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Characterization of Phenylpropene O-Methyltransferases from Sweet Basil: Facile Change of Substrate Specificity and Convergent Evolution within a Plant O-Methyltransferase Family
Open accessAbstract
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 CVOMT1 and EOMT1 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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Cited by
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Chong, J., Poutaraud, A., & Hugueney, P. (2009) · Plant Science · doi:10.1016/j.plantsci.2009.05.012 · Cited by 664
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Pichersky, E., & Lewinsohn, E. (2011) · Annual Review of Plant Biology · doi:10.1146/annurev-arplant-042110-103814 · Cited by 523
Self-citationDudareva, N., Martin, D., Kish, C. M., Kolosova, N., Gorenstein, N., Fäldt, J., Miller, B., & Bohlmann, J. (2003) · The Plant Cell · doi:10.1105/tpc.011015 · Cited by 466
Koeduka, T., Fridman, E., Gang, D. R., Vassão, D. G., Jackson, B. L., Kish, C. M., Orlova, I., Spassova, S. M., Lewis, N. G., Noel, J. P., et al. (2006) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0603732103 · Cited by 417
Self-citationBiosynthesis of cannflavins A and B from Cannabis sativa L.
Rea, K. A., Casaretto, J. A., Al-Abdul-Wahid, M. S., Sukumaran, A., Geddes-McAlister, J., Rothstein, S. J., & Akhtar, T. A. (2019) · Phytochemistry · doi:10.1016/j.phytochem.2019.05.009 · Cited by 112
“For example, the first group of type 1 plant OMTs depicted in our phylogenetic analysis includes enzymes that utilize a broad array of aromatic substrates - from simple phenolic compounds, such as chavicol, guaiacol and orcinol (Gang et al., 2002; Scalliet et al., 2006; Akhtar et al., 2013), to more complex heterocycl…”
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Metadata
- Authors
- Gang, D. R., Lavid, N., Zubieta, C., Chen, F., Beuerle, T., Lewinsohn, E., Noel, J. P., & Pichersky, E.
- Venue
- The Plant Cell
- Publisher
- Oxford University Press (OUP)
- Published
- 2002-02
- Volume
- 14
- Issue
- 2
- Pages
- 505-519
- ISSN
- 1040-4651 (ISSN-L)
- 1532-298X
- OpenAlex
- W2153472178
- Cited by
- 243
- References
- 0
- FWCI
- 3.46
- Type
- journal article
- Language
- en
- Open access
- bronze
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- CoChat. (2026). Citation check: Characterization of Phenylpropene O-Methyltransferases from Sweet Basil: Facile Change of Substrate Specificity and Convergent Evolution within a Plant O-Methyltransferase Family. https://app.cochat.ai/papers/10.1105/tpc.010327
- The paper
- Gang, D. R., Lavid, N., Zubieta, C., Chen, F., Beuerle, T., Lewinsohn, E., Noel, J. P., & Pichersky, E. (2002). Characterization of Phenylpropene O-Methyltransferases from Sweet Basil: Facile Change of Substrate Specificity and Convergent Evolution within a Plant O-Methyltransferase Family. The Plant Cell. https://doi.org/10.1105/tpc.010327
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