Biosynthesis of eugenol and cinnamic aldehyde in Cinnamomum zeylanicum

Senanayake, U.M.; Wills, R. B. H.; Lee, T.H.

doi:10.1016/0031-9422(77)80125-8

Cited by 26 publications

(20 citation statements)

References 6 publications

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“…However, surprisingly little is known about the biosynthesis of eugenol and chavicol, the simplest phenylpropenes, and their derivatives. Labeling experiments of leaf segments with radioactive Phe indicated that Phe is their initial precursor (Manitto et al, 1974;Klischies et al, 1975;Manitto et al, 1975;Senanayake et al, 1977). Based on these results, two proposed biosynthetic pathways to these and related phenylpropenes are illustrated in Figure 1.…”

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confidence: 90%

“…Conflicting reports based only on feeding radioactive precursors to whole leaf tissues suggested that eugenol is formed from the monolignol precursor coniferyl alcohol (Klischies et al, 1975;see Fig. 1) or is instead formed via an undefined mechanism involving methylation and decarboxylation (Manitto et al, 1974(Manitto et al, , 1975Senanayake et al, 1977) of the hydroxycinnamic acids (see potential methylated intermediates in Fig. 1).…”

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confidence: 99%

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An Investigation of the Storage and Biosynthesis of Phenylpropenes in Sweet Basil

et al. 2001

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Plants that contain high concentrations of the defense compounds of the phenylpropene class (eugenol, chavicol, and their derivatives) have been recognized since antiquity as important spices for human consumption (e.g. cloves) and have high economic value. Our understanding of the biosynthetic pathway that produces these compounds in the plant, however, has remained incomplete. Several lines of basil (Ocimum basilicum) produce volatile oils that contain essentially only one or two specific phenylpropene compounds. Like other members of the Lamiaceae, basil leaves possess on their surface two types of glandular trichomes, termed peltate and capitate glands. We demonstrate here that the volatile oil constituents eugenol and methylchavicol accumulate, respectively, in the peltate glands of basil lines SW (which produces essentially only eugenol) and EMX-1 (which produces essentially only methylchavicol). Assays for putative enzymes in the biosynthetic pathway leading to these phenylpropenes localized many of the corresponding enzyme activities almost exclusively to the peltate glands in leaves actively producing volatile oil. An analysis of an expressed sequence tag database from leaf peltate glands revealed that known genes for the phenylpropanoid pathway are expressed at very high levels in these structures, accounting for 13% of the total expressed sequence tags. An additional 14% of cDNAs encoded enzymes for the biosynthesis of S-adenosyl-methionine, an important substrate in the synthesis of many phenylpropenes. Thus, the peltate glands of basil appear to be highly specialized structures for the synthesis and storage of phenylpropenes, and serve as an excellent model system to study phenylpropene biosynthesis.

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An Investigation of the Storage and Biosynthesis of Phenylpropenes in Sweet Basil

et al. 2001

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“…4, A and B), with the ratio of the latter to the former ranging from 1.4 to 1.6 in all floral tissues and throughout the lifespan of the flower. Manitto et al, 1974;Senanayake et al, 1977). An alternative pathway involving caffeoyl acid COA and CCOMT is…”

Section: Iemt Activity In Flower Parts and Its Temporal Variationmentioning

confidence: 99%

“…Little is known about the enzymatic steps leading to eugenol and isoeugenol, although pulse-chase experiments with radioactive precursors have clearly shown that they are ultimately derived from Phe, with p-coumaric acid as an intermediate (Manitto et al, 1974;Senanayake et al, 1977). It is important to note that our investigation did not address the question of whether an early step in the biosynthesis of eugenol and isoeugenol involves the 3'-hydroxyl methylation of caffeic acid by COMT or, alternatively, the 3'-hydroxyl methylation of caffeoyl CoA by CCOMT (or neither) (Fig.…”

