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来自……腐根的新的氢过氧化和20,24-环氧达玛烷三萜类化合物

New hydroperoxylated and 20,24-epoxylated dammarane triterpenes from the rot roots of .

作者信息

Shang Jia-Huan, Sun Wen-Jie, Zhu Hong-Tao, Wang Dong, Yang Chong-Ren, Zhang Ying-Jun

机构信息

State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China.

University of Chinese Academy of Sciences, Beijing, China.

出版信息

J Ginseng Res. 2020 May;44(3):405-412. doi: 10.1016/j.jgr.2019.01.008. Epub 2019 Feb 6.

Abstract

BACKGROUND

Root rot is a serious destructive disease of , a famous cultivated araliaceous herb called Sanqi or Tianqi in Southwest China.

METHODS

The chemical substances of Sanqi rot roots were explored by chromatographic techniques. MS, 1D/2D-NMR, and single crystal X-ray diffraction were applied to determine the structures. Murine macrophage RAW264.7 and five human cancer cell lines were used separately for evaluating the antiinflammatory and cytotoxic activities.

RESULTS AND CONCLUSION

Thirty dammarane-type triterpenes and saponins were isolated from the rot roots of . Among them, seven triterpenes, namely, 20()-dammar-25-ene-24()-hydroperoxyl-3,6,12,20-tetrol (), 20()-dammar-3-oxo-23-ene-25-hydroperoxyl-6,12,20-triol (), 20()-dammar-12-oxo-23-ene-25-hydroperoxyl-3,6,20-triol (), 20()-dammar-3-oxo-23-ene-25-hydroperoxyl-12,20-diol (), 20(),24()-epoxy-3,4--dammar-25-hydroxy-12-one-3-oic acid (), 20(),24()-epoxy-3,4--dammar-25-hydroxy-12-one-3-oic acid methyl ester (), and 6-hydroxy-22,23,24,25,26,27-hexanordammar-3,12,20-trione (), are new compounds. In addition, 12 known ones (- and -) were reported in Sanqi for the first time. The new Compound showed comparable antiinflammatory activity on inhibition of NO production to the positive control, whereas the known compounds , , , and displayed moderate cytotoxicities against five human cancer cell lines. The results will provide scientific basis for understanding the chemical constituents of Sanqi rot roots and new candidates for searching antiinflammatory and antitumor agents.

摘要

背景

根腐病是中国西南部著名的栽培五加科草本植物三七(又称田七)的一种严重破坏性病害。

方法

采用色谱技术对三七腐烂根中的化学物质进行探索。应用质谱、一维/二维核磁共振和单晶X射线衍射来确定结构。分别使用小鼠巨噬细胞RAW264.7和五种人类癌细胞系来评估抗炎和细胞毒活性。

结果与结论

从三七腐烂根中分离出30种达玛烷型三萜和皂苷。其中,七种三萜,即20(S)-达玛-25-烯-24(R)-氢过氧基-3,6,12,20-四醇(化合物1)、20(S)-达玛-3-氧代-23-烯-25-氢过氧基-6,12,20-三醇(化合物2)、20(S)-达玛-12-氧代-23-烯-25-氢过氧基-3,6,20-三醇(化合物3)、20(S)-达玛-3-氧代-23-烯-25-氢过氧基-12,20-二醇(化合物4)、20(S),24(R)-环氧-3,4-开环-达玛-25-羟基-12-酮-3-酸(化合物5)、20(S),24(R)-环氧-3,4-开环-达玛-25-羟基-12-酮-3-酸甲酯(化合物6)和6-羟基-22,23,24,25,26,27-六去甲达玛-3,12,20-三酮(化合物7),是新化合物。此外,12种已知化合物(化合物8至化合物19)首次在三七中被报道。新化合物7在抑制NO产生方面表现出与阳性对照相当的抗炎活性,而已知化合物8、9、10和11对五种人类癌细胞系显示出中等细胞毒性。这些结果将为了解三七腐烂根的化学成分提供科学依据,并为寻找抗炎和抗肿瘤药物提供新的候选化合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7035/7195571/8ff47cf2f9f4/gr1.jpg

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