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. 2018 Oct 4;8:14796. doi: 10.1038/s41598-018-32967-1

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© The Author(s) 2018

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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PRISE family reduction reactions. (A) Substrates and products for NADPH-dependent reduction reactions for PmMOR, CrIS and Dl5ß –POR. (i) Reductive cyclisation reaction of 8-oxogeranial postulated for CrIS and PmMOR. (ii) Double bond reduction reaction at the 5-position of the A ring of progesterone catalyzed by Dl5ß –POR. (iii) Reduction of the aldehyde (top) and alkene (bottom) of citral by PmMOR yielding alcohol and reduced products. (B) ¹H NMR spectrum of an overnight reaction of PmMOR with NADPH and 8-oxogeranial. The chemical shifts and coupling patterns correspond to the starting material, 8-oxogeranial or nepetalactol and are indicated.