Phenylpropanoid Glucoside Research Articles

An early salicylic acid-, pathogen- and elicitor-inducible tobacco glucosyltransferase: role in compartmentalization of phenolics and H 2O 2 metabolism

Treatment of tobacco cell suspension cultures with a fungal elicitor of defense responses resulted in an early accumulation of the phenylpropanoid glucosyltransferase TOGT, along with the rapid synthesis and secretion of scopolin, the glucoside of scopoletin. Elicitor-triggered extracellular accumulation of the aglycone scopoletin and of free caffeic and ferulic acids could only be revealed in the presence of diphenylene iodonium, an inhibitor of extracellular H 2O 2 production. Our results strongly support a role for TOGT in the elicitor-stimulated production of transportable phenylpropanoid glucosides, followed by the release of free antioxidant phenolics into the extracellular medium and subsequent H 2O 2 scavenging.

Secondary Metabolites in Transformed Root Cultures of Campanula glomerata

Summary The transformed roots of Campanula glomerata L. var. dahurica Fish., induced by infection with Agrobacterium rhizogenes MAFF 03-01724, produced the anthocyanins cyanidin 3-glucoside and cyanidin 3-rutinoside, a flavonoid rutin and a phenylpropanoid glucoside coniferin, together with the polyacetylene constituents lobetyol, lobetyolin and lobetyolinin. Although illumination was inhibiting for root proliferation, it was an essential factor for the accumulation of anthocyanin and flavonoid in the tissues. Addition of benzyladenine (BA) to the medium also promoted the accumulation of phenolics (anthocyanins, rutin and coniferin) in the roots. Polyacetylene production in the roots was not greatly affected by either illumination or BA treatment.

Phenylpropanoid Glycosides from Daphne oleoides.

A new phenylpropanoid glucoside, daphnenoside, was isolated in addition to coniferin, conferinoside, syringin and syringinoside, from the n-butanol soluble fraction of Daphne oleoides SCHREB (Thymelaeaceae). Structures were characterized on the basis of spectroscopic methods.

TWO PHENYLPROPANOID GLUCOSIDES FROM GLINUS LOTOIDES L. VAR. DICTAMNOIDES

A new phenylpropanoid glucoside (dictamnoside A) and another known one (Citrusin C) were isolated from the chloroform-soluble fraction of Glinus lotoides L. var. dictamnoides extract. Their structures were determined by means of spectroscopic methods.

Iridoid and phenylpropanoid glucosides from Tecoma capensis

Leaves of Tecoma capensis contain, together with tecomoside, large quantities of it's benzoic and cinnamic esters. A novel glucoside was isolated and, by spectroscopic and chemical data, characterized as 7- O-( p-methoxy) benzoyl tecomoside. Flowers of T. capensis contain only tecomoside, together with two phenylethanoid-derived glucosides, cornoside and it's rearranged aglycone, halleridone, and rengioside B.

Wahlenbergioside, a phenylpropanoid glucoside from Wahlenbergia marginata

Wahlenbergioside, a new hydroxymethylglutaroyl phenylpropanoid glucoside, and a known compound, lobetyolin, were isolated from the methanol extract of Wahlenbergia marginata. The structures were determined by spectroscopic analysis and chemical degradations.

Antifeedant activity of two phenylpropanoid glucosides from Aegiphila obducta against Chilo partellus larvae

Two phenylpropanoid glucosides, namely acetylmartynoside A and 4″-O-acetylmartynoside, isolated from Aegiphila obducta (Verbenaceae) were studied for insect antifeedant activity against fourth-instar larvae of Chilo partellus (Lepidoptera: Pyralidae). Acetylmartynoside A showed weak antifeedant activity at all the concentrations tested while 4″-O-acetylmartynoside showed strong antifeedant activity, particularly at the higher concentrations of 400 and 500 μg/disk.

A new phenylpropanoid glucoside and other constituents of Oenanthe javanica.

Three glucosides (1-3), together with known phenylpropanoids and polyacetylenes were isolated from Oenanthe javanica Blume (DC.). Glucoside 1, named oenanthoside A, is a new phenylpropanoid glucoside and was determined to be 2,3-methylenedioxy-5-allylphenyl beta-D-glucopyranoside, mainly by NMR techniques. Glucosides 2 and 3 were identified as eugenyl beta-D-glucopyranoside and pinoresinol beta-D-glucopyranoside, respectively. These were found for the first time in this plant.

Phenylpropanoid glycosides of Prunus ssiori

Two new bitter phenylpropanoid glucosides, 2-(3,4-methylenedioxyphenyl)-ethyl-(6- O-caffeoyl)- β- d-glucopyranoside and 3- O-caffeoyl-β- d-fructofuranosyl, 2,3,4,6-tetra- O-acetyl- α- d-glucopyranoside, have been isolated together with the known compounds, 6- O-caffeoyl- d-glucopyranoside and 2-(3,4-dihydroxyphenyl)-ethyl-(6- O-caffeoyl)-β- d-glucopyranoside, from the bark of Prunus ssiori. The structures of the isolated compounds have been established by extensive spectroscopic studies.

A phenylpropanoid glucoside from Perilla frutescens

The glycosidic constituents of two varieties of Perilla frutescens have been compared. A new phenylpropanoid glucoside named perilloside E has been isolated from the fresh leaves of the purple type plant. The structure was determined on the basis of spectral and chemical evidence.

