{"title":"深海发酵真菌赤曲霉 YPGA10 的麦角甾醇衍生物和 25,28-二羟麦角甾醇诱导人结肠癌 SW620 细胞凋亡的作用","authors":"Zhen Zhang, Yuanli Li, Huannan Wang, Wei Xu, Chunying Wang, Huabin Ma, Fang Zhong, Jiazhi Ou, Zhuhua Luo, Hai-Bin Luo and Zhongbin Cheng*, ","doi":"10.1021/acs.jnatprod.4c00154","DOIUrl":null,"url":null,"abstract":"<p >Ten new ergone derivatives (<b>1</b>–<b>10</b>) and five known analogues (<b>11</b>–<b>15</b>) were isolated from the deep-sea-derived fungus <i>Aspergillus terreus</i> YPGA10. The structures including the absolute configurations were established by detailed analysis of the NMR spectroscopic data, HRESIMS, ECD calculation, and coupling constant calculation. All the structures are characterized by a highly conjugated 25-hydroxyergosta-4,6,8(14),22-tetraen-3-one nucleus. Structurally, compound <b>2</b> bearing a 15-carbonyl group and compounds <b>5</b>–<b>7</b> possessing a 15β-OH/OCH<sub>3</sub> group are rarely encountered in ergone derivatives. Bioassay results showed that compounds <b>1</b> and <b>11</b> demonstrated cytotoxic effects on human colon cancer SW620 cells with IC<sub>50</sub> values of 8.4 and 3.1 μM, respectively. Notably, both compounds exhibited negligible cytotoxicity on the human normal lung epithelial cell BEAS-2B. Compound <b>11</b> was selected for preliminary mechanistic study and was found to inhibit cell proliferation and induce apoptosis in human colon cancer SW620 cells. In addition, compound <b>1</b> displayed cytotoxic activity against five human leukemia cell lines with IC<sub>50</sub> values ranging from 5.7 to 8.9 μM. Our study demonstrated that compound <b>11</b> may serve as a potential candidate for the development of anticolorectal cancer agents.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-06-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Ergone Derivatives from the Deep-Sea-Derived Fungus Aspergillus terreus YPGA10 and 25,28-Dihydroxyergone-Induced Apoptosis in Human Colon Cancer SW620 Cells\",\"authors\":\"Zhen Zhang, Yuanli Li, Huannan Wang, Wei Xu, Chunying Wang, Huabin Ma, Fang Zhong, Jiazhi Ou, Zhuhua Luo, Hai-Bin Luo and Zhongbin Cheng*, \",\"doi\":\"10.1021/acs.jnatprod.4c00154\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >Ten new ergone derivatives (<b>1</b>–<b>10</b>) and five known analogues (<b>11</b>–<b>15</b>) were isolated from the deep-sea-derived fungus <i>Aspergillus terreus</i> YPGA10. The structures including the absolute configurations were established by detailed analysis of the NMR spectroscopic data, HRESIMS, ECD calculation, and coupling constant calculation. All the structures are characterized by a highly conjugated 25-hydroxyergosta-4,6,8(14),22-tetraen-3-one nucleus. Structurally, compound <b>2</b> bearing a 15-carbonyl group and compounds <b>5</b>–<b>7</b> possessing a 15β-OH/OCH<sub>3</sub> group are rarely encountered in ergone derivatives. Bioassay results showed that compounds <b>1</b> and <b>11</b> demonstrated cytotoxic effects on human colon cancer SW620 cells with IC<sub>50</sub> values of 8.4 and 3.1 μM, respectively. Notably, both compounds exhibited negligible cytotoxicity on the human normal lung epithelial cell BEAS-2B. Compound <b>11</b> was selected for preliminary mechanistic study and was found to inhibit cell proliferation and induce apoptosis in human colon cancer SW620 cells. In addition, compound <b>1</b> displayed cytotoxic activity against five human leukemia cell lines with IC<sub>50</sub> values ranging from 5.7 to 8.9 μM. Our study demonstrated that compound <b>11</b> may serve as a potential candidate for the development of anticolorectal cancer agents.</p>\",\"PeriodicalId\":47,\"journal\":{\"name\":\"Journal of Natural Products \",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2024-06-10\",\"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.4c00154\",\"RegionNum\":2,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MEDICINAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Natural Products ","FirstCategoryId":"99","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.jnatprod.4c00154","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
Ergone Derivatives from the Deep-Sea-Derived Fungus Aspergillus terreus YPGA10 and 25,28-Dihydroxyergone-Induced Apoptosis in Human Colon Cancer SW620 Cells
Ten new ergone derivatives (1–10) and five known analogues (11–15) were isolated from the deep-sea-derived fungus Aspergillus terreus YPGA10. The structures including the absolute configurations were established by detailed analysis of the NMR spectroscopic data, HRESIMS, ECD calculation, and coupling constant calculation. All the structures are characterized by a highly conjugated 25-hydroxyergosta-4,6,8(14),22-tetraen-3-one nucleus. Structurally, compound 2 bearing a 15-carbonyl group and compounds 5–7 possessing a 15β-OH/OCH3 group are rarely encountered in ergone derivatives. Bioassay results showed that compounds 1 and 11 demonstrated cytotoxic effects on human colon cancer SW620 cells with IC50 values of 8.4 and 3.1 μM, respectively. Notably, both compounds exhibited negligible cytotoxicity on the human normal lung epithelial cell BEAS-2B. Compound 11 was selected for preliminary mechanistic study and was found to inhibit cell proliferation and induce apoptosis in human colon cancer SW620 cells. In addition, compound 1 displayed cytotoxic activity against five human leukemia cell lines with IC50 values ranging from 5.7 to 8.9 μM. Our study demonstrated that compound 11 may serve as a potential candidate for the development of anticolorectal cancer agents.
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.
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