Dingwei Gong , Baoping Xie , Yijun Sun , Yuanyuan Cheng , Xiaofei Tian , Zhengzheng Zhou , Li-Wen Tian
{"title":"Daldiconoids A-G:Daldinia concentrica 子实体中的 3,4-癸烷三萜类化合物及其抗炎活性。","authors":"Dingwei Gong , Baoping Xie , Yijun Sun , Yuanyuan Cheng , Xiaofei Tian , Zhengzheng Zhou , Li-Wen Tian","doi":"10.1016/j.phytochem.2024.114201","DOIUrl":null,"url":null,"abstract":"<div><p>Seven undescribed 3,4-secolanostane triterpenoids, daldiconoids A-G (<strong>1</strong>–<strong>7</strong>), were isolated from the fruiting bodies of <em>Daldinia concentrica</em>. Daldiconoid A (<strong>1</strong>) was a highly modified 4,6,28,29-tetranorlanostane triterpenoid alkaloid featuring an unusual <em>δ</em>-lactam fused with a flanking cyclopentenone architecture. Their structures were determined by spectroscopic data, NMR calculations coupled with the DP4+ analysis, X-ray single-crystal diffraction, and chemical transformation. The plausible biosynthetic pathway for <strong>1</strong> was proposed. Compounds <strong>1</strong>, <strong>2</strong>, and <strong>4</strong>–<strong>6</strong> inhibited the expressions of IL-1<em>β</em>, IL-6, and TNF-<em>α</em> in lipopolysaccharide stimulated RAW264.7 cells at a concentration of 10 μM. Mechanistically, Compounds <strong>1</strong> and <strong>2</strong> blocked the JAK2/STAT3 signaling pathway induced by lipopolysaccharide.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2000,"publicationDate":"2024-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Daldiconoids A-G: 3,4-Secolanostane triterpenoids from the fruiting bodies of Daldinia concentrica and their anti-inflammatory activity\",\"authors\":\"Dingwei Gong , Baoping Xie , Yijun Sun , Yuanyuan Cheng , Xiaofei Tian , Zhengzheng Zhou , Li-Wen Tian\",\"doi\":\"10.1016/j.phytochem.2024.114201\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Seven undescribed 3,4-secolanostane triterpenoids, daldiconoids A-G (<strong>1</strong>–<strong>7</strong>), were isolated from the fruiting bodies of <em>Daldinia concentrica</em>. Daldiconoid A (<strong>1</strong>) was a highly modified 4,6,28,29-tetranorlanostane triterpenoid alkaloid featuring an unusual <em>δ</em>-lactam fused with a flanking cyclopentenone architecture. Their structures were determined by spectroscopic data, NMR calculations coupled with the DP4+ analysis, X-ray single-crystal diffraction, and chemical transformation. The plausible biosynthetic pathway for <strong>1</strong> was proposed. Compounds <strong>1</strong>, <strong>2</strong>, and <strong>4</strong>–<strong>6</strong> inhibited the expressions of IL-1<em>β</em>, IL-6, and TNF-<em>α</em> in lipopolysaccharide stimulated RAW264.7 cells at a concentration of 10 μM. Mechanistically, Compounds <strong>1</strong> and <strong>2</strong> blocked the JAK2/STAT3 signaling pathway induced by lipopolysaccharide.</p></div>\",\"PeriodicalId\":20170,\"journal\":{\"name\":\"Phytochemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.2000,\"publicationDate\":\"2024-06-26\",\"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/S0031942224002383\",\"RegionNum\":2,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"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/S0031942224002383","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
Daldiconoids A-G: 3,4-Secolanostane triterpenoids from the fruiting bodies of Daldinia concentrica and their anti-inflammatory activity
Seven undescribed 3,4-secolanostane triterpenoids, daldiconoids A-G (1–7), were isolated from the fruiting bodies of Daldinia concentrica. Daldiconoid A (1) was a highly modified 4,6,28,29-tetranorlanostane triterpenoid alkaloid featuring an unusual δ-lactam fused with a flanking cyclopentenone architecture. Their structures were determined by spectroscopic data, NMR calculations coupled with the DP4+ analysis, X-ray single-crystal diffraction, and chemical transformation. The plausible biosynthetic pathway for 1 was proposed. Compounds 1, 2, and 4–6 inhibited the expressions of IL-1β, IL-6, and TNF-α in lipopolysaccharide stimulated RAW264.7 cells at a concentration of 10 μM. Mechanistically, Compounds 1 and 2 blocked the JAK2/STAT3 signaling pathway induced by lipopolysaccharide.
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.