Biosynthesis of the major scent components 3,5‐dimethoxytoluene and 1,3,5‐trimethoxybenzene by novel rose <i>O</i>‐methyltransferases

Scalliet, Gabriel; Journot, Noellie; Jullien, Frédéric; Baudino, Sylvie; Magnard, Jean‐Louis; Channelière, Stéphanie; Vergne, Philippe; Dumas, Christian; Bendahmane, Mohammed; Cock, J. Mark; Hugueney, Philippe

doi:10.1016/s0014-5793(02)02956-3

Cited by 81 publications

(81 citation statements)

References 17 publications

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“…A flavonol OMT from Catharanthus roseus was shown to perform two sequential O-methylations (Cacace et al, 2003). Similarly, orcinol OMT was reported to carry out two sequential O-methylations in rose (Rosa 3 hybrida) scent biosynthesis (Lavid et al, 2002;Scalliet et al, 2002). Sequential methylation has also been reported for certain N-methyltransferases (Nuccio et al, 2000;Charron et al, 2002), but these proteins possess a different structural domain.…”

Section: Benzylisoquinoline (Rs)-norlaudanosoline Was Not Accepted mentioning

confidence: 91%

Characterization of Three O-Methyltransferases Involved in Noscapine Biosynthesis in Opium Poppy

2012

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Noscapine is a benzylisoquinoline alkaloid produced in opium poppy (Papaver somniferum) and other members of the Papaveraceae. It has been used as a cough suppressant and more recently was shown to possess anticancer activity. However, the biosynthesis of noscapine in opium poppy has not been established. A proposed pathway leading from (S)-reticuline to noscapine includes (S)-scoulerine, (S)-canadine, and (S)-N-methylcanadine as intermediates. Stem cDNA libraries and latex extracts of eight opium poppy cultivars displaying different alkaloid profiles were subjected to massively parallel pyrosequencing and liquid chromatographytandem mass spectrometry, respectively. Comparative transcript and metabolite profiling revealed the occurrence of three cDNAs encoding O-methyltransferases designated as SOMT1, SOMT2, and SOMT3 that correlated with the accumulation of noscapine in the eight cultivars. SOMT transcripts were detected in all opium poppy organs but were most abundant in aerial organs, where noscapine primarily accumulates. SOMT2 and SOMT3 showed strict substrate specificity and regiospecificity as 9-Omethyltransferases targeting (S)-scoulerine. In contrast, SOMT1 was able to sequentially 9-and 2-O-methylate (S)-scoulerine, yielding (S)-tetrahydropalmatine. SOMT1 also sequentially 39-and 7-O-methylated both (S)-norreticuline and (S)-reticuline with relatively high substrate affinity, yielding (S)-tetrahydropapaverine and (S)-laudanosine, respectively. The metabolic functions of SOMT1, SOMT2, and SOMT3 were investigated in planta using virus-induced gene silencing. Reduction of SOMT1 or SOMT2 transcript levels resulted in a significant decrease in noscapine accumulation. Reduced SOMT1 transcript levels also caused a decrease in papaverine accumulation, confirming the selective roles for these enzymes in the biosynthesis of both alkaloids in opium poppy.

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Section: Benzylisoquinoline (Rs)-norlaudanosoline Was Not Accepted mentioning

confidence: 91%

Characterization of Three O-Methyltransferases Involved in Noscapine Biosynthesis in Opium Poppy

2012

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“…Many modern rose varieties synthesize a related compound, 3,5-dimethoxytoluene (Flament et al, 1993), from orcinol (3,5-dihydroxytoluene) by two successive methylations. The orcinol O-methyltransferases responsible for these reactions have been characterized Scalliet et al, 2002). Orcinol O-methyltransferases can also carry out the last two methylation steps of 1,3,5-trimethoxybenzene biosynthesis but are incapable of efficiently methylating phloroglucinol, explaining the absence of 1,3,5-trimethoxybenzene from the floral scent of modern rose varieties.…”

