Unusual ingenoids from  Euphorbia erythradenia  Bioss. with pro-apoptotic effects

Zarei, Seyed Mohammad; Ayatollahi, Abdul Majid; Ghanadian, Mustafa; Kobarfard, Farzad; Aghaei, Mahmoud; Choudhary, M. Iqbal; Fallahian, Faranak

doi:10.1016/j.fitote.2013.08.016

Cited by 17 publications

(14 citation statements)

References 13 publications

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“…To assess the effects of isolates on the viability of breast cancer cell lines, standard MTT assays were performed on MCF-7 and MDA-MB 468 human cancer cells, in vitro (Zarei et al 2013). As shown in Figure …”

Section: Resultsmentioning

confidence: 99%

New macrocyclic diterpenes fromEuphorbia connataBoiss. with cytotoxic activities on human breast cancer cell lines

Shadi

Saeidi

Ghanadian

et al. 2014

Natural Product Research

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Acetone:chloroform (1:2) extract of the aerial parts of Euphorbia connata Boiss. (Euphorbiaceae) was investigated for its diterpenoids. This led to the isolation of one known and two new diterpenes, belonging to the pentahydroxy-13(17)-epoxy-8,10(18)-myrsinadiene and tetrahydroxy-5,6-epoxy-14-oxo-jatropha-11(E)-ene classes. The structures were elucidated based on (13)C and (1)H NMR as well as 2D NMR, IR and MS spectra and the cytotoxicity for compounds 1-3 were evaluated by using MTT assay against two human breast cancer cell lines. Myrsinane-type compounds - 3,7,14,15-tetraacetyl-5-propanoyl-13(17)-epoxy-8,10(18)-myrsinadiene (1) and 3,7,10,14,15-pentaacetyl-5-butanoyl-13,17-epoxy-8-myrsinene (2) - exhibited moderate inhibitory effects, with IC50 values of 24.53 ± 3.39 and 26.67 ± 1.41 μM against the MDA-MB cell line, and 37.73 ± 3.41 and 34.57 ± 2.12 μM against the MCF-7 cell line, respectively. Jatrophane-type diterpene - 5,6-epoxy-8,9,15-triacetyl-3-benzoyl-14-oxo-jatropha-11(E)-ene (3) - showed weak cytotoxicity, with IC50 values of 55.67 ± 7.09 μM against MDA-MB, and moderate cytotoxicity with IC50 values of 24.33 ± 3.21 μM against MCF-7 cell line.

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Section: Resultsmentioning

confidence: 99%

New macrocyclic diterpenes fromEuphorbia connataBoiss. with cytotoxic activities on human breast cancer cell lines

Shadi

Saeidi

Ghanadian

et al. 2014

Natural Product Research

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“…These fractions were studied for cytotoxic activity using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide standard method against ovarian and colon cancer cells. [1920] Detailed description of this study is published by authors elsewhere. [20] The cytotoxicity screening revealed that Fr.b2, Fr.b4, and Fr.b8 were the most cytotoxic fractions.…”

Section: Methodsmentioning

confidence: 99%

Isolation and Identification of Two Phenolic Compounds from a Moderately Cytotoxic Fraction of Cousinia verbascifolia Bunge

2017

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Background:Little information is available about chemical components of the Cousinia genus. A primary cytotoxicity screening on Cousinia verbascifolia showed moderate cytotoxic activity against OVCAR-3 ovarian and HT-29 colon cancer cells. Therefore, the aim of this study is a phytochemical investigation to identify the compounds responsible for this bioactivity.Materials and Methods:Extraction was done through percolation and fractionations by reverse phase column chromatography and normal column chromatography. Using standard 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay Fr.b8 with moderate cytotoxicity was selected for identification of major components. Fr.b8 was subjected to polyamide column chromatography. More purification was done using a new modified recycle high-performance liquid chromatography (HPLC) with flow splitter.Results:Two known compounds: Apigenin (flavone) and caffeic acid (phenolic acid) were obtained from phenolic bioactive fraction for the first time from this plant.Conclusions:Apigenin and caffeic acid with known antitumor and matrix metalloproteinase inhibitory effects seem to be the bioactive components responsible for moderate cytotoxicity of phenolic fraction. Recycle HPLC following with flow splitting is a new method useful for isolation of closely eluted compounds in HPLC chromatogram.

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“… Electron ionization mass fragmentation pattern of 4′-methoxy-luteolin-7-phosphate. Cleavage of ring C by retro-Diels-Alder (RDA) mechanism led to A (m/z 231) and B (m/z 117) ions( 16 ). …”

Section: Resultsmentioning

confidence: 99%

“…Molecular formula was determined by 13 C-NMR data (broad band and distortionless enhancement by polarization transfer (DEPT)) and negative ESI/MS m/z 285 [M-H] - as C 15 H 10 O 6 . The UV spectrum showed absorption maxima at 264 and 350 nm characteristic of flavones( 16 ). The 1 H-NMR spectrum displayed two meta coupled doublets at δ H 6.26 (1H, d, J = 1.6 Hz) and 6.45 (1H, d, J = 1.6 Hz) attributed to H-6 and H-8, a singlet proton at δ H 6.51 (1H, s, H-3) two ortho coupled proton signals at δ H 6.97 (1H, d, J = 8.…”

Section: Discussionmentioning

confidence: 99%

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Flavone constituents of Phlomis bruguieri Desf. with cytotoxic activity against MCF-7 breast cancer cells

et al. 2018

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Phlomis bruguieri (P. bruguieri) is a large genus in the Lamiaceae family, with a wide variety distributed in Euro-Asia, Central Asia, Iran, and China. Phlomis flowers have been used as herbal tea for gastrointestinal disturbances, protection of liver and cardiovascular systems. The aim of this study was to analyse phytochemical of flavonoid constituents in semi polar fraction of P. bruguieri. Methanol extract of plant material (4 kg) yielded 361 g dark green concentrated extract gum. After preliminary fractionation by normal column chromatography on silica gel, Fr. 2 eluted with chloroform: methanol (90:10) selected as semi polar fraction and was more purified using different chromatography columns on silica gel, polyamide SC6 and Sephadex LH-20 adsorbents. Finally one new and three known flavonoids (1-4) were characterized in semi polar fraction. Isolated structures were identified using 1H-NMR, 13C-NMR, 31P-NMR, HSQC, HMBC, negative ESI mass, and UV spectra using different shift reagents. Using standard MTT assay, cytotoxicity of isolated new compound was done against michigan cancer foundation-7 (MCF-7) breast cancer cells. Phytochemical analysis of P. bruguieri resulted in identification of one new 4’-methoxy-luteolin-7-phosphate and three known flavones including luteolin, apigenin, and tricin for the first time in this plant. In MTT cytotoxicity test, 4’-methoxy-luteolin-7-phosphate showed cytotoxicity with IC50 value of 43.65 ± 8.56 μM agasint MCF-7 breast cancer cells.

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Unusual ingenoids from Euphorbia erythradenia Bioss. with pro-apoptotic effects

Cited by 17 publications

References 13 publications

New macrocyclic diterpenes fromEuphorbia connataBoiss. with cytotoxic activities on human breast cancer cell lines

New macrocyclic diterpenes fromEuphorbia connataBoiss. with cytotoxic activities on human breast cancer cell lines

Isolation and Identification of Two Phenolic Compounds from a Moderately Cytotoxic Fraction of Cousinia verbascifolia Bunge

Flavone constituents of Phlomis bruguieri Desf. with cytotoxic activity against MCF-7 breast cancer cells

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