Novel neo-clerodane diterpenoids from Teucrium quadrifarium and their anti-ferroptosis effect

IF 4.8 3区化学 Q1 CHEMISTRY, MEDICINAL

Natural Products and Bioprospecting Pub Date : 2025-01-06 DOI:10.1007/s13659-024-00489-1

Huan Wang, Han-Fei Liu, Xiao-Qiao Yang, Yu-Qiong Liao, Fen-Cong Pan, Jin-Yu Li, Hua-Yong Lou, Wei-Dong Pan

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Abstract

Teucrifarides A–D (1–4), four previously unreported neo-clerodane-type diterpenoids, combined with sixteen known analogs (5–20), were purified from Teucrium quadrifarium. The absolute forma of compounds 1–4 were determined via spectroscopic and ECD calculation methods, together with X-ray crystallography experiments. Among them, compound 1 possessed a 5,20-epoxy ring featuring a unique cage-like 12-oxatricyclo [5.3.2.0^1,6]undecane skeleton. Meanwhile, 2 incorporated a 6,20-epoxy ring with a novel 12-oxatricyclo [6.2.2.0^2,7]undecane skeleton. Compounds 1 and 12 exhibited significant inhibitory effects against HT-22 cells ferroptosis induced by RSL3, with EC₅₀ values of 11.8 ± 1.0 μM, and 4.52 ± 1.24 μM, respectively. Moreover, ROS accumulation in HT22 cells treated with compound 1 was also observed.

Graphical Abstract

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新克罗丹二萜类化合物及其抗铁下垂作用

Teucrifarides A-D（1-4）是4个未被报道的新氯罗旦型二萜类化合物，与16个已知的类似物（5-20）结合从Teucrium quadriarium中分离得到。化合物1 ~ 4的绝对形态通过光谱学、ECD计算方法及x射线晶体学实验确定。其中，化合物1具有一个5,20-环氧环，具有独特的笼状12-氧杂环[5.3.2.01,6]十一烷骨架。与此同时，2将6,20-环氧环与新的12-氧环[6.2.2.02,7]十一烷骨架结合在一起。化合物1和12对RSL3诱导的HT-22细胞铁下垂有明显的抑制作用，EC50值分别为11.8±1.0 μM和4.52±1.24 μM。此外，化合物1处理的HT22细胞中也观察到ROS的积累。图形抽象

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来源期刊

Natural Products and Bioprospecting CHEMISTRY, MEDICINAL-

CiteScore

8.30

自引率

2.10%

发文量

审稿时长

13 weeks

期刊介绍： Natural Products and Bioprospecting serves as an international forum for essential research on natural products and focuses on, but is not limited to, the following aspects: Natural products: isolation and structure elucidation Natural products: synthesis Biological evaluation of biologically active natural products Bioorganic and medicinal chemistry Biosynthesis and microbiological transformation Fermentation and plant tissue cultures Bioprospecting of natural products from natural resources All research articles published in this journal have undergone rigorous peer review. In addition to original research articles, Natural Products and Bioprospecting publishes reviews and short communications, aiming to rapidly disseminate the research results of timely interest, and comprehensive reviews of emerging topics in all the areas of natural products. It is also an open access journal, which provides free access to its articles to anyone, anywhere.