Investigation of glucosinolates in the desert plant Ochradenus baccatus (Brassicales: Resedaceae). Unveiling glucoochradenin, a new arabinosylated glucosinolate

Beny Trabelcy; Nicka Chinkov; Michal Samuni-Blank; Mayan Merav; Ido Izhaki; Shmuel Carmeli; Yoram Gerchman

doi:10.1016/j.phytochem.2021.112760

Investigation of glucosinolates in the desert plant Ochradenus baccatus (Brassicales: Resedaceae). Unveiling glucoochradenin, a new arabinosylated glucosinolate

Beny Trabelcy, Nicka Chinkov, Michal Samuni-Blank, Mayan Merav, Ido Izhaki, Shmuel Carmeli, Yoram Gerchman

Research output: Contribution to journal › Article › peer-review

Abstract

Here we describe the structure elucidation and quantification of six glucosinolates (GSLs) from the roots of the desert plant Ochradenus baccatus, Delile 1813 (family Resedaceae; order Brassicales). The structure elucidation was established on the corresponding enzymatically desulfated derivatives of the native GSLs of the plant. Among these GSLs we describe the previously undescribed 2″-O-(α-L-arabinopyranosyloxy)benzylglucosinolate (1a), for which we propose the name glucoochradenin. The other five glucosinolates (2a-6a) were (2S)-2-hydroxy-2-phenylethylglucosinolate (2a; glucobarbarin), 2″-O-(α-L-rhamnopyranosyloxy)benzylglucosinolate (3a), benzylglucosinolate (4a; glucotropaeolin), indol-3-ylmethylglucosinolate (5a; glucobrassicin) and phenethylglucosinolate (6a; gluconasturtiin), all elucidated as their desulfo-derivatives, 2b-6b respectively). Structures were elucidated by MS and 1D and 2D-NMR techniques, the identity of the arabinose verified by ion chromatography, and the absolute configuration of the sugar units determined by hydrolysis, coupling to cysteine methyl-ester and phenyl isothiocyanate followed by HPLC-MS analysis of the resulted diastereomers. Response factors were generated for desulfo-2″-O-(α-L-arabinopyranosyloxy)benzylglucosinolate and for desulfo-2″-O-(α-L-rhamnopyranosyloxy)benzylglucosinolate and all six GSLs were quantified, indicating that the root of O. baccatus is rich in GSLs (Avg. 61.3 ± 10.0 μmol/g DW and up to 337.2 μmol/g DW).

Original language	English
Article number	112760
Journal	Phytochemistry
Volume	187
DOIs	https://doi.org/10.1016/j.phytochem.2021.112760
State	Published - Jul 2021

Bibliographical note

Funding Information:
Funding from the Middle East Regional Cooperation Program (project number TA-MOU-08-M28-013 ) and the Israel Science Foundation ( #189/08 ) is gratefully acknowledged. We are grateful to Dr. Michael Reichelt and Prof. Dr. Jonathan Gershenzon from the Department of Biochemistry at the Max Planck Institute for Chemical Ecology in Jena, Germany, for their help in developing the HPLC purification procedure. We also wish to thank Dr. Yael S. Balazs and Dr. Shifi Kababya of the Technion NMR center and Ms. Larisa Panz of the Technion MS center for their help in characterizing the compounds described here. We thank the reviewers of the manuscript for their time investment and fruitful suggestions that remarkably improved the final version of manuscript.

Funding Information:
Funding from the Middle East Regional Cooperation Program (project number TA-MOU-08-M28-013) and the Israel Science Foundation (#189/08) is gratefully acknowledged. We are grateful to Dr. Michael Reichelt and Prof. Dr. Jonathan Gershenzon from the Department of Biochemistry at the Max Planck Institute for Chemical Ecology in Jena, Germany, for their help in developing the HPLC purification procedure. We also wish to thank Dr. Yael S. Balazs and Dr. Shifi Kababya of the Technion NMR center and Ms. Larisa Panz of the Technion MS center for their help in characterizing the compounds described here. We thank the reviewers of the manuscript for their time investment and fruitful suggestions that remarkably improved the final version of manuscript.

Publisher Copyright:
© 2021 Elsevier Ltd

Keywords

Aromatic glucosinolates
Desert plants
Glycosylated glucosinolates
NMR
Ochradenus baccatus (Resedaceae)
Quantitative variation
Response factors
Root
Structure elucidation

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Plant Science
Horticulture

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10.1016/j.phytochem.2021.112760

