Abstract
Flavonoids are a group of natural products with a great structural diversity, widely distributed in plant kingdom. They play an important role in plant growth, development and defense against aggressors. Flavonoids show a huge variety of biological activities such as antioxidant, anti-inflammatory, anti-mutagenic, antimicrobial and antitumor, being able to modulate a large diversity of cellular enzymatic activities. Among natural flavonoids, some classes comprise chiral molecules including flavanones, flavan-3-ols, isoflavanones, and rotenoids, which have one or more stereogenic centers. Interestingly, in some cases, individual compounds of enantiomeric pairs have shown different antitumor activity. In nature, these compounds are mainly biosynthesized as pure enantiomers. Nevertheless, they are often isolated as racemates, being necessary to carry out their chiral separation to perform enantioselectivity studies. Synthetic chiral flavonoids with promising antitumor activity have also been obtained using diverse synthetic approaches. In fact, several new chiral bioactive flavonoids have been synthesized by enantioselective synthesis. Particularly, flavopiridol was the first cyclin-dependent kinase (CDK) inhibitor which entered clinical trials. The chiral pool approaches using amino acid as chiral building blocks have also been reported to achieve small libraries of chrysin derivatives with more potent in vitro growth inhibitory effect than chrysin, reinforcing the importance of the introduction of chiral moieties to improve antitumor activity. In this work, a literature review of natural and synthetic chiral flavonoids with antitumor activity is reported for the first time.
Highlights
Cancer is a heterogeneous disease resulting from uncontrolled proliferation and deregulation of the cell cycle, producing abnormal cells that are often able to invade and metastasize other organs from the body [1]
The results suggested that this flavanone (7) was able to prevent the progression of this type of cancer, mitigating the processes of invasion, migration and proliferation on MDA-MB-231 cells
OCH3 the R-enantiomer (23) exhibited weak cytotoxicity in HepG2 cells. These results suggest the importance of the stereochemistry for the antitumor activity of leucoflavonine
Summary
Cancer is a heterogeneous disease resulting from uncontrolled proliferation and deregulation of the cell cycle, producing abnormal cells that are often able to invade and metastasize other organs from the body [1]. According to World Health Organization (WHO), cancer was responsible for about 9.6 million deaths worldwide in 2018, being the second leading cause of death after cardiovascular diseases [2]. The growing incidence associated with cancer diseases along with problems of multiple side effects and resistance inherent to classical chemotherapeutic agents renders the search for new compounds with antitumor effects increasingly urgent [4]. Nature is an interesting source of new anticancer drugs [5]. Some of the drugs currently in therapeutics as anticancer agents are natural products or derived from natural products, most of them being chiral [6]. Pharmaceuticals 2021, 14, 1267 with relevant biological activities, including antitumor by being able to interfere with carcinogenesis processes [8]
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