New Diterpenoids from<i>Euphorbia sieboldiana</i>

Jia, Zhong‐Jian; Ding, Yili

doi:10.1055/s-2006-960208

Cited by 21 publications

(13 citation statements)

References 2 publications

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“…The above mentioned spectroscopic feature, combined with the degrees of unsaturation, revealed that 3 should be an ent ‐atisane diterpene. Comparison of the NMR spectra of 3 with those of ent ‐atisane‐3 β ,16 α ,17‐triol showed that they are similar in structure. The difference is that the chemical shifts of the methyl C(19) have significantly shifted downfield in 3 as compared with that in ent ‐atisane‐3 β ,16 α ,17‐triol.…”

Section: Resultsmentioning

confidence: 79%

Terpenes from Euphorbia antiquorum and Their in Vitro Anti‐HIV Activity

Dong

Chen

et al. 2018

Chemistry & Biodiversity

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Three new compounds (1 - 3), including two euphane type triterpenes, 24,24-dimethoxy-25,26,27-trinoreuphan-3β-ol (1) and (24S)-24-hydroperoxyeupha-8,25-dien-3β-ol (2), and an ent-atisine diterpene, ent-atisane-3α,16α,17-triol (3), were isolated from an acetone extract of the stems of Euphorbia antiquorum, together with eight known diterpenes (4 - 11). The structures of compounds (1 - 11) were elucidated using NMR and MS spectroscopic methods. Compound 7 showed moderate activity against HIV-1 replication in vitro (EC = 1.38 μm).

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Section: Resultsmentioning

confidence: 79%

Terpenes from Euphorbia antiquorum and Their in Vitro Anti‐HIV Activity

Dong

Chen

et al. 2018

Chemistry & Biodiversity

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“…Fifteen known diterpenoids, namely, ingenol ( 3 ) [12], (3 β ,12 α )-3,12-dihydroxyisopimara-7,15-dien-2-one ( 7 ) [8], ent -l6 α ,17-dihydroxyatisan-3-one ( 9 ) [11], ent -(3 α ,5 β ,8 α ,9 β ,10 α ,12 α )-3-hydroxyatis-16-en-14-one ( 10 ) [8], ent -(5 β ,8 α ,9 β ,10 α ,11 α ,12 α )-11-hydroxyatis-16-ene-3,14-dione ( 11 ) [8], ent -(5 β ,8 α ,9 β ,10 α ,11 α ,12 α )-3,14-dioxoatis-16-en-11-yl acetate ( 12 ) [8], jolkinolide E ( 13 ) [13, 14], 7 β -hydroxy- ent -abieta-8(14),13(15)-dien-12 α ,16-olide ( 14 ) [15], pekinenal ( 15 ) [16], pekinenin A ( 16 ) [17], pekinenin D ( 17 ) [18], ent -l6 β ,17-isopropylidenedioxy kauran-3 β -ol ( 18 ) [19], jolkinol A ( 19 ) [20], jolkinol A′ ( 20 ) [20], and 3 β ,5 α ,20-trihydroxy-15 β -cinnamoyloxy-14-oxolathyra-6 Z ,12 E -diene ( 21 ) [21], were also isolated and identified by comparison of their spectroscopic data with those reported values in the literatures.…”

Section: Resultsmentioning

confidence: 99%

Antifeedant and Antiviral Diterpenoids from the Fresh Roots of Euphorbia jolkinii

Huang

Luo

et al. 2014

Nat. Prod. Bioprospect.

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The perennial herbaceous plant Euphorbia jolkinii (Euphorbiaceae) is a noxious weed widely distributed in the grasslands of northwestern Yunnan and has greatly threatened the local biodiversity. Phytochemical investigation on the fresh roots of E. jolkinii afforded six new diterpenoids 1, 2, 4–6, and 8, together with fifteen known diterpenoids. Their structures were elucidated on the basis of 1D and 2D NMR and other spectroscopic methods. Casbane, lathyrane, abietane, and ent-kaurane diterpenoids were reported from this plant for the first time. Selected compounds were evaluated for their antifeedant and anti-RSV (respiratory syncytial virus) activities. Compound 2 and ingenol (3) exhibited moderate antifeedant activity against a generalist insect herbivore, Spodoptera exigua, with EC50 values of 17.88 and 17.71 μg/cm2 respectively. Compound 19 showed significant anti-RSV activity, with 50 % inhibition (IC50) value of 10.0 μM and selective index of 8.0. Compounds 1 and 2 were less active against RSV virus, both with IC50 value of 25 μM, and with selective indices of 1.0 and 3.2 respectively. These findings provided new evidence for the biological functions and utilization of the diversified diterpenoid metabolites in the roots of this rich but harmful plant.Graphical AbstractElectronic supplementary materialThe online version of this article (doi:10.1007/s13659-014-0009-3) contains supplementary material, which is available to authorized users.

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“…The 1 H-NMR and 13 C-NMR data of hydrolysate are shown in Table S1 and Figure S3. Compared to the literature [18,19], the hydrolysate was determined to be ingenol and the conversion process between compounds 3-O-EZ and ingenol is shown in Figure 1.…”

Section: Resultsmentioning

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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New Diterpenoids fromEuphorbia sieboldiana

Cited by 21 publications

References 2 publications

Terpenes from Euphorbia antiquorum and Their in Vitro Anti‐HIV Activity

Terpenes from Euphorbia antiquorum and Their in Vitro Anti‐HIV Activity

Antifeedant and Antiviral Diterpenoids from the Fresh Roots of Euphorbia jolkinii

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

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