New cycloartane-type ester triterpenes from Euphorbia pterococca and biological evaluation

Benabdelaziz, Imane; Gómez‐Ruiz, Santiago; Benkhaled, Mohammed; Carralero, Sandra; Schenker, Patricia; Salm, Andrea; Gertsch, Jürg; Haba, Hamada

doi:10.1016/j.fitote.2018.02.027

Cited by 15 publications

(9 citation statements)

References 34 publications

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“…[21,22] The signals at δ H 3.28 (dd, J = 4.8, 11.1 Hz)/δ C 79.0 were assigned to an oxymethine at H-3/C-3, its large coupling constant value indicated a 3β-configured hydroxyl group. [23][24][25] H-3 exhibited 1 H-1 H COSY to H-2 and HMBC cross peaks to C-4, C-5, C-29, and C-30, assuring this assignment ( Figure 3). The signals at δ H 4.72 and 4.66 (each brs, H-21)/δ C 105.9 (C-21) and 157.0 (C-20) referred to the existence of an exomethylene moiety in 2.…”

Section: Characterization Of the Isolated Metabolitesmentioning

confidence: 63%

“…The 1 H NMR revealed a pair of doublets at δ H 0.55 and 0.33 (each d, J =3.4 Hz, H‐19a,b), which displayed HSQC correlations to the carbon at δ C 29.6 and HMBC cross peaks to C‐1, C‐5, C‐8, C‐9, and C‐10 (Figure ), characteristic of C‐9/C‐10 cyclopropyl methylene group of a cycloartan‐3‐ol triterpenoid . The signals at δ H 3.28 (dd, J =4.8, 11.1 Hz)/δ C 79.0 were assigned to an oxymethine at H‐3/C‐3, its large coupling constant value indicated a 3β‐configured hydroxyl group . H‐3 exhibited 1 H‐ 1 H COSY to H‐2 and HMBC cross peaks to C‐4, C‐5, C‐29, and C‐30, assuring this assignment (Figure ).…”

Section: Resultsmentioning

confidence: 99%

“…The NOESY cross peaks of H‐3/H‐5, H 3 ‐28, and H 3 ‐30 and H 3 ‐28/H‐17 designated the α‐orientation of these protons. Moreover, H‐29 exhibited a cross peak to H‐8 and H‐18, suggesting their β‐configuration . Thus, the cyclocuneatol structure was assigned as cycloart‐20‐en‐3β‐ol.…”

Section: Resultsmentioning

confidence: 99%

“…[26] 18, suggesting their β-configuration. [24,27,28] Thus, the cyclocuneatol structure was assigned as cycloart-20-en-3β-ol.…”

Section: Characterization Of the Isolated Metabolitesmentioning

confidence: 99%

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Cyclocuneatol and Cuneatannin, New Cycloartane Triterpenoid and Ellagitannin Glycoside from Euphorbia cuneata

et al. 2019

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Phytochemical investigation of the aerial parts of Euphorbia cuneata Vahl. (Euphorbiaceae) revealed new cycloartane triterpenoid, cyclocuneatol (2) and new ellagitannin glycoside, cuneatannin (11), along with nine known metabolites: β‐sitosterol (1), 3β‐hydroxycycloart‐25‐ene‐24‐one (3), cycloart‐25‐ene‐3β,24β‐diol (4), cycloart‐23Z‐ene‐3β,25‐diol (5), 2R‐naringenin (6), β‐sitosterol‐3‐O‐β‐D‐glucopyranoside (7), quercetin (8), kaempferol‐7‐O‐β‐glucoside (9), and 2R‐naringenin‐7‐O‐β‐glucoside (10). Their chemical structures were identified by detailed analyses of physical, chemical, and spectral data as well as comparison with literature. Their cytotoxic activity was assessed towards HepG2, MCF7, and HCT116 cancer cell lines by sulphorhodamine B test (SRB). It is noteworthy that 3 and 4 demonstrated the most significant activity towards HepG2, MCF7, and HCT116 cells (IC50 2.6, 2.7, and 2.4 μM, respectively for 3 and 3.4, 4.1, and 5.3 μM, respectively for 4) in comparison with doxorubicin (IC50 0.18, 0.6, and 0.2 μM, respectively).

