Euphorhelipanes A and B, Triglyceride-Lowering <i>Euphorbia</i> Diterpenoids with a Bicyclo[4.3.0]nonane Core from <i>Euphorbia helioscopia</i>

Li, Wei; Tang, Ya-Qi; Chen, Shixin; Tang, Gui‐Hua; Gan, Li‐She; Li, Chan; Rao, Yong; Huang, Zhi‐Shu; Yin, Sheng

doi:10.1021/acs.jnatprod.8b00780

Cited by 26 publications

(14 citation statements)

References 20 publications

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“…Euphorbia helioscopia L., a well-known medicinal herb widely distributed in Europe, Asia, and North Africa, has been used for many years by local populations as a folk medicine due to its various biological activities . Previous phytochemical investigations have revealed that the metabolites of this plant are characterized by multiesterified jatrophane diterpenes and their derivatives. , Recently, heliojatrones A and B, two jatrophane-derived diterpenes bearing an unprecedented densely functionalized bicyclo[8.3.0]tridecane framework, were discovered from this plant and are the sole examples of diterpenes possessing a 5/10 fused ring system . In an ongoing project to discover structurally unique and biologically significant metabolites from medicinal plants, E. helioscopia was selected for investigation.…”

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confidence: 99%

Macrocyclic Diterpenoids from Euphorbia helioscopia and Their Potential Anti-inflammatory Activity

Cheng

Song

et al. 2019

J. Nat. Prod.

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Guided by 1 H 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 lipopolysaccharidestimulated RAW 264.7 cells. Compound 1 showed an IC 50 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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confidence: 99%

Macrocyclic Diterpenoids from Euphorbia helioscopia and Their Potential Anti-inflammatory Activity

Cheng

Song

et al. 2019

J. Nat. Prod.

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“…The presence of 3,4-(methylenedioxy) cinnamyl moiety was reported for the first time in the species as seen in kansuijatrophanol C ( 179 ) and D ( 180 ) [ 65 ] jatrophane-type diterpenoids. Equally, from the whole plant ethanol extracts of E. helioscopia , euphorhelipanes A ( 244 ) and B ( 245 ) [ 99 ] diterpenoids with a 4-(5,5-dimethylheptan-2-yl)-2,7-dimethylbicyclo [4.3.0] nonane skeleton structure were isolated. These compounds are examples of unique diterpenes possessing a 5/6 fused carbon system isolated from Euphorbia species for the first time and are postulated to have originated from jatrophane.…”

Section: Lower Diterpenesmentioning

confidence: 99%

Euphorbia Diterpenes: An Update of Isolation, Structure, Pharmacological Activities and Structure–Activity Relationship

et al. 2021

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Euphorbia species have a rich history of ethnomedicinal use and ethnopharmacological applications in drug discovery. This is due to the presence of a wide range of diterpenes exhibiting great structural diversity and pharmacological activities. As a result, Euphorbia diterpenes have remained the focus of drug discovery investigations from natural products. The current review documents over 350 diterpenes, isolated from Euphorbia species, their structures, classification, biosynthetic pathways, and their structure–activity relationships for the period covering 2013–2020. Among the isolated diterpenes, over 20 skeletal structures were identified. Lathyrane, jatrophane, ingenane, ingenol, and ingol were identified as the major diterpenes in most Euphorbia species. Most of the isolated diterpenes were evaluated for their cytotoxicity activities, multidrug resistance abilities, and inhibitory activities in vitro, and reported good activities with significant half-inhibitory concentration (IC50) values ranging from 10–50 µM. The lathyranes, isopimaranes, and jatrophanes diterpenes were further found to show potent inhibition of P-glycoprotein, which is known to confer drug resistance abilities in cells leading to decreased cytotoxic effects. Structure–activity relationship (SAR) studies revealed the significance of a free hydroxyl group at position C-3 in enhancing the anticancer and anti-inflammatory activities and the negative effect it has in position C-2. Esterification of this functionality, in selected diterpenes, was found to enhance these activities. Thus, Euphorbia diterpenes offer a valuable source of lead compounds that could be investigated further as potential candidates for drug discovery.

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“…Combined with biosynthetic considerations, the relative configurations of these diterpenoids can be confidently correlated with their absolute configurations . Although jatrophane diterpenoids from E. helioscopia have been reported with various significant biological activities, − few studies have correlated these molecules with antipsoriasis effects. The petroleum ether fraction was identified as the active fraction of E. helioscopia , and isolation led to 17 new diterpenoids, named heliojatrone D ( 1 ) and helioscopids A–P ( 2 – 17 ), along with 11 known analogues ( 18 – 28 ).…”

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confidence: 99%

Jatrophane Diterpenoids with Kv1.3 Ion Channel Inhibitory Effects from Euphorbia helioscopia

et al. 2022

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Chemical investigation of bioactive components from the whole plant of Euphorbia helioscopia resulted in the isolation and identification of 17 new jatrophane diterpenoids, namely, heliojatrone D (1) and helioscopids A−P (2−17), along with 11 known analogues (18−28). The structural elucidation of the new diterpenoids was achieved by the comprehensive analysis of HRESIMS, NMR, and X-ray crystallographic data, as well as using electronic circular dichroism. Structurally, heliojatone D (1) is the fourth natural diterpenoid with a rare bicyclo[8.3.0]tridecane skeleton. The inhibitory effect of the isolated diterpenoids against Kv1.3 ion channels was evaluated in a human embryonic kidney 293 cell model transfected with plasmid encoding Kv1.3, resulting in the identification of a series of potent Kv1.3 ion channel inhibitors, with the most active ones (2 and 15) showing IC 50 values of 0.9 μM.

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Euphorhelipanes A and B, Triglyceride-Lowering Euphorbia Diterpenoids with a Bicyclo[4.3.0]nonane Core from Euphorbia helioscopia

Cited by 26 publications

References 20 publications

Macrocyclic Diterpenoids from Euphorbia helioscopia and Their Potential Anti-inflammatory Activity

Macrocyclic Diterpenoids from Euphorbia helioscopia and Their Potential Anti-inflammatory Activity

Euphorbia Diterpenes: An Update of Isolation, Structure, Pharmacological Activities and Structure–Activity Relationship

Jatrophane Diterpenoids with Kv1.3 Ion Channel Inhibitory Effects from Euphorbia helioscopia

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