Emission of 2-phenylethanol from its β-d-glucopyranoside and the biogenesis of these compounds from [2H8] l-phenylalanine in rose flowers

Hayashi, Shunsuke; Yagi, Kensuke; Ishikawa, Takashi; Kawasaki, Mikio; Asai, Tatsuo; Picone, Joanne M.; Turnbull, Colin; Hiratake, Jun; Sakata, Kanzo; Takada, Masayasu; Ogawa, Koji; Watanabe, Naoharu

doi:10.1016/j.tet.2003.10.130

Cited by 28 publications

(40 citation statements)

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“…'Hoh-Jun.' 5) In our previous study, 6) we have confirmed that 2-phenyl-N-glucosylacetamidiumbromide, a glycone-specific -glucosidase inhibitor, inhibited the hydrolysis of 2PE -Glc in an enzymatic reaction by using enzymes prepared from the petals of these roses. 2-Phenyl-N-glucosyl-acetamidiumbromide also partially inhibited the emission of 2PE from rose petals.…”

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confidence: 54%

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Purification and Characterization of β-Glucosidase Involved in the Emission of 2-Phenylethanol from Rose Flowers

Sakai

Tomita

Hirata

et al. 2008

Bioscience, Biotechnology, and Biochemistry

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-Glucosidase was partially purified from Rosa 'HohJun' petals. The enzyme was highly specific for such -D-glucopyranosides as 2-phenylethyl -D-glucopyranoside. The optimal activity was observed at pH 6.0 and 35 C. The enzymes were composed with two proteins (160 and 155 kDa) by blue native-PAGE, and were classified in a family 1 glucosidase based on LC-MS/MS analyses.Key words: -glucosidase; Rosa 'Hoh-Jun'; petal; 2-phenylethyl -D-glucopyranoside; blue native-PAGE Such flower scent compounds as 2-phenylethanol (2PE), geraniol and benzylalcohol have been reported to be present in the form of monoglycosides and/or diglycosides in plant tissues.1,2) These glyco-conjugates of volatile compounds are hydrolysed by -glucosidase or endoglycosidase, e.g., -primeverosidase, to release the volatile compounds for emission from plant tissues. 3,4) In some flowers, floral scent emission is concurrent with an increase in -glucosidase activity.3) 2-Phenylethyl -D-glucopyranoside (2PE -Glc) is one of the main glycoconjugates in such Damask roses as Rosa damascena Mill. and R. 'Hoh-Jun.' 5) In our previous study, 6) we have confirmed that 2-phenyl-N-glucosylacetamidiumbromide, a glycone-specific -glucosidase inhibitor, inhibited the hydrolysis of 2PE -Glc in an enzymatic reaction by using enzymes prepared from the petals of these roses. 2-Phenyl-N-glucosyl-acetamidiumbromide also partially inhibited the emission of 2PE from rose petals. These results indicate the involvement of -glucosidase in the emission of 2PE from rose flowers. To elucidate the role of -glucosidase, we purified and characterized the enzyme from R. 'HohJun' petals.The -glucosidase activity was measured in a standard assay by the method of Yamamoto et al.7) with some modifications. The reaction mixture (200 ml) consisting of 5 mM 2PE -Glc and an enzyme solution in a 50 mM citrate buffer (pH 6.0) was incubated for 15 min at 30 C. The reaction was quenched by adding a 0.1 M trichloroacetic acid solution (100 ml). The amount of 2PE released from 2PE -Glc was analyzed by HPLC under the following conditions: column, RP-18GP Aqua (5 mm, 4:6 Â 150 mm); detection, 205 nm; column temperature, 40 C; sample temperature, 15 C; injection volume, 20 ml; mobile phase A, a 10 mM phosphate buffer (pH 6.0); mobile phase B, acetonitrile; gradient condition, 35-70% of B over 10 min; flow rate, 1 ml/ min. 2PE was detected at 3.3 min. One unit of enzyme activity is defined as the amount releasing 1 mmole of 2PE per min. The glycosidic compounds of the volatile aglycones were chemically prepared according to the reported methods. 6) Protein concentration was measured by using a DC protein assay kit (Bio-Rad), with bovine serum albumin as a standard.Cell free extracts were prepared from lyophilized R. 'Hoh-Jun' flower petals (0.5 g, stages 4 to 6) with 100 ml of buffer A (0.1 M potassium phosphate at pH 7.5, containing 0.5% 3-[(3-cholamidopropyl)-dimethylamino]-1-propanesulfonate (CHAPS), 1 mM ED-TA, 2 mM DTT, 0.5 mM PMSF, and 1% glycerol) and 1 g of Polyclar 10. After centrifuging at...

