A systematic review on biological activities of prenylated flavonoids

Figures & data

Figure 1. Chemical structure of prenylated flavonoids: R₆, R₈, R₃′, R₅′, one or more prenyl can be found in these positions as prenylated flavonoids: R₂′, R₄′, R₃, R₅, R₇, can be –H, --OH or other functional groups.

Table 1. Summary on bioactivities of prenylated flavonoids.

Bioactivity	Percentage (%)
Antibacterial activity	19
Anti-inflammatory activity	7
Anti-oxidant activity	12
Anti-virus activity	3
Anti-allergic	2
Cytotoxicity	25
Osteogenic activity	3
Estrogenic activity	7
Larvicidal activity	3
Enzyme inhibition or protection	19

Table 2. Summary on structure--bioactivity relationship of prenylated flavonoids.

	Number	Position	Type	Mechanism	References
Antibacterial activity	Various	C-8↑	Prenyl; Lavandulyl; Isoprenyl	Prenylation increases the lipophilicity of flavonoids	Oh et al. (2011); Hatano et al. (2000)
Anti-inflammatory activity	Various	Various↑	Various	Unclear	Peluso et al. (2010); Jones et al. (1996); Huang et al. (2009); Simpson et al. (2010)
Anti-oxidant activity	Various	Various↑	Various	Unclear	Kumazawa et al. (2007); Lee et al. (2006); Dufall et al. (2003); Park et al. (2006); Jung et al. (2008); Jayasinghe et al. (2008)
Anti-virus activity	Two	C-5/C-6↑	Prenyl	Unclear	Feng et al. (2010); Khaomek et al. (2008)
Anti-allergy	One	Various↑	Prenyl; Lavandulyl	Unclear	Quan et al. (2008)
Cytotoxicity	Four	C-3↑ C-8↑	Prenyl; Isoprenyl; farnesyl; geranyl	Prenylated flavonoids have greater binding energies than those of the non-prenylated flavonoids	Dat et al. (2010); Cassidy and Serzer (2010); Ma et al. (2011); Halabalaki et al. (2006); Wu et al. (2008)
Osteogenic activity	One	C-6↓ C-8↑	Prenyl	Unclear	Zhang et al. (2008); Ming et al. (2011)
Estrogenic activity	One	C-8↑	Prenyl	Unclear	Kretzschmar et al. (2010); Milligan et al. (2002)
Larvicidal activity	One/Two	Inactive	Prenyl	Unclear	Omisore et al. (2005); Niu et al. (2010)
Enzyme inhibitor and enhancer	Various	C-8↑	Prenyl; Lavandulyl	Prenylation increases the lipophilic chain length to enhance the function of flavonoids skeleton	Kenéz et al. (2007); Habtemariam, (2012); Stec and Li (2012); Cho et al. (2011); Jang et al. (2008); Oh et al. (2005); Kim et al. (2003); Jung et al. (2010, 2012)

Number, Position, Type describe the characters of prenyl group. Mechanism shows how these factors affect the bioactivities of prenylated flavonoids.

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