Showing papers on "Flavanone published in 2010"
TL;DR: In this paper, the authors reported on the extraction of polyphenols especially flavanones from orange peel by using ethanol as a food grade solvent, and the best yield of extraction was reached for a particle size of 2.cm2.
581 citations
TL;DR: In this paper, the effects of microwave treatment on the phenolic compounds and antioxidant capacity of citrus mandarin pomace were evaluated, and the results indicated that appropriate microwave treatment could be an efficient process to liberate and activate the bound phenolic compound and to enhance the antioxidant activity of citrus pOMace.
155 citations
TL;DR: A large interindividual variation was observed, this being consistent for each individual after the intake of the different beverages, suggesting that flavanone bioavailability is also dependent on the occurrence of specific microbiota that is able to remove the rutinosides from the juice glycosides, which results in aglycones that are then absorbed from the gut.
Abstract: Orange juice is a very rich source of dietary flavanones. The effect of flavanone concentration and solubility of orange beverages on their bioavailability has been studied in a crossover study with 10 healthy volunteers. Five different beverages with different flavanone concentrations were evaluated. Commercial orange juices (29.2-70.3 mg of flavanones/100 mL) were compared with experimental orange beverages in which the flavanone concentration was enhanced (110.2 mg/100 mL). Hesperetin and naringenin glucuronides and sulfates were detected and quantified in plasma and urine. The study shows that the solubility of the flavanones, and particularly that of hesperidin, in the juice is a key factor for the bioavailability as flavanone excretion and the C(max) in plasma correlate well with the soluble flavanone concentration in the juice, whereas it has no correlation with the total flavanone intake. In addition, a large interindividual variation was observed, this being consistent for each individual after the intake of the different beverages, suggesting that flavanone bioavailability is also dependent on the occurrence of specific microbiota that is able to remove the rutinosides from the juice glycosides, which results in aglycones that are then absorbed from the gut.
136 citations
TL;DR: Some chalcone derivatives synthesized were found to possess aldose reductase inhibition and antioxidant activities in‐vitro as well as inhibition in the accumulation of sorbitol in the tissues in‐ vitro.
Abstract: Aldose reductase, the key enzyme of the polyol pathway, and oxidative stress are known to play important roles in the complications of diabetes. A drug with potent inhibition of aldose reductase and oxidative stress, therefore, would be a most promising drug for the prevention of diabetic complications. The purpose of this study was to develop new compounds with these dual-effects through synthesis of chalcone derivatives and by examining the structure-activity relationships on the inhibition of rat lens aldose reductase as well as on antioxidant effects. A series of 35 flavonoid derivatives were synthesized by Winget's condensation, oxidation, and reduction of appropriate acetophenones with appropriate benzaldehydes. The inhibitory activity of these derivatives on rat lens aldose reductase and their antioxidant effects, measured using Cu2+ chelation and radical scavenging activities on 1,1-diphenyl-picrylhydrazyl in-vitro, were evaluated. Their effect on sorbitol accumulation in the red blood cells, lenses and sciatic nerves of streptozotocin-induced diabetic rats was also estimated. Among the new flavonoid derivatives synthesized, those with the 2′,4′-dihydroxyl groups in the A ring such as 2,4,2′,4′-tetrahydroxychalcone (22), 2,2′,4′-trihydroxychalcone (11), 2′,4′-dihydroxy-2,4-dimethylchalcone (21) and 3,4,2′,4′-tetrahydroxychalcone (18) were found to possess the highest rat lens aldose reductase inhibitory activity in-vitro, their IC50 values (concentration of inhibitors giving 50% inhibition of enzyme activity) being 1.6 times 10−7, 3.8 times 10−7, 4.0 times 10−7 and 4.6 times 10−7 M, respectively. All of the chalcones tested except 3, 18, 23 with o-dihydroxy or hydroquinone moiety showed a weak free radical scavenging activity. In the in-vivo experiments, however, compound 18 with o-dihydroxy moiety in the B ring showed the strongest inhibitory activity in the accumulation of sorbitol in the tissues. It also showed the strongest activity in transition metal chelation and free radical scavenging activity. Of the 35 4,2′-dihydroxyl and 2′,4′-dihydroxyl derivatives of flavonoid synthesized, including chalcone, flavone, flavanone, flavonol and dihydrochalcone, some chalcone derivatives synthesized were found to possess aldose reductase inhibition and antioxidant activities in-vitro as well as inhibition in the accumulation of sorbitol in the tissues in-vivo. 3,4,2′,4′-Tetrahydroxychalcone (18, butein) was the most promising compound for the prevention or treatment of diabetic complications.
