title: Antimutagenicity of mono-, di-, and tricaffeoylquinic acid derivatives isolated from sweetpotato (Ipomoea batatas L.) leaf.
abstract: The caffeoylquinic acid derivatives, 3-mono-O-caffeoylquinic acid (chlorogenic acid, ChA), 3,4-di-O-caffeoylquinic acid (3,4-diCQA), 3,5-di-O-caffeoylquinic acid (3,5-diCQA), 4,5-di-O-caffeoylquinic acid (4,5-diCQA) and 3,4,5-tri-O-caffeoylquinic acid (3,4,5-triCQA), and caffeic acid (CA) were isolated from the sweetpotato (Ipomoea batatas L.) leaf. We examined the antimutagenicity of these caffeoylquinic acid compounds to promote new uses of the sweetpotato leaf. These caffeoylquinic acid derivatives effectively inhibited the reverse mutation induced by Trp-P-1 on Salmonella typhimurium TA 98. The antimutagenicity of these derivatives was 3,4,5-triCQA > 3,4-diCQA = 3,5-diCQA = 4,5-diCQA > ChA in this order. There was no difference in the antimutagenicity of all dicaffeoylquinic acid derivatives. A comparison of the activities and structures of these compounds suggested that the number of caffeoyl groups bound to quinic acid played a role in the antimutagenicity of the caffeoylquinic acid derivatives. The sweetpotato leaves contained distinctive polyphenolic components with a high content of mono-, di-, and tricaffeoylquinic acid derivatives and could be a source of physiological functions.
authors.affiliation: Department of Upland Farming Research, National Agricultural Research Center for Kyushu Okinawa Region, Miyakonojo, Miyazaki 885-0091, Japan. mak825@affrc.go.jp
authors.forename: Makoto
authors.initials: M
authors.lastname: Yoshimoto
authors.forename: Shoji
authors.initials: S
authors.lastname: Yahara
authors.forename: Shigenori
authors.initials: S
authors.lastname: Okuno
authors.forename: Md Shahidul
authors.initials: MS
authors.lastname: Islam
authors.forename: Koji
authors.initials: K
authors.lastname: Ishiguro
authors.forename: Osamu
authors.initials: O
authors.lastname: Yamakawa
mesh_terms: D016587:Antimutagenic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002243:Carbolines / Q000633:toxicity; D002851:Chromatography, High Pressure Liquid; D027723:Ipomoea batatas / Q000737:chemistry*; D009152:Mutagenicity Tests; D010636:Phenols / Q000032:analysis; D018515:Plant Leaves / Q000737:chemistry; D011801:Quinic Acid / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D012486:Salmonella typhimurium / Q000187:drug effects / Q000235:genetics
chemical_list: D016587:Antimutagenic Agents; D002243:Carbolines; D010636:Phenols; C472707:caffeoylquinic acid; D011801:Quinic Acid; C019132:3-amino-1,4-dimethyl-5H-pyrido(4,3-b)indole