ABSTRACT
The first synthesis of alphitonin-4-O-ß-D-glucopyranoside (1) was described. Since, the nitrile group, a strong hydrogen bond acceptor with a significant solvation shell, is considered to have capacity comparable to sugar for facilitating the cell membrane permeation of the molecules, several alphitonin-4-O-ß-D-glucopyranoside and maesopsin-4-O-ß-D-glucopyranoside analogues were prepared by replacing glucopyranose moieties with acetonitrile groups. Immunostimulating activity evaluation on lymphocyte proliferation indicated that the compound 7 with an acetonitrile group at OH-4 of alphitonin had a strong stimulation effect on lymphocyte proliferation. Interestingly, when tested against the normal cell NIH/3T3, 7 had no inhibition even at the concentration of 100 µg/mL.
Subject(s)
Glucans/chemical synthesis , Glucans/pharmacology , Animals , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Glucans/chemistry , Lymphocytes/drug effects , Mice , Molecular Structure , NIH 3T3 Cells , RabbitsABSTRACT
A new, reliable, and convenient protection-free one-pot method for the synthesis of aureusidin (1) is described. The present synthetic approach involves the condensation of 4,6-dihydroxybenzofuranone with 3,4-dihydroxybenzaldehyde in the presence of concentrated HCl to afford aureusidin (1) in good yield with high purity. This procedure offers a short and simple route for the preparation of aureusidin (1), a bioactive natural product from several vegetal species, as well as for synthesis of other aurones.
