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. 2019 Feb 6;9:1477. doi: 10.1038/s41598-018-38047-8

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© The Author(s) 2019

Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.

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The proportion of (−)-trans-verbenol and (+)-trans-verbenol produced by CYP6DE1 or female MPB in assays or treatments, respectively, with different ratios of (−)-α-pinene and (+)-α-pinene. A series of enantiomeric ratios of (−)-α-pinene and (+)-α-pinene were used as either a substrate for CYP6DE1 enzyme assays or in treatment assays with female MPB. The enantiomeric ratios of the corresponding trans-verbenol products were measured. CYP6DE1 assays were performed with N = 3 replicates; MPB treatment assay were performed with N = 3 replicates.