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Identification of iridoid synthases from Nepeta species: Iridoid cyclization does not determine nepetalactone stereochemistry

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Identification of iridoid synthases from Nepeta species : Iridoid cyclization does not determine nepetalactone stereochemistry. / Sherden, Nathaniel H.; Lichman, Benjamin; Caputi, Lorenzo; Zhao, Dongyan; Kamileen, Mohamed O.; Buell, C. Robin; O'Connor, Sarah E.

In: PHYTOCHEMISTRY, Vol. 145, 01.01.2018, p. 48-56.

Research output: Contribution to journalArticlepeer-review

Harvard

Sherden, NH, Lichman, B, Caputi, L, Zhao, D, Kamileen, MO, Buell, CR & O'Connor, SE 2018, 'Identification of iridoid synthases from Nepeta species: Iridoid cyclization does not determine nepetalactone stereochemistry', PHYTOCHEMISTRY, vol. 145, pp. 48-56. https://doi.org/10.1016/j.phytochem.2017.10.004

APA

Sherden, N. H., Lichman, B., Caputi, L., Zhao, D., Kamileen, M. O., Buell, C. R., & O'Connor, S. E. (2018). Identification of iridoid synthases from Nepeta species: Iridoid cyclization does not determine nepetalactone stereochemistry. PHYTOCHEMISTRY, 145, 48-56. https://doi.org/10.1016/j.phytochem.2017.10.004

Vancouver

Sherden NH, Lichman B, Caputi L, Zhao D, Kamileen MO, Buell CR et al. Identification of iridoid synthases from Nepeta species: Iridoid cyclization does not determine nepetalactone stereochemistry. PHYTOCHEMISTRY. 2018 Jan 1;145:48-56. https://doi.org/10.1016/j.phytochem.2017.10.004

Author

Sherden, Nathaniel H. ; Lichman, Benjamin ; Caputi, Lorenzo ; Zhao, Dongyan ; Kamileen, Mohamed O. ; Buell, C. Robin ; O'Connor, Sarah E. / Identification of iridoid synthases from Nepeta species : Iridoid cyclization does not determine nepetalactone stereochemistry. In: PHYTOCHEMISTRY. 2018 ; Vol. 145. pp. 48-56.

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@article{808d696895264f63a2b03aadf4dfac1f,
title = "Identification of iridoid synthases from Nepeta species: Iridoid cyclization does not determine nepetalactone stereochemistry",
abstract = "Nepetalactones are iridoid monoterpenes with a broad range of biological activities produced by plants in the Nepeta genus. However, none of the genes for nepetalactone biosynthesis have been discovered. Here we report the transcriptomes of two Nepeta species, each with distinctive profiles of nepetalactone stereoisomers. As a starting point for investigation of nepetalactone biosynthesis in Nepeta, these transcriptomes were used to identify candidate genes for iridoid synthase homologs, an enzyme that has been shown to form the core iridoid skeleton in several iridoid producing plant species. Iridoid synthase homologs identified from the transcriptomes were cloned, heterologously expressed, and then assayed with the 8-oxogeranial substrate. These experiments revealed that catalytically active iridoid synthase enzymes are present in Nepeta, though there are unusual mutations in key active site residues. Nevertheless, these enzymes exhibit similar catalytic activity and product profile compared to previously reported iridoid synthases from other plants. Notably, four nepetalactone stereoisomers with differing stereochemistry at the 4α and 7α positions – which are generated during the iridoid synthase reaction – are observed at different ratios in various Nepeta species. This work strongly suggests that the variable stereochemistry at these 4α and 7α positions of nepetalactone diastereomers is established further downstream in the iridoid pathway in Nepeta. Overall, this work provides a gateway into the biosynthesis of nepetalactones in Nepeta.",
keywords = "Iridoid, Natural product biosynthesis, Short chain alcohol dehydrogenase, Terpenoid",
author = "Sherden, {Nathaniel H.} and Benjamin Lichman and Lorenzo Caputi and Dongyan Zhao and Kamileen, {Mohamed O.} and Buell, {C. Robin} and O'Connor, {Sarah E.}",
note = "{\textcopyright}2017 The Author(s).",
year = "2018",
month = jan,
day = "1",
doi = "10.1016/j.phytochem.2017.10.004",
language = "English",
volume = "145",
pages = "48--56",
journal = "PHYTOCHEMISTRY",
issn = "0031-9422",
publisher = "Elsevier Limited",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - Identification of iridoid synthases from Nepeta species

T2 - Iridoid cyclization does not determine nepetalactone stereochemistry

AU - Sherden, Nathaniel H.

