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奥利弗氏獐牙菜中的裂环烯醚萜苷及其生物活性。

Seco-iridoid glycosides from the Gentiana olivieri Griseb and their bioactivities.

机构信息

State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, People's Republic of China; University of Chinese Academy of Sciences, Beijing 100039, People's Republic of China.

State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, People's Republic of China.

出版信息

Phytochemistry. 2023 Nov;215:113839. doi: 10.1016/j.phytochem.2023.113839. Epub 2023 Aug 31.

DOI:10.1016/j.phytochem.2023.113839
PMID:37657663
Abstract

The ethanol extract of the Gentiana olivieri Griseb plant was subjected to an investigation to ascertain the presence of its iridoid constituents. By means of HPLC and TLC monitoring, a total of thirteen previously unreported seco-iridoid glucosides olivierisecoside A-M, as well as seven known seco-iridoid glycosides and one known iridoid glycoside were isolated. Their structures were elucidated by a comprehensive spectroscopic data analysis and ECD calculations. The absolute configuration of olivierisecoside D was further confirmed through single-crystal X-ray diffraction analysis. All the identified compounds were characterized as aromatic conjugated seco-iridoid glucosides, with olivierisecoside F-I representing a particularly rare subtype known as the morroniside type seco-iridoids. In vitro testing of the isolated compounds revealed their potential anti-inflammatory and hepatoprotective effects. The results showed olivieroside B and 6'-gentisoyl-8-epi-kingiside have good anti-inflammatory activities in LPS induced RAW264.7 cells. Additionally, olivierisecoside M exhibited some improvements in PA-induced L02 and HepG2 cells damage, known compound loganin showed slight hepatoprotective effect in PA-induced HepG2 cells damage.

摘要

对秦艽植物的乙醇提取物进行了研究,以确定其裂环环烯醚萜类成分的存在。通过 HPLC 和 TLC 监测,共分离得到 13 种以前未报道的裂环环烯醚萜葡萄糖苷 olivierisecoside A-M,以及 7 种已知的裂环环烯醚萜糖苷和 1 种已知的环烯醚萜糖苷。通过全面的光谱数据分析和 ECD 计算阐明了它们的结构。通过单晶 X 射线衍射分析进一步确定了 olivierisecoside D 的绝对构型。所有鉴定的化合物均被表征为芳香共轭裂环环烯醚萜葡萄糖苷,其中 olivierisecoside F-I 代表一种特别罕见的亚型,称为 morroniside 型裂环环烯醚萜。对分离化合物的体外测试表明它们具有潜在的抗炎和保肝作用。结果表明,olivieroside B 和 6'-gentisoyl-8-epi-kingiside 在 LPS 诱导的 RAW264.7 细胞中具有良好的抗炎活性。此外,olivierisecoside M 对 PA 诱导的 L02 和 HepG2 细胞损伤有一定的改善作用,已知化合物马钱苷对 PA 诱导的 HepG2 细胞损伤有轻微的保肝作用。

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