122 citations
TL;DR: The qualitative and quantitative compositions of chinotto juice in two different maturation periods were determined via chromatographic separation of extracted aliquots of juice of Citrus x myrtifolia Raf.
Abstract: The qualitative and quantitative compositions of chinotto juice in two different maturation periods were determined via chromatographic separation of extracted aliquots of juice of Citrus × myrtifolia Raf. by using reverse-phase LC-DAD-ESI-MS-MS. This provides a comprehensive chromatographic evaluation of 11 compounds (furanocoumarins and flavonoids C- and O-glycosides). Five flavonoids and two furanocoumarins were identified for the first time in chinotto juice: two C-glucosides (vicenin-2 and lucenin-2 4′-methyl ether), two O-glycosides (narirutin and rhoifolin), and a 3-hydroxy-3-methylglutaryl flavanone (brutieridin). Bergapten and epoxybergamottin were the primary furanocoumarins found. Overall, the juice from immature chinotto fruits is richer in bioactive compounds than that obtained from ripe fruits. The free radical and superoxide anion scavenging activities of juice from both green and ripe fruits were assessed, and results showed that the former is much more efficient in scavenging radical and ...
104 citations
TL;DR: In vitro and in planta evidence is provided that the rice P450 CYP93G2 protein encoded by Os06g01250 is a functional flavanone 2-hydroxylase, conclusively assigned as the first enzyme that channels flavanones to C-glycosylflavone biosynthesis in rice.
Abstract: C-Glycosylflavones are ubiquitous in the plant kingdom, and many of them have beneficial effects on human health. They are a special group of flavonoid glycosides in which the sugars are C-linked to the flavone skeleton. It has been long presumed that C-glycosylflavones have a different biosynthetic origin from O-glycosylflavonoids. In rice (Oryza sativa), a C-glucosyltransferase (OsCGT) that accepts 2-hydroxyflavanone substrates and a dehydratase activity that selectively converts C-glucosyl-2-hydroxyflavanones to 6C-glucosylflavones were recently described. In this study, we provide in vitro and in planta evidence that the rice P450 CYP93G2 protein encoded by Os06g01250 is a functional flavanone 2-hydroxylase. CYP93G2 is related to the CYP93B subfamily, which consists of dicot flavone synthase II enzymes. In the presence of NADPH, recombinant CYP93G2 converts naringenin and eriodictyol to the corresponding 2-hydroxyflavanones. In addition, CYP93G2 generates 2-hydroxyflavanones, which are modified by O-glycosylation in transgenic Arabidopsis (Arabidopsis thaliana). Coexpression of CYP93G2 and OsCGT in Arabidopsis resulted in the production of C-glucosyl-2-hydroxyflavanones in the dibenzoylmethane tautomeric form. The same structure was reported previously for the in vitro OsCGT reaction products. Thus, CYP93G2 generates 2-hydroxyflavanone substrates from flavanones for C-glucosylation by OsCGT in planta. Furthermore, knocking down Os06g01250 in rice (O. sativa subsp. japonica 'Zhonghua 11') preferentially depleted the accumulation of C-glycosylapigenin, C-glycosylluteolin, and C-glycosylchrysoeriol but did not affect the levels of tricin, which is frequently present as O-glycosides in cereals. Taken together, our work conclusively assigned CYP93G2 as the first enzyme that channels flavanones to C-glycosylflavone biosynthesis in rice.
96 citations
TL;DR: A new series of synthetic flavones, thioflavones, and flavanones has been synthesized and evaluated as potential inhibitors of monoamine oxidase isoforms (MAO-A and -B) and the most active series is the flavanone one with higher selective inhibitory activity against MAO-B.
86 citations
TL;DR: Structural-activity analysis showed that the furan rings of the polyphenols were essential for neuraminidase inhibitory activity, and that this activity was enhanced by the apioside group on the chalcone and flavanone backbone.
85 citations
TL;DR: Strong inhibitory effects of flavonoids on CYP1 activities require the 2-3 double bond on the C-ring, suggesting chemopreventive flavonoid for E(2) related breast cancer; and binding specificity of these methoxyflavonoids is based on the interactions between the methoxy groups and specific CYP 1s residues.
