C-prenylated flavonoids with potential cytotoxic activity against solid tumor cell lines

Chemical Characterization, α-Glucosidase, α-Amylase and Lipase Inhibitory Properties of the Australian Honey Bee Propolis

“…Owing to the prenylated side chains, which can enhance cell membrane permeability, the prenylated flavonoids generally show stronger biological activities than their non-prenylated precursors [43,44]. They have been known to possess a wide range of biological properties, such as antifungal [45], antimicrobial [46,47], antiviral [48,49], antiinflammatory [50], anticancer [47,51,52], anti-arthritic [50], anti-osteoporosis [52,53], antilipid [54], and α-glucosidase inhibitory activities [55], in both in vitro and in vivo studies. More recently, the synergistic effects of some of the prenylated flavonoids in combination with conventional antibiotics, including vancomycin, ciprofloxacin, and methicillin, against the multidrug-resistant Staphylococcus aureus bacterial strain have been reported [56].…”

Prenylated Flavonoids with Potential Antimicrobial Activity: Synthesis, Biological Activity, and In Silico Study

“…However, since prenylated flavonoids often exist at trace levels in their natural sources that make further biological studies difficult, it may be useful to synthesize prenylated flavonoids in appreciable quantities and at low costs to allow future biological studies [ 4 ]. Compounds of this type exhibit significant effects in the insect–plant interaction [ 5 ] as well as antifungal [ 6 ], antimicrobial [ 7 ], antiviral [ 8 , 9 ], anti-inflammatory [ 10 ], and anticancer [ 11 ] activities and anti-lipid properties, both in vitro and in vivo [ 12 ]. The C-prenylation of flavonoids seems to be crucial to the biological activities of these compounds, which may lead to enhanced cell membrane targeting and thus increased intracellular activity [ 13 ].…”

8‐Prenylflavanones through Microwave Promoted Tandem Claisen Rearrangement/6‐endo‐trig Cyclization and Cross Metathesis

“…for C 18 H 16 O 2 [M + ] 264.1150, found 264.1155. Analytical data of 13aa : [ 5 ] yellowish solid. 1 H NMR (400 MHz, CDCl 3 ): δ = 13.19 (s, 1H), 7.92 (d, J = 15.5 Hz, 1H), 7.82 (dd, J = 8.1, 1.2 Hz, 1H), 7.71–7.63 (m, 3H), 7.47–7.42 (m, 3H), 7.39 (dm, J = 7.4 Hz, 1H), 6.92 (t, J = 7.7 Hz, 1H), 6.07 (ddt, J = 16.9, 10.3, 6.6 Hz, 1H), 5.16–5.09 (m, 2H), 3.48 (d, J = 6.6 Hz, 2H) ppm; 13 C NMR (100 MHz, CDCl 3 ): δ = 194.1, 161.8, 145.4, 136.6, 136.3, 134.9, 131.0, 129.8, 129.2, 128.8, 127.9, 120.7, 119.7, 118.5, 116.2, 33.7 ppm; IR (ATR): ν̃ = 2923 (w), 1636 (s), 1594 (m), 1571 (s), 1476 (m), 1434 (m), 1345 (s), 1305 (m), 1231 (s), 1105 (m) cm –1 ; HRMS (EI): m/z calcd.…”

“…[1,2] Bioactivities of these compounds such as antibacterial and anti-oxidant activity, cytotoxicity and estrogenic activity modulation, have been summarized and discussed in several recent reviews. [3][4][5][6] Prenyl substituents generally increase the bioactivities of flavonoids. This has been attributed to an enhanced membrane permeability, which is caused by the higher lipophilicity compared to the analogous non-prenylated natural products.…”