Ting-Ting Zhou , Man-Wen Zhang , Yan-Chun Liu , Xiao-Nian Li , Yan Liu , Kai Guo , Sheng-Hong Li
{"title":"从 Leucosceptrum canum 中提取的具有免疫抑制作用的白三烯和五正白三烯酯类化合物。","authors":"Ting-Ting Zhou , Man-Wen Zhang , Yan-Chun Liu , Xiao-Nian Li , Yan Liu , Kai Guo , Sheng-Hong Li","doi":"10.1016/j.phytochem.2024.114185","DOIUrl":null,"url":null,"abstract":"<div><p>Five undescribed leucosesterterpane sesterterpenoids, leucosceptrines A−E, two undescribed penta-<em>nor</em>-leucosesterterpane (C<sub>20</sub>) sesterterpenoids, <em>nor</em>-leucosceptrines A and B, and three known analogues, were obtained from the aerial parts of <em>Leucosceptrum canum</em> of Chinese origin. Leucosceptrines A−C are the first examples of leucosesterterpane-type sesterterpenoids with unclosed dihydropyran rings and reverse configurations at chiral centers C-4 and/or C-12. <em>Nor</em>-leucosceptrines A and B possesses an unusual penta-<em>nor</em>-leucosesterterpane skeleton. Their structures were unambiguously elucidated through comprehensive spectroscopic analyses and single-crystal X-ray diffraction. A plausible biogenetic pathway for these sesterterpenoids was proposed. The immunosuppressive effects of these isolates on the secretion of the cytokine IFN-γ by T cells stimulated with anti-CD3/CD28 monoclonal antibodies were observed with different potencies.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2000,"publicationDate":"2024-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Immunosuppressive leucosesterterpane and penta-nor-leucosesterterpane sesterterpenoids from Leucosceptrum canum\",\"authors\":\"Ting-Ting Zhou , Man-Wen Zhang , Yan-Chun Liu , Xiao-Nian Li , Yan Liu , Kai Guo , Sheng-Hong Li\",\"doi\":\"10.1016/j.phytochem.2024.114185\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Five undescribed leucosesterterpane sesterterpenoids, leucosceptrines A−E, two undescribed penta-<em>nor</em>-leucosesterterpane (C<sub>20</sub>) sesterterpenoids, <em>nor</em>-leucosceptrines A and B, and three known analogues, were obtained from the aerial parts of <em>Leucosceptrum canum</em> of Chinese origin. Leucosceptrines A−C are the first examples of leucosesterterpane-type sesterterpenoids with unclosed dihydropyran rings and reverse configurations at chiral centers C-4 and/or C-12. <em>Nor</em>-leucosceptrines A and B possesses an unusual penta-<em>nor</em>-leucosesterterpane skeleton. Their structures were unambiguously elucidated through comprehensive spectroscopic analyses and single-crystal X-ray diffraction. A plausible biogenetic pathway for these sesterterpenoids was proposed. The immunosuppressive effects of these isolates on the secretion of the cytokine IFN-γ by T cells stimulated with anti-CD3/CD28 monoclonal antibodies were observed with different potencies.</p></div>\",\"PeriodicalId\":20170,\"journal\":{\"name\":\"Phytochemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.2000,\"publicationDate\":\"2024-06-12\",\"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/S003194222400222X\",\"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/S003194222400222X","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}
引用次数: 0
摘要
研究人员从中国产的Leucosceptrum canum的气生部分获得了五种未曾描述过的单桉树酯类化合物(leucosceptrines A-E)、两种未曾描述过的五正桉树酯类化合物(C20)(nor-leucosceptrines A 和 B)以及三种已知的类似物。Leucosceptrines A-C 是首例具有非封闭二氢吡喃环和手性中心 C-4 和/或 C-12 反向构型的白果三萜类化合物。Nor-leucosceptrines A 和 B 具有不寻常的五-正亮氨酸酯烷骨架。通过全面的光谱分析和单晶 X 射线衍射,它们的结构得到了明确的阐释。提出了这些酯类化合物的合理生物遗传途径。观察到这些分离物对小鼠脾细胞在抗 CD3/CD28 单克隆抗体刺激下分泌细胞因子 IFN-γ 的免疫抑制作用具有不同的效力。
Immunosuppressive leucosesterterpane and penta-nor-leucosesterterpane sesterterpenoids from Leucosceptrum canum
Five undescribed leucosesterterpane sesterterpenoids, leucosceptrines A−E, two undescribed penta-nor-leucosesterterpane (C20) sesterterpenoids, nor-leucosceptrines A and B, and three known analogues, were obtained from the aerial parts of Leucosceptrum canum of Chinese origin. Leucosceptrines A−C are the first examples of leucosesterterpane-type sesterterpenoids with unclosed dihydropyran rings and reverse configurations at chiral centers C-4 and/or C-12. Nor-leucosceptrines A and B possesses an unusual penta-nor-leucosesterterpane skeleton. Their structures were unambiguously elucidated through comprehensive spectroscopic analyses and single-crystal X-ray diffraction. A plausible biogenetic pathway for these sesterterpenoids was proposed. The immunosuppressive effects of these isolates on the secretion of the cytokine IFN-γ by T cells stimulated with anti-CD3/CD28 monoclonal antibodies were observed with different potencies.
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.