Diterpenes from Euphorbia segetalis

Jakupovic, Jasmin; Jeske, Frank; Morgenstern, T.; Tsichritzis, F.; Marco, J. Alberto; Berendsohn, Walter G.

doi:10.1016/s0031-9422(97)00830-3

Cited by 71 publications

(68 citation statements)

References 14 publications

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“…The present results are in agreement with the previously-reported isolation of ingenol-3-mebutate (25) in E. peplus extract [56], and also the isolation of other ingenane esters in E. peplus and in E. segetalis extracts [57,58]. The detection of 13-O-isobutyryl-12-deoxyphorbol-20-acetate (22) was also supported by the isolation of dideoxyphorbol esters in E. pithyusa ssp.…”

Section: Analysis Of Euphorbia Extracts Using Targeted Lc-ms 2 Methodssupporting

confidence: 93%

LC-MS2-Based dereplication of Euphorbia extracts with anti-Chikungunya virus activity

et al. 2015

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Recently, phorbol esters from Euphorbiaceae have been shown to elicit potent and selective antiviral activity on the replication of Chikungunya virus (CHIKV) in cell culture. With the objective to found new compounds with anti-CHIKV activities, 45 extracts from various plant parts of 11 Mediterranean Euphorbia and one Mercurialis species were evaluated for selective inhibition of CHIKV replication. All EtOAc extracts, especially those prepared from latex, exhibited significant and selective antiviral activity in a Chikungunya virus-cell-based assay. An LC-MS(2) dereplication method was then developed to investigate whether known diterpenoids with anti-CHIKV activity, such as the potent anti-CHIKV 12-O-tetradecanoylphorbol-13-acetate (TPA), phorbol-12,13-didecanoate, and prostratin as well as 24 other commercially available diterpenoids of tigliane-, ingenane-, and daphnane-type for which the anti-CHIKV activity have been established in advance (Nothias-Scaglia et al. 2015), were present in the Euphorbia extracts. Only ingenol-3-mebutate, 13-O-isobutyryl-12-deoxyphorbol-20-acetate, and ingenol-3,20-dibenzoate, all exhibiting weak anti-CHIKV activities, were detected in the EtOAc extracts of Euphorbia peplus, Euphorbia segetalis ssp. pinea, and Euphorbia pithyusa ssp. pithyusa. Given the potent anti-CHIKV activities of these Euphorbia extracts, the present study suggested that their antiviral activities are probably due to untargeted diterpenoids.

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Section: Analysis Of Euphorbia Extracts Using Targeted Lc-ms 2 Methodssupporting

confidence: 93%

LC-MS2-Based dereplication of Euphorbia extracts with anti-Chikungunya virus activity

et al. 2015

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“…The IR spectrum of 1 exhibited the characteristic absorptions of a hydroxyl group, carbonyl groups and an aromatic ring. Its EI mass spectrum displayed a weak molecular ion peak at m/z = 656, a base peak at m/ z = 105 [C 6 , [9], [13]. When comparing the NMR spectra, the Me-16, which appears as a doublet (d = 0.85, J = 7.2 Hz) and has a 13 C resonance at d C = 10.2 in compound 2, is displayed as a lower field singlet (d = 1.57) and located at an oxygenated carbon (d C 89.8), in the spectrum of portlandicine.…”

Section: Resultsmentioning

confidence: 99%

“…The relative stereochemistry of 1 was deduced from a NOESY spectrum and the J H-H values [8], [9], [13]. The NOE interactions of the a-oriented H-4, taken as a reference point on a biogenetic basis [14], Compounds 1 ± 3 were examined for their MDR-reversing activity on L5178 mouse lymphoma cells.…”

Section: Resultsmentioning

confidence: 99%

Rearranged Jatrophane-Type Diterpenes fromEuphorbiaSpecies. Evaluation of their Effects on the Reversal of Multidrug Resistance

et al. 2004

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The rearranged jatrophane-type diterpenes ( 1 - 3), isolated from the Me (2)CO extracts of Euphorbia portlandica and Euphorbia segetalis, were examined for their effects on multidrug resistance (MDR) in mouse lymphoma cells. Compounds 2 and 3 revealed to be active with the latter being more active than the positive control verapamil, a known resistance modifier. The new compound 1, named portlandicine, was isolated from Euphorbia portlandica and its structure characterised by high-field NMR spectroscopic methods including 2D NMR techniques: COSY, HMQC, HMBC and NOESY. The known diterpene 2, together with aleuritolic acid ( 4), oleanolic acid ( 5), and betulin diacetate ( 6), were also isolated from the same species.

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“…The use of Euphorbia species in the remedy of skin illness and asthma has been postponed [14][15][16]. Previous phytochemical studies on E. paralias led to the identification of several terpenes such as pre-segetanin, segetanin A, segetanin B [17], segetenes A, segetenes B, paralinone A, paralinone B [18], segetane diterpenes, jatrophanes and paralianes [19][20][21][22][23]. Some flavonoids were isolated from this plant, such as quercetin, hyperoside and kaempferol 3-β-D-glucoside [24]; one phytosterol was isolated, β-sitosterol [24].…”

Section: Introductionmentioning

confidence: 99%

Total phenolic compounds, antioxidant potential and α-glucosidase inhibition by Tunisian Euphorbia paralias L.

Hlila¹,

Majouli²,

Harzallah‐Skhiri³

et al. 2016

J Coast Life Med

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Diterpenes from Euphorbia segetalis

Cited by 71 publications

References 14 publications

LC-MS2-Based dereplication of Euphorbia extracts with anti-Chikungunya virus activity

LC-MS2-Based dereplication of Euphorbia extracts with anti-Chikungunya virus activity

Rearranged Jatrophane-Type Diterpenes fromEuphorbiaSpecies. Evaluation of their Effects on the Reversal of Multidrug Resistance

Total phenolic compounds, antioxidant potential and α-glucosidase inhibition by Tunisian Euphorbia paralias L.

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