Ellagitannin oligomers and a neolignan from pomegranate arils and their inhibitory effects on the formation of advanced glycation end products.
Two new ellagitannin oligomers, pomegraniins A (7, tetramer) and B (8, pentamer), and a new glucose ester of neolignan, pomegralignan (19), together with six known ellagitannins, were isolated from the arils and pericarps of Punica granatum L. (pomegranate). The structures of the new compounds were elucidated based on spectroscopic analyses and chemical evidence. The known ellagitannins included oligomers such as oenothein B (4), eucalbanin B (5), and eucarpanin T1 (6), in addition to the known ellagitannin monomers such as punicalagin (1), punicalin (2), and punicacortein C (3). This paper therefore represents the first report concerning the isolation of ellagitannin oligomers from pomegranate. Examination of the inhibitory activities of the polyphenolic constituents from pomegranate towards the formation of advanced glycation end products (AGEs) revealed that all ellagitannins tested were more potent inhibitors than aminoguanidine, which was used as a positive control, and pomegraniin A (7) showed the most potent effect.
Faculty of Health and Welfare Science, Okayama Prefectural University, 111 Kuboki, Soja, Okayama 719-1197, Japan; Division of Pharmaceutical Sciences, Okayama University Graduate School of Medicine, Dentistry, Pharmaceutical Sciences, 1-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan. Electronic address: hito@fhw.oka-pu.ac.jp.
Hideyuki
H
Ito
Division of Pharmaceutical Sciences, Okayama University Graduate School of Medicine, Dentistry, Pharmaceutical Sciences, 1-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan.
Peng
P
Li
Division of Pharmaceutical Sciences, Okayama University Graduate School of Medicine, Dentistry, Pharmaceutical Sciences, 1-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan.
Mayuko
M
Koreishi
Osaka Techno Center, Morishita Jintan Co., Ltd., 2-11-1 Tsudayamate, Hirakata, Osaka 573-0128, Japan.
Akifumi
A
Nagatomo
Osaka Techno Center, Morishita Jintan Co., Ltd., 2-11-1 Tsudayamate, Hirakata, Osaka 573-0128, Japan.
Norihisa
N
Nishida
Division of Pharmaceutical Sciences, Okayama University Graduate School of Medicine, Dentistry, Pharmaceutical Sciences, 1-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan.
Takashi
T
Yoshida
D000975:Antioxidants / Q000737:chemistry*; D005638:Fruit / Q000737:chemistry*; D017127:Glycation End Products, Advanced / Q000737:chemistry*; D047348:Hydrolyzable Tannins / Q000737:chemistry*; D017705:Lignans / Q000737:chemistry*; D029561:Lythraceae / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry*
D000975:Antioxidants; D017127:Glycation End Products, Advanced; D047348:Hydrolyzable Tannins; D017705:Lignans; D010936:Plant Extracts; C013515:ellagitannin
Advanced glycation end products; Ellagitannin oligomer; Pomegralignan; Pomegranate; Pomegraniin; Punica granatum