AU - Lichman, Benjamin

AU - Caputi, Lorenzo

AU - Zhao, Dongyan

AU - Kamileen, Mohamed O.

AU - Buell, C. Robin

AU - O'Connor, Sarah E.

N1 - ©2017 The Author(s).

PY - 2018/1/1

Y1 - 2018/1/1

N2 - Nepetalactones are iridoid monoterpenes with a broad range of biological activities produced by plants in the Nepeta genus. However, none of the genes for nepetalactone biosynthesis have been discovered. Here we report the transcriptomes of two Nepeta species, each with distinctive profiles of nepetalactone stereoisomers. As a starting point for investigation of nepetalactone biosynthesis in Nepeta, these transcriptomes were used to identify candidate genes for iridoid synthase homologs, an enzyme that has been shown to form the core iridoid skeleton in several iridoid producing plant species. Iridoid synthase homologs identified from the transcriptomes were cloned, heterologously expressed, and then assayed with the 8-oxogeranial substrate. These experiments revealed that catalytically active iridoid synthase enzymes are present in Nepeta, though there are unusual mutations in key active site residues. Nevertheless, these enzymes exhibit similar catalytic activity and product profile compared to previously reported iridoid synthases from other plants. Notably, four nepetalactone stereoisomers with differing stereochemistry at the 4α and 7α positions – which are generated during the iridoid synthase reaction – are observed at different ratios in various Nepeta species. This work strongly suggests that the variable stereochemistry at these 4α and 7α positions of nepetalactone diastereomers is established further downstream in the iridoid pathway in Nepeta. Overall, this work provides a gateway into the biosynthesis of nepetalactones in Nepeta.

AB - Nepetalactones are iridoid monoterpenes with a broad range of biological activities produced by plants in the Nepeta genus. However, none of the genes for nepetalactone biosynthesis have been discovered. Here we report the transcriptomes of two Nepeta species, each with distinctive profiles of nepetalactone stereoisomers. As a starting point for investigation of nepetalactone biosynthesis in Nepeta, these transcriptomes were used to identify candidate genes for iridoid synthase homologs, an enzyme that has been shown to form the core iridoid skeleton in several iridoid producing plant species. Iridoid synthase homologs identified from the transcriptomes were cloned, heterologously expressed, and then assayed with the 8-oxogeranial substrate. These experiments revealed that catalytically active iridoid synthase enzymes are present in Nepeta, though there are unusual mutations in key active site residues. Nevertheless, these enzymes exhibit similar catalytic activity and product profile compared to previously reported iridoid synthases from other plants. Notably, four nepetalactone stereoisomers with differing stereochemistry at the 4α and 7α positions – which are generated during the iridoid synthase reaction – are observed at different ratios in various Nepeta species. This work strongly suggests that the variable stereochemistry at these 4α and 7α positions of nepetalactone diastereomers is established further downstream in the iridoid pathway in Nepeta. Overall, this work provides a gateway into the biosynthesis of nepetalactones in Nepeta.

KW - Iridoid

KW - Natural product biosynthesis

KW - Short chain alcohol dehydrogenase

KW - Terpenoid

UR - http://www.scopus.com/inward/record.url?scp=85032291510&partnerID=8YFLogxK

U2 - 10.1016/j.phytochem.2017.10.004

DO - 10.1016/j.phytochem.2017.10.004

M3 - Article

C2 - 29091815

AN - SCOPUS:85032291510

VL - 145

SP - 48

EP - 56

JO - PHYTOCHEMISTRY

JF - PHYTOCHEMISTRY

SN - 0031-9422

ER -