Water-soluble phenolic glycosides from leaves of Alangium premnifolium

Kijima, Hidehiko; Ide, Toshinori; Otsuka, Hideaki; Ogimi, Choei; Hirata, Eiji; Takushi, Anki; Takeda, Yoshio

doi:10.1016/s0031-9422(96)00760-1

Cited by 39 publications

(25 citation statements)

References 11 publications

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“…Thus, the molecular formula of 1 was determined to be C 17 H 26 O 11 . Spectroscopic data including the specific rotation, [] D 23 À17.7 (c=0.5, MeOH), agreed well with previously reported data (Kijima et al, 1997), and therefore, the planar structure of 1 was determined to be as in Fig. 1.…”

Section: Resultssupporting

confidence: 87%

Isolation of α-glusosidase inhibitors from hyssop ( Hyssopus officinalis )

et al. 2004

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Section: Resultssupporting

confidence: 87%

Isolation of α-glusosidase inhibitors from hyssop ( Hyssopus officinalis )

et al. 2004

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“…Although syringoylglycerol 9-O-b-D-glucopyranoside has been isolated from Alangium premnifolium (Kijima et al 1997) and Hyssopus officinalis as a a-glucosidase inhibitor (Matsuura et al 2004), it has not previously been reported as a plant growth inhibitory compound. Starch breakdown during the germination of seeds is the results of the concerted action of a-amylase, b-amylase, a debranching enzyme and a-glucosidase (Sun and Henson 1991).…”

Section: Resultsmentioning

confidence: 99%

Stable Agrobacterium-mediated transformation of embryogenic tissues from Pinus pinaster Portuguese genotypes

et al. 2006

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When seedlings of lettuce, cress, rice and wheat were incubated with the leachate of wheat straw, the roots growth of lettuce and garden cress were particularly inhibited. The leachate of wheat straw (100 g eq./l) showed 80.5 and 79.4% inhibition for lettuce and cress roots, respectively. The inhibitory activity was stronger as the concentration of wheat straw leachate was greater. This result indicates that allelochemical(s) inhibiting the roots growth of lettuce and cress are leached from the wheat straw into the water. Two potent compounds were isolated from the leachate of the wheat straw and identified as syringoylglycerol 9-O-b-D-glucopyranoside and L-tryptophan by spectral analyses. Syringoylglycerol 9-O-b-D-glucopyranoside inhibited the roots growth of lettuce and cress at concentrations greater than 0.1 and 10.0 lM, respectively. On the other hand, L-tryptophan inhibited the roots growth of lettuce and cress at concentrations greater than 0.1 and 1.0 lM, respectively. The content of syringoylglycerol 9-O-b-D-glucopyranoside and L-tryptophan in the leachate of wheat straw (100 g eq./l) was 18.4 ± 0.7 and 6.2 ± 0.6 lM, respectively. Syringoylglycerol 9-O-b-D-glucopyranoside (18.4 lM) showed 21.5 and 13.5% inhibition in the lettuce and cress roots assay, respectively. On the other hand, 6.2 lM of L-tryptophan showed 47.5 and 35.0% inhibition in the lettuce and cress roots assay, respectively. These results suggested that L-tryptophan may be a major contributor to the allelopathy in aqueous leachate of wheat straw and syringoylglycerol 9-O-b-D-glucopyranoside may be a minor contributor.

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“…Analysis of MS/MS spectra of these glycosides revealed two major sugar moieties conjugated to guaiacol, MeSA, and eugenol: (1) a dihexose-pentose moiety, and (2) a malonyl dihexose-pentose moiety. Triglycosides of volatiles consisting of different sugar combinations have been reported in plants before (Herderich et al, 1992;Bilia et al, 1994;Kijima et al, 1997). Also, malonylation of sugar moieties is a common feature in several plants (Withopf et al, 1997;Kazuma et al, 2003;D'Auria et al, 2007;Kogawa et al, 2007).…”

Section: Emission Of Php Volatiles From Tomato Fruit Upon Tissue Disrmentioning

confidence: 99%

A Role for Differential Glycoconjugation in the Emission of Phenylpropanoid Volatiles from Tomato Fruit Discovered Using a Metabolic Data Fusion Approach

Tikunov

Vos²,

González-Paramás³

et al. 2009

Plant Physiology

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A role for differential glycoconjugation in the emission of phenylpropanoid volatiles from ripening tomato fruit (Solanum lycopersicum) upon fruit tissue disruption has been discovered in this study. Application of a multiinstrumental analytical platform for metabolic profiling of fruits from a diverse collection of tomato cultivars revealed that emission of three discriminatory phenylpropanoid volatiles, namely methyl salicylate, guaiacol, and eugenol, took place upon disruption of fruit tissue through cleavage of the corresponding glycoconjugates, identified putatively as hexose-pentosides. However, in certain genotypes, phenylpropanoid volatile emission was arrested due to the corresponding hexose-pentoside precursors having been converted into glycoconjugate species of a higher complexity: dihexose-pentosides and malonyl-dihexose-pentosides. This glycoside conversion was established to occur in tomato fruit during the later phases of fruit ripening and has consequently led to the inability of red fruits of these genotypes to emit key phenylpropanoid volatiles upon fruit tissue disruption. This principle of volatile emission regulation can pave the way to new strategies for controlling tomato fruit flavor and taste.

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Water-soluble phenolic glycosides from leaves of Alangium premnifolium

Cited by 39 publications

References 11 publications

Isolation of α-glusosidase inhibitors from hyssop ( Hyssopus officinalis )

Isolation of α-glusosidase inhibitors from hyssop ( Hyssopus officinalis )

Stable Agrobacterium-mediated transformation of embryogenic tissues from Pinus pinaster Portuguese genotypes

A Role for Differential Glycoconjugation in the Emission of Phenylpropanoid Volatiles from Tomato Fruit Discovered Using a Metabolic Data Fusion Approach

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