Anti-inflammatory 5,6,7,8-tetrahydro-2-(2-phenylethyl) chromone derivatives from the stems of Aquilaria sinensis.

IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL
Xia Liu, Min Yu, Jie Chen, Bin Hu, Jia-Bo Huang, Wei-Qun Yang, Zhong-Xiang Zhao
{"title":"Anti-inflammatory 5,6,7,8-tetrahydro-2-(2-phenylethyl) chromone derivatives from the stems of Aquilaria sinensis.","authors":"Xia Liu, Min Yu, Jie Chen, Bin Hu, Jia-Bo Huang, Wei-Qun Yang, Zhong-Xiang Zhao","doi":"10.1016/j.fitote.2024.106312","DOIUrl":null,"url":null,"abstract":"<p><p>Three previously undescribed 5,6,7,8-tetrahydro-2-(2-phenylethyl)chromones, (5S,6R,7S,8S)-8-chloro-5-ethoxy-6,7-dihydroxy-2-[2-(4'-methoxyphenyl)ethyl]-5,6,7,8-tetrahydrochromone (1), (5R,6S,7R,8R)-8-chloro-5-ethoxy-6,7-dihydroxy-2-(2- phenylethyl)-5,6,7,8-tetrahydrochromone (2), (5S,6R,7S,8R)-5,8-dichloro-6,7- dihydroxy-2-[2-(4'-methoxyphenyl)ethyl]-5,6,7,8-tetrahydrochromone (3), and 28 known analogues (4-31) were isolated from the stems of Aquilaria sinensis. Their structures were characterized by the spectroscopic methods, and the absolute configuration was resolved by circular dichroism (CD) spectroscopy. Bioactivity evaluation indicated that compounds 3-8 had significant inhibition effect in the production of NO in an inflammatory cell model with relatively lower IC<sub>50</sub> values of 5.54, 11.44, 3.68, 7.15, 10.26 and 13.04 μM, respectively, compared to the positive control Indomethacin (IC<sub>50</sub> = 23.03 μM).</p>","PeriodicalId":12147,"journal":{"name":"Fitoterapia","volume":" ","pages":"106312"},"PeriodicalIF":2.5000,"publicationDate":"2024-11-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Fitoterapia","FirstCategoryId":"3","ListUrlMain":"https://doi.org/10.1016/j.fitote.2024.106312","RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
引用次数: 0

Abstract

Three previously undescribed 5,6,7,8-tetrahydro-2-(2-phenylethyl)chromones, (5S,6R,7S,8S)-8-chloro-5-ethoxy-6,7-dihydroxy-2-[2-(4'-methoxyphenyl)ethyl]-5,6,7,8-tetrahydrochromone (1), (5R,6S,7R,8R)-8-chloro-5-ethoxy-6,7-dihydroxy-2-(2- phenylethyl)-5,6,7,8-tetrahydrochromone (2), (5S,6R,7S,8R)-5,8-dichloro-6,7- dihydroxy-2-[2-(4'-methoxyphenyl)ethyl]-5,6,7,8-tetrahydrochromone (3), and 28 known analogues (4-31) were isolated from the stems of Aquilaria sinensis. Their structures were characterized by the spectroscopic methods, and the absolute configuration was resolved by circular dichroism (CD) spectroscopy. Bioactivity evaluation indicated that compounds 3-8 had significant inhibition effect in the production of NO in an inflammatory cell model with relatively lower IC50 values of 5.54, 11.44, 3.68, 7.15, 10.26 and 13.04 μM, respectively, compared to the positive control Indomethacin (IC50 = 23.03 μM).

从旱莲草茎中提取的 5,6,7,8-四氢-2-(2-苯基乙基)铬酮衍生物具有抗炎作用。
(5R,6S,7R,8R)-8-氯-5-乙氧基-6,7-二羟基-2-(2-苯基乙基)-5,6,7,8-四氢苯并吡喃酮(2)、(5S,6R,7S,8R)-5,8-二氯-6,7-二羟基-2-[2-(4'-甲氧基苯基)乙基]-5,6,7,8-四氢苯并吡喃酮(3),以及 28 种已知的类似物(4-31)。通过光谱方法对它们的结构进行了表征,并通过圆二色性(CD)光谱解析了它们的绝对构型。生物活性评价表明,化合物 3-8 在炎症细胞模型中对 NO 的产生有显著的抑制作用,与阳性对照吲哚美辛(IC50 = 23.03 μM)相比,其 IC50 值分别为 5.54、11.44、3.68、7.15、10.26 和 13.04 μM,相对较低。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 求助全文
来源期刊
Fitoterapia
Fitoterapia 医学-药学
CiteScore
5.80
自引率
2.90%
发文量
198
审稿时长
1.5 months
期刊介绍: Fitoterapia is a Journal dedicated to medicinal plants and to bioactive natural products of plant origin. It publishes original contributions in seven major areas: 1. Characterization of active ingredients of medicinal plants 2. Development of standardization method for bioactive plant extracts and natural products 3. Identification of bioactivity in plant extracts 4. Identification of targets and mechanism of activity of plant extracts 5. Production and genomic characterization of medicinal plants biomass 6. Chemistry and biochemistry of bioactive natural products of plant origin 7. Critical reviews of the historical, clinical and legal status of medicinal plants, and accounts on topical issues.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信