A systematic review on biological activities of prenylated flavonoids

Abstract

Context: Prenylated flavonoids are a unique class of naturally occurring flavonoids that exist especially for the plant's self-defensive strategy. This special class of flavonoids increases the bioactivities of their backbone flavonoids with non-prenylation; therefore, prenylated flavonoids have more potential to be developed and utilized. Objective: The number, position and type of the prenyl group on the flavonoids backbone structure may have close relationships with the bioactivities of flavonoids. Methods: PubMed and WEB OF KNOWLEDGEÕ were used to search articles published in English between 1 January 2002 and 31 December 2012, which discuss the structure-activity relationship between prenylated flavonoids and their bioactivities. Results: It is proposed that the prenyl-moiety makes the backbone compound more lipophilic, which leads to its high affinity with cell membranes. The prenylation brings the flavonoids with enhancement of antibacterial, anti-inflammatory, antioxidant, cytotoxicity, larvicidal as well as estrogenic activities. However, it is reported that the prenyl-moiety decreases the bioavailability and plasma absorption of prenylated flavonoids. Conclusion: The prenyl group affects the bioactivities of flavonoids in certain ways, while the action mechanisms and the structure-activity relationship as well as more in vivo studies even clinical validation trials need to be further investigated.

Effect of substituted stilbenes on platelet function

“…However, oral bioavailability of resveratrol is poor due to rapid and extensive metabolism, with the formation of several metabolites many of which biologically inactive, like resveratrol glucuronides and resveratrol sulfates [8]. Some natural derivatives of resveratrol (1a), like pterostilbene (1b) [9], while sharing with resveratrol most of the biologic activities, have a higher in vivo bioavailability [10]. Furthermore, prenylation of natural or semisynthetic phenols increases several of their actions, such as the antibacterial, antioxidant and anti-inflammatory activities, by increasing their cellular uptake, and indeed oxyprenylated polyphenols have proven to be valuable, biologically active phytochemicals [9].…”

Prenylated Flavonoids from Roots of Glycyrrhiza uralensis Induce Differentiation of B16-F10 Melanoma Cells

“…In recent years, flavonoids, especially the prenylated ones, have attracted extensive attention because of its resulting radicals can enhance their biological activities [15]. In this study, several flavonoids, including GF-1, 2, 4, 6, and 9, were found to contain a substituent of prenyl moiety or dimethylpyran (formation from prenyl) in their structures.…”

“…According to their variations of backbone and substitution, flavonoids can be classified into different subclasses, providing an extremely diverse range of derivatives. Among them, prenylated flavonoids have attracted considerable attention due to their promising and diverse bioactivities [15]. For example, the prenylated substituted chalcones were shown to be cytotoxic in MCF-7, HT-29, and A-2780 cancer cells, whereas the conversion of a chalcone to a favanone resulted in reduced antiproliferative activity [23].…”

Prenylated flavanone derivatives isolated from Erythrina addisoniae are potent inducers of apoptotic cell death

“…& Dalz. afforded six further compounds (1)(2)(3)(4)(5)(6). The 1 H-and 13 C-NMR spectra of compound 1 showed resonances for 25 carbons and 28 protons.…”

“…The genus Erythrina is known to contain prenylated flavonoid derivatives 1 , which were reported to possess interesting biological and pharmacological properties 2 . In traditional medicine, extracts prepared from Erythrina spp.…”