Prenylation enhances the biological activity of dietary flavonoids by altering their bioavailability

Figures & data

Figure 1. Chemical structures of prenyl flavonoids in edible plants.

Table 1. Prenylation enhances biological activities of parent flavonoids.

Position	Parent flavonoid	Enhanced activity	Experimental model	Ref
3-prenyl	Luteolin	Inhibition of tyrosinase	In vitro	[30]
6-prenyl	Apigenin	Inhibition of melanin byosynthesis	B16 melanoma cells	[31]
5’-prenyl	Chalcone	Inhibition of α-glucosidase	In vitro	[32]
8-prenyl	Quercetin
8-prenyl	Quercetin	Inhibition of MAPKs	LAW264.7 cells	[22]
8 or 6-prenyl	Naringenin	Estrogenic activity	MCF-7 cells	[34,35]
8-prenyl	Naringenin	Bone maintenance	Calvarial osteoblasts	[36]
8-prenyl	Naringenin	Muscle maintenance	C57BL6 mice	[38]

Figure 2. High accumulation of prenyl flavonoids in the tissues. Mukai et al. [38,65] demonstrated higher tissue accumulation of prenyl flavonoids by comparison with parent flavonoids. Mice were fed each flavonoid mixed in a diet for more than 2 weeks, and the concentrations were analyzed by high-performance liquid chromatography. (A) Accumulation of 8PN and naringenin in the gastronomic muscle [38], (B) 8PQ and quercetin in the liver and kidney [65]. Data are modified from previous reports [38,65]. Data represent the mean ± S.E (n = 4). Asterisks indicate significant differences analyzed by two-sided Student’s t-test (p < 0.05).

Figure 3. Conversion of XN to 8PN [56,59,60].

Figure 4. Prenylation enhances the biological activity of dietary flavonoids by increasing their bioaccumulation.

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