Jie DONG , Haibo LI , Mi ZHOU , Xinsheng YAO , Jianliang GENG , Yang YU
{"title":"牛膝草果实中的四种新的二芳基庚酸类化合物和两种新的萜类化合物及其抗炎活性。","authors":"Jie DONG , Haibo LI , Mi ZHOU , Xinsheng YAO , Jianliang GENG , Yang YU","doi":"10.1016/S1875-5364(24)60723-5","DOIUrl":null,"url":null,"abstract":"<div><div>Four previously unreported diarylheptanoids (<strong>1a</strong>/<strong>1b</strong>−<strong>2a</strong>/<strong>2b</strong>), one undescribed sesquiterpenoid (<strong>8</strong>), one new diterpenoid (<strong>12</strong>), and twelve known analogs were isolated from the fruits of <em>Alpinia oxyphylla</em>. The structural elucidation of these compounds was achieved through a comprehensive analysis of spectroscopic data, single-crystal X-ray diffraction, electronic circular dichroism (ECD), and modified Mosher’s method. Enantiomeric mixtures (<strong>1a</strong>/<strong>1b</strong>, <strong>2a</strong>/<strong>2b</strong>, <strong>3a</strong>/<strong>3b</strong>, <strong>4a</strong>/<strong>4b</strong>, and <strong>5a</strong>/<strong>5b</strong>) were separated on a chiral column using acetonitrile-water mixtures as eluents. Among them, compounds <strong>3a</strong>/<strong>3b</strong> and <strong>4a</strong>/<strong>4b</strong> were isolated as optically pure enantiomers in the initial chiral separation. Furthermore, most of the isolates were evaluated for their inhibitory effects against the production of nitric oxide (NO) and interleukin-6 (IL-6) in lipopolysaccharide (LPS)-induced RAW264.7 macrophages. Interestingly, <strong>2</strong> and <strong>4</strong> showed significant inhibitory activities against NO production with IC<sub>50</sub> values of 33.65 and 9.88 μmol·L<sup>−1</sup> (hydrocortisone: IC<sub>50</sub> 34.26 μmol·L<sup>−1</sup>), respectively. Additionally, they also partially reduced the secretion of IL-6.</div></div>","PeriodicalId":10002,"journal":{"name":"Chinese Journal of Natural Medicines","volume":"22 10","pages":"Pages 929-936"},"PeriodicalIF":4.0000,"publicationDate":"2024-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Four new diarylheptanoids and two new terpenoids from the fruits of Alpinia oxyphylla and their anti-inflammatory activities\",\"authors\":\"Jie DONG , Haibo LI , Mi ZHOU , Xinsheng YAO , Jianliang GENG , Yang YU\",\"doi\":\"10.1016/S1875-5364(24)60723-5\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Four previously unreported diarylheptanoids (<strong>1a</strong>/<strong>1b</strong>−<strong>2a</strong>/<strong>2b</strong>), one undescribed sesquiterpenoid (<strong>8</strong>), one new diterpenoid (<strong>12</strong>), and twelve known analogs were isolated from the fruits of <em>Alpinia oxyphylla</em>. The structural elucidation of these compounds was achieved through a comprehensive analysis of spectroscopic data, single-crystal X-ray diffraction, electronic circular dichroism (ECD), and modified Mosher’s method. Enantiomeric mixtures (<strong>1a</strong>/<strong>1b</strong>, <strong>2a</strong>/<strong>2b</strong>, <strong>3a</strong>/<strong>3b</strong>, <strong>4a</strong>/<strong>4b</strong>, and <strong>5a</strong>/<strong>5b</strong>) were separated on a chiral column using acetonitrile-water mixtures as eluents. Among them, compounds <strong>3a</strong>/<strong>3b</strong> and <strong>4a</strong>/<strong>4b</strong> were isolated as optically pure enantiomers in the initial chiral separation. Furthermore, most of the isolates were evaluated for their inhibitory effects against the production of nitric oxide (NO) and interleukin-6 (IL-6) in lipopolysaccharide (LPS)-induced RAW264.7 macrophages. Interestingly, <strong>2</strong> and <strong>4</strong> showed significant inhibitory activities against NO production with IC<sub>50</sub> values of 33.65 and 9.88 μmol·L<sup>−1</sup> (hydrocortisone: IC<sub>50</sub> 34.26 μmol·L<sup>−1</sup>), respectively. Additionally, they also partially reduced the secretion of IL-6.</div></div>\",\"PeriodicalId\":10002,\"journal\":{\"name\":\"Chinese Journal of Natural Medicines\",\"volume\":\"22 10\",\"pages\":\"Pages 929-936\"},\"PeriodicalIF\":4.0000,\"publicationDate\":\"2024-10-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chinese Journal of Natural Medicines\",\"FirstCategoryId\":\"3\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S1875536424607235\",\"RegionNum\":2,\"RegionCategory\":\"医学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"INTEGRATIVE & COMPLEMENTARY MEDICINE\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chinese Journal of Natural Medicines","FirstCategoryId":"3","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S1875536424607235","RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"INTEGRATIVE & COMPLEMENTARY MEDICINE","Score":null,"Total":0}
Four new diarylheptanoids and two new terpenoids from the fruits of Alpinia oxyphylla and their anti-inflammatory activities
Four previously unreported diarylheptanoids (1a/1b−2a/2b), one undescribed sesquiterpenoid (8), one new diterpenoid (12), and twelve known analogs were isolated from the fruits of Alpinia oxyphylla. The structural elucidation of these compounds was achieved through a comprehensive analysis of spectroscopic data, single-crystal X-ray diffraction, electronic circular dichroism (ECD), and modified Mosher’s method. Enantiomeric mixtures (1a/1b, 2a/2b, 3a/3b, 4a/4b, and 5a/5b) were separated on a chiral column using acetonitrile-water mixtures as eluents. Among them, compounds 3a/3b and 4a/4b were isolated as optically pure enantiomers in the initial chiral separation. Furthermore, most of the isolates were evaluated for their inhibitory effects against the production of nitric oxide (NO) and interleukin-6 (IL-6) in lipopolysaccharide (LPS)-induced RAW264.7 macrophages. Interestingly, 2 and 4 showed significant inhibitory activities against NO production with IC50 values of 33.65 and 9.88 μmol·L−1 (hydrocortisone: IC50 34.26 μmol·L−1), respectively. Additionally, they also partially reduced the secretion of IL-6.
期刊介绍:
The Chinese Journal of Natural Medicines (CJNM), founded and sponsored in May 2003 by China Pharmaceutical University and the Chinese Pharmaceutical Association, is devoted to communication among pharmaceutical and medical scientists interested in the advancement of Traditional Chinese Medicines (TCM). CJNM publishes articles relating to a broad spectrum of bioactive natural products, leading compounds and medicines derived from Traditional Chinese Medicines (TCM).
Topics covered by the journal are: Resources of Traditional Chinese Medicines; Interaction and complexity of prescription; Natural Products Chemistry (including structure modification, semi-and total synthesis, bio-transformation); Pharmacology of natural products and prescription (including pharmacokinetics and toxicology); Pharmaceutics and Analytical Methods of natural products.