Three rare anti-inflammatory sesquiterpene lactones from Magnolia grandiflora

IF 4 2区 医学 Q1 INTEGRATIVE & COMPLEMENTARY MEDICINE Chinese Journal of Natural Medicines Pub Date : 2024-03-01 DOI:10.1016/S1875-5364(24)60601-1
Shuangyu XU , Feng ZHANG , Linlan TAO , Yangming JIANG , Tao HUANG , Yanan LI , Zhanxing HU , Jue YANG , Xiaojiang HAO , Chunmao YUAN
{"title":"Three rare anti-inflammatory sesquiterpene lactones from Magnolia grandiflora","authors":"Shuangyu XU ,&nbsp;Feng ZHANG ,&nbsp;Linlan TAO ,&nbsp;Yangming JIANG ,&nbsp;Tao HUANG ,&nbsp;Yanan LI ,&nbsp;Zhanxing HU ,&nbsp;Jue YANG ,&nbsp;Xiaojiang HAO ,&nbsp;Chunmao YUAN","doi":"10.1016/S1875-5364(24)60601-1","DOIUrl":null,"url":null,"abstract":"<div><p>Four new sesquiterpene lactones (SLs) (<strong>1</strong>–<strong>4</strong>), along with a biosynthetically related SL (<strong>5</strong>), have been isolated from the leaves of <em>Magnolia grandiflora</em>. Magrandate A (<strong>1</strong>) is notable as the first C18 homogemarane type SL, featuring a unique 1,7-dioxaspiro[4.4]nonan-6-one core. Compounds <strong>2</strong> and <strong>3</strong>, representing the first instances of chlorine-substituted gemarane-type SL analogs in natural products, were also identified. The structures of these isolates were elucidated through a combination of spectroscopic data analysis, electronic circular dichroism calculations, and X-ray single-crystal diffraction analysis. All isolates demonstrated anti-inflammatory activity in lipopolysaccharide-stimulated RAW264.7 cells. Notably, <strong>3</strong>–<strong>5</strong> showed a significant inhibitory effect on nitric oxide production, with IC<sub>50</sub> values ranging from 0.79 to 4.73 μmol·L<sup>−1</sup>. Additionally, <strong>4</strong> and <strong>5</strong> exhibited moderate cytotoxic activities against three cancer cell lines, with IC<sub>50</sub> values between 3.09 and 11.23 μmol·L<sup>−1</sup>.</p></div>","PeriodicalId":10002,"journal":{"name":"Chinese Journal of Natural Medicines","volume":null,"pages":null},"PeriodicalIF":4.0000,"publicationDate":"2024-03-01","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/S1875536424606011","RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"INTEGRATIVE & COMPLEMENTARY MEDICINE","Score":null,"Total":0}
引用次数: 0

Abstract

Four new sesquiterpene lactones (SLs) (14), along with a biosynthetically related SL (5), have been isolated from the leaves of Magnolia grandiflora. Magrandate A (1) is notable as the first C18 homogemarane type SL, featuring a unique 1,7-dioxaspiro[4.4]nonan-6-one core. Compounds 2 and 3, representing the first instances of chlorine-substituted gemarane-type SL analogs in natural products, were also identified. The structures of these isolates were elucidated through a combination of spectroscopic data analysis, electronic circular dichroism calculations, and X-ray single-crystal diffraction analysis. All isolates demonstrated anti-inflammatory activity in lipopolysaccharide-stimulated RAW264.7 cells. Notably, 35 showed a significant inhibitory effect on nitric oxide production, with IC50 values ranging from 0.79 to 4.73 μmol·L−1. Additionally, 4 and 5 exhibited moderate cytotoxic activities against three cancer cell lines, with IC50 values between 3.09 and 11.23 μmol·L−1.

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
从广玉兰中提取的三种罕见的抗炎倍半萜内酯
从广玉兰的叶子中分离出了四种新的倍半萜内酯(SLs)(1-4)以及一种生物合成相关的 SL(5)。Magnrandate A(1)是第一个 C18 同根香豆内酯型 SL,具有独特的 1,7-二氧杂螺[4.4]壬烷-6-酮核心。化合物 2 和 3 也被鉴定出来,它们代表了天然产物中氯取代的吉玛烷型 SL 类似物的首次出现。通过结合光谱数据分析、电子圆二色性计算和 X 射线单晶衍射分析,阐明了这些分离物的结构。所有分离物在脂多糖刺激的 RAW264.7 细胞中都表现出抗炎活性。值得注意的是,3-5 对一氧化氮的产生有明显的抑制作用,IC50 值在 0.79 至 4.73 μmol-L-1 之间。此外,4 和 5 对三种癌细胞株具有中等程度的细胞毒性活性,IC50 值介于 3.09 和 11.23 μmol-L-1 之间。
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 去求助
来源期刊
Chinese Journal of Natural Medicines
Chinese Journal of Natural Medicines INTEGRATIVE & COMPLEMENTARY MEDICINE-PHARMACOLOGY & PHARMACY
CiteScore
7.50
自引率
4.30%
发文量
2235
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.
期刊最新文献
Advances in intelligent mass spectrometry data processing technology for in vivo analysis of natural medicines Chiral resolution of furofuran lignans and their derivatives from the stems of Dendrobium 'Sonia' Cyclocarysaponins A–J, dammarane-type triterpenoid glycosides from the leaves of Cyclocarya paliurus Four new diarylheptanoids and two new terpenoids from the fruits of Alpinia oxyphylla and their anti-inflammatory activities Highly oxygenated clerodane furanoditerpenoids from the leaves and twigs of Croton yunnanensis
×
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
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 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 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1