75 citations
TL;DR: A new application of Julia-Kocienski olefination for the synthesis of chalcones and flavanones has been described in this article, where 2-(Benzo[d]thiazol-2-ylsulfonyl)-1-(2-hydroxyphenyl)ethanone reacted with the aromatic aldehydes to furnish flavanone in good yields via one-pot intra-molecular cyclization.
73 citations
TL;DR: Nine geranylated flavanones isolated from the fruits of Paulownia tomentosa and two from the roots of Morus alba were examined for cytotoxicity to selected human cancer cell lines and normal human fibroblasts, and showed different levels of cytotoxic activity.
Abstract: Nine geranylated flavanones isolated from the fruits of Paulownia tomentosa (4-12) and two from the roots of Morus alba (13 and 14) were examined for cytotoxicity to selected human cancer cell lines and normal human fibroblasts. Cytotoxicity was determined in vitro using a calcein AM cytotoxicity assay. Cytotoxicity for the THP-1 monocytic leukemia cell line was tested using erythrosin B cell staining. The geranylated compounds tested were compared with the known simple flavanone standards taxifolin (1), naringenin (2), and hesperetin (3) and with the standard anticancer drugs olomoucine II, diaziquone, and oxaliplatin and the antineoplastic compound camptothecin, and showed different levels of cytotoxicity. The effects of structural changes on cytotoxic activity, including geranyl substitution of the flavanone skeleton and the oxidation pattern of ring B of the flavanones, are discussed.
TL;DR: It is revealed that 3-deoxyanthocyanidin accumulation and SbDFR3 expression were induced by methyl jasmonate treatment in sorghum roots but the stimulation effects were antagonized by salicylic acid.
Abstract: 3-Deoxyanthocyanidins are the unique phytoalexins synthesized by sorghum in response to fungal inoculation. They are structurally related to anthocyanins but the final steps of their pathogen-inducible biosynthesis are not fully understood. We have identified new flavonoid structural genes from the recently completed sorghum BTx623 genome sequence. The biochemical functions of the different expressed sorghum genes were established in planta by complementation in the appropriate Arabidopsis transparent testa mutants. There is a family of nine chalcone synthase genes which are all inducible by fungal inoculation in sorghum seedlings. Specific dihydroflavonol 4-reductase (DFR) genes responsive to conditions which stimulated anthocyanin accumulation (SbDFR1) or 3-deoxyanthocyanidin production (SbDFR3) were identified. Recombinant SbDFR1 and SbDFR3 were found to function as typical DFRs by accepting dihydroflavonol substrates. On the other hand, both DFRs showed substantially lower but detectable NADPH-dependent activities toward flavanones. Reduction of flavanones to flavan-4-ols is a reaction step required for 3-deoxyanthocyanidin production. Flavanone 3-hydroxylase (F3H) converts flavanones to dihydroflavonols for anthocyanin biosynthesis. In sorghum seedlings, expression of two F3H genes was either absent or strongly suppressed during the accumulation of 3-deoxyanthocyanidins. Under such conditions, most flavanones are expected to be reduced by the pathogen-induced SbDFR3 for the formation of flavan-4-ols. Our work also revealed that 3-deoxyanthocyanidin accumulation and SbDFR3 expression were induced by methyl jasmonate treatment in sorghum roots but the stimulation effects were antagonized by salicylic acid.
TL;DR: Phylogenetic analyses of the subfamily of plant CYP93B enzymes indicate the evolution of a gene encoding a flavone synthase which originally catalyzed the direct conversion of flavanones into flavones, via early gene duplication into a less efficient enzyme with an altered catalytic mechanism.
TL;DR: The use of nano-LC technique for the resolution of flavanones optical isomers allowed to achieve good resolutions in shorter analysis time compared to the results reported in literature with conventional HPLC.
TL;DR: The crude MeOH extract from the leaves of Baccharis retusa DC showed potential against Leishmania sp.
Abstract: In the course of selection of new bioactive compounds from Brazilian flora, the crude MeOH extract from the leaves of Baccharis retusa DC. (Asteraceae) showed potential against Leishmania sp. and Trypanosoma cruzi. Chromatographic fractionation of the dichloromethane phase from MeOH extract yielded great amounts of the bioactive derivative, which was characterized as 5,6,7-trihydroxy-4'-methoxyflavanone. The structure of this compound was established on the basis of spectroscopic data analysis, mainly nuclear magnetic resonance and mass spectrometry.
TL;DR: A series of new flavanone derivatives of farrerol was synthesized by a convenient method and exhibited good pharmacological activity and the preliminary structure-activity relationships were described.
