Antiplatelet Flavonoids from Seeds of Psoralea corylifolia

Abstract

The MeOH extract of the seeds of Psoralea corylifolia L. was found to inhibit the aggregation of rabbit platelets induced by arachidonic acid, collagen, and platelet activating factor. Bioassay-directed fractionation led to the isolation of three flavonoids, isobavachalcone (1), neobavaiso-flavone (2), and bavachin (3). Compounds 1 and 2 inhibited platelet aggregation.

Constituents of Psoralea corylifolia Fruits and Their Effects on Methicillin-Resistant Staphylococcus aureus

“…Among them, the following 15 were identified as known compounds by comparison of their spectral data with those in the literature: corylifol C (3) [5], bavachinin (4) [11], bavachin (5) [12], neobavaisoflavone (6) [11], corylin (7) [13], corylifol A (8) [5], 8-prenyldaidzin (9) [14,15], isobavachalcone (10) [11], corylifol B (11) [5], bakuchiol (12) (16) [18], and isopsoralen (17) [19] (Figure 1). The remaining two compounds were regarded as novel and named bakuisoflavone (1) and bakuflavanone (2) (Figure 1). Their structures were characterized as follows.…”

“…Among these compounds, two new compounds, bakuisoflavone (1) and bakuflavanone (2), were elucidated to be 4′,7-dihydroxy-3′-(2-hydroxy-3-methyl-3-butenyl)-isoflavone and 4′,7-dihydroxy-3′-(2-hydroxy-3-methyl-3-butenyl)-flavanone, respectively. The antibacterial effects of the isolated compounds, which were categorized as a flavone (3), flavanones (2, 4 and 5), isoflavones (1, 6, 7, 8 and 9), chalcones (10 and 11), meroterpenes (12, 13, 14 and 15), and coumarins (16 and 17), were examined.…”

“…Some of these compounds exhibit antioxidant [1], antiplatelet [2], estrogenic [3], immunomodulatory, and antitumor properties [4]. Antibacterial effects of several constituents on Staphylococcus aureus and S. epidermidis [5] have been reported.…”

“…On the other hand, compounds 13-15, each of which is oxidized at the terminal prenyl group, showed weaker antibacterial effects than that observed for bakuchiol (12), which is unoxidized at the terminal prenyl group. Similarly, bakuisoflavone (1) and bakuflavanone (2), in which the prenyl group is oxidized to 2-hydroxy-3-methyl-3-butenyl group in each structure, showed weaker antibacterial effects than those of the corresponding unoxidized compounds, bavachin (5) and neobavaisoflavone (6). Therefore, we assumed that hydroxylation of the prenyl group weakened the antibacterial effects.…”

Inhibitory Effects of Bakuchiol, Bavachin, and Isobavachalcone Isolated fromPiper longumon Melanin Production in B16 Mouse Melanoma Cells

“…[17][18][19] 2 has been reported to show an antiallergic effect, 20) and 3 has been reported to show antioxidative and antiplatelet activities. 17,21) Recently, 2 and 3 were found to inhibit the activity of acyl-CoA: cholesterol acyltransferase (ACAT), 22) but, their inhibitory activities against melanin biosynthesis have not been reported before. In recent reports, several prenylated flavonoids isolated from Artocapus heterophyllus were found to suppress melanin biosynthesis without inhibiting tyrosinase activity.…”