Abscisic acid related compounds and lignans in prunes (Prunus domestica L.) and their oxygen radical absorbance capacity (ORAC).
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.
Kikuzaki
Hiroe
H
Division of Food and Health Sciences, Graduate School of Human Life Science, Osaka City University, 3-138, Sugimoto 3, Sumiyoshi, Osaka 558-8585, Japan.
Kayano
Shin-ichi
S
Fukutsuka
Naoko
N
Aoki
Asuka
A
Kasamatsu
Kumi
K
Yamasaki
Yuka
Y
Mitani
Takahiko
T
Nakatani
Nobuji
N
D000040:Abscisic Acid / Q000031:analogs & derivatives* / Q000032:analysis / Q000737:chemistry; D016166:Free Radical Scavengers / Q000737:chemistry; D005638:Fruit / Q000737:chemistry*; D017705:Lignans / Q000032:analysis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D027861:Prunus / Q000737:chemistry*; D017382:Reactive Oxygen Species / Q000737:chemistry*; D013053:Spectrophotometry
D016166:Free Radical Scavengers; D017705:Lignans; D017382:Reactive Oxygen Species; D000040:Abscisic Acid