TL;DR: The in vivo testing involved measuring the cytoprotective effect of chosen flavanones against alloxan-induced diabetes in mice and the antioxidant activity relationship of geranyl or prenyl-substituted flavonoids with different substitutions at the B and C ring was discussed.
Abstract: Antiradical and cytoprotective activities of several flavanones isolated from Paulownia tomentosa (Thunb.) Steud. (Scrophulariaceae) have been evaluated using different in vitro and in vivo methods. The capacity of flavanones to scavenge radicals was measured in vitro by means of DPPH and ABTS assays, the inhibition of hydroxyl radicals produced in Fenton reactions, FRAP, scavenging superoxide radicals using enzymatic and nonenzymatic assays and the inhibition of peroxynitrite-induced nitration of tyrosine. The in vivo testing involved measuring the cytoprotective effect of chosen flavanones against alloxan-induced diabetes in mice. The activity of tested compounds was expressed either as a Trolox® equivalent or was compared with rutin or morine as known antioxidant compounds. The highest activity in most tests was observed for diplacone and 3´-O-methyl-5´-hydroxydiplacone, and the structure vs. the antioxidant activity relationship of geranyl or prenyl-substituted flavonoids with different substitutions at the B and C ring was discussed.
TL;DR: In this article, the glucuronides of naringenin (4'- and 7-O-beta-d-glucuronides) and hesperetin (3' and 7' O-β-dglucurides) in grapefruit and orange, respectively, were chemically synthesized.
Abstract: Flavanone glucuronides are the major phenolic metabolites detected in human plasma after consumption of citrus fruits. As such, they might display significant cardioprotective effects. In this work, glucuronides of naringenin (4'- and 7-O-beta-d-glucuronides) and hesperetin (3'- and 7-O-beta-d-glucuronides), the major flavanone aglycones in grapefruit and orange, respectively, have been chemically synthesized. On the one hand, the most reactive hydroxyl group, C7-OH, was protected by selective benzoylation to allow subsequent glucuronidation of C4'-OH (naringenin) or C3'-OH (hesperetin) (B-ring). On the other hand, the selective debenzoylation at C7-OH of the perbenzoylated flavanone aglycones allowed glucuronidation at the same position (A-ring). After careful deprotection, the target compounds were purified and characterized by nuclear magnetic resonance and mass spectrometry.
TL;DR: Cytotoxicity and antitubulin activity of these five flavones, as well as 5,3'-dihydroxy-3,7,4'-trimethoxyflavone (= ayanin) and intermediate 6,8-dibromo-ayanin (8), were evaluated.
Abstract: Semisynthesis of 5,3′-dihydroxy-3,6,7,8,4′-pentamethoxyflavone (1), a natural flavone that binds with high affinity to tubulin, was performed from hesperidin, the very abundant Citrus flavanone, by a five-step sequence. The last step of the synthesis also gave rise to 5,3′-dihydroxy-3,6,7,4′-tetramethoxyflavone (= casticin or vitexicarpin) (10), 5,3′-dihydroxy-3,7,8,4′-tetramethoxyflavone (= gossypetin 3,7,8,4′-tetramethyl ether) (11), and, unexpectedly, 5,7,3′-trihydroxy-3,6,8,4′-tetramethoxyflavone (12) and 5,3′-dihydroxy-8-dimethylamino-3,6,7,4′-tetramethoxyflavone (= 8-dimethylaminocasticin) (13). Cytotoxicity and antitubulin activity of these five flavones, as well as 5,3′-dihydroxy-3,7,4′-trimethoxyflavone (= ayanin) (14) and intermediate 6,8-dibromo-ayanin (8), were evaluated. Comparison of the responses confirmed and clarified the influence of the A-ring substitution pattern on the biological activity.
TL;DR: These compounds were studied for their anti-glycation and antioxidant properties and the structures of new compounds 1 and 2 were deduced on the basis of spectroscopic evidence.
Abstract: 4′-O-[β-D-Apiosyl(1→2)]-β-D-glucosyl]-5-hydroxyl-7-O-sinapylflavanone (1), 3-(4-acetoxy-3,5-dimethoxy)-phenyl-2E-propenyl-β-D-glucopyranoside (2), 3-(4-hydroxy-3,5-dimethoxy)-phenyl-2E-propenyl-β-D-glucopyranoside (3), 5,7-dimethoxy-4′-O-β-D-glucopyranoside flavanone (4), 4′,5-dimethoxy-7-hydroxy flavanone (5), and 5,7-dimethoxy-4′-hydroxy flavanone (6), were isolated from the organic extracts of Viscum album L. (European Mistletoe). These compounds were studied for their anti-glycation and antioxidant properties. The structures of new compounds 1 and 2 were deduced on the basis of spectroscopic evidence.
