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Review
. 2023 Apr;46(4):207-272.
doi: 10.1007/s12272-023-01443-4. Epub 2023 Apr 14.

Phytochemistry and pharmacology of natural prenylated flavonoids

Hua-Wei Lv  1 , Qiao-Liang Wang  1 , Meng Luo  1 , Meng-Di Zhu  2 , Hui-Min Liang  1 , Wen-Jing Li  1 , Hai Cai  1 , Zhong-Bo Zhou  3 , Hong Wang  1 , Sheng-Qiang Tong  4 , Xing-Nuo Li  5
Affiliations
Review

Phytochemistry and pharmacology of natural prenylated flavonoids

Hua-Wei Lv et al. Arch Pharm Res. 2023 Apr.

Abstract

Prenylated flavonoids are a special kind of flavonoid derivative possessing one or more prenyl groups in the parent nucleus of the flavonoid. The presence of the prenyl side chain enriched the structural diversity of flavonoids and increased their bioactivity and bioavailability. Prenylated flavonoids show a wide range of biological activities, such as anti-cancer, anti-inflammatory, neuroprotective, anti-diabetic, anti-obesity, cardioprotective effects, and anti-osteoclastogenic activities. In recent years, many compounds with significant activity have been discovered with the continuous excavation of the medicinal value of prenylated flavonoids, and have attracted the extensive attention of pharmacologists. This review summarizes recent progress on research into natural active prenylated flavonoids to promote new discoveries of their medicinal value.

Keywords: Anti-cancer; Anti-inflammatory; Pharmacological activity; Phytochemistry; Prenylated flavonoid.

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Conflict of interest statement

The authors declare that there is no conflict of interest.

Figures

Fig. 1
Fig. 1
Statistics for the families (A); numbers in parentheses are the statistics for the genus/species. Statistics for genera from Fabaceae (B), Moraceae (C), and Euphoriaceae (D); numbers in parentheses are the statistics for species
Fig. 2
Fig. 2
Statistics for the number of prenylated flavonoids
Fig. 3
Fig. 3
Basic skeleton of flavonoids and prenyl groups
Fig. 4
Fig. 4
Biosynthesis of the chalcone skeleton and the different classes of flavonoids. Enzyme names are abbreviated as follows: PAL phenylalanine ammonia lyase; C4H cinnamate 4-hydroxylase; CPR cytochrome P450 reductase; TAL tyrosine ammonia lyase; 4CL 4-coumarate-CoA ligase; CHS chalcone synthase; CHR chalcone reductase; CHI chalcone isomerase; F3H flavanone 3-hydroxylase; FNS flavone synthas; IFS isoflavone synthase; HID 2-hydroxyisoflavanone dehydratase; FLS flavonol synthase; DFR dihydroflavonol 4-reductase; I2′H isoflavone hydroxylase; IFR isoflavone reductase; PTS pterocarpan synthase.
Fig. 5
Fig. 5
Biosynthesis of the prenylated flavonoids (I)
Fig. 6
Fig. 6
Biosynthesis of the prenylated flavonoids (II).
Fig. 7
Fig. 7
Chemical structures of prenylated flavones (1–261)
Fig. 7
Fig. 7
Chemical structures of prenylated flavones (1–261)
Fig. 7
Fig. 7
Chemical structures of prenylated flavones (1–261)
Fig. 7
Fig. 7
Chemical structures of prenylated flavones (1–261)
Fig. 7
Fig. 7
Chemical structures of prenylated flavones (1–261)
Fig. 7
Fig. 7
Chemical structures of prenylated flavones (1–261)
Fig. 7
Fig. 7
Chemical structures of prenylated flavones (1–261)
Fig. 8
Fig. 8
Chemical structures of prenylated flavonones (262–567)
Fig. 8
Fig. 8
Chemical structures of prenylated flavonones (262–567)
Fig. 8
Fig. 8
Chemical structures of prenylated flavonones (262–567)
Fig. 8
Fig. 8
Chemical structures of prenylated flavonones (262–567)
Fig. 8
Fig. 8
Chemical structures of prenylated flavonones (262–567)
Fig. 8
Fig. 8
Chemical structures of prenylated flavonones (262–567)
Fig. 8
Fig. 8
Chemical structures of prenylated flavonones (262–567)
Fig. 9
Fig. 9
Chemical structures of prenylated chalcones (568–657)
Fig. 9
Fig. 9
Chemical structures of prenylated chalcones (568–657)
Fig. 10
Fig. 10
Chemical structures of prenylated dihydrochalcones (658–689)
Fig. 11
Fig. 11
Chemical structures of prenylated isoflavones (690–908)
Fig. 11
Fig. 11
Chemical structures of prenylated isoflavones (690–908)
Fig. 11
Fig. 11
Chemical structures of prenylated isoflavones (690–908)
Fig. 11
Fig. 11
Chemical structures of prenylated isoflavones (690–908)
Fig. 11
Fig. 11
Chemical structures of prenylated isoflavones (690–908)
Fig. 12
Fig. 12
Chemical structures of prenylated flavans (909–943)
Fig. 13
Fig. 13
Chemical structures of prenylated isoflavans (944–1005)
Fig. 13
Fig. 13
Chemical structures of prenylated isoflavans (944–1005)
Fig. 14
Fig. 14
Chemical structures of prenylated flavonostilbenes and biflavonoids (1006–1036)
Fig. 15
Fig. 15
SARs of prenylated flavonoids with cytotoxicity (I)
Fig. 16
Fig. 16
SARs of prenylated flavonoids with cytotoxicity (II).
Fig. 17
Fig. 17
SARs of prenylated flavonoids with PPARγ agonist activity
Fig. 18
Fig. 18
SARs of prenylated flavonoids with antifungal activity against Z. parabailii
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