Synthesis and immunosuppressive activity of l-rhamnopyranosyl flavonoids

Organic & Biomolecular Chemistry Pub Date: 2006-06-08 DOI: 10.1039/B604521A

Abstract

Astilbin, a flavonoid isolated from different plants, shows diverse biological activities. This paper reports the synthesis and immunosuppressive activity of seven analogues of astilbin, which may shed light on the structure–activity relationship of the compounds. The following glycosyl flavonoids, 6-α-L-rhamnopyranosyloxyflavanone (20), 3-α-L-rhamnopyranosyloxyflavone (22), 3-α-L-rhamnopyranosyloxyflavanone (24), 3-α-L-rhamnopyranosyloxychromanone (26), 4-α-L-rhamnopyranosyloxychromanol (27), 7-hydroxy-3-α-L-rhamnopyranosyloxyflavanone (30) and 4′-hydroxy-3-α-L-rhamnopyranosyloxyflavanone (32) were prepared respectively by glycosylation of 6-hydroxyflavanone (1), 3-hydroxyflavone (2), 3-hydroxyflavanone (5), 3-hydroxychromanone (8), 4-chromanol (9), 7-benzyloxy-3-hydroxyflavanone (12), 4′-benzyloxy-3-hydroxyflavanone (15). Among them, compounds 5, 8, 12 and 15 were synthesized from flavanone (3), 4-chromanone (6), 7-hydroxyflavanone (10) and 4′-hydroxyflavanone (13) respectively. Similar to astilbin (4), compounds 22, 24, 26, 30 and 32 significantly inhibited the single mixed lymphocytes reaction (sMLR) and enhanced the apoptosis of spleen cells isolated from mice with sheep red blood cell-induced delayed-type hypersensitivity respectively. However, compound 20 only showed a slight tendency to inhibit sMLR at higher concentration. Both compounds 20 and 27 did not influence the cell apoptosis. These data suggest that the following factors play essential roles in determining the biological activity of the flavonoids: the position at which the sugar is linked to the flavone, the presence of carbonyl on C-4 and phenol hydroxyl group in A or B ring. However, the presence of a B ring is unfavorable for the biological activity and the double bond at C(2)–C(3) in C-ring shows little effect on the activity.

Graphical abstract: Synthesis and immunosuppressive activity of l-rhamnopyranosyl flavonoids
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