Prenylated Isoflavonoids: Botanical Distribution, Structures, Biological Activities and Biotechnological Studies. An Update (1995 – 2006)

Abstract

In contrast with the parent class of flavonoids, the distribution of the isoflavonoid class in the plant kingdom is relatively limited, probably owing to the sporadic occurrence of isoflavone synthase. Isoflavonoids have been mostly found in the subfamily Fabaceae/Papilionoideae of the Leguminosae family. Isoprenoid-substituted (also called complex) isoflavonoids are expressed from a smaller number of plants, as a result of the similarly restricted distribution of prenyltransferases (PT-ase). After the reviews of Tanara & Ibrahim (1995), Boland & Donnelly (1997), the Handbook of Flavonoids by Harborne & C ( Handbook of Flavonoids, 1999), and the paper by Harborne and Williams (2000) few other reports concern the distribution and the biological activity of complex isoflavonoids, except a list of isoflavonoids produced from non leguminous plants. This review deals with an update of the literature on isoprenylated isoflavonoids in the years 1995-2006 and is focused on the following highlights. 1. Natural sources of complex isoflavonoids (2000-2006); 2. Chemical structure variety: new entries (2000-2006) 3. Biological activities and a possible structure-activity relationship (1995-2006) 4. In vitro production and microbial metabolism (1995-2006).

Molecular Characterization of a Membrane-bound Prenyltransferase Specific for Isoflavone from Sophora flavescens

“…Many prenylated aromatic compounds, such as flavonoids, coumarins, xanthones, and phloroglucinols, have been identified in various medicinal plants, and their biological and pharmacological activities have been studied. In particular, prenylated isoflavonoids found mainly in the Leguminosae family have drawn much attention as phytoalexins (32), in addition to some beneficial activities for humans (1,8). Studies on plant prenyltransferase genes for the prenylation of native polyphenolic compounds has begun from the identification of SfN8DT-1, the first flavonoid-specific plant prenyltransferase.…”

“…Out of diverse flavonoid cores, prenylated isoflavones particularly draw the attention of many researchers as notably valuable compounds due to their attractive biological activities (1,8). For instance, anthelmintic and phytoestrogen activities have been reported in prenylated isoflavonoids isolated from Tadehagi triquetrum (9).…”

Molecular Characterization and Phylogenetic Analysis of Two Novel Regio-specific Flavonoid Prenyltransferases from Morus alba and Cudrania tricuspidata

“…These compounds are hybrid molecules that contain structurally divergent flavonoid skeletons and extensively modified prenyl moieties with different chain lengths, and these compounds exhibit a wide range of biological activities, e.g. antioxidative, antitumor, antibacterial, antiviral, and estrogenic activities (1,3). Notably, the substitution of the flavonoid ring system with prenyl group(s) contributes strongly to these biological activities because the prenyl group(s) increases the lipophilicity of the flavonoids and confers to these molecules a strong affinity to biological membranes that results in greater bioavailability (6).…”

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

“…[1,2] Prenylation often improves the affinity for biomembranes and the interaction with proteins of a compound, [2] and therefore dramatically increases the biological activity. 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.…”

“…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.…”