Zheng Niu, Chun-Yan Chen, Yan Zhou, Guan-Ke Liu, Bing-Yang Zhang, Mahmood Brobbey Oppong, De-Qin Zhang, Tie Yao, Feng Qiu
{"title":"茵陈花中半萜二聚体的表征及相关化合物的结构修正","authors":"Zheng Niu, Chun-Yan Chen, Yan Zhou, Guan-Ke Liu, Bing-Yang Zhang, Mahmood Brobbey Oppong, De-Qin Zhang, Tie Yao, Feng Qiu","doi":"10.1021/acs.jnatprod.4c00269","DOIUrl":null,"url":null,"abstract":"<p><p>Sesquiterpene dimers are mainly found in the Asteraceae family. However, conflicting reports on the structures of these compounds can be found in the literature. Herein, we describe ten sesquiterpene dimers isolated from the flowers of <i>Inula japonica</i>, including configurational revisions of japonicone H (<b>1</b>-<b>1</b>), japonicone D (<b>2</b>-<b>1</b>), inulanolide A (<b>4</b>-<b>1</b>), japonicone X (<b>5</b>-<b>1</b>), and inulanolide F (<b>5</b>-<b>2</b>) to compounds <b>1</b>, <b>2</b>, <b>4</b>, and <b>5</b>, respectively. Five new related metabolites (<b>3</b> and <b>6</b>-<b>9</b>) are also described. Application of GIAO NMR/DP4+ analyses and ECD/OR calculations enabled us to revise the absolute configurations of an additional 13 sesquiterpene dimers isolated from plants of the genus <i>Inula</i>. Compounds <b>1</b>, <b>2</b>, <b>4</b>, and <b>6</b> exhibited inhibition of nitric oxide production in lipopolysaccharide activated RAW264.7 macrophages with IC<sub>50</sub> values of 4.07-10.00 μM.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-07-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Characterization of Sesquiterpene Dimers from the Flowers of <i>Inula japonica</i> and the Structural Revisions of Related Compounds.\",\"authors\":\"Zheng Niu, Chun-Yan Chen, Yan Zhou, Guan-Ke Liu, Bing-Yang Zhang, Mahmood Brobbey Oppong, De-Qin Zhang, Tie Yao, Feng Qiu\",\"doi\":\"10.1021/acs.jnatprod.4c00269\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>Sesquiterpene dimers are mainly found in the Asteraceae family. However, conflicting reports on the structures of these compounds can be found in the literature. Herein, we describe ten sesquiterpene dimers isolated from the flowers of <i>Inula japonica</i>, including configurational revisions of japonicone H (<b>1</b>-<b>1</b>), japonicone D (<b>2</b>-<b>1</b>), inulanolide A (<b>4</b>-<b>1</b>), japonicone X (<b>5</b>-<b>1</b>), and inulanolide F (<b>5</b>-<b>2</b>) to compounds <b>1</b>, <b>2</b>, <b>4</b>, and <b>5</b>, respectively. Five new related metabolites (<b>3</b> and <b>6</b>-<b>9</b>) are also described. Application of GIAO NMR/DP4+ analyses and ECD/OR calculations enabled us to revise the absolute configurations of an additional 13 sesquiterpene dimers isolated from plants of the genus <i>Inula</i>. Compounds <b>1</b>, <b>2</b>, <b>4</b>, and <b>6</b> exhibited inhibition of nitric oxide production in lipopolysaccharide activated RAW264.7 macrophages with IC<sub>50</sub> values of 4.07-10.00 μM.</p>\",\"PeriodicalId\":47,\"journal\":{\"name\":\"Journal of Natural Products \",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2024-07-26\",\"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://doi.org/10.1021/acs.jnatprod.4c00269\",\"RegionNum\":2,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/7/9 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MEDICINAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Natural Products ","FirstCategoryId":"99","ListUrlMain":"https://doi.org/10.1021/acs.jnatprod.4c00269","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/7/9 0:00:00","PubModel":"Epub","JCR":"Q2","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
Characterization of Sesquiterpene Dimers from the Flowers of Inula japonica and the Structural Revisions of Related Compounds.
Sesquiterpene dimers are mainly found in the Asteraceae family. However, conflicting reports on the structures of these compounds can be found in the literature. Herein, we describe ten sesquiterpene dimers isolated from the flowers of Inula japonica, including configurational revisions of japonicone H (1-1), japonicone D (2-1), inulanolide A (4-1), japonicone X (5-1), and inulanolide F (5-2) to compounds 1, 2, 4, and 5, respectively. Five new related metabolites (3 and 6-9) are also described. Application of GIAO NMR/DP4+ analyses and ECD/OR calculations enabled us to revise the absolute configurations of an additional 13 sesquiterpene dimers isolated from plants of the genus Inula. Compounds 1, 2, 4, and 6 exhibited inhibition of nitric oxide production in lipopolysaccharide activated RAW264.7 macrophages with IC50 values of 4.07-10.00 μM.
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.