Highly oxygenated and structurally diverse diterpenoids from Euphorbia helioscopia

Wang, Wan-Ping; Jiang, Kun; Zhang, Ping; Shen, Kaikai; Qu, Shi‐Jin; Yu, Xiaoping; Tan, Chen

doi:10.1016/j.phytochem.2017.10.012

Cited by 43 publications

(23 citation statements)

References 23 publications

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“…All of the NMR spectroscopic evidence led to the establishment of an ent-atisane-type diterpenoid scaffold for 1, as depicted in Figure 1. 18,19,43 The cross-peaks in the NOESY spectrum and Chem3D simulations permitted the elucidation of the configuration of compound 1. The NOE interactions observed for H 3 -18/H- regarded as trans-fused, with H-9 in a β-position, the C-13−C-14 bridge linkage moiety on its α-face, and the C-19 hydroxymethyl group found to occupy an α-axial position.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Bioactive Diterpenoids from the Stems of Euphorbia antiquorum

Liang

Shi

et al. 2019

J. Nat. Prod.

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A total of 18 diterpenoids, including 10 new analogues (1−10), were isolated from Euphorbia antiquorum. The structures were characterized by spectroscopic techniques, and circular dichroism data analysis was adopted to confirm the absolute configurations of 1−10. Compounds 1− 9 were classified as ent-atisane diterpenoids, and 10 was assigned as an ent-kaurane diterpenoid. The biological evaluation of nitric oxide (NO) production inhibition was conducted, and all of these isolates showed the property of inhibiting NO generation in lipopolysaccharide-induced BV-2 cells. Further research on molecular docking disclosed the affinities between the diterpenoids obtained and inducible nitric oxide synthase.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Bioactive Diterpenoids from the Stems of Euphorbia antiquorum

Liang

Shi

et al. 2019

J. Nat. Prod.

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“…30 Compound 6 (anomaluone) was obtained as white powder and its molecular formula of C 20 analysis of NMR data revealed 6 to be an entkaurane-type diterpenoid and reported in the literature as anomaluone (please see supplemental materials S1-S3). 4,10 The configuration of compound 6 was confirmed by ROESY experiment between H-18/H-5, H-5/H-9, H-9/H-15, H-17/ H-14β, H-14α/H-20, H-20/H-19, 31 shown in Figure 1(b), and negative optical rotation [α] 20 D -75.9 (c 0.32, MeOH), agreed with the majority of entkauranes characterized for negative optical rotation. 9 Compound 7 (16-epiabbeokutone), white powder, had a molecular formula of C 20 H 32 O 3 based on the [M + ] at m/z 320.2348 (calculated for, 320.2346) in the HRTOFMS.…”

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confidence: 85%

An Antiproliferative ent-Kaurane Diterpene Isolated from the Roots of Mallotus japonicus Induced Apoptosis in Leukemic Cells

Lee

Thủy

Lee

et al. 2020

Natural Product Communications

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Mallotus japonicus has been evaluated for the treatment of dermatitis, inflammatory conditions, and cancer. Diterpenes, one of the major constituents of M. japonicus, possess various pharmacological effects. In this study, 2 known diterpenes, anomaluone (6) and 16-epiabbeokutone (7), along with other known compounds, 2-hydroxy ferulic acid (1), bergenin (2), gallocatechin (3), catechin (4), erythro,erythro-1-[4-[2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-(hydroxymethyl) ethoxy]-3,5-dimethoxyphenyl]-1,2,3- propanetriol (5), and gallincin (8), were isolated from M. japonicus. Cytotoxicity assays in blood cancer cell models demonstrated that M. japonicus compounds possess potent antiproliferative activity. In addition, treatment with compound 6 increased the number of apoptotic cells, led to cell-cycle arrest at the subG0/G1 phase, and decreased the number of cells in the S and G2/M phases. Compound 6 also displayed potent mitochondrial depolarization effects in Jurkat cells. These findings revealed that the cytotoxic effects of 6 were mediated by intracellular signaling, possibly through a mechanism involving upregulation of mitochondrial reactive oxygen species. Thus, compound 6 could be a potential multi-target therapeutic agent for leukemia.

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“…Euphorbiaceae; chloroplast genome; Illumina sequencing; phylogenetic analysis Euphorbia helioscopia Linn. is a traditional Chinese medicine of Euphorbiaceae, which contains terpenes (iridoids, sesquiterpenoids, diterpenoids, triterpenoids), steroids, flavonoids, acetophenones, tannins, phenylpropanoids, cerebrosides and so on (Shi et al 2008;Wang et al 2018). Euphorbia helioscopia L. was used to treat malignant tumors and chronic obstructive pulmonary diseases such as cough, phlegm-turbidity, asthma and chronic bronchitis (Chen et al 1979;Cheng et al 2015).…”

Section: Euphorbia Helioscopia;mentioning

confidence: 99%

“…Euphorbia helioscopia L. was used to treat malignant tumors and chronic obstructive pulmonary diseases such as cough, phlegm-turbidity, asthma and chronic bronchitis (Chen et al 1979;Cheng et al 2015). Modern pharmacological research shows that Euphorbia diterpenoids have anti-cancer effects (Wang et al 2018).…”

Section: Euphorbia Helioscopia;mentioning

confidence: 99%

Characterization of the complete chloroplast genome of Euphorbia helioscopia Linn. (Euphorbiaceae), a traditional Chinese medicine

Liang

Zhang

2019

Mitochondrial DNA Part B

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Euphorbia helioscopia Linn. known as a traditional Chinese medicine of Euphorbiaceae, which contains terpenes, steroids, flavonoids, acetophenones, tannins, phenylpropanoids, cerebrosides and so on. Euphorbia helioscopia L. was used to treat malignant tumors and chronic obstructive pulmonary diseases such as cough, phlegm-turbidity, asthma, and chronic bronchitis. The complete chloroplast genome was assembled by Illumina paired-end reads data. The length of circular cp genome distribution in 160,041 bp, containing a large single-copy region (LSC) of 88,832 bp, a small single-copy region (SSC) of 17,145 bp and a pair of inverted repeat (IR) regions of 27,032 bp. In addition, 11 genes possess a single intron, while the other two genes (ycf3, clpP) have a couple of introns. The GC content of entire Euphorbia helioscopia L. cp genome, LSC, SSC and IR regions are 35.9, 33.1, 30.3, and 42.3%, respectively. From the NJ phylogenetic tree analysis showed that Euphorbia helioscopia L. and Euphorbia esula are closely related to each other within the family Euphorbiaceae.

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Highly oxygenated and structurally diverse diterpenoids from Euphorbia helioscopia

Cited by 43 publications

References 23 publications

Bioactive Diterpenoids from the Stems of Euphorbia antiquorum

Bioactive Diterpenoids from the Stems of Euphorbia antiquorum

An Antiproliferative ent-Kaurane Diterpene Isolated from the Roots of Mallotus japonicus Induced Apoptosis in Leukemic Cells

Characterization of the complete chloroplast genome of Euphorbia helioscopia Linn. (Euphorbiaceae), a traditional Chinese medicine

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