Shu-Fei Yu, Jin-Na Zhao, Bo Li, Yan-Jun Ding, Ming-Yue He, Zhi-Hang Wu, Lu Chen, Ze Li, Yan-Liang Qu, Jian Huang, Xian-Mei Piao*, Jin-Hui Wang* and Li-Bo Wang*,
{"title":"砂砂果中倍半萜吲哚类生物碱A和B。","authors":"Shu-Fei Yu, Jin-Na Zhao, Bo Li, Yan-Jun Ding, Ming-Yue He, Zhi-Hang Wu, Lu Chen, Ze Li, Yan-Liang Qu, Jian Huang, Xian-Mei Piao*, Jin-Hui Wang* and Li-Bo Wang*, ","doi":"10.1021/acs.jnatprod.5c00539","DOIUrl":null,"url":null,"abstract":"<p >Two unprecedented 4/9/5-membered ring sesquiterpene-indole alkaloids, amomaxyz A (<b>1</b>) and B (<b>2</b>), along with one known compound caryolane-1,9β-diol (<b>3</b>), were isolated from the fruit of <i>Amomum maximum</i> Roxb. Their structures and absolute configurations were elucidated through comprehensive spectroscopic analyses, including NMR, electronic circular dichroism (ECD), X-ray single-crystal diffraction, and DP4 probability analysis of calculated NMR data. Biological evaluation revealed distinct anti-inflammatory and anticancer activities. <b>1</b> demonstrated dose-dependent anti-inflammatory activity by suppressing NO release in LPS/IFN-γ-activated RAW264.7 macrophages (25.9% at 10 μM, 29.9% at 20 μM; <i>P</i> < 0.01), while <b>2</b> and <b>3</b> exhibited weaker effects. Moreover, <b>1</b> (IC<sub>50</sub> = 30.62 μM) and <b>2</b> (IC<sub>50</sub> = 23.43 μM) showed moderate inhibitory effects against HepG2 cells, which reveals the potential of their biological activity.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 7","pages":"1791–1796"},"PeriodicalIF":3.6000,"publicationDate":"2025-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Amomaxyz A and B, Sesquiterpene-Indole Alkaloids from Fruits of Amomum maximum Roxb\",\"authors\":\"Shu-Fei Yu, Jin-Na Zhao, Bo Li, Yan-Jun Ding, Ming-Yue He, Zhi-Hang Wu, Lu Chen, Ze Li, Yan-Liang Qu, Jian Huang, Xian-Mei Piao*, Jin-Hui Wang* and Li-Bo Wang*, \",\"doi\":\"10.1021/acs.jnatprod.5c00539\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >Two unprecedented 4/9/5-membered ring sesquiterpene-indole alkaloids, amomaxyz A (<b>1</b>) and B (<b>2</b>), along with one known compound caryolane-1,9β-diol (<b>3</b>), were isolated from the fruit of <i>Amomum maximum</i> Roxb. Their structures and absolute configurations were elucidated through comprehensive spectroscopic analyses, including NMR, electronic circular dichroism (ECD), X-ray single-crystal diffraction, and DP4 probability analysis of calculated NMR data. Biological evaluation revealed distinct anti-inflammatory and anticancer activities. <b>1</b> demonstrated dose-dependent anti-inflammatory activity by suppressing NO release in LPS/IFN-γ-activated RAW264.7 macrophages (25.9% at 10 μM, 29.9% at 20 μM; <i>P</i> < 0.01), while <b>2</b> and <b>3</b> exhibited weaker effects. Moreover, <b>1</b> (IC<sub>50</sub> = 30.62 μM) and <b>2</b> (IC<sub>50</sub> = 23.43 μM) showed moderate inhibitory effects against HepG2 cells, which reveals the potential of their biological activity.</p>\",\"PeriodicalId\":47,\"journal\":{\"name\":\"Journal of Natural Products \",\"volume\":\"88 7\",\"pages\":\"1791–1796\"},\"PeriodicalIF\":3.6000,\"publicationDate\":\"2025-06-27\",\"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.5c00539\",\"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.5c00539","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
Amomaxyz A and B, Sesquiterpene-Indole Alkaloids from Fruits of Amomum maximum Roxb
Two unprecedented 4/9/5-membered ring sesquiterpene-indole alkaloids, amomaxyz A (1) and B (2), along with one known compound caryolane-1,9β-diol (3), were isolated from the fruit of Amomum maximum Roxb. Their structures and absolute configurations were elucidated through comprehensive spectroscopic analyses, including NMR, electronic circular dichroism (ECD), X-ray single-crystal diffraction, and DP4 probability analysis of calculated NMR data. Biological evaluation revealed distinct anti-inflammatory and anticancer activities. 1 demonstrated dose-dependent anti-inflammatory activity by suppressing NO release in LPS/IFN-γ-activated RAW264.7 macrophages (25.9% at 10 μM, 29.9% at 20 μM; P < 0.01), while 2 and 3 exhibited weaker effects. Moreover, 1 (IC50 = 30.62 μM) and 2 (IC50 = 23.43 μM) showed moderate inhibitory effects against HepG2 cells, which reveals the potential of their biological activity.
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.