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confidence: 54%

“…The glycosidic compounds of the volatile aglycones were chemically prepared according to the reported methods. 6) Protein concentration was measured by using a DC protein assay kit (Bio-Rad), with bovine serum albumin as a standard.…”

mentioning

confidence: 99%

Purification and Characterization of β-Glucosidase Involved in the Emission of 2-Phenylethanol from Rose Flowers

Sakai

Tomita

Hirata

et al. 2008

Bioscience, Biotechnology, and Biochemistry

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“…6,7) It became clear that a PLP-dependent enzyme was involved in the conversion of L-Phe into PAld (routes B and C in Scheme 1) and that an enzymecatalyzing reduction of PAld was involved in 2PE production in the presence of NADPH.…”

Section: Resultsmentioning

confidence: 99%

“…6) Furthermore, we showed by feeding experiments that 2PE and 2PEG were synthesized with retention of the -hydrogen atom of L-Phe. 7) These results strongly suggested that the biosynthetic pathway of 2PE from L-Phe must be different from those already proposed, because thehydrogen atom of L-Phe must be abstracted to yield either of the intermediates, phenylpyruvate or phenylacetic acid.…”

mentioning

confidence: 83%

Production of 2-Phenylethanol in Roses as the Dominant Floral Scent Compound fromL-Phenylalanine by Two Key Enzymes, a PLP-Dependent Decarboxylase and a Phenylacetaldehyde Reductase

Sakai

Hirata

Sayama

et al. 2007

Bioscience, Biotechnology, and Biochemistry

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“…Eugenol (clove essence) is a reduced version of coniferyl alcohol, a lignin precursor (13). Phenylacetaldehyde, a compound present in tomato fruit (14), is derived from phenylalanine by decarboxylation and oxidative removal of the amino group (15). Shortening of the three-carbon side chain of phenylalanine-derived hydroxycinnamates to one carbon also leads to aromatic building blocks such as benzoic acid and benzaldehyde (16).…”

Section: Pv Biosynthetic Pathways Branch Off From Primary Metabolismmentioning

confidence: 99%

Biosynthesis of Plant Volatiles: Nature's Diversity and Ingenuity

Pichersky

Noel

Dudareva

2006

Science

838

525

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Plant volatiles (PVs) are lipophilic molecules with high vapor pressure that serve various ecological roles. The synthesis of PVs involves the removal of hydrophilic moieties and oxidation/ hydroxylation, reduction, methylation, and acylation reactions. Some PV biosynthetic enzymes produce multiple products from a single substrate or act on multiple substrates. Genes for PV biosynthesis evolve by duplication of genes that direct other aspects of plant metabolism; these duplicated genes then diverge from each other over time. Changes in the preferred substrate or resultant product of PV enzymes may occur through minimal changes of critical residues. Convergent evolution is often responsible for the ability of distally related species to synthesize the same volatile.Plant volatiles (PV) are typically lipophilic liquids with high vapor pressures. Nonconjugated PVs can cross membranes freely and evaporate into the atmosphere when there are no barriers to diffusion. The number of identified volatile chemicals synthesized by various plants exceeds 1000 and is likely to grow as more plants are examined with new methods for detecting and analyzing quantities of volatiles that are often minute (1-3).PVs serve multiple functions in both floral and vegetative organs, and these roles are not always related to their volatility (1). Most PVs are restricted to specific lineages and are involved in species-specific ecological interactions, leading to their designation as specialized, or secondary, metabolites (4). To humans, pollinator-attracting floral scents have been a source of olfactory pleasure since antiquity, and we also use a large number of aromatic plants as flavorings, preservatives, and herbal remedies (5). Flower and herb aromas may contain many individual chemicals, sometimes with very little overlap in the PV profiles of even closely related species (6). It is unlikely that the observed differences are due entirely to differential gene expression. That most PVs are restricted to a few lineages, both ancient and derived, argues for frequent changes in enzymatic profiles through evolution. Considerable diversity and fast rates of change have also been observed in nonvolatile specialized metabolites in plants, raising similar questions regarding the underlying evolutionary mechanisms (7).Improvements in analytical techniques and molecular and biochemical methods have made PVs one of the best-studied groups of plant secondary metabolites. Here we describe

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Emission of 2-phenylethanol from its β-d-glucopyranoside and the biogenesis of these compounds from [2H8] l-phenylalanine in rose flowers

Cited by 28 publications

References 27 publications

Purification and Characterization of β-Glucosidase Involved in the Emission of 2-Phenylethanol from Rose Flowers

Purification and Characterization of β-Glucosidase Involved in the Emission of 2-Phenylethanol from Rose Flowers

Production of 2-Phenylethanol in Roses as the Dominant Floral Scent Compound fromL-Phenylalanine by Two Key Enzymes, a PLP-Dependent Decarboxylase and a Phenylacetaldehyde Reductase

Biosynthesis of Plant Volatiles: Nature's Diversity and Ingenuity

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