TL;DR: The isolated compounds were used for the development and validation of a HPLC-method which enables the determination of these bioactive substances in C. coggygria wood and could represent valuable markers for the identification and quality control of the plant.
Abstract: Phytochemical investigations of Cotinus coggygria Scop. wood, a medicinal and tinctorial plant used since antiquity, resulted in the isolation and structure elucidation of the novel C-3/C-3'' dimer of butin (3',4',7-trihydroxyflavanone) and other known compounds: gallic acid and its methyl ester; catechin; profisetinidins: fisetinidol-(4α→8)-(+)-catechin and epifisetinidol-(4β→8)-(+)-catechin; flavanonols: fustin and dihydroquercetagetin; flavanones: butin and eriodictyol; flavonols: fisetin and quercetin; the chalcone butein and the aurone sulfuretin. The isolated compounds were used for the development and validation of a HPLC-method which enables the determination of these bioactive substances in C. coggygria extracts. Separation was possible on an ether-linked phenyl column material, using as mobile phase mixtures of water, methanol, and acetonitrile with 0.02% trifluoroacetic acid. Sensitivity, selectivity, linearity, precision, accuracy, and repeatability of the method were verified and assured suitability for its intended use. LC-MS experiments performed in positive and negative electrospray ionization mode confirmed the identity of analytes and allowed unambiguous assignment of all peaks of interest. The analysis of different C. coggygria samples revealed that sulfuretin (0.38-0.69%) and fustin (0.33-0.59%) dominated, followed by dihydroquercetagetin (0.12-0.35%), a rare flavanonol derivative with a 5,6,7-trihydroxysubstituted A-ring. The new natural compound C-3/C-3'' flavanone dimer occurred in concentrations of 0.03-0.06%; the two latter compounds could represent valuable markers for the identification and quality control of C. coggygria wood.
TL;DR: Several species of the Artocarpus genus (Moraceae) have been investigated their natural product and the secondary metabolitessuccessfully being isolatad from ArtocARPus genus consist of terpenoid, flavonoids, stilbenoid, arylbenzofuran, neolignan, and adductDiels-Alder.
Abstract: Hakim A. 2010. The diversity of secondary metabolites from Genus Artocarpus (Moraceae). Nusantara Bioscience 2:146-156.Several species of the Artocarpus genus (Moraceae) have been investigated their natural product. The secondary metabolitessuccessfully being isolatad from Artocarpus genus consist of terpenoid, flavonoids, stilbenoid, arylbenzofuran, neolignan, and adductDiels-Alder. Flavonoid group represent the compound which is the most found from Artocarpus plant. The flavonoids compound whichare successfully isolated from Artocarpus plant consist of the varied frameworks like chalcone, flavanone, flavan-3-ol, simple flavone,prenylflavone, oxepinoflavone, pyranoflavone, dihydrobenzoxanthone, furanodihydrobenzoxanthone, pyranodihydrobenzoxanthone,quinonoxanthone, cyclopentenoxanthone, xanthonolide, dihydroxanthone. Key words: Artocarpus, Moraceae, flavonoid, Diels-Alder, secondary metabolites.
TL;DR: Six new Flavanones with dihydrofuran moiety and two known flavanones were isolated from the stem bark of Erythrina abyssinica and their structures were elucidated on the basis of spectroscopic and physicochemical analyses.
Abstract: As the insulin and leptin signaling pathway can be regulated by PTP1B, it has been suggested that compounds that reduce PTP1B activity or expression levels can be used for treating type 2 diabetes and obesity. In the course of our screening efforts on new PTP1B inhibitors, six new flavanones ( 1- 6) with dihydrofuran moiety and two known flavanones ( 7 and 8) were isolated from the stem bark of Erythrina abyssinica (Leguminosae). Their structures were elucidated on the basis of spectroscopic (including UV, CD, MS, 1D, and 2D NMR) and physicochemical analyses. With the exception of 3 and 5, the compounds inhibited PTP1B activity in an IN VITRO assay with IC (50) values ranging from 15.2 +/- 1.2 to 19.6 +/- 2.3 microM, whereas RK-682 as a positive control displayed an IC (50) value of 4.7 +/- 0.5 microM.