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Section: Characterization Of the Isolated Metabolitesmentioning

confidence: 63%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…[26] 18, suggesting their β-configuration. [24,27,28] Thus, the cyclocuneatol structure was assigned as cycloart-20-en-3β-ol.…”

Section: Characterization Of the Isolated Metabolitesmentioning

confidence: 99%

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Cyclocuneatol and Cuneatannin, New Cycloartane Triterpenoid and Ellagitannin Glycoside from Euphorbia cuneata

et al. 2019

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“…Antitrypanosomal activity was first evaluated against epimastigotes of T. cruzi (Y strain obtained from ATCC) by the XTT assay (51,52). Since all known antichagasic agents show toxicity also against the epimastigote form, we used this screening as a preselective assay.…”

Section: In Vitro Activity Against T Cruzi Epimastigotesmentioning

confidence: 99%

Phylobioactive hotspots identified through multidimensional profiling of botanical drugs used to treat Chagas disease in Bolivia and Dioscorides’ De Materia Medica

Salm

Krishnan

Collu

et al. 2019

Preprint

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Globally, more than six million people are infected with Trypanosoma cruzi, the causative protozoan parasite of the vector-borne Chagas disease (CD). In Bolivia, CD is hyperendemic and a major health problem among indigenous communities. Although botanical drugs are used widely among different ethnic groups in Bolivia, studies challenging the hypothesis that effective antitrypanosomal medicinal agents were identified empirically are lacking. We conducted a cross-sectional ethnopharmacological field study in Bolivia among different ethnic groups in the Chaco, Chiquitanía and Inter-Andean valleys. We compared botanical drugs used in Bolivia in the context of CD with botanical drugs from unrelated indications from the Mediterranean De Materia Medica (DMM) compiled by Dioscorides two thousand years ago. A total of 775 ethyl acetate plant extracts with and without ethnomedical indications for CD treatment were profiled against T. cruzi epimastigote and procyclic T. brucei proliferation, parasite release from T. cruzi trypomastigote infected cells, as well as for host cell cytotoxicity in vitro. Inhibition of parasite release was monitored using a flow cytometry-based celluar assay. At 25 µg/mL, less than 5% of all extracts exhibited selective toxicity for T. cruzi. We found no evidence that ethnomedicine-inspired bioprospecting significantly increased the probability of finding selective antichagasic botanical drugs. The ethnomedical data further indicate a discrepancy between local and scientific concepts about CD among the studied ethnic groups. Intriguingly, the phylobioactive anthraquinone hotspot identified in this study matched the antichagasic activity of Senna chloroclada, the taxon with the strongest consensus for treating CD among the Izoceño-Guaraní. Selected antitrypanosomal plant extracts from DMM were subjected to HPLC-based activity profiling and targeted isolation of active compounds yielding sesquiterpene lactones, naphtoquinones and anthraquinones. Because the anthraquinone emodin selectively and potently inhibited T. cruzi in host cell infection, we performed a preliminary structure-activity relationship analysis for the 9,10-anthracenedione scaffold, exploring the impact of differential hydroxylation. This study shows that the multidimensional phylobioactivity-guided identification of antichagasic natural products enables comparative bioprospecting and is suitable to challenge ethnopharmacological hypotheses. Author summaryChagas disease (CD) is a parasitic disease caused by the protozoan Trypanosoma cruzi. In Bolivia, CD is a major health problem among indigenous communities, which frequently use traditional medicine to treat the chronic symptoms of the disease related to cardiomyopathy. However, the ethnomedical context of the use of such remedies is largely unclear and it remains unknown whether the botanical drugs have any effect on parasitemia. In a field study among different ethnic groups in the Chaco, Chiquitanía and Inter-Andean valleys the authors collected ethnobotanical and ethnopharmac...

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Phytochemical Composition, Antioxidant and Antibacterial Activities of Crude Extracts from the Species Euphorbia Atlantica Coss.

Mouffouk¹,

Gómez‐Ruiz

Benkhaled³

et al. 2019

Pharm Chem J

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New cycloartane-type ester triterpenes from Euphorbia pterococca and biological evaluation

Cited by 15 publications

References 34 publications

Cyclocuneatol and Cuneatannin, New Cycloartane Triterpenoid and Ellagitannin Glycoside from Euphorbia cuneata

Cyclocuneatol and Cuneatannin, New Cycloartane Triterpenoid and Ellagitannin Glycoside from Euphorbia cuneata

Phylobioactive hotspots identified through multidimensional profiling of botanical drugs used to treat Chagas disease in Bolivia and Dioscorides’ De Materia Medica

Phytochemical Composition, Antioxidant and Antibacterial Activities of Crude Extracts from the Species Euphorbia Atlantica Coss.

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