Synthesis and anticancer effect of chrysin derivatives

Zheng, Xiaohui; Meng, Weidong; Xu, Yuan; Cao, Ji; Qing, Feng‐Ling

doi:10.1016/s0960-894x(02)01081-8

Cited by 140 publications

(74 citation statements)

References 16 publications

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“…Numerous studies in vitro have shown a close relationship between the chemical structure and the biological activity of genistein derivatives, whereby their basic structure can be modified to increase or decrease their biological activity (Kim et al, 2003;Gao et al, 2001). As part of our current work (Zheng et al, 2003), searching for anticancer substances, we describe herein the synthesis of genistein derivatives and their anticancer activities against leukocythemia (HL-60), colorectal adenocarcinoma (HT-29), and human gastric adenocarcinoma (SGC-7901) cell lines.…”

Section: Introductionmentioning

confidence: 89%

Synthesis and cytotoxic activity of genistein derivatives

Zheng

Liu

et al. 2009

Med Chem Res

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Section: Introductionmentioning

confidence: 89%

Synthesis and cytotoxic activity of genistein derivatives

Zheng

Liu

et al. 2009

Med Chem Res

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“…Amongst various naturally occurring flavonoids, very few semi-synthetic derivatives of chrysin have been developed by different researchers and evaluated for broad spectrum biological activities viz. antimicrobial [17,19], anticancer [25][26][27][28], anti-inflammatory, vasodilating, immune modulating, neuro-protective, antidiabetic and many more [17,[29][30][31]. The encouraging biological profiles of the flavonoids particularly of chrysin and in continuation of our current research interests [32] on searching and development of antimicrobial agent from natural resources led us to extend our work towards the synthesis of some new chrysin derivatives and their biological evaluations.…”

Section: Introductionmentioning

confidence: 96%

Synthesis of Some New Chrysin Derivatives and Their Biological Assessment as Antibacterial, Antibiofilm and Antifungal Agent

Bhowmik¹,

Daş²,

Ghosh³

et al. 2018

Asian J. Chem.

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Some new derivatives of natural chrysin have been synthesized and evaluated for antibacterial, antibiofilm and antifungal activities. Three compounds, namely 2a, 2e, 2i showed excellent activities (MIC 14.0-18.3 µg/mL) against six bacterial and two fungal type strains while most of the other compounds showed comparatively low to moderate values of such activities. Significant antibiofilm and bactericidal activities (MBC ranges from 17-20 µg/mL) were also observed for 2a, 2e, 2i against pneumonia causing two bacterial strains. This study further indicated that the chrysin compounds with 7-O-alkyl type substitution were much more effective than corresponding aryl substituted congeners which signifies that 7-O position of chrysin is crucial for antimicrobial activities. Thus, this article would contribute to further design and development of potential antimicrobial agents via structural modulation of natural chrysin, which is a potential molecular skeleton with diverse biological activities.

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“…Halogenation of the 6-and 8-positions of the phenylchromen ring is a modication that has been found to enhance the antioxidant activity and lipophilicity of several avonoids, and render them more potent in inhibiting the proliferation of cancer cell lines compared to their precursor NPs. 6,7 Further, methylation of specically the 7-hydroxyl of apigenin to produce genkwanin signicantly alters the anticancer activities. 8 Based on these studies, we hypothesized that methylating the 7-position in addition to brominating the 6-and 8-positions of apigenin would enhance its anticancer activity.…”

Section: Introductionmentioning

confidence: 99%

Combining semi-synthesis with plant and microbial biocatalysis: new frontiers in producing a chemical arsenal against cancer

et al. 2018

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Natural products (NPs) that exhibit anticancer activities are frequently not potent enough to be used clinically as therapeutics. Semi-synthesis and metabolic engineering are promising approaches for producing more efficacious derivatives of anticancer NPs (ACNPs), but each technique alone can be inefficient at obtaining specific ACNP derivatives that may be suspected to have enhanced anticancer activity. Here, we demonstrate that the methods of semi-synthesis and biocatalysis can be used as modules in succession and in different combinations to produce 6,8-dibromogenkwanin, a derivative of the ACNP apigenin. Further, we demonstrated that soybean seed coats can be used as a biocatalyst to convert brominated flavonoids into multiple derivatives. A strength of the combinatorial (bio)synthesis approach was that the order of the modules could be rearranged to increase the yield of the desired product. At lower treatment concentration (5 mM), 6,8-dibromogenkwanin exhibited enhanced antiproliferative activities against HT-29 colorectal adenocarcinoma cancer cells under normoxic and hypoxic conditions compared to its ACNP precursors, but not at higher concentrations. Dose-response analyses suggested that dibromogenkwanin had a distinct mode-of-action compared to apigenin. Thus, this proof-of-concept paper demonstrates combinatorial (bio)synthesis as an approach that can be used to produce novel chemistries for anticancer research.

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Synthesis and anticancer effect of chrysin derivatives

Cited by 140 publications

References 16 publications

Synthesis and cytotoxic activity of genistein derivatives

Synthesis and cytotoxic activity of genistein derivatives

Synthesis of Some New Chrysin Derivatives and Their Biological Assessment as Antibacterial, Antibiofilm and Antifungal Agent

Combining semi-synthesis with plant and microbial biocatalysis: new frontiers in producing a chemical arsenal against cancer

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