory effects against concanavalin A-induced T lymphocyte proliferation and lipopolysaccharide-induced B lymphocyte proliferation, with IC
50 values ranging from 2.33 to 4.22 μM. Spectasteroid F also showed excellent antimultidrug resistance activity, which remarkable enhanced the inhibitory activity of PTX on the colony formation of SW620/Ad300 cells., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier Ltd. All rights reserved.)- Published
- 2024
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