Chemical Constituents from Euphorbia kansui

Zhang, Qiao; Zhou, Qin-Rong; Lou, Jian-Wei; Chen, Peidong; Yao, Weifeng; Tao, Weiwei; Tang, Yuping; Dai, Guan-Cheng; Wang, Kun; Zhang, Li

doi:10.3390/molecules22122176

Cited by 15 publications

(7 citation statements)

References 20 publications

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“…were consistent with those reported from the identical tetracyclic scaffold of tirucalla-8,24-diene-3β,11β-diol-7-one[56]. Euphorol M (3) was isolated as an optically active white amorphous solid, the molecular formula of which was established as C30H52O3 based on its negative-ion mode HRESIMS data (m/z 459.3803, calcd for C30H52O3-H, 459.3844).…”

supporting

confidence: 84%

Further terpenoids from Euphorbia tirucalli

et al. 2019

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The phytochemical investigation of Euphorbia tirucalli L. (Euphorbiaceae) yielded four new compounds, including a rare cadalene-type sesquiterpene (tirucadalenone), two tirucallane triterpenoids, euphorol L and euphorol M, with the latter being described as an epimeric mixture, and a euphane triterpene, namely, euphorol N, together with 7 known compounds. Their structures and absolute configurations were elucidated from analysis of 1D (1H, J-modulated 13 C) and 2D NMR (HSQC, HMBC and NOESY), high-resolution mass spectrometry (HRESIMS), optical rotation, and GIAO NMR shift calculation followed by CP3 analysis, along with comparison with literature reports. All these compounds were tested for cytotoxicity against K562, MCF-7 and/or and HepG2 tumor cell lines. Only tirucadalenone displayed a mild cytotoxic activity. Graphical abstractFour previously undescribed terpenoids: a cadalene (1), two tirucallanes (2 and 3a/3b), and a euphane (4) were isolated from Euphorbia tirucalli L. ACCEPTED MANUSCRIPT

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supporting

confidence: 84%

Further terpenoids from Euphorbia tirucalli

et al. 2019

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“…3- O -( 2′E,4′Z -Decadienoyl)-20- O -acetylingenol (3-O-EZ) was extracted from EK and purified in our laboratory (purity determined by HPLC-UV were more than 98%) [9]. Acetonitrile and formic acid of HPLC grade were purchased from Merck Co. (Darmstadt, Germany).…”

Section: Methodsmentioning

confidence: 99%

“…Previous studies showed that the structure type of the compounds in EK including diterpenes, triterpenes, flavonoids, phenolic and acids. Among them, diterpenoids (ingenane and jatrophane type) and triterpenoids are the major bioactive components from EK, and are responsible for the toxicity effect of EK [9,10]. In contrast to the triterpenoids, the diterpenoids of EK exhibit stronger cytotoxic activity, indicating that EK may exert systemic toxicity effect mainly though the actions of diterpenoids.…”

Section: Introductionmentioning

confidence: 99%

Toxicity Reduction of Euphorbia kansui Stir-Fried with Vinegar Based on Conversion of 3-O-(2′E,4′Z-Decadi-enoyl)-20-O-acetylingenol

