Biocatalytic synthesis, structural elucidation, antioxidant capacity and tyrosinase inhibition activity of long chain fatty acid acylated derivatives of phloridzin and isoquercitrin

Ziaullah,; Bhullar, Khushwant S.; Warnakulasuriya, Sumudu N.; Rupasinghe, H.P. Vasantha

doi:10.1016/j.bmc.2012.11.034

Cited by 57 publications

(56 citation statements)

References 46 publications

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“…15 Q3G was acylated with long chain fatty acid esters as previously described in Ziaullah et al 18 In the current study, we investigated the antiproliferative and cytotoxic properties of six long chain fatty acid esters of Q3G to investigate whether the acylation enhances its biological action and finally to elucidate the mechanism of action of the novel compounds.…”

Section: Discussionmentioning

confidence: 99%

“…The compounds for the study were synthesized as previously described by Ziaullah et al 18 Briefly, in a round bottom flask, defined quantities of Q3G and individual fatty acids were dissolved in acetone. Enzymatic reactions were initiated by the addition of lipase (Novozyme 435 Õ ); with an activity of 10,000 propyl laurate units).…”

Section: Synthesis Of the Long Chain Fatty Acid Esters Of Q3gmentioning

confidence: 99%

“…Hepatocellular carcinoma is the most common form of liver cancer, which represents the fifth worldwide malignancy and third cause of mortality among cancer-related death. The novel compounds for this study were prepared using enzymatic acylation as previously described by Ziaullah et al 18 …”

Section: Introductionmentioning

confidence: 99%

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Antiproliferative activity of long chain acylated esters of quercetin-3-O-glucoside in hepatocellular carcinoma HepG2 cells

Sudan

Rupasinghe

2015

Exp Biol Med (Maywood)

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Despite their strong role in human health, poor bioavailability of flavonoids limits their biological effects in vivo. Enzymatically catalyzed acylation of fatty acids to flavonoids is one of the approaches of increasing cellular permeability and hence, biological activities. In this study, six long chain fatty acid esters of quercetin-3-O-glucoside (Q3G) acylated enzymatically and were used for determining their antiproliferative action in hepatocellular carcinoma cells (HepG2) in comparison to precursor compounds and two chemotherapy drugs (Sorafenib and Cisplatin). Fatty acid esters of Q3G showed significant inhibition of HepG2 cell proliferation by 85 to 90% after 6 h and 24 h of treatment, respectively. The cell death due to these novel compounds was associated with cell-cycle arrest in S-phase and apoptosis observed by DNA fragmentation, fluorescent microscopy and elevated caspase-3 activity and strong DNA topoisomerase II inhibition. Interestingly, Q3G esters showed significantly low toxicity to normal liver cells than Sorafenib (P < 0.05), a chemotherapy drug for hepatocellular carcinoma. Among all, oleic acid ester of Q3G displayed the greatest antiproliferation action and a high potential as an anti-cancer therapeutic. Overall, the results of the study suggest strong antiproliferative action of these novel food-derived compounds in treatment of cancer.

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Section: Discussionmentioning

confidence: 99%

Section: Synthesis Of the Long Chain Fatty Acid Esters Of Q3gmentioning

confidence: 99%

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Antiproliferative activity of long chain acylated esters of quercetin-3-O-glucoside in hepatocellular carcinoma HepG2 cells

Sudan

Rupasinghe

2015

Exp Biol Med (Maywood)

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“…The procedure used was described by Sirat et al [19] and modified by Ziaullah et al [20]. The concentration of the fractions demonstrating 50% activity were calculated as an inhibitory concentration (IC 50 ) and compared with a control in terms of mean±standard deviation (SD).…”

Section: Anti-tyrosinase Activitymentioning

confidence: 99%

Polyphenol characterization, anti-oxidant, anti-proliferation and anti-tyrosinase activity of cranberry pomace