Section: Biosynthesis Of Methyleugenol and Isomethyleugenol And The Ementioning

confidence: 99%

Floral Scent Production in Clarkia breweri (Onagraceae) (II. Localization and Developmental Modulation of the Enzyme S-Adenosyl-L-Methionine:(Iso)Eugenol O-Methyltransferase and Phenylpropanoid Emission)

et al. 1997

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Here we report that petal tissue was responsible for the bulk of the phenylpropanoid emission. The activity of S-adenosyl-i-methionine:(iso)eugenol O-methyltransferase (IEMT), a nove1 enzyme that catalyzes the methylation of the para-4'-hydroxyl of both eugenol and (iso)eugenol to methyleugenol and isomethyleugenol, respectively, was also highest i n petal tissue. IEMT activity was absent from floral tissues of plants not emitting (iso)methyleugenol. A C. breweri cDNA clone encoding IEMT was isolated, and its sequence was shown t o have 70% identity t o S-adenosyl-L-methionine:caffeic acid Omethyltransferase. l h e protein encoded by this cDNA can use eugenol and isoeugenol as substrates, but not caffeic acid. Steadystate IEMT mRNA levels were positively correlated with levels of IEMT activity in the tissues, and no IEMT mRNA was observed in flowers that do not emit (iso)methyleugenol. Overall, the data show that the floral emission of (iso)methyleugenol is controlled at the site of emission, that a positive correlation exists between volatile emission and IEMT activity, and that control of the level of IEMT activity is exerted at a pretranslational step.Flowers of many plants attract pollinators by producing and emitting a complex mixture of low-molecular-weight volatile compounds. Floral scents may function as both long-and short-distance attractants and nectar guides to a variety of animal pollinators (for review, see Dobson, 1993). Since insects are able to distinguish between complex floral scent mixtures, discriminatory visitation based on floral scent has important implications for population structure and reproductive isolation (Dodson et al

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“…Conflicting reports have left the question open of how the allyl/propenyl side chain of the phenylpropenes is formed (Manitto et al, 1974(Manitto et al, , 1975Klischies et al, 1975;Senanayake et al, 1977). Other steps in the pathway, however, have been investigated further.…”

Section: Introductionmentioning

confidence: 99%

Characterization of Phenylpropene O-Methyltransferases from Sweet Basil

et al. 2002

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Some basil varieties are able to convert the phenylpropenes chavicol and eugenol to methylchavicol and methyleugenol, respectively. Chavicol O -methyltransferase (CVOMT) and eugenol O -methyltransferase (EOMT) cDNAs were isolated from the sweet basil variety EMX-1 using a biochemical genomics approach. These cDNAs encode proteins that are 90% identical to each other and very similar to several isoflavone O -methyltransferases such as IOMT, which catalyzes the 4 -O -methylation of 2,7,4 -trihydroxyisoflavanone. On the other hand, CVOMT1 and EOMT1 are related only distantly to (iso)eugenol OMT from Clarkia breweri , indicating that the eugenol O -methylating enzymes in basil and C. breweri evolved independently. Transcripts for CVOMT1 and EOMT1 were highly expressed in the peltate glandular trichomes on the surface of the young basil leaves. The CVOMT 1 and EOMT 1 cDNAs were expressed in Escherichia coli , and active proteins were produced. CVOMT1 catalyzed the O -methylation of chavicol, and EOMT1 also catalyzed the O -methylation of chavicol with equal efficiency to that of CVOMT1, but it was much more efficient in O -methylating eugenol. Molecular modeling, based on the crystal structure of IOMT, suggested that a single amino acid difference was responsible for the difference in substrate discrimination between CVOMT1 and EOMT1. This prediction was confirmed by site-directed mutagenesis, in which the appropriate mutants of CVOMT1 (F260S) and EOMT1 (S261F) were produced that exhibited the opposite substrate preference relative to the respective native enzyme.

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Biosynthesis of eugenol and cinnamic aldehyde in Cinnamomum zeylanicum

Cited by 26 publications

References 6 publications

An Investigation of the Storage and Biosynthesis of Phenylpropenes in Sweet Basil

An Investigation of the Storage and Biosynthesis of Phenylpropenes in Sweet Basil

Floral Scent Production in Clarkia breweri (Onagraceae) (II. Localization and Developmental Modulation of the Enzyme S-Adenosyl-L-Methionine:(Iso)Eugenol O-Methyltransferase and Phenylpropanoid Emission)

Characterization of Phenylpropene O-Methyltransferases from Sweet Basil

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