Section: Amino Acid-derived Flavor Compoundsmentioning

confidence: 99%

Biosynthesis of plant‐derived flavor compounds

Schwab¹,

Davidovich‐Rikanati²,

Lewinsohn³

2008

The Plant Journal

952

704

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SummaryPlants have the capacity to synthesize, accumulate and emit volatiles that may act as aroma and flavor molecules due to interactions with human receptors. These low-molecular-weight substances derived from the fatty acid, amino acid and carbohydrate pools constitute a heterogenous group of molecules with saturated and unsaturated, straight-chain, branched-chain and cyclic structures bearing various functional groups (e.g. alcohols, aldehydes, ketones, esters and ethers) and also nitrogen and sulfur. They are commercially important for the food, pharmaceutical, agricultural and chemical industries as flavorants, drugs, pesticides and industrial feedstocks. Due to the low abundance of the volatiles in their plant sources, many of the natural products had been replaced by their synthetic analogues by the end of the last century. However, the foreseeable shortage of the crude oil that is the source for many of the artifical flavors and fragrances has prompted recent interest in understanding the formation of these compounds and engineering their biosynthesis. Although many of the volatile constituents of flavors and aromas have been identified, many of the enzymes and genes involved in their biosynthesis are still not known. However, modification of flavor by genetic engineering is dependent on the knowledge and availability of genes that encode enzymes of key reactions that influence or divert the biosynthetic pathways of plant-derived volatiles. Major progress has resulted from the use of molecular and biochemical techniques, and a large number of genes encoding enzymes of volatile biosynthesis have recently been reported.

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“…2; Lavid et al, 2002;Scalliet et al, 2002). In previous studies, we characterized OOMTs from Chinese rose (Rosa chinensis) cv Old Blush (Scalliet et al, 2002(Scalliet et al, , 2006, and preliminary experiments showed that resveratrol could be methylated by purified recombinant OOMT1 from cv Old Blush. Therefore, we searched grapevine public EST collections for OOMT homologs.…”

Section: Biosynthesis Of Pterostilbene In Grapevine Leaves Infected Wmentioning

confidence: 99%

“…Therefore, we hypothesized that the putative ROMT enzyme was more likely to resemble rose OOMTs, which catalyze the biosynthesis of the dimethylated molecule 3,5-dimethoxytoluene ( Fig. 2; Lavid et al, 2002;Scalliet et al, 2002). Identification of OOMT homologs among grapevine EST collections allowed the cloning of a candidate ROMT cDNA from Cabernet Sauvignon.…”

Section: Characterization Of a Novel Romt From Grapevinementioning

confidence: 99%

“…In roses (Rosa spp. ), orcinol O-methyltransferases (OOMTs) have been shown to catalyze the methylation of orcinol to yield the volatile phenolic ether 3,5-dimethoxytoluene, a major compound of rose scent Scalliet et al, 2002). Starting from these results, we used a candidate gene approach to identify a previously uncharacterized ROMT involved in the biosynthesis of pterostilbene in grapevine.…”

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confidence: 99%

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A Stress-Inducible Resveratrol O-Methyltransferase Involved in the Biosynthesis of Pterostilbene in Grapevine

et al. 2008

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Stilbenes are considered the most important phytoalexin group in grapevine (Vitis vinifera) and they are known to contribute to the protection against various pathogens. The main stilbenes in grapevine are resveratrol and its derivatives and, among these, pterostilbene has recently attracted much attention due both to its antifungal and pharmacological properties. Indeed, pterostilbene is 5 to 10 times more fungitoxic than resveratrol in vitro and recent studies have shown that pterostilbene exhibits anticancer, hypolipidemic, and antidiabetic properties. A candidate gene approach was used to identify a grapevine resveratrol O-methyltransferase (ROMT) cDNA and the activity of the corresponding protein was characterized after expression in Escherichia coli. Transient coexpression of ROMT and grapevine stilbene synthase in tobacco (Nicotiana benthamiana) using the agroinfiltration technique resulted in the accumulation of pterostilbene in tobacco tissues. Taken together, these results showed that ROMT was able to catalyze the biosynthesis of pterostilbene from resveratrol both in vitro and in planta. ROMT gene expression in grapevine leaves was induced by different stresses, including downy mildew (Plasmopara viticola) infection, ultraviolet light, and AlCl 3 treatment.

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Biosynthesis of the major scent components 3,5‐dimethoxytoluene and 1,3,5‐trimethoxybenzene by novel rose O‐methyltransferases

Cited by 81 publications

References 17 publications

Characterization of Three O-Methyltransferases Involved in Noscapine Biosynthesis in Opium Poppy

Characterization of Three O-Methyltransferases Involved in Noscapine Biosynthesis in Opium Poppy

Biosynthesis of plant‐derived flavor compounds

A Stress-Inducible Resveratrol O-Methyltransferase Involved in the Biosynthesis of Pterostilbene in Grapevine

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