Prenylation enhances cytotoxicity of apigenin and liquiritigenin in rat H4IIE hepatoma and C6 glioma cells

Cytotoxic Constituents of Propolis from Myanmar and Their Structure-Activity Relationship

“…This activity enhancement may be due to the increase of the lipophilicity resulting in the enhancement of interaction with cancer cell membrane. 30,31) In conclution, the cytotoxicity of 13 cylcoartane-type triterpenes and four prenylated flavanones, isolated from propolis collected in Myanmar, were tested against a panel of six different cancer cell lines. 3a,27-Dihydroxycycloart-24E-en-26-oic acid (3) and (2S)-5,7-dihydroxy-4Ј-methoxy-8,3Ј-diprenylflavanone (14) displayed the most potent cytotoxicity among the tested cylcoartane-type triterpenes and flavanones, respectively.…”

Prenylation of Aromatic Secondary Metabolites: A New Frontier for Development of Novel Drugs

“…Watjen and co-workers [20] analyzed the antioxidative potential and cytotoxic effects of two prenylflavonoids (Figure 4), licoflavone C (24) and and isobavachin (26) in comparison to their non prenylated analogues, apigenin (23) , liquiritigen (25) and apigenin glucoside (27). They discovered that compounds 24 and 26 showed good cytotoxic activity against C6 glioma and H4IIE hepatoma cells with IC 50 of 42 ± 5 and 96 ± 19 µmol/L respectively.…”

Prenylation of Flavonoids by Using a Dimethylallyltryptophan Synthase, 7‐DMATS, from Aspergillus fumigatus

“…Diverse biological and pharmacological activities such as antifungal, antibacterial, antiviral, antiparasitic, anti-inflammatory, antitumor, cancer chemoprevention, estrogenic, and antiestrogenic activities have been described for prenylated flavonoids. [1][2][3] Due to the broad pharmacological activities of prenylated flavonoids, various strategies have been developed for their regioselective chemical synthesis, especially for C-prenylated derivatives. [4,5] Meanwhile, significant progress has also been made in the identification of enzymes that catalyze the transfer of prenyl moieties onto the flavonoid skeleton.…”