Structure–activity relationships of flavonoid-induced cytotoxicity on human leukemia cells

Plochmann, Kathrin; Korte, Gabriele; Koutsilieri, Eleni; Richling, Elke; Riederer, Peter; Rethwilm, Axel; Schreier, Peter; Scheller, Carsten

doi:10.1016/j.abb.2007.02.003

Cited by 131 publications

(108 citation statements)

References 25 publications

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“…Flavonoids have been shown to exert minimal effects on normal cells with a significant cytotoxic activity against various human cancer cells. This makes flavonoids ideal agents for developing anticancer drugs (Plochmann et al 2007;Ben Sghaier et al 2011). Although most of the biological actions of flavonoids depend on their structure, this point is still unclear for anticancer activity.…”

Section: Introductionmentioning

confidence: 99%

Flavonoids ofCalligonum polygonoidesand their cytotoxicity

Ahmed

Moawad

Owis

et al. 2016

Pharmaceutical Biology

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Context Calligonum polygonoides L. subsp. comosum L' Hér. (Polygonaceae), locally known as ''arta'', is a slow-growing small leafless desert shrub. Objective Isolation, structure elucidation and evaluation of cytotoxic activity of flavonoids from C. polygonoides aerial parts. Materials and methods Flavonoids in the hydroalcoholic extract of the of C. polygonoides were isolated and purified using column chromatography and preparative HPLC. The structures of the isolated flavonoids were elucidated on the basis of spectroscopic data including 2D NMR techniques. The cytotoxic activity of the isolated flavonoids (6.25, 25, 50 and 100 mg/mL) was evaluated against liver HepG2 and breast MCF-7 cancer cell lines using sulphorhodamine-B assay.00 -n-butyl glucuronide) (1), and 13 known flavonoids, quercetin 3-O-b-D-(6 00 -n-butyl glucuronide) (2), kaempferol-3-O-b-D-(6 00 -methyl glucuronide) (3), quercetin-3-O-b-D-(6 00 -methyl glucuronide) (4), quercetin-3-O-glucuronide (5), kaempferol-3-O-glucuronide (6), quercetin-3-O-a-rhamnopyranoside (7), astragalin (8), quercetin-3-O-glucopyranoside (9), taxifolin (10), (+)-catechin (11), dehydrodicatechin A (12), quercetin (13), and kaempferol (14), were isolated from the aerial parts of C. polygonoides. Quercetin showed significant cytotoxic activity against HepG2 and MCF-7 cell lines with IC 50 values of 4.88 and 0.87 mg/mL, respectively. Structure-activity relationships were analyzed by comparing IC 50 values of several pairs of flavonoids differing in one structural element. Discussion and conclusion The activity against breast cancer cell lines decreased by glycosylation at C-3. The presence of 2,3-double bond in ring C, carbonyl group at C-4 and 3',4'-dihydroxy substituents in ring B are essential structural requirements for the cytotoxic activity against breast cancer cells. ARTICLE HISTORY

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Section: Introductionmentioning

confidence: 99%

Flavonoids ofCalligonum polygonoidesand their cytotoxicity

Ahmed

Moawad

Owis

et al. 2016

Pharmaceutical Biology

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“…The higher methoxylated compounds were significantly more toxic than the less methoxylated molecules. 19 Our results revealed that the cytotoxic activity of flavones decreased when 3'-hydroxyl was methylated (1-3), while the effect of 7-OH on the cytotoxic activity was uncertain. Furthermore, the existence of 3-Gal seemed to attenuate the cytotoxic activity of these compounds, suggesting that the sugar moiety could reduce the cytotoxic activity and that glycoside had a weaker cytotoxic activity than the corresponding aglycones, respectively.…”

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confidence: 81%

Flavonoids from Cleistocalyx operculatus Buds and their Cytotoxic Activity

Min¹,

Cuong²,

Lee³

et al. 2010

Bulletin of the Korean Chemical Society

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“…Indeed, flavonoids have been demonstrated to reveal cytotoxic activities towards numerous human cancer cells, whilst having little or no effect on normal cells. This has led to interest in the development of potential flavonoid-based chemotherapeutics for anticancer treatment (34)(35)(36)(37). Traditional Chinese herbs, which depend predominantly on empirical medication, have been used for thousands of years in the treatment of numerous diseases, often with few adverse effects.…”

Section: Resultsmentioning

confidence: 99%

Flavonoids from Artemisia sacrorum Ledeb. and their cytotoxic activities against human cancer cell lines

Yuan

et al. 2016

Experimental and Therapeutic Medicine

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Abstract. Flavonoids have been demonstrated to have cytotoxic activities toward numerous human cancer cells, whereas they have little or no effect on normal cells. The numerous flavonoids in traditional Chinese herbs may be promising candidates for the development of novel anti-cancer drugs. Our previous study demonstrated that CH 2 Cl 2 and 95% ethanol eluate (EE) fractions have the strongest cytotoxic activities against human cancer cell lines of the 9 fractions separated from Artemisia sacrorum Ledeb., which is widely used to prevent and treat diverse diseases in Northeast China. In the present study, 8 flavonoids were isolated from the 95% EE fraction of Artemisia sacrorum Ledeb. The chemical structures of the compounds were elucidated by extensive spectroscopic analyses. The following 5 flavonoids were isolated for the first time from this plant: Jaceosidin, kaempferol, quercetin, luteolin and quercitrin. A total of 2 flavonoids from the CH 2 Cl 2 fraction and 8 flavonoids from the 95% EE fraction were examined to evaluate their cytotoxic activities against human SK-HEP-1 hepatoma cancer cells and human HeLa cervical cancer cells, respectively. The results revealed that 2 flavonoids had marked cytotoxic activities against HeLa cells.

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Structure–activity relationships of flavonoid-induced cytotoxicity on human leukemia cells

Cited by 131 publications

References 25 publications

Flavonoids ofCalligonum polygonoidesand their cytotoxicity

Flavonoids ofCalligonum polygonoidesand their cytotoxicity

Flavonoids from Cleistocalyx operculatus Buds and their Cytotoxic Activity

Flavonoids from Artemisia sacrorum Ledeb. and their cytotoxic activities against human cancer cell lines

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