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中国特有的珍稀濒危植物的植物化学与生物学研究。第二十五部分。来自中国秦岭地区两种濒危松科植物的结构多样的三萜类和二萜类化合物及其生物活性。

Phytochemical and biological studies on rare and endangered plants endemic to China. Part XXV. Structurally diverse triterpenoids and diterpenoids from two endangered Pinaceae plants endemic to the Chinese Qinling Mountains and their bioactivities.

作者信息

Jiang Wei, Zhao Ze-Yu, Tong Ying-Peng, Ma Guang-Lei, Zang Yi, Osman Ezzat E A, Jin Ze-Xin, Xiong Juan, Li Jia, Hu Jin-Feng

机构信息

Institute of Natural Medicine and Health Products, School of Pharmaceutical Sciences, Zhejiang Provincial Key Laboratory of Plant Ecology and Conservation, Taizhou University, Zhejiang, 318000, PR China; School of Life Science and Technology, Wuhan Polytechnic University, Hubei, 430023, PR China; Department of Natural Medicine, School of Pharmacy, Fudan University, Shanghai, 201203, PR China.

Institute of Natural Medicine and Health Products, School of Pharmaceutical Sciences, Zhejiang Provincial Key Laboratory of Plant Ecology and Conservation, Taizhou University, Zhejiang, 318000, PR China; Department of Natural Medicine, School of Pharmacy, Fudan University, Shanghai, 201203, PR China.

出版信息

Phytochemistry. 2022 Nov;203:113366. doi: 10.1016/j.phytochem.2022.113366. Epub 2022 Aug 12.

Abstract

A joint phytochemical investigation on the MeOH extracts of the twigs and needles of two endangered Pinaceae plants endemic to the Chinese Qinling Mountains, Picea neoveitchii (an evergreen spruce) and Larix potaninii var. chinensis (a deciduous larch), led to the isolation and characterization of 34 and 24 structurally diverse terpenoids, respectively. Among them, seven are previously undescribed, including a picane-type [i.e., 14(13 → 12)abeo-12αH-serratane] (neoveitchin A) and a serratane-type (neoveitchin B) triterpenoids, and an abietane-type (neoveitchin C) as well as four labdane-type (potalarxins A-D) diterpenoids. Their structures and absolute configurations were established by extensive spectroscopic methods and/or X-ray diffraction analyses. All isolates were evaluated for their inhibitory activities against the human protein tyrosine phosphatase 1B (PTP1B). Serrat-14-en-3α,21β-diol, betulinic acid, 3β-hydroxy-11-ursen-13(28)-olide, ursolic acid, and oleanolic acid were found to have considerable inhibitory effects against PTP1B, with IC values ranging from 1.1 to 18.1 μM. The interactions of the bioactive triterpenoids with PTP1B were thereafter performed by employing molecular docking studies. In addition, 7-oxo-dehydroabietic acid (an abietane-type diterpenoid) and mangiferonic acid (a cycloartane-type triterpenoid) inhibited acetyl-coenzyme A carboxylase 1 (ACC1), with IC values of 3.4 and 6.6 μM, respectively.

摘要

对中国秦岭地区特有的两种濒危松科植物——新麦吊云杉(一种常绿云杉)和太白红杉(一种落叶落叶松)的嫩枝和针叶的甲醇提取物进行了联合植物化学研究,分别分离并鉴定了34种和24种结构多样的萜类化合物。其中,有7种是以前未描述过的,包括一种樟烷型[即14(13→12)失碳-12αH-锯齿烷](新麦吊云杉素A)和一种锯齿烷型(新麦吊云杉素B)三萜类化合物,以及一种枞酸型(新麦吊云杉素C)和四种半日花烷型(太白红杉素A-D)二萜类化合物。通过广泛的光谱方法和/或X射线衍射分析确定了它们的结构和绝对构型。对所有分离物进行了针对人蛋白酪氨酸磷酸酶1B(PTP1B)的抑制活性评估。发现锯齿-14-烯-3α,21β-二醇、桦木酸、3β-羟基-11-乌苏-13(28)-烯酸、熊果酸和齐墩果酸对PTP1B具有相当大的抑制作用,IC值范围为1.1至18.1μM。此后,通过分子对接研究对生物活性三萜类化合物与PTP1B的相互作用进行了研究。此外,7-氧代脱氢枞酸(一种枞酸型二萜类化合物)和芒果酮酸(一种环阿尔廷烷型三萜类化合物)抑制乙酰辅酶A羧化酶1(ACC1),IC值分别为3.4和6.6μM。

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