Fei Liu , Qin Li , Yongqi Li , Hong Liao , Weiguang Sun , Jianguo Li , Chunmei Chen , Yonghui Zhang , Hucheng Zhu
{"title":"刺曲霉中第二种具有免疫抑制活性的17-非梭菌二萜类A-D。","authors":"Fei Liu , Qin Li , Yongqi Li , Hong Liao , Weiguang Sun , Jianguo Li , Chunmei Chen , Yonghui Zhang , Hucheng Zhu","doi":"10.1016/j.phytochem.2025.114414","DOIUrl":null,"url":null,"abstract":"<div><div>Chemical investigation on the secondary metabolites of <em>Aspergillus aculeatus</em> led to the identification of ten modified fusicoccane-type diterpenoids aculeanoids A–J (<strong>1</strong>–<strong>10</strong>). Their structures and absolute configurations were characterized by comprehensive spectroscopic analysis, DP4+ analysis, Mo<sub>2</sub>(OAc)<sub>4</sub>-induced ECD, single-crystal X-ray diffractions, and ECD calculations. Compounds <strong>1</strong>–<strong>4</strong> belong to a rare class of 17-<em>nor</em> fusicoccane diterpenoids, with only one previously reported example. Biologically, compounds <strong>6</strong>, <strong>7</strong>, and <strong>10</strong> exhibited significant immunosuppressive activities against con A-induced T cell proliferation with IC<sub>50</sub> values ranging from 2.44 to 5.26 <em>μ</em>M and LPS-induced B cell proliferation with IC<sub>50</sub> values ranging from 4.18 to 5.78 <em>μ</em>M, which provided more possibilities with the treatment of organ transplantation and various autoimmune diseases.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"233 ","pages":"Article 114414"},"PeriodicalIF":3.4000,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Aculeanoids A–D, the second 17-nor fusicoccane diterpenoids with immunosuppressive activity from Aspergillus aculeatus\",\"authors\":\"Fei Liu , Qin Li , Yongqi Li , Hong Liao , Weiguang Sun , Jianguo Li , Chunmei Chen , Yonghui Zhang , Hucheng Zhu\",\"doi\":\"10.1016/j.phytochem.2025.114414\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Chemical investigation on the secondary metabolites of <em>Aspergillus aculeatus</em> led to the identification of ten modified fusicoccane-type diterpenoids aculeanoids A–J (<strong>1</strong>–<strong>10</strong>). Their structures and absolute configurations were characterized by comprehensive spectroscopic analysis, DP4+ analysis, Mo<sub>2</sub>(OAc)<sub>4</sub>-induced ECD, single-crystal X-ray diffractions, and ECD calculations. Compounds <strong>1</strong>–<strong>4</strong> belong to a rare class of 17-<em>nor</em> fusicoccane diterpenoids, with only one previously reported example. Biologically, compounds <strong>6</strong>, <strong>7</strong>, and <strong>10</strong> exhibited significant immunosuppressive activities against con A-induced T cell proliferation with IC<sub>50</sub> values ranging from 2.44 to 5.26 <em>μ</em>M and LPS-induced B cell proliferation with IC<sub>50</sub> values ranging from 4.18 to 5.78 <em>μ</em>M, which provided more possibilities with the treatment of organ transplantation and various autoimmune diseases.</div></div>\",\"PeriodicalId\":20170,\"journal\":{\"name\":\"Phytochemistry\",\"volume\":\"233 \",\"pages\":\"Article 114414\"},\"PeriodicalIF\":3.4000,\"publicationDate\":\"2025-05-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Phytochemistry\",\"FirstCategoryId\":\"99\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0031942225000378\",\"RegionNum\":2,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2025/1/21 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q2\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Phytochemistry","FirstCategoryId":"99","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0031942225000378","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/1/21 0:00:00","PubModel":"Epub","JCR":"Q2","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
Aculeanoids A–D, the second 17-nor fusicoccane diterpenoids with immunosuppressive activity from Aspergillus aculeatus
Chemical investigation on the secondary metabolites of Aspergillus aculeatus led to the identification of ten modified fusicoccane-type diterpenoids aculeanoids A–J (1–10). Their structures and absolute configurations were characterized by comprehensive spectroscopic analysis, DP4+ analysis, Mo2(OAc)4-induced ECD, single-crystal X-ray diffractions, and ECD calculations. Compounds 1–4 belong to a rare class of 17-nor fusicoccane diterpenoids, with only one previously reported example. Biologically, compounds 6, 7, and 10 exhibited significant immunosuppressive activities against con A-induced T cell proliferation with IC50 values ranging from 2.44 to 5.26 μM and LPS-induced B cell proliferation with IC50 values ranging from 4.18 to 5.78 μM, which provided more possibilities with the treatment of organ transplantation and various autoimmune diseases.
期刊介绍：
Phytochemistry is a leading international journal publishing studies of plant chemistry, biochemistry, molecular biology and genetics, structure and bioactivities of phytochemicals, including ''-omics'' and bioinformatics/computational biology approaches. Phytochemistry is a primary source for papers dealing with phytochemicals, especially reports concerning their biosynthesis, regulation, and biological properties both in planta and as bioactive principles. Articles are published online as soon as possible as Articles-in-Press and in 12 volumes per year. Occasional topic-focussed special issues are published composed of papers from invited authors.
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