Characterization of Benzylalcohol Acetyltransferases in Scented and Non-Scented Clarkia Species

Nam, Kee‐Hyun; Dudareva, Natalia; Pichersky, Eran

doi:10.1093/oxfordjournals.pcp.a029623

Cited by 24 publications

(22 citation statements)

References 16 publications

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“…In addition, the enzymes encoded by such transcripts have higher affinity with substrates other than benzylalcohol (e.g. heptanol; Nam et al, 1999). (Enzymes that can react with more than one substrate are not uncommon in secondary metabolism; see Wang and Pichersky, 1999.)…”

Section: Evolution Of Floral Scentmentioning

confidence: 99%

Biochemical and Molecular Genetic Aspects of Floral Scents

2000

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The chemical composition of floral scents has been extensively investigated for hundreds of years because of the commercial value of floral volatiles in perfumery. More recently, several ecological studies have examined the roles of floral scent in the biology of the plant. However, in contrast to the chemical emphasis of the perfumers and the organismal emphasis of the ecologists, until recently, there have been few studies concerning the biochemical synthesis of floral scent compounds and the enzymes and genes that control these processes. In fact, our recent investigation into the biogenesis of floral scent production in Clarkia breweri, an annual plant native to California that served as our model organism, and our even more recent work on the scent of the cultivated snapdragon (Antirrhinum majus) represent the only examples to date (to our knowledge) in which isolation of enzymes and genes involved in the de novo synthesis of scent compounds in the flower have been reported. In this Update we review the research leading to our work, report our findings, and discuss implications for future directions of the field.

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Section: Evolution Of Floral Scentmentioning

confidence: 99%

Biochemical and Molecular Genetic Aspects of Floral Scents

2000

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“…All attempts to clone the gene residing on the BAC clone AL391151 via RT-PCR using total RNA from various plant tissues were unsuccessful. Because this gene has only one intron, the putative open reading frame was amplified from genomic DNA, and the introns were spliced out as described by Nam et al (1999) by using the following two pairs of primers (front pair, forward primer 5Ј-AATGTCCGGGT-CACTCACGTT and backward primer 5Ј-GCATTTCAAGCGCGTGA-CCTGCATGAGCAT-3Ј; back pair, forward primer 5Ј-CCTTTGATGC-TCATGCAGGTCACGCGCTTGAAATGC-3Ј and backward primer 5Ј-TTACAGAGAAGACATGATCAA-3Ј). The resulting 1,387-nt DNA fragment was again cloned as described above.…”

Section: Cloning Of Bebt and Its Homologs From Arabidopsis And Tobaccomentioning

confidence: 99%

Characterization of an Acyltransferase Capable of Synthesizing Benzylbenzoate and Other Volatile Esters in Flowers and Damaged Leaves of Clarkia breweri

2002

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A cDNA encoding a protein with 456 amino acids whose sequence shows considerable similarity to plant acyltransferases was identified among 750 Clarkia breweri flower expressed sequence tags. The cDNA was expressed in Escherichia coli, and the protein produced was shown to encode the enzyme benzoyl-coenzyme A (CoA):benzyl alcohol benzoyl transferase (BEBT). BEBT catalyzes the formation of benzylbenzoate, a minor constituent of the C. breweri floral aroma, but it also has activity with a number of other alcohols and acyl CoAs. The BEBTgene is expressed in different parts of the flowers with maximal RNA transcript levels in the stigma, and no expression was observed in the leaves under normal conditions. However, BEBT expression was induced in damaged leaves, reaching a maximum 6 h after damage occurred. We also show here that a closely related tobacco (Nicotiana tabacum) gene previously shown to be induced in leaves after being challenged by phytopathogenic bacteria also has BEBT activity, whereas the most similar protein to BEBT in the Arabidopsis proteome does not use benzoyl CoA as a substrate and instead can use acetyl CoA to catalyze the formation of cis-3-hexen-1-yl acetate, a green-leaf volatile.

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“…In the case of isoeugenol O-methyl transferase (IEMT), only 7 amino acid substitutions were required to cause a diverged function from the precursor, ca!eic acid O-methyl transferase (COMT) (Wang and Pichersky, 1999). Transcriptional and translational regulatory integration into a tissue speci"c biochemical pathway must have then occurred (Wang et al, 1997;Nam et al, 1999). Finally, evolution of osmophores might occur, but there is evidence that this may not be necessary, at least in Clarkia breweri (Raguso and Pichersky, 1995).…”

Section: Relative Weighting Of Stepmatricesmentioning

confidence: 99%

Character coding of secondary chemical variation for use in phylogenetic analyses

Barkman

2001

Biochemical Systematics and Ecology

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A coding procedure is presented for secondary chemical data whereby putative biogenetic pathways are coded as phylogenetic characters with enzymatic conversions between compounds representing the corresponding character states. A character state tree or stepmatrix allows direct representation of the secondary chemical biogenetic pathway and avoids problems of non-independence associated with coding schemes that score presence/absence of individual compounds. Stepmatrices are the most biosynthetically realistic character de"nitions because individual and population level polymorphisms can be scored, reticulate enzymatic conversions within pathways may be represented, and down-weighting of pathway loss versus gain is possible. The stepmatrix approach uni"es analyses of secondary chemicals, allozymes, and developmental characters because the biological unity of the pathway, locus, or character ontogeny is preserved. Empirical investigation of the stepmatrix and character state tree coding methods using #oral fragrance data in Cypripedium (Orchidaceae) resulted in cladistic relationships which were largely congruent with those suggested from recent DNA and allozyme studies. This character coding methodology provides an e!ective means for including secondary compound data in total evidence studies. Furthermore, ancestral state reconstructions provide a phylogenetic context within which biochemical pathway evolution may be studied.

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Characterization of Benzylalcohol Acetyltransferases in Scented and Non-Scented Clarkia Species

Cited by 24 publications

References 16 publications

Biochemical and Molecular Genetic Aspects of Floral Scents

Biochemical and Molecular Genetic Aspects of Floral Scents

Characterization of an Acyltransferase Capable of Synthesizing Benzylbenzoate and Other Volatile Esters in Flowers and Damaged Leaves of Clarkia breweri

Character coding of secondary chemical variation for use in phylogenetic analyses

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