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Stereoselective synthesis of procyanidin B3-3-O-gallate and 3,3″-di-O-gallate, and their abilities as antioxidant and DNA polymerase inhibitor |
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| Authors: | Akiko Saito Mana Emoto Akira Tanaka Yuki Doi Kazuaki Shoji Yoshiyuki Mizushina Hiroshi Ikawa Hiromi Yoshida Nobuyasu Matsuura Noriyuki Nakajima |
| Institution: | aBiotechnology Center, Toyama Prefecture, Kosugi, Toyama 939-0398, Japan bDepartment of Biosources Science, College of Technology, Kosugi, Toyama 939-0398, Japan cBiotechnology Research Center, Toyama Prefectural University, Kosugi, Toyama 939-0398, Japan dBiotechnology Section, Agricultural Experiment Station, Toyama Agricultural Research Center, Yoshioka, Toyama 939-8153, Japan eDepartment of Nutritional Science, Kobe-Gakuin University, Nishi-ku, Kobe, Hyogo 651-2180, Japan fHigh Technology Research Center, Kobe-Gakuin University, Nishi-ku, Kobe, Hyogo 651-2180, Japan gDepartment of Life Science, Faculty of Science, Okayama University of Science, Ridai-cho, Okayama 700-0005, Japan |
| Abstract: | A simple method for the synthesis of procyanidin B3 substituted with a galloyl group at the 3 and 3″ position is described. Condensation of a benzylated catechin-3-O-gallate electrophile with a nucleophile, catechin and catechin-3-O-gallate, proceeded smoothly and stereoselectively to afford the corresponding dimer gallates, procyanidin B3-3-O-gallate and procyanidin B3-3,3″-di-O-gallate, in good yields. Further, their antioxidant activities on UV-induced lipid peroxide formation, DPPH radical scavenging activity and inhibitory activity of DNA polymerase were also investigated. Among three procyanidin B3 congeners (procyanidin B3, 3-O-gallate and 3,3″-di-O-gallate), the 3,3″-di-O-gallate derivative showed the strongest antioxidant and radical scavenging activity. Interestingly, the 3-O-gallate derivative was the strongest inhibitor of mammalian DNA polymerase  with IC50 value of 0.26 μM, although it showed the weakest antioxidant and radical scavenging activity. It became apparent that the presence of a galloyl group at the C-3 position in the proanthocyanidin oligomer was very important for biological activity, however, the antioxidant activity of these compounds was not parallel to the DNA polymerase inhibitory activity. |
| Keywords: | Proanthocyanidin Procyanidin B3 Galloyl ester Antioxidant activity DPPH radical scavenging activity DNA polymerase inhibitor Stereoselective synthesis |
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