Germination Inhibitor in<i>Citrus unshu</i>Fruit Peelings: (+)-Abscisyl β-D-Glucopyranoside

Yamauchi, Satoshi; Abe, Fumiko; Kinoshita, Yoshiro

doi:10.1271/bbb.59.1968

Cited by 2 publications

(3 citation statements)

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“…The 14 known compounds were determined as dehydrovomifoliol ( 2 ) [16], 3-oxo- α -ionol 9- O -β- d -glucoside ( 3 ) [17], roseoside ( 4 ) [17], 3-oxo-9- O -β- d -glucosyloxy-4,6 E -megastigmadien ( 5 ) [18], 4-oxo-β-ionol 9- O -β- d -glucoside ( 6 ) [9], cannabiside D ( 7 ) [19], dendranthemoside B ( 8 ) [20], icariside B2 ( 9 ) [21], officinoside A ( 10 ) [22], abscisic acid ( 12 ) [23], abscisyl β- d -glucoside ( 13 ) [24], 9 E -abscisic acid ( 14 ) [25], 9 E -abscisyl β- d -glucoside ( 15 ) [26], and 9 E -abscisic alcohol β- d -glucoside ( 16 ) [12] by comparing their spectroscopic data with those reported in the literature (see Supplementary Materials).…”

Section: Resultsmentioning

confidence: 99%

Carotenoid-Derived Flavor Precursors from Averrhoa carambola Fresh Fruit

Jia

Yang

et al. 2019

Molecules

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The fruit of Averrhoa carambola L. (Oxalidaceae), commonly known as star fruit or carambola, is popular in tropical and subtropical regions. Carotenoid-derived components, mainly C13- and C15-norisoprenoids, contribute greatly to the flavor of star fruit. Previously reported norisoprenoids were tentatively identified by GC-MS analysis after enzymatic hydrolysis. To gain accurate information about glycosidically bound flavor precursors in star fruit, a phytochemical study was conducted, which led to the isolation of 16 carotenoid derivatives—One new C13-norisoprenoid glucoside, (5R,6S,7E,9R)-5,6,9-trihydroxy-7-megastigmene 9-O-β-d-glucoside (1); one new C15-norisoprenoid, (6S,7E,10S)-Δ9,15-10-hydroxyabscisic alcohol (11); and 14 known ones, of which 12 were in glucoside form. The structures of the two new compounds were elucidated on the basis of extensive spectroscopic data analysis and chemical reaction. Compound 11 was a rare C15-norisoprenoid with a double bond between C-9 and C-15, and its possible biogenetic pathway was proposed. The known compounds were identified by comparison of their mass and nuclear magnetic resonance (NMR) data with those reported in the literature. The structure identification of one new (1) and seven known (3–7, 9, and 10) C13-norisoprenoid glucosides from the genus Averrhoa for the first time enriches the knowledge of carotenoid-derived flavor precursors in star fruit.

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Section: Resultsmentioning

confidence: 99%

Carotenoid-Derived Flavor Precursors from Averrhoa carambola Fresh Fruit

Jia

Yang

et al. 2019

Molecules

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“…Compounds 5 − 9 were identified on the basis of their NMR and MS data, and their optical rotations to be (+)-abscisic acid ( 5 ) (), (+)-β- d -glucopyranosyl abscisate ( 6 ) ( , ), (6 S , 9 R )-roseoside ( 7 ) (), (+)-pinoresinol mono-β- d -glucopyranoside ( 8 ) () and 3-(β- d -glucopyranosyloxymethyl)-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-(2 R ,3 S )-dihydrobenzofuran ( 9 ) (), respectively. This is the first report on the isolation of compounds 1 − 9 from prunes.…”

Section: Resultsmentioning

confidence: 99%

“…(+)- β - d -Glucopyranosyl Abscisate (6) ( , ). Colorless viscous liquid, [α] 23 D +153.7° ( c 0.44, MeOH).…”

Section: Methodsmentioning

confidence: 99%

Abscisic Acid Related Compounds and Lignans in Prunes (Prunus domestica L.) and Their Oxygen Radical Absorbance Capacity (ORAC)

Kikuzaki

Kayano

Fukutsuka

et al. 2003

J. Agric. Food Chem.

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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.

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Germination Inhibitor inCitrus unshuFruit Peelings: (+)-Abscisyl β-D-Glucopyranoside

Cited by 2 publications

References 1 publication

Carotenoid-Derived Flavor Precursors from Averrhoa carambola Fresh Fruit

Carotenoid-Derived Flavor Precursors from Averrhoa carambola Fresh Fruit

Abscisic Acid Related Compounds and Lignans in Prunes (Prunus domestica L.) and Their Oxygen Radical Absorbance Capacity (ORAC)

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