Jin-Ling Chang, Yu-Tian Gan, Yin-Hui Zhou, Xiao-Gang Peng, Zuo-Ye Xie, Xianggao Meng, Shu-Ming Li and Han-Li Ruan*,
{"title":"Asperustins A–J: Austocystins with Immunosuppressive and Cytotoxic Activities from Aspergillus ustus NRRL 5856","authors":"Jin-Ling Chang, Yu-Tian Gan, Yin-Hui Zhou, Xiao-Gang Peng, Zuo-Ye Xie, Xianggao Meng, Shu-Ming Li and Han-Li Ruan*, ","doi":"10.1021/acs.jnatprod.3c01243","DOIUrl":null,"url":null,"abstract":"<p >Ten new (<b>1</b>–<b>10</b>) and nine known (<b>11</b>–<b>19</b>) austocystins, along with four known anthraquinones (<b>20</b>–<b>23</b>), were isolated from the culture of <i>Aspergillus ustus</i> NRRL 5856 by bioactivity-guided fractionation. The structures of the new compounds were elucidated by spectroscopic data analysis, X-ray crystallographic study, the modified Mosher’s method, [Rh<sub>2</sub>(OCOCF3)<sub>4</sub>]-induced ECD spectral analysis, and comparison of the experimental ECD spectra with those of the similar analogues. Compounds <b>1</b>–<b>8</b> represent the first examples of austocystins with a C-4′ oxygenated substitution. The absolute configuration of 1″-hydroxy austocystin D (<b>11</b>) was determined by single-crystal X-ray diffraction and consideration of its biosynthetic origin. Compounds <b>5</b>, <b>9</b>, and <b>11</b> exhibited significant inhibitory effects against the proliferation of ConA-induced T cells with IC<sub>50</sub> values of 1.1, 1.0, and 0.93 μM, respectively. Furthermore, these compounds suppressed the expression of IL-6 in a dose-dependent manner. Compounds <b>10</b>–<b>12</b> and <b>14</b> showed pronounced cytotoxicities against MCF-7 with IC<sub>50</sub> values of 3.9, 1.3, 0.46, and 2.3 μM, respectively.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-03-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Natural Products ","FirstCategoryId":"99","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.jnatprod.3c01243","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
引用次数: 0
Abstract
Ten new (1–10) and nine known (11–19) austocystins, along with four known anthraquinones (20–23), were isolated from the culture of Aspergillus ustus NRRL 5856 by bioactivity-guided fractionation. The structures of the new compounds were elucidated by spectroscopic data analysis, X-ray crystallographic study, the modified Mosher’s method, [Rh2(OCOCF3)4]-induced ECD spectral analysis, and comparison of the experimental ECD spectra with those of the similar analogues. Compounds 1–8 represent the first examples of austocystins with a C-4′ oxygenated substitution. The absolute configuration of 1″-hydroxy austocystin D (11) was determined by single-crystal X-ray diffraction and consideration of its biosynthetic origin. Compounds 5, 9, and 11 exhibited significant inhibitory effects against the proliferation of ConA-induced T cells with IC50 values of 1.1, 1.0, and 0.93 μM, respectively. Furthermore, these compounds suppressed the expression of IL-6 in a dose-dependent manner. Compounds 10–12 and 14 showed pronounced cytotoxicities against MCF-7 with IC50 values of 3.9, 1.3, 0.46, and 2.3 μM, respectively.
期刊介绍:
The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained.
Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.
When new compounds are reported, manuscripts describing their biological activity are much preferred.
Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.