3-O-(2'E ,4'Z-decadienoyl)-20-O-acetylingenol
3-O-(2′E,4′Z-decadienoyl)-20-O-acetylingenol, one toxic terpenoid from raw Gansui. It has strong cytotoxicity against human normal cell lines L-O2 and GES-1 with dose-dependent relationships .
It shows antinematodal activity against the nematode, Bursaphelenchus xylophilus, at a minimum effective dose (MED) of 5 microg/cotton ball. 3-O-(2'E,4'Z-decadienoyl)-20-O-acetylingenol induces the cytotoxicity of intestinal epithelial cells of rats (IEC-6 cells) depends on induction of cell apoptosis via mitochondrial pathway and cell cycle arrest.3-O-(2'E,4'Z-decadienoyl)-20-O-acetylingenol, kansuinine B and kansuinine A can markedly promote SPL proliferation and NO production by PMphi at concentrations from 0.78 to 12.50 microg/mL, hence the they are believed to be important proinflammatory components of the roots of E. kansui.
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Ultra-performance liquid chromatography-quadrupole/time-of-flight mass spectrometry analysis of the impact of processing on toxic components of Kansui Radix[Reference:
WebLink]
Kansui Radix (Gansui in Chinese), the dried tuber of Euphorbia kansui, is a Chinese medicinal herb commonly used for the treatment of oedema and ascites with dyspnea. Because of its toxic nature, the herb is usually processed with vinegar to reduce the toxicity. A report has shown that the contents of toxic terpenoids in Gansui decreased after processing with vinegar. However, comprehensive comparison of the chemical profiles between vinegar-processed and raw Gansui has not yet been conducted.
METHODS AND RESULTS:
An ultra-high-performance liquid chromatography in conjunction with ultra-high resolution quadrupole time-of-flight mass spectrometry (UHPLC UHD Q-TOF MS/MS) method was developed for the analysis of chemical profiles of vinegar-processed and raw Gansui in this study.Results showed that processing with vinegar caused conspicuous chemical changes. Among the altered components,
11 toxic terpenoids, 3-O-benzoyl-13-O- dodecanoylingenol/20-O-benzoyl-13-O-dodecanoylingenol, kansuinine D, kansuinine A, 3-O-benzoyl-13-O-dodecanoylingenol/20-O-benzoyl-13-O-dodecanoylingenol, 3-O- benzoylingenol/20-O-benzoylingenol, 20-O-(2′E,4′Z-decadienoyl)ingenol/20-O-(2′E,4′E- decadienoyl)ingenol/3-O-(2′E,4′Z-decadienoyl)ingenol/3-O-(2′E,4′E-decadienoyl)ingenol, 3-O-(2'E ,4'Z-decadienoyl)-20-deoxyingenol,3-O-(2′E,4′Z-,ecadienoyl)-5-O-acetylingenol,3-O-(2'E ,4'Z-decadienoyl)-20-O-acetylingenol ,3-O-(2,3-dimethylbutanoyl)-13-O-dodecanoylingenol, were tentatively identified. The contents of most of these terpenoids were obviously decreased after processing with reductions of 6.66–95.25 %.
CONCLUSIONS:
Our findings could help us understand the chemical basis for the toxicity reduction of Gansui afforded by processing with vinegar. Further investigations are warranted to establish the relationship between processing-induced chemical changes and the reduction of toxicity of Gansui.
