Macrocyclic Diterpenoids from Euphorbia helioscopia and Their Potential Anti-inflammatory Activity
Posted on 2019-09-24 - 19:37
Guided by 1H NMR spectroscopic
experiments using the
aromatic protons as probes, 11 macrocyclic diterpenes (1–11) were isolated from the aerial parts of Euphorbia helioscopia. Their full three-dimensional structures,
including absolute configurations, were established unambiguously
by spectroscopic analysis and single-crystal X-ray crystallographic
experiments. Among the isolated compounds, compound 1 is the third member thus far of a rare class of Euphorbia diterpenes featuring an unusual 5/10 fused ring system, and 2–4 are new jatrophane diterpenes. Based
on the NMR data of the jatrophane diterpenes obtained in this study
as well as those with crystallographic structures reported in the
literature, the correlations of the chemical shifts of the relevant
carbons and the configurations of C-2, C-13, and C-14 of their flexible
macrocyclic ring were considered. Moreover, the anti-inflammatory
activities of 1–11 were investigated
by monitoring their inhibitory effects on nitric oxide production
in lipopolysaccharide-stimulated RAW 264.7 cells. Compound 1 showed an IC50 of 7.4 ± 0.6 μM, which might
be related to the regulation of the NF-κB signaling pathway
by suppressing the translocation of the p65 subunit and the consequent
reduction of IL-6 and TNF-α secretions.
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Su, Jun-Cheng; Cheng, Wen; Song, Jian-Guo; Zhong, Yuan-Lin; Huang, Xiao-Jun; Jiang, Ren-Wang; et al. (2019). Macrocyclic Diterpenoids from Euphorbia helioscopia and Their Potential Anti-inflammatory Activity. ACS Publications. Collection. https://doi.org/10.1021/acs.jnatprod.9b00519
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AUTHORS (10)
JS
Jun-Cheng Su
WC
Wen Cheng
JS
Jian-Guo Song
YZ
Yuan-Lin Zhong
XH
Xiao-Jun Huang
RJ
Ren-Wang Jiang
YL
Yao-Lan Li
ML
Man-Mei Li
WY
Wen-Cai Ye
YW
Ying Wang