<i>O</i>-Methyltransferases Involved in the Biosynthesis of Volatile Phenolic Derivatives in Rose Petals

Lavid, Noa; Wang, Jihong; Shalit, Moshe; Guterman, Inna; Bar, Einat; Beuerle, Till; Menda, Naama; Shafir, Sharoni; Zamir, Dani; Adam, Zach; Vainstein, Alexander; Weiss, David; Pichersky, Eran; Lewinsohn, Efraim

doi:10.1104/pp.005330

Cited by 149 publications

(131 citation statements)

References 30 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: 89%

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: 89%

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

2012

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“…hydroxyl groups of orcinol at positions 3 and 5 to yield the dimethylated molecule 3,5-dimethoxytoluene ( Fig. 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.…”

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%

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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“…Several genes encoding enzymes involved in benzenoid biosynthesis have been identified from C. breweri (Dudareva et al, 1998;D'Auria et al, 2002), snapdragon (Antirrhinum majus) (Murfitt et al, 2000), and rose (Rosa hybrida) (Lavid et al, 2002). Only two corresponding cDNAs have been identified from petunia petals, S-adenosyl-L-Met:benzoic acid carboxyl methyltransferase (BSMT) and benzoyl-CoA:benzyl alcohol/phenylethanol benzoyltransferase (BPBT) (Negre et al, 2003;Boatright et al, 2004).…”

Section: Introductionmentioning

confidence: 99%

ODORANT1Regulates Fragrance Biosynthesis in Petunia Flowers

et al. 2005

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Floral scent is important to plant reproduction because it attracts pollinators to the sexual organs. Therefore, volatile emission is usually tuned to the foraging activity of the pollinators. In Petunia hybrida, volatile benzenoids determine the floral aroma. Although the pathways for benzenoid biosynthesis have been characterized, the enzymes involved are less well understood. How production and emission are regulated is unknown. By targeted transcriptome analyses, we identified ODORANT1 (ODO1), a member of the R2R3-type MYB family, as a candidate for the regulation of volatile benzenoids in Petunia hybrida cv W115 (Mitchell) flowers. These flowers are only fragrant in the evening and at night. Transcript levels of ODO1 increased before the onset of volatile emission and decreased when volatile emission declined. Downregulation of ODO1 in transgenic P. hybrida Mitchell plants strongly reduced volatile benzenoid levels through decreased synthesis of precursors from the shikimate pathway. The transcript levels of several genes in this pathway were reduced by suppression of ODO1 expression. Moreover, ODO1 could activate the promoter of the 5-enol-pyruvylshikimate-3-phosphate synthase gene. Flower pigmentation, which is furnished from the same shikimate precursors, was not influenced because color and scent biosynthesis occur at different developmental stages. Our studies identify ODO1 as a key regulator of floral scent biosynthesis.

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O-Methyltransferases Involved in the Biosynthesis of Volatile Phenolic Derivatives in Rose Petals

Cited by 149 publications

References 30 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

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

ODORANT1Regulates Fragrance Biosynthesis in Petunia Flowers

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