title: Syntheses of procyanidin B2 and B3 gallate derivatives using equimolar condensation mediated by Yb(OTf)3 and their antitumor activities.
abstract: Synthesis of procyanidin B2 and B3 gallate derivatives, 3-O-gallate, 3"-O-gallate, and 3,3"-di-O-gallate, were synthesized using equimolar condensation mediated by Yb(OTf)3. Synthesized compounds showed significant antitumor effects against human prostate PC-3 cell lines. Their activities were weaker than well-known EGCG and prodelphinidin B3.
authors.affiliation: Graduate School of Agriculture, Sciences of Functional Foods, Shinshu University, 8304 Minami-Minowa Kami-Ina, Nagano 399-4598, Japan.
authors.forename: Manato
authors.initials: M
authors.lastname: Suda
authors.forename: Miyuki
authors.initials: M
authors.lastname: Katoh
authors.forename: Kazuya
authors.initials: K
authors.lastname: Toda
authors.forename: Kiriko
authors.initials: K
authors.lastname: Matsumoto
authors.forename: Koichiro
authors.initials: K
authors.lastname: Kawaguchi
authors.forename: Sei-ichi
authors.initials: S
authors.lastname: Kawahara
authors.forename: Yasunao
authors.initials: Y
authors.lastname: Hattori
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Fujii
authors.forename: Hidefumi
authors.initials: H
authors.lastname: Makabe
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D044946:Biflavonoids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002392:Catechin / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D005707:Gallic Acid / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D008297:Male; D008698:Mesylates / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D044945:Proanthocyanidins / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011471:Prostatic Neoplasms / Q000188:drug therapy
chemical_list: D000970:Antineoplastic Agents; D044946:Biflavonoids; D008698:Mesylates; D009942:Organometallic Compounds; D044945:Proanthocyanidins; C479580:procyanidin B2; C479581:procyanidin B3; C518808:ytterbium(III) triflate; D005707:Gallic Acid; D002392:Catechin
keywords: Antitumor; Condensation; Lewis acid; Polyphenol; Procyanidin gallate