Linusitamarin, a New Phenylpropanoid Glucoside from Linum usitatissimum

From the defatted meal of flaxseed (Linum usitatissimum), a novel phenylpropanoid glucoside, linusitamarin [1], was isolated, along with a number of known compounds. The structure of 1 was determined by spectroscopic analysis.

Two phenylpropanoid glucosides from Penstemon procerus

Besides the known iridoids, euphroside and plantarenaloside, two phenylpropanoid glucosides of novel type have been isolated from Penstemon procerus. The structure of these compounds has been elucidated on the basis of their spectral data.

Neolignans and a phenylpropanoid glucoside from Illicium difengpi

Six new constituents comprising three 2-phenyldihydrobenzofuranpropanol-type neolignans, two 1-phenyl-2-phenoxypropane-1,3-diols, and 4- O-(2-hydrox

Three biologically active phenylpropanoid glucosides from Myriophyllum verticillatum

Three novel phenylpropanoid glucosides have been isolated from a methanolic extract of Myriophyllum verticillatum and their structures defined by spectroscopic methods and chemical degradations. The biological activity of these compounds on the cyanobacterium Synechococcus leopoliensis has been investigated.

New aurone glucosides and new phenylpropanoid glucosides from Bidens pilosa.

Three new glucosides of (Z)-6, 7, 3', 4'-tetrahydroxyaurone, (Z)-7-O-β-D-glucopyranosyl-6, 7, 3', 4'-tetrahydroxyaurone, (Z)-6-O-(6-O-p-coumaroyl-β-D-glucopyranosyl)-6, 7, 3', 4'-tetrahydroxyaurone, (Z)-6-O-(6-O-acetyl-β-D-glucopyranosyl)-6, 7, 3', 4'-tetrahydroxyaurone, together with (Z)-6-O-β-D-glucopyranosyl-6, 7, 3', 4'-tetrahydroxyaurone, and two new phenylpropanoid glucosides, 4-O-(6-O-p-coumaroyl-β-D-glucopyranosyl)-p-coumaric acid and 4-O-(2-O-acetyl-6-O-p-coumaroyl-β-D-glucopyranosyl)-p-coumaric acid, have been isolated from the fresh leaves of Bidens pilosa. These structures have been elucidated on the basis of spectral data and chemical correlation.

Identification of an Agrobacterium tumefaciens virulence gene inducer from the pinaceous gymnosperm Pseudotsuga menziesii.

Inducible T-strand mobilization from the Ti plasmid of Agrobacterium tumefaciens to the genome of a plant host is mediated by the activation of a cascade of bacterial virulence genes. It is initiated when the bacterium senses the presence of a low molecular weight inducer secreted by the plant. Although many hydroxyphenylpropanoid and phenolic compounds can activate the virulence cascade, the only native inducers that have been identified to date are acetosyringone and hydroxyacetosyringone. A new inducer, the phenylpropanoid glucoside coniferin, has now been isolated from Pseudotsuga menziesii (Douglas-fir). Agrobacterium strains that were more tumorigenic on gymnosperms were more effectively induced by coniferin.

Flavonol and phenylpropanoid glycosides from Lilium cordatum

Four flavonol glycosides and four phenyl-propanoid glucosides were isolated from a methanolic petal extract of Lilium cordatum. These structures were established as isorhamnetin 3-glucoside, 3-glucoside-7-rhamnoside, 3-rutinoside and 3-rutinoside-7-rhamnoside and isoeugenol, p-propenylphenol, coniferyl alcohol and p-coumaryl alcohol glucosides, respectively.

Polar Constituents ofCalceolaria ascendens1

A new phenylpropanoid glucoside, 1'- O-beta- D-(3,4-dihydroxy-beta-phenyl)-ethyl-4'- O-caffeoyl-beta- D-apiosyl-(1'''-->3')-glucopyranoside, named calceolarioside E, was isolated from CALCEOLARIA ASCENDENS Lind., together with two other phenylpropanoid glucosides, verbascoside and forsythoside A, and cyclohexanols rengyol, isorengyol, and 4-hydroxy-4-(2'-hydroxyethyl)-cyclohexanone.

Cyanogenic and phenylpropanoid glucosides from Prunus grayana

In a chemical examination of the bark of Prunus grayana, three new phenylpropanoid glucosides, grayanoside A, grayanoside B and grayanin, have been isolated. The structures of these compounds have been established to be 2-(4-hydroxyphenyl)ethyl-(6- O-feruloyl)-β- D-glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl-(6- O-feruloyD-β- D-gluco and (2 R)-[(6- O-caffeoyl)-β- D-glucopyranosyloxy]benzeneacetonitrile, respectively, on the basis of the spectroscopic studies and the chemical evidence.

Phenolic glucosides from Prunus grayana

A new bitter phenylpropanoid glucoside, 2-(4-hydroxyphenyl)-ethyl-(6-O-caffeoyl)-β-D-glucopyranoside and a new bitter tannin-related compound, 3,4,5-trimethoxybenzoyl-β-D-glucopyranoside, have been isolated together with known compounds, 2-(3,4-dihydroxyphenyl)-ethyl-(6-O-caffeoyl)-β-D-glucopyranoside, 2-(3,4-dihydroxyphenyl)-ethyl-β-D-glucopyranoside and 6-O-caffeoyl-D-glucopyranose, from the bark of Prunus grayana. The structures of these compounds have been established on the basis of spectroscopic studies and chemical evidence.