Zhang

Zhou

et al. 2019

Molecules

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The dried roots of Euphorbia kansui S.L.Liou ex S.B.Ho have long been used to treat edema in China. However, the severe toxicity caused by Euphorbia kansui (EK) has seriously restricted its clinical application. Although EK was processed with vinegar to reduce its toxicity, the detailed mechanisms of attenuation in toxicity of EK stir-fried with vinegar (VEK) have not been well delineated. Diterpenoids are the main toxic ingredients of EK, and changes in these after processing may be the underlying mechanism of toxicity attenuation of VEK. 3-O-(2′E,4′Z-decadienoyl)-20-O-acetylingenol (3-O-EZ) is one of the diterpenoids derived from EK, and the content of 3-O-EZ was significantly reduced after processing. This study aims to explore the underlying mechanisms of toxicity reduction of VEK based on the change of 3-O-EZ after processing with vinegar. Based on the chemical structure of 3-O-EZ and the method of processing with vinegar, simulation experiments were carried out to confirm the presence of the product both in EK and VEK and to enrich the product. Then, the difference of peak area of 3-O-EZ and its hydrolysate in EK and VEK were detected by ultra-high-performance liquid chromatography (UPLC). Furthermore, the toxicity effect of 3-O-EZ and its hydrolysate, as well as the underlying mechanism, on zebrafish embryos were investigated. The findings showed that the diterpenoids (3-O-EZ) in EK can convert into less toxic ingenol in VEK after processing with vinegar; meanwhile, the content of ingenol in VEK was higher than that of EK. More interestingly, the ingenol exhibited less toxicity (acute toxicity, developmental toxicity and organic toxicity) than that of 3-O-EZ, and 3-O-EZ could increase malondialdehyde (MDA) content and reduce glutathione (GSH) content; cause embryo oxidative damage by inhibition of the succinate dehydrogenase (SDH) and superoxide dismutase (SOD) activity; and induce inflammation and apoptosis by elevation of IL-2 and IL-8 contents and activation of the caspase-3 and caspase-9 activity. Thus, this study contributes to our understanding of the mechanism of attenuation in toxicity of VEK, and provides the possibility of safe and rational use of EK in clinics.

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“…Euphorbia kansui Liou is a classical traditional Chinese medicine (TCM), which dried root has long been used to treat asthma, edema, ascites [1]. There are many secondary metabolites in E. kansui , diterpense and triterpenes are the main compounds, which show anti-virus, skin irritating and modulation of multidrug resistance effects [2,3,4].…”

Section: Introductionmentioning

confidence: 99%

MicroRNAome Profile of Euphorbia kansui in Response to Methyl Jasmonate

Tian

Zhang

et al. 2019

IJMS

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miRNAs play vital regulatory roles in different plant developmental stages and in plant response to biotic and abiotic stresses. However, information is limited on the miRNA regulatory mechanism to methyl jasmonate (MeJA). In this study, we used the microRNAome profile to illustrate the relevant regulatory mechanisms of Euphorbia kansui in response to methyl jasmonate (MeJA) through Illumina RNA-Seq. As a result, we identified 875 miRNAs corresponding to 11,277 target mRNAs, among them, 168 known miRNA families representing 6019 target mRNAs sequences were obtained. 452 miRNA-mRNA pairs presented an anti-correlationship (Cor < −0.50 and p-value of correlation ≤ 0.05). The miRNA with a fold change ≥ 2 and a p (p-Value) < 0.05 in pairwise comparison were identified as significant differentially expressed miRNAs (DEMs). The DEMs in MeJA treatment of 0, 24, 36 and 48 h were compared by using Short Time Expression Miner (STEM) cluster and 4 significant gene profiles (p-value ≤ 0.02) were identified. Through the kyoto encyclopedia of genes and genomes (KEGG) pathway and gene ontology (GO) enrichment analysis on all miRNA targets, we identified 33 mRNAs in terpenoid biosynthesis, which were regulated by miRNAs under MeJA treatment, so the miRNA maybe involved in the response of E. kansui plant to exogenous MeJA and the results would provide very useful information on illustrating the regulatory mechanism of E. kansui and also provide an overall view of the miRNAs response to MeJA stress of a non-model plant.

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Chemical Constituents from Euphorbia kansui

Cited by 15 publications

References 20 publications

Further terpenoids from Euphorbia tirucalli

Further terpenoids from Euphorbia tirucalli

Toxicity Reduction of Euphorbia kansui Stir-Fried with Vinegar Based on Conversion of 3-O-(2′E,4′Z-Decadi-enoyl)-20-O-acetylingenol

MicroRNAome Profile of Euphorbia kansui in Response to Methyl Jasmonate

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