Abstract
A one-step synthesis of phloretin derivatives 2–11 from phloretin in good to excellent yields is reported. Their structures were characterized by 1H-NMR, 13C-NMR and MS, and the structures of 8 and 11 were determined by X-ray diffraction analysis. A mechanism for the formation of 9–11 is proposed. Compared with the anticancer drug docetaxel, phloretin, phloretin derivatives and phlorizin exhibited moderate cytotoxicity toward the MDA-MB-231, SPC-A1, A549, MCF-7 and EC109 cell lines. Among all of the tested compounds, 7 exhibited the strongest cytotoxicity toward the five cell lines and was more active than docetaxel in MDA-MB-231 cells. Our findings suggest that these derivatives hold great promise for further development as anticancer agents.
Highlights
Phloretin, a naturally occurring flavonoid, belongs to the dihydrochalcone chemical class and consists of a C6-C3-C6 skeleton structure [1,2,3]
To improve the bioavailability of phloretin and investigate the antitumor activities of phloretin derivatives compared with docetaxel, the synthesis of a series of phloretin derivatives was accomplished and their antitumor activity has been evaluated against various cancer cell lines, including A549, SPC-A1, EC109, MCF-7 and MDA-MB-231 cells
The synthesis of a series of phloretin derivatives is outlined in Scheme 1, starting from phloretin (1), which is commercially available
Summary
A naturally occurring flavonoid, belongs to the dihydrochalcone chemical class and consists of a C6-C3-C6 skeleton structure (two aromatic rings connected by a C3 chain, Figure 1) [1,2,3]. Phloretin is primarily found in apples, pears, and other succulent fruits. It exhibits various biological and pharmacological activities, such as anti-inflammatory, anticancer [4], antimutagenic and anticarcinogenic activities, and has been used as a cosmeceutical ingredient [5,6,7]. Since its discovery more than 170 years ago, phlorizin has been widely investigated in biofilm research and the field of human medicine [13,14,15,16,17,18]. Phloretin and its derivatives have a broad and important role in various fields of human health and have become a focus of natural products research. Little research has been performed regarding the antitumor activities of phloretin derivatives, except for phlorizin and its derivatives. To improve the bioavailability of phloretin and investigate the antitumor activities of phloretin derivatives compared with docetaxel, the synthesis of a series of phloretin derivatives was accomplished and their antitumor activity has been evaluated against various cancer cell lines, including A549 (human lung cancer cell line), SPC-A1 (human non-small-cell lung cancer cell line), EC109 (human esophageal cancer cell line), MCF-7 (human breast adenocarcinoma cell line) and MDA-MB-231 (human breast cancer cell line) cells
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