Systematic synthesis of galloyl-substituted procyanidin B1 and B2, and their ability of DPPH radical scavenging activity and inhibitory activity of DNA polymerases.
Six galloyl-substituted procyanidin B1 and B2, 3-O-gallate, 3''-O-gallate, and 3,3''-di-O-gallate, were systematically synthesized with the condensation method using TMSOTf as a catalyst. Their ability of DPPH radical scavenging activity and DNA polymerase inhibitory activity were also investigated. The results indicated that the galloyl group of these compounds is very important for both activities. 3,3''-Di-O-gallate dimers acted as strong inhibitor against DNA polymerase alpha and beta, whereas the desgalloyl and monogalloyl compounds did not exhibit any appreciable inhibitory activity against the DNA polymerase beta.
Saito
Akiko
A
Biotechnology Center, Toyama Prefecture, Kosugi, Toyama 939-0398, Japan.
Mizushina
Yoshiyuki
Y
Ikawa
Hiroshi
H
Yoshida
Hiromi
H
Doi
Yuki
Y
Tanaka
Akira
A
Nakajima
Noriyuki
N
D000818:Animals; D044946:Biflavonoids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001713:Biphenyl Compounds; D002384:Catalysis; D002392:Catechin / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002417:Cattle; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D016166:Free Radical Scavengers / Q000737:chemistry*; D005707:Gallic Acid / Q000737:chemistry; D008968:Molecular Conformation; D019384:Nucleic Acid Synthesis Inhibitors; D010851:Picrates / Q000737:chemistry*; D044945:Proanthocyanidins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D051381:Rats; D013329:Structure-Activity Relationship
D044946:Biflavonoids; D001713:Biphenyl Compounds; D004791:Enzyme Inhibitors; D016166:Free Radical Scavengers; D019384:Nucleic Acid Synthesis Inhibitors; D010851:Picrates; D044945:Proanthocyanidins; C479579:procyanidin B1; C479580:procyanidin B2; D005707:Gallic Acid; D002392:Catechin; C004931:1,1-diphenyl-2-picrylhydrazyl