Aspersterols A-D, Ergostane-Type Sterols with an Unusual Unsaturated Side Chain from the Deep-Sea-Derived Fungus Aspergillus unguis
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Title
- Aspersterols A-D, Ergostane-Type Sterols with an Unusual Unsaturated Side Chain from the Deep-Sea-Derived Fungus Aspergillus unguis
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Author(s)
- Cao, Van Anh; Kwon, Joo-Hee; Kang, Jong Soon; Lee, Hwa-Sun; Heo, Chang-Su; Shin, Hee Jae
- KIOST Author(s)
- Lee, Hwa Sun(이화선); Heo, Chang Su(허창수); Shin, Hee Jae(신희재)
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Alternative Author(s)
- Cao Van Anh; 이화선; 허창수; 신희재
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Publication Year
- 2022-09
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Abstract
- Four previously undescribed ergostane-type sterols, aspersterols A-D (1-4), were isolated from a deep-sea-derived fungus, Aspergillus unguis IV17-109. The structures of the new compounds were determined by extensive analyses of their spectroscopic data, pyridine-induced deshielding effect, Mosher's method, and electronic circular dichroism calculations. The key feature of these sterols is the presence of a rare unsaturated side chain with conjugated double bonds at delta(17) and delta(22). The absolute configuration of C-24 in the side chain was determined by hydrogenation and comparing C-13 NMR chemical shifts of the hydrogenated products with literature values. In addition, aspersterol A (1) is the second representative of anthrasteroids with a hydroxy group at the C-2 position. Compound 1 showed cytotoxicity against six cancer cell lines, with GI50 values of 3.4 +/- 0.3 to 4.5 +/- 0.7 mu M, while 2-4 showed anti-inflammatory activity, with IC50 values ranging from 11.6 +/- 1.6 to 19.5 +/- 1.2 mu M.
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ISSN
- 0163-3864
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URI
- https://sciwatch.kiost.ac.kr/handle/2020.kiost/43178
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DOI
- 10.1021/acs.jnatprod.2c00398
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Bibliographic Citation
- Journal of Natural Products, v.85, no.9, pp.2177 - 2183, 2022
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Publisher
- American Chemical Society
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Type
- Article
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Language
- English
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Document Type
- Article; Early Access
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