Two New Enzymes of Rosmarinic Acid Biosynthesis from Cell Cultures of Coleus blumei: Hydroxyphenylpyruvate Reductase and Rosmarinic Acid Synthase

Petersen, Maike; Alfermann, A. W.

doi:10.1515/znc-1988-7-804

Cited by 79 publications

(57 citation statements)

References 13 publications

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“…The two moieties of the parallel pathways are connected by hydroxycinnamoyl-CoA : hydroxyphenyllactate hydroxycinnamoyl transferase (RAS) catalyzing a transesterification reaction. 36,37) Chemically, RA is an ester of caffeic acid with 3,4-dihydroxyphenyl lactic acid, but biologically, it is formed from 4-coumaroyl-4′-hydroxyphenyllactate. 36) RAS is an enzyme that uses caffeoylCoA and 3-(3,4-dihydroxyphenyl)lactate to produce CoA and RA.…”

Section: Discussionmentioning

confidence: 99%

Molecular Cloning and Characterization of Genes Involved in Rosmarinic Acid Biosynthesis from <i>Prunella vulgaris</i>

Kim

Shin

Tuấn

et al. 2014

Biological & Pharmaceutical Bulletin

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Prunella vulgaris L., commonly known as "self-heal" or "heal-all," is a perennial herb with a long history of medicinal use. Phenylalanine ammonia-lyase (PAL), cinnamate 4-hydroxylase (C4H), and 4-coumarate:coenzyme-A (CoA) ligase (4CL) are important enzymes in the phenylpropanoid pathway and in the accumulation of rosmarinic acid (RA), which is a major secondary metabolite in P. vulgaris. In this study, we isolated cDNAs encoding PvPAL, PvC4H, and Pv4CL from P. vulgaris using rapid amplification of cDNA ends polymerase chain reaction (PCR). The amino acid sequence alignments of PvPAL, PvC4H, and Pv4CL showed high sequence identity to those of other plants. Quantitative real-time PCR analysis was used to determine the transcript levels of genes involved in RA biosynthesis in the flowers, leaves, stems, and roots of P. vulgaris. The transcript levels of PvPAL, PvC4H, and Pv4CL1 were the highest in flowers, whereas Pv4CL2 was the highest in roots. High-performance liquid chromatography analysis also showed the highest RA content in the flowers (3.71 mg/g dry weight). We suggest that the expression of the PvPAL, PvC4H, and Pv4CL1 genes is correlated with the accumulation of RA. Our results revealed that P. vulgaris flowers are appropriate for medicinal usage, and our findings provide support for increasing RA production in this plant.

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Section: Discussionmentioning

confidence: 99%

Molecular Cloning and Characterization of Genes Involved in Rosmarinic Acid Biosynthesis from <i>Prunella vulgaris</i>

Kim

Shin

Tuấn

et al. 2014

Biological & Pharmaceutical Bulletin

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“…were established from a dark-grown callus culture which was a gift from Dr. B. Ulbrich (Rh6ne-Poulenc-Rorer, Cologne, FRG). The cultures were maintained as described previously (Petersen and Alfermann 1988). For stimulation of RA accumulation, 7-d-old ceils were transferred from a growth medium with 2% sucrose to a production medium with 4% sucrose.…”

Section: Methodsmentioning

confidence: 99%

“…Several isoforms of tyrosine aminotransferase were found to be active in cell cultures of Anchusa officinalis (De-Eknamkul and Ellis 1987b;Mizukami and Ellis 1991) and, subsequently, DOPA was no longer considered to be an essential intermediate of the RA biosynthetic pathway. In 1988, two new enzymes of RA biosynthesis, hydroxyphenylpyruvate reductase and RA synthase, were isolated and characterized from cell cultures of C. blumei (Petersen and Alfermann 1988;H/iusler et al 1991;Petersen 1991). In these cultures RA biosynthesis was stimulated by raising the sucrose content of the medium from 2 to 4%.…”

Section: Introductionmentioning

confidence: 99%

Proposed biosynthetic pathway for rosmarinic acid in cell cultures of Coleus blumei Benth

Petersen

Häusler

Karwatzki

et al. 1993

Planta

111

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Abstract.A biosynthetic pathway for rosmarinic acid is proposed. This pathway is deduced from studies of the enzymes detectable in preparations from suspension cells of Coleus blumei. Phenylalanine is transformed to 4-coumaroyl-CoA by the enzymes of the general phenylpropanoid pathway: phenylalanine ammonia-lyase (EC 4.3.1.5), cinnamic acid 4-hydroxylase (EC 1.14.13.11) and hydroxycinnamic acid:CoA ligase (EC 6.2.1.12). Tyrosine is metabolized to 4-hydroxyphenyllactate by tyrosine aminotransferase (EC 2.6.1.5) and hydroxyphenylpyruvate reductase. The ester can be formed from 4-coumaroyl-CoA and 4-hydroxyphenyllactate by the catalytic activity of rosmarinic acid synthase with concomitant release ofCoA. Microsomal hydroxylase activities introduce the hydroxyl groups at positions 3 and 3' of the aromatic rings of the ester 4-coumaroyl-4'-hydroxyphenyllactate giving rise to rosmarinic acid.

