Scabrosteroids A–D, Four Pyrrolidinone–Ergosterol Heterodimers from <i>Penicillium scabrosum</i> FXI744

Scabrosteroids A-D (<b>1</b>-<b>4</b>), four novel steroidal heterodimers, were isolated from <i>Penicillium scabrosum</i> FXI744. These compounds represent the first naturally occurring pyrrolidinone-ergosterol hybrids, linked by a C-3/C-3' bond between pyrrolidinone and ergosterol moieties. Their structural elucidation, including the determination of absolute configurations, was accomplished using HRESIMS, NMR, X-ray crystallography, and ECD calculation. A plausible biosynthetic pathway for these metabolites was proposed. Biological evaluation revealed that compounds <b>1</b>-<b>4</b> inhibited NO production with IC<sub>50</sub> values ranging from 9.5 to 14.4 μM, and compounds <b>1</b> and <b>4</b> also showed moderate <i>in</i> <i>vitro</i> immunosuppressive effects.

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Publication Details

Journal
Organic Letters
Published
2025-06-09
DOI
https://doi.org/10.1021/acs.orglett.5c01729
Citations
5
Primary Topic
Steroid Chemistry and Biochemistry
Type
article
Field-Weighted Citation Impact
4.03

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article

Scabrosteroids A–D, Four Pyrrolidinone–Ergosterol Heterodimers from Penicillium scabrosum FXI744

Chunlun Qin, Wanpeng Li, Ting Zhou, Hanli Ruan et al.
5 citations
Organic Letters
Steroid Chemistry and Biochemistry
4.03
article

Scabrosteroids A–D, Four Pyrrolidinone–Ergosterol Heterodimers from Penicillium scabrosum FXI744

Chunlun Qin, Wanpeng Li, Ting Zhou, Hanli Ruan, Zheng Li, Jia-Yun Hu, Yin-Hui Zhou
article en
5 citations

Abstract

Scabrosteroids A-D (<b>1</b>-<b>4</b>), four novel steroidal heterodimers, were isolated from <i>Penicillium scabrosum</i> FXI744. These compounds represent the first naturally occurring pyrrolidinone-ergosterol hybrids, linked by a C-3/C-3' bond between pyrrolidinone and ergosterol moieties. Their structural elucidation, including the determination of absolute configurations, was accomplished using HRESIMS, NMR, X-ray crystallography, and ECD calculation. A plausible biosynthetic pathway for these metabolites was proposed. Biological evaluation revealed that compounds <b>1</b>-<b>4</b> inhibited NO production with IC<sub>50</sub> values ranging from 9.5 to 14.4 μM, and compounds <b>1</b> and <b>4</b> also showed moderate <i>in</i> <i>vitro</i> immunosuppressive effects.

Organic LettersVol. 27(24)
Huazhong University of Science and Technology (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 6%
Steroid Chemistry and Biochemistry
4.03
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