Kikuzaki Hiroe, Kayano Shin-ichi, Fukutsuka Naoko, Aoki Asuka, Kasamatsu Kumi, Yamasaki Yuka, Mitani Takahiko, Nakatani Nobuji
Division of Food and Health Sciences, Graduate School of Human Life Science, Osaka City University, 3-138, Sugimoto 3, Sumiyoshi, Osaka 558-8585, Japan.
J Agric Food Chem. 2004 Jan 28;52(2):344-9. doi: 10.1021/jf034954v.
Four new abscisic acid related compounds (1-4), together with (+)-abscisic acid (5), (+)-beta-D-glucopyranosyl abscisate (6), (6S,9R)-roseoside (7), and two lignan glucosides ((+)-pinoresinol mono-beta-D-glucopyranoside (8) and 3-(beta-D-glucopyranosyloxymethyl)-2- (4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-(2R,3S)-dihydrobenzofuran (9)) were isolated from the antioxidative ethanol extract of prunes (Prunus domestica L.). The structures of 1-4 were elucidated on the basis of NMR and MS spectrometric data to be rel-5-(3S,8S-dihydroxy-1R,5S-dimethyl-7-oxa-6-oxobicyclo[3,2,1]oct-8-yl)-3-methyl-2Z,4E-pentadienoic acid (1), rel-5-(3S,8S-dihydroxy-1R,5S-dimethyl-7-oxa-6-oxobicyclo[3,2,1]oct-8-yl)-3-methyl-2Z,4E-pentadienoic acid 3'-O-beta-d-glucopyranoside (2), rel-5-(1R,5S-dimethyl-3R,4R,8S-trihydroxy-7-oxa-6-oxobicyclo[3,2,1]oct-8-yl)-3-methyl-2Z,4E-pentadienoic acid (3), and rel-5-(1R,5S-dimethyl-3R,4R,8S-trihydroxy-7-oxabicyclo[3,2,1]- oct-8-yl)-3-methyl-2Z,4E-pentadienoic acid (4). The antioxidant activities of these isolated compounds were evaluated on the basis of oxygen radical absorbance capacity (ORAC). The ORAC values of abscisic acid related compounds (1-7) were very low. Two lignans (8 and 9) were more effective antioxidants whose ORAC values were 1.09 and 2.33 micromol of Trolox equiv/micromol, respectively.
从李子（Prunus domestica L.）的抗氧化乙醇提取物中分离出四种新的脱落酸相关化合物（1-4），以及（+）-脱落酸（5）、（+）-β-D-吡喃葡萄糖基脱落酸酯（6）、（6S,9R）-蔷薇糖苷（7）和两种木脂素糖苷（（+）-松脂醇单-β-D-吡喃葡萄糖苷（8）和3-（β-D-吡喃葡萄糖氧基甲基）-2-（4-羟基-3-甲氧基苯基）-5-（3-羟丙基）-7-甲氧基-（2R,3S）-二氢苯并呋喃（9））。根据核磁共振和质谱数据阐明了1-4的结构，分别为rel-5-（3S,8S-二羟基-1R,5S-二甲基-7-氧杂-6-氧代双环[3,2,1]辛-8-基）-3-甲基-2Z,4E-戊二烯酸（1）、rel-5-（3S,8S-二羟基-1R,5S-二甲基-7-氧杂-6-氧代双环[3,2,1]辛-8-基）-3-甲基-2Z,4E-戊二烯酸3'-O-β-D-吡喃葡萄糖苷（2）、rel-5-（1R,5S-二甲基-3R,4R,8S-三羟基-7-氧杂-6-氧代双环[3,2,1]辛-8-基）-3-甲基-2Z,4E-戊二烯酸（3）和rel-5-（1R,5S-二甲基-3R,4R,8S-三羟基-7-氧杂双环[3,2,1]-辛-8-基）-3-甲基-2Z,4E-戊二烯酸（4）。基于氧自由基吸收能力（ORAC）对这些分离出的化合物的抗氧化活性进行了评估。脱落酸相关化合物（1-7）的ORAC值非常低。两种木脂素（8和9）是更有效的抗氧化剂，其ORAC值分别为1.09和2.33微摩尔Trolox当量/微摩尔。