Rupasinghe¹,

Neir²,

Parmar³

2016

FFHD

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Citation: Parmar I., Neir S.V., and Rupasinghe HPV. Polyphenol characterization, anti-oxidant, anti-proliferation and anti-tyrosinase activity of cranberry pomace. Functional Foods in Health and Disease 2016; 6(11):754-768 ABSTRACT Background: Cranberry pomace (CP), an underutilized by-product from juice processing, contains a wide range of biologically active compounds that can be recovered and used in a variety of applications in functional foods and nutraceuticals. Methods:In this study, analytical chemical techniques such as solvent extractions and characterization of extracts in respect with their phenolic content were performed using ultrahigh performance liquid chromatography mass spectrometry (UPLC-MS) and spectrophotometry. Crude CP extract and its phenolic acids, flavonols, anthocyanins and proanthocyanidins-rich fractions were then evaluated for their anti-oxidant capacity, tyrosinase inhibitory activity, and anti-proliferation activity against hepatocellular carcinoma HepG2 cells. Results:On a dry weight basis, the different CP fractions contained seven major anthocyanins (0.1-125 mg/g), six major phenolic acids (0.8-31 mg/g), seven flavonols (1-126 mg/g) and five flavan-3-ols (0.1-12 mg/g). Fractions rich in flavonols exhibited the most potent antioxidant capacities with ferric ion reducing antioxidant power values of 1.8-1.9 mmole/g and 2, 2-diphenyl-1-picrylhydrazyl radical scavenging IC 50 values of 15.1-15.2 mg/L respectively. On the other hand, fractions rich in phenolic acids and flavan-3-ol monomers demonstrated the most potent anti-tyrosinase activity (IC 50 =6.1-6.2 mg/L) and anti-proliferative activity (IC 50 =7.8-15.8 mg/L). Generally, all the fractions exhibited a dose-response relationship in the selected biological activity assays. Conclusion: This study suggests an effective utilization of CP to obtain biologically active fractions with potential to be used in functional foods and nutraceuticals designed for the prevention of chronic diseases associated with oxidative stress.

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“…β-Sitosterol and its glucoside have profound anti-inflammatory activity (Bouic et al, 1996). In addition, flavonoids have been discovered to have antiinflammatory activity (Ziaullah et al, 2013). More specifically, rutin is widely used in treating ailments through its anti-inflammatory activities (Yang et al, 2008).…”

Section: Resultsmentioning

confidence: 99%

Chemical and biological study of Mentha suaveolens Ehrh. cultivated in Egypt

El-Kashoury¹,

El‐Askary²,

Kandil³

et al. 2014

J. Med. Plants Res.

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Investigation of the different fractions of the ethanolic extract of the aerial parts of M. suaveolens growing in Egypt yielded nine compounds; two new triterpenes [3β-acetyl -22α-hydroxy ursa-12,20-diene (compound 1) and 2α, 3β-dihydroxy-olean-18-en-29-oic acid (compound 7)] and nine known compounds: a sterol and its glucoside; β-sitosterol (compound 2) and β-sitosterol-3-O-β-D-glucoside (compound 4), a triterpene; oleanolic acid (compound 3), two monoterepenes; dihydrolimonene (compound 5) and 7-hydroxy-p-cymene (compound 6), two flavonoids; isoquercitrin (compound 8) and rutin (compound 9) which were isolated from M. suaveolens Ehrh. for the first time. The structures of the isolated compounds were identified by spectral data (UV, MS, 1D and 2D-NMR) and comparison with authentic samples. Moreover, the ethanolic extract showed potent analgesic activity as compared to indomethacin. The ethyl acetate fraction was the most potent as anti-inflammatory (88%), followed by the ethanolic extract (82.9%) as compared with indomethacin. The ethanolic extract and its four subfractions showed a moderate inhibitory activity against the tested human pathogenic bacteria.

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Biocatalytic synthesis, structural elucidation, antioxidant capacity and tyrosinase inhibition activity of long chain fatty acid acylated derivatives of phloridzin and isoquercitrin

Cited by 57 publications

References 46 publications

Antiproliferative activity of long chain acylated esters of quercetin-3-O-glucoside in hepatocellular carcinoma HepG2 cells

Antiproliferative activity of long chain acylated esters of quercetin-3-O-glucoside in hepatocellular carcinoma HepG2 cells

Polyphenol characterization, anti-oxidant, anti-proliferation and anti-tyrosinase activity of cranberry pomace

Chemical and biological study of Mentha suaveolens Ehrh. cultivated in Egypt

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