ArticlePlant physiology2016
The α-Terpineol to 1,8-Cineole Cyclization Reaction of Tobacco Terpene Synthases.
Article in Plant physiology, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed, 25 citations in OpenAlex.
- Reinvestigation of the mechanism and selectivity of 1,8-cineole synthase usingChemical science · 2026Article
- Genetic blueprint of herbaceous peony floral scent: evidence from terpene synthase, Nudix hydrolase, and prenyltransferase.Horticulture research · 2026Article
- Effects of drought duration on terpene profiles, physiological responses, and terpene-related gene expression in rosemary.BMC plant biology · 2026Article
- Molecular insights into Valencene synthase (SgTPS-V) and its role in sesquiterpenoid biosynthesis.BMC plant biology · 2026Article
- The comprehensive review of eucalyptol: synthesis, metabolism, and therapeutic applications in disease treatment.Molecular biology reports · 2025Review
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- Sub-Tissue Localization of Phytochemicals inPlants (Basel, Switzerland) · 2021Article
- Redesigning the Molecular Choreography to Prevent Hydroxylation in Germacradien-11-ol Synthase Catalysis.ACS catalysis · 2021Article
- Direct formation of the sesquiterpeonid ether liguloxide by a terpene synthase in Senecio scandens.Plant molecular biology · 2021Article
- GC-MS Composition and Olfactory Profile of Concretes from the Flowers of FourMolecules (Basel, Switzerland) · 2020Article
- Taming the Reactivity of Monoterpene Synthases To Guide Regioselective Product Hydroxylation.Chembiochem : a European journal of chemical biology · 2020Article
- Article
- Enzyme-Catalyzed Intramolecular Enantioselective Hydroalkoxylation.Journal of the American Chemical Society · 2017Article
- Exploring Blueberry Aroma Complexity by Chromatographic and Direct-Injection Spectrometric Techniques.Frontiers in plant science · 2017Article
Corrections and comments
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Authors and funding
7 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Flowers of Nicotiana species emit a characteristic blend including the cineole cassette monoterpenes. This set of terpenes is synthesized by multiproduct enzymes, with either 1,8-cineole or α-terpineol contributing most to the volatile spectrum, thus referring to cineole or terpineol synthase, respectively. To understand the molecular and structural requirements of the enzymes that favor the biochemical formation of α-terpineol and 1,8-cineole, site-directed mutagenesis, in silico modeling, and semiempiric calculations were performed. Our results indicate the formation of α-terpineol by a nucleophilic attack of water. During this attack, the α-terpinyl cation is stabilized by π-stacking with a tryptophan side chain (tryptophan-253). The hypothesized catalytic mechanism of α-terpineol-to-1,8-cineole conversion is initiated by a catalytic dyad (histidine-502 and glutamate-249), acting as a base, and a threonine (threonine-278) providing the subsequent rearrangement from terpineol to cineol by catalyzing the autoprotonation of (S)-(-)-α-terpineol, which is the favored enantiomer product of the recombinant enzymes. Furthermore, by site-directed mutagenesis, we were able to identify amino acids at positions 147, 148, and 266 that determine the different terpineol-cineole ratios in Nicotiana suaveolens cineole synthase and Nicotiana langsdorffii terpineol synthase. Since amino acid 266 is more than 10 Å away from the active site, an indirect effect of this amino acid exchange on the catalysis is discussed.
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