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“…A p-coumaroyl-CoA:shikimic acid p-coumaroyl transferase (CST) and a p-coumaroyl-CoA:4-hydroxyphenyllactic acid p-coumaroyl transferase (CPLT) had been identified in other plant species (Ulbrich and Zenk, 1980;Petersen and Alfermann, 1988;Petersen, 1991;Lofty et al, 1992). Therefore, we examined the enzymatic activities present in our basil lines that can synthesize p-coumarate esters such as p-coumaroyl shikimate and p-coumaroyl 4-hydroxyphenyllactic acid.…”

Section: Partial Purification and Properties Of Basil Hydroxycinnamoymentioning

confidence: 99%

Differential Production of meta Hydroxylated Phenylpropanoids in Sweet Basil Peltate Glandular Trichomes and Leaves Is Controlled by the Activities of Specific Acyltransferases and Hydroxylases

et al. 2002

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Sweet basil (Ocimum basilicum) peltate glandular trichomes produce a variety of small molecular weight phenylpropanoids, such as eugenol, caffeic acid, and rosmarinic acid, that result from meta hydroxylation reactions. Some basil lines do not synthesize eugenol but instead synthesize chavicol, a phenylpropanoid that does not contain a meta hydroxyl group. Two distinct acyltransferases, p-coumaroyl-coenzyme A:shikimic acid p-coumaroyl transferase and p-coumaroyl-coenzyme A:4-hydroxyphenyllactic acid p-coumaroyl transferase, responsible for the production of p-coumaroyl shikimate and of p-coumaroyl 4-hydroxyphenyllactate, respectively, were partially purified and shown to be specific for their substrates. p-Coumaroyl-coenzyme A:shikimic acid p-coumaroyl transferase is expressed in basil peltate glands that are actively producing eugenol and is not active in glands of noneugenol-producing basil plants, suggesting that the levels of this activity determine the levels of synthesis of some meta-hydroxylated phenylpropanoids in these glands such as eugenol. Two basil cDNAs encoding isozymes of cytochrome P450 CYP98A13, which meta hydroxylates p-coumaroyl shikimate, were isolated and found to be highly similar (90% identity) to the Arabidopsis homolog, CYP98A3. Like the Arabidopsis enzyme, the basil enzymes were found to be very specific for p-coumaroyl shikimate. Finally, additional hydroxylase activities were identified in basil peltate glands that convert p-coumaroyl 4-hydroxyphenyllactic acid to its caffeoyl derivative and p-coumaric acid to caffeic acid.Basil (Ocimum basilicum) plants synthesize significant quantities of phenylpropanoid derivatives that contain an hydroxyl group at the meta position on the aromatic ring. Several of these compounds, such as eugenol, rosmarinic acid, and caffeic acid (Fig. 1), are found in high concentrations in specialized structures that are located on the surface of the aerial parts of the plant and are known as peltate glandular trichomes (glands; Gang et al., 2001). These specialized metabolites have been found in other plant species as well, but the nature of the enzymes that catalyze the meta hydroxylation has so far remained poorly understood.One of the difficulties in identifying the enzymes catalyzing the 3-hydroxylations in the phenylpropanoid pathways is that they appear to be found at very low abundance in the tissues examined (Petersen, 1997). We have recently shown (Gang et al., 2001) that, as in peppermint (Mentha ϫ piperita; Gershenzon et al., 1992;McCaskill and Croteau, 1995), the basil gland cells can be removed from the plant and studied in isolation from the rest of the plant, greatly facilitating biochemical and molecular investigations of a single, fully differentiated cell type (Gershenzon et al., 1992;McCaskill et al., 1992;McCaskill and Croteau, 1995;Lange et al., 2000;Gang et al., 2001). Furthermore, because these gland cells are so highly specialized for production of plantspecialized metabolites, the enzymes in these metabolic pathways are highly express...

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Two New Enzymes of Rosmarinic Acid Biosynthesis from Cell Cultures of Coleus blumei: Hydroxyphenylpyruvate Reductase and Rosmarinic Acid Synthase

Cited by 79 publications

References 13 publications

Molecular Cloning and Characterization of Genes Involved in Rosmarinic Acid Biosynthesis from <i>Prunella vulgaris</i>

Molecular Cloning and Characterization of Genes Involved in Rosmarinic Acid Biosynthesis from <i>Prunella vulgaris</i>

Proposed biosynthetic pathway for rosmarinic acid in cell cultures of Coleus blumei Benth

Differential Production of meta Hydroxylated Phenylpropanoids in Sweet Basil Peltate Glandular Trichomes and Leaves Is Controlled by the Activities of Specific Acyltransferases and Hydroxylases

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