Biologically active prenylated flavonoids from the genus Sophora and their structure–activity relationship—A review

Abstract

The genus Sophora (Fabaceae) has been used in traditional medicine for years. Prenylated flavonoids are one of the constituents of Sophora species that play important roles in their biological properties. Different classes of prenylated flavonoids are produced by Sophora spp. including prenylated flavonol (e.g., sophoflavescenol), prenylated flavanone (e.g., sophoraflavanone G), prenylated flavonostilbene (e.g., alopecurones A and B), and prenylated chalcone (kuraridin). Prenylated flavonoids have a more lipophilic structure, which leads to its high affinity to the cell membranes and enhancement of the biological activity, which includes cytotoxicity, antibacterial, anti‐inflammatory, and estrogenic activities. However, it is reported that prenylation decreases the plasma absorption but increases the tissue accumulation. The presence of the prenyl or lavandulyl groups on C8 position of flavonoids plays an important role in the biological activity. It seems that prenylated flavonoids have the potential to be developed as new drugs or supplements for human health.

Davidones F and G, Two Novel Flavonoids from Sophora davidii (Franch.) Skeels

“…Compounds 3 – 13 exhibited inactive to weak activities, increasing GLUT-4 translocation by 0.56–0.88 folds, respectively. Initial examination of the structure–activity relationship inferred that the prenylated groups in compounds 1 and 2 might contribute to their enhanced GLUT-4 translocation activity [ 6 , 12 , 25 , 26 , 27 ].…”

“…Notably, for the prenylated flavonoids, prenylation increased the lipophilicity of flavonoids, which resulted in an increased affinity to biological receptors [6]. To enhance our understanding of the chemical and biological diversity of the Sophora species, the chemical investigation of S. davidii led to the isolation of one new prenylated flavanone, davidone F (1), with a novel seven-membered oxygen ring, and one new prenylated flavanonol, davidone G (2), together with one known flavanonol (3), two known chalcones (5)(6), four known isoflavones (7)(8)(9)(10)(11)(12) and one known flavonol (13) (Figure 1). Additionally, we describe the isolation, structure elucidation and GLUT-4 translocation activities of these isolated compounds.…”

LaPT2 Gene Encodes a Flavonoid Prenyltransferase in White Lupin

“…In addition, prenylated flavonoids also possess considerable health-promoting properties for human health (De Naeyer et al, 2004;Ahmed-Belkacem et al, 2005;Han et al, 2006). In particular, prenylated flavonols, such as the methylated 8-prenylkaempferol (also called sophoflavescenol), showed cytotoxicity against the different cancer cell lines as well as antidiabetic and anti-Alzheimer activities (Jung et al, 2011;Boozari et al, 2019).…”

Phytochemical investigation using GC/MS analysis and evaluation of antimicrobial and cytotoxic activities of the lipoidal matter of leaves of Sophora secundiflora and Sophora tomentosa

“…Also, it was used for the treatment of hypertension in Taiwan folk medicine [12]. A myriad of active compounds including alkaloids, flavonoids, steroids, and triterpenoids compounds were isolated from the genus Sophora [13][14][15][16].…”