TL;DR: The results indicated that kaempferol, a well known and widely distributed flavonoid in the plant kingdom, was the most active antiproteasomal agent, followed by apigenin, eriodictyol-7-O-β-D-glucuronopyranoside, 3,5-dihydroxyphenethyl alcohol-3-O
TL;DR: Two flavanone glycosides were isolated from the aerial part of Launeae arborescens (Asteraceae), which were identified as hesperidin and naringin, which are the most abundant flavonoids in the edible parts of many species of citrus fruits.
TL;DR: In this article, metabolically engineered Saccharomyces cerevisiae expressing 4-coumaroyl:CoA-ligase (4CL) and chalcone synthase (CHS) was explored as a platform for producing non-natural flavanones and dihydrochalcones.
Abstract: Flavonoids are plant phenolic compounds that have many interesting medicinal properties. Therefore, there is interest in the synthesis of non-natural flavonoids as they may possess new or enhanced biological activities. In this study, metabolically engineered Saccharomyces cerevisiae expressing 4-coumaroyl:CoA-ligase (4CL) and chalcone synthase (CHS) was explored as a platform for producing non-natural flavanones and dihydrochalcones. By precursor addition of cinnamic acid analogues to the engineered yeast, numerous non-natural flavanones and dihydrochalcones were formed in vivo. Also, several CHS derailment products were formed. Of the isolated compounds, one flavanone and three derailment products were found to be novel compounds.
TL;DR: Seven new compounds including three flavanone glycosides, visartisides A-C (1-3), three glycoside acyl esters, visArtisides D-F (4-6), and one diphenylpropane glyCoside (7) were isolated from the leaves and stems of Viscum articulatum and structure elucidation of 1-7 was based on spectroscopic data analysis.
Abstract: Seven new compounds including three flavanone glycosides, visartisides A−C (1−3), three glycoside acyl esters, visartisides D−F (4−6), and one diphenylpropane glycoside, (4′-hydroxy-2′,3′,6′,3′′-tetramethoxy-1,3-diphenylpropane)-4′′-O-β-d-glucopyranoside (7), along with four known flavanone glycosides (8−11) were isolated from the leaves and stems of Viscum articulatum. The structure elucidation of 1−7 was based on spectroscopic data analysis. Biological evaluation showed that 1, 2, and 10 exhibited antioxidant activity using a DPPH method and that compounds 1, 3, and 11 were active in a lipopolysaccharide-induced nitric oxide assay.
TL;DR: In this article, a series reaction scheme involving the Claisen-Schmidt condensation between 2′-hydroxyacetophenone and benzaldehyde was used to synthesize flavanone.
TL;DR: X-ray structure and detailed (1)H-NMR analysis of both new compounds, as well as the study of their antiproliferative activity, suggest that the mechanism of biological activity may be different for these ruthenium compounds compared to cisplatin.
Abstract: Synthesis, structure and properties of two new flavanone complexes of Ru(ii) are described. The new complexes form during the reaction of ruthenium(iii) chloride with 3-aminoflavone (3-af) dissolved in an aliphatic alcohol. The formed products depend on the alcohol used and were found to be: cis-dichloridobis(3-imino-2-methoxyflavanone)ruthenium(ii)·3H(2)O (1) from a methanolic solution and cis-dichloridobis(3-imino-2-ethoxyflavanone)ruthenium(ii)·2H(2)O (2) from an ethanolic solution, in which the original ligand 3-af had been converted by dehydrogenative alcoholysis to an entirely new ligand. This paper presents the X-ray structure and detailed (1)H-NMR analysis of both new compounds, as well as the study of their antiproliferative activity. The coordination of Ru(ii) is octahedral with [RuCl(2)N(2)O(2)] chromophores, having trans chlorides and common Ru-L distances. Both 1 and 2 are highly cytotoxic towards the cisplatin resistant EJ and L1210 cell lines, and both complexes are as active as cisplatin in the sensitive cell lines. They display the ability to overcome cisplatin resistance in the drug resistant sub-lines EJcisR and L1210R. The present evidence suggests that the mechanism of biological activity may be different for these ruthenium compounds compared to cisplatin.
TL;DR: Synthesis of stilbene-fused chalcones and flavanones were successfully completed and molecules were designed in a way to mimic the structural features of both "stilbenes and chalCones" or "stILbene and Flavanones" at the same time, and synthesized by three steps.