A New DNA‐Intercalative Cytotoxic Allylic Xanthone from Swertia corymbosa

Abstract

Phytochemical investigation of the CHCl3 fraction of Swertia corymbosa resulted in the isolation of a new 3-allyl-2,8-dihydroxy-1,6-dimethoxy-9H-xanthen-9-one (1), along with four known xanthones, gentiacaulein (3), norswertianin (4), 1,3,6,8-tetrahydroxyxanthone (5), and 1,3-dihydroxyxanthone (6). Structure of compound 1 was elucidated with the aid of IR, UV, NMR, and MS data, and chemical transformation via new allyloxy xanthone derivative (2). Compounds 1-6 exhibited various levels of antioxidant and anti-α-glucosidase activities. Absorption and fluorescence spectroscopic studies on 1-6 indicated that these compounds could interact with calf thymus DNA (CT-DNA) through intercalation and with bovine serum albumin (BSA) in a static quenching process. Compound 1 was found to be significantly cytotoxic against human cancer cell lines HeLa, HCT116, and AGS, and weakly active against normal NIH 3T3 cell line.

Antitumor Activity of the Xanthonoside XGAc in Triple-Negative Breast, Ovarian and Pancreatic Cancer by Inhibiting DNA Repair

“…By promoting S-phase arrest, these compounds impair DNA replication [24]. Consistently, previous evidence has indicated that xanthone derivatives may interact with DNA through intercalation, suppressing its replication in cancer cells [11,12].…”

“…Xanthones are O-heteroaromatic tricyclic scaffolds, which provide a wide range of derivatives with several biological responses, representing a privileged structure for anticancer drug development [10]. Particularly, this class of oxygen-containing heterocyclic compounds can intercalate into the base group pairs of DNA due to the appropriate planarity of the xanthone ring, causing DNA damage in cancer cells through non-covalent interaction with DNA [11,12]. In addition, the glycosidic moiety of natural glycosides of flavonoids and xanthones may exhibit biological activities that positively affect the antitumor activity [13].…”

Synthesis and Molecular Docking Studies of Alkoxy- and Imidazole-Substituted Xanthones as α-Amylase and α-Glucosidase Inhibitors

“…Considering structural similarities among other molecules, inhibition was much stronger for those containing the C-1 allyl group ( 7 , 9b , and 11b ). The data suggest that a molecule with an allyl or substituted aryl group has better affinity for the amino acid residues of the α-glucosidase enzyme and thus enhanced bioactivity, which owes itself to π-sticking or hydrophobic effects [ 11 , 21 , 37 ], as well as interactions with the halogen atoms substituted at the phenyl groups or at the alkyl side chain [ 36 , 38 , 47 ].…”

“…Several heterocyclic compounds containing oxygen and nitrogen are relevant for designing and developing new drugs. For instance, xanthone is a dibenzo-γ-pyrone heterocycle that has drawn the attention of researchers due to its broad spectrum of biological activity [ 8 , 9 , 10 , 11 ]. Xanthone derivatives are oxygenated heterocyclic compounds that occur as secondary metabolites in some families of higher plants (Guttiferae, Gentianaceae, Moraceae, Clusiaceae, and Polygalaceae).…”

Antimicrobial Compounds from Drypetes staudtii

“…It would be worthwhile to investigate medicinal plants used to treat wounds in folk medicines for the identification of new lead antimicrobial compounds. In our continuing efforts to discover new bioactive natural products from ethnomedicinal plants , we have collected stems and bark of D . staudtii from Nigeria based on its reported ethnomedicinal properties.…”