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@article{d11c8f7bf0174ab8b5e9161590070418,

title = "Investigation of glucosinolates in the desert plant Ochradenus baccatus (Brassicales: Resedaceae). Unveiling glucoochradenin, a new arabinosylated glucosinolate",

abstract = "Here we describe the structure elucidation and quantification of six glucosinolates (GSLs) from the roots of the desert plant Ochradenus baccatus, Delile 1813 (family Resedaceae; order Brassicales). The structure elucidation was established on the corresponding enzymatically desulfated derivatives of the native GSLs of the plant. Among these GSLs we describe the previously undescribed 2″-O-(α-L-arabinopyranosyloxy)benzylglucosinolate (1a), for which we propose the name glucoochradenin. The other five glucosinolates (2a-6a) were (2S)-2-hydroxy-2-phenylethylglucosinolate (2a; glucobarbarin), 2″-O-(α-L-rhamnopyranosyloxy)benzylglucosinolate (3a), benzylglucosinolate (4a; glucotropaeolin), indol-3-ylmethylglucosinolate (5a; glucobrassicin) and phenethylglucosinolate (6a; gluconasturtiin), all elucidated as their desulfo-derivatives, 2b-6b respectively). Structures were elucidated by MS and 1D and 2D-NMR techniques, the identity of the arabinose verified by ion chromatography, and the absolute configuration of the sugar units determined by hydrolysis, coupling to cysteine methyl-ester and phenyl isothiocyanate followed by HPLC-MS analysis of the resulted diastereomers. Response factors were generated for desulfo-2″-O-(α-L-arabinopyranosyloxy)benzylglucosinolate and for desulfo-2″-O-(α-L-rhamnopyranosyloxy)benzylglucosinolate and all six GSLs were quantified, indicating that the root of O. baccatus is rich in GSLs (Avg. 61.3 ± 10.0 μmol/g DW and up to 337.2 μmol/g DW).",

keywords = "Aromatic glucosinolates, Desert plants, Glycosylated glucosinolates, NMR, Ochradenus baccatus (Resedaceae), Quantitative variation, Response factors, Root, Structure elucidation",

author = "Beny Trabelcy and Nicka Chinkov and Michal Samuni-Blank and Mayan Merav and Ido Izhaki and Shmuel Carmeli and Yoram Gerchman",

note = "Funding Information: Funding from the Middle East Regional Cooperation Program (project number TA-MOU-08-M28-013 ) and the Israel Science Foundation ( #189/08 ) is gratefully acknowledged. We are grateful to Dr. Michael Reichelt and Prof. Dr. Jonathan Gershenzon from the Department of Biochemistry at the Max Planck Institute for Chemical Ecology in Jena, Germany, for their help in developing the HPLC purification procedure. We also wish to thank Dr. Yael S. Balazs and Dr. Shifi Kababya of the Technion NMR center and Ms. Larisa Panz of the Technion MS center for their help in characterizing the compounds described here. We thank the reviewers of the manuscript for their time investment and fruitful suggestions that remarkably improved the final version of manuscript. Funding Information: Funding from the Middle East Regional Cooperation Program (project number TA-MOU-08-M28-013) and the Israel Science Foundation (#189/08) is gratefully acknowledged. We are grateful to Dr. Michael Reichelt and Prof. Dr. Jonathan Gershenzon from the Department of Biochemistry at the Max Planck Institute for Chemical Ecology in Jena, Germany, for their help in developing the HPLC purification procedure. We also wish to thank Dr. Yael S. Balazs and Dr. Shifi Kababya of the Technion NMR center and Ms. Larisa Panz of the Technion MS center for their help in characterizing the compounds described here. We thank the reviewers of the manuscript for their time investment and fruitful suggestions that remarkably improved the final version of manuscript. Publisher Copyright: {\textcopyright} 2021 Elsevier Ltd",

year = "2021",

month = jul,

doi = "10.1016/j.phytochem.2021.112760",

language = "English",

volume = "187",

journal = "Phytochemistry",

issn = "0031-9422",

publisher = "Elsevier",

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TY - JOUR

T1 - Investigation of glucosinolates in the desert plant Ochradenus baccatus (Brassicales

T2 - Resedaceae). Unveiling glucoochradenin, a new arabinosylated glucosinolate

AU - Trabelcy, Beny

AU - Chinkov, Nicka

AU - Samuni-Blank, Michal

AU - Merav, Mayan

AU - Izhaki, Ido

AU - Carmeli, Shmuel

AU - Gerchman, Yoram

N1 - Funding Information: Funding from the Middle East Regional Cooperation Program (project number TA-MOU-08-M28-013 ) and the Israel Science Foundation ( #189/08 ) is gratefully acknowledged. We are grateful to Dr. Michael Reichelt and Prof. Dr. Jonathan Gershenzon from the Department of Biochemistry at the Max Planck Institute for Chemical Ecology in Jena, Germany, for their help in developing the HPLC purification procedure. We also wish to thank Dr. Yael S. Balazs and Dr. Shifi Kababya of the Technion NMR center and Ms. Larisa Panz of the Technion MS center for their help in characterizing the compounds described here. We thank the reviewers of the manuscript for their time investment and fruitful suggestions that remarkably improved the final version of manuscript. Funding Information: Funding from the Middle East Regional Cooperation Program (project number TA-MOU-08-M28-013) and the Israel Science Foundation (#189/08) is gratefully acknowledged. We are grateful to Dr. Michael Reichelt and Prof. Dr. Jonathan Gershenzon from the Department of Biochemistry at the Max Planck Institute for Chemical Ecology in Jena, Germany, for their help in developing the HPLC purification procedure. We also wish to thank Dr. Yael S. Balazs and Dr. Shifi Kababya of the Technion NMR center and Ms. Larisa Panz of the Technion MS center for their help in characterizing the compounds described here. We thank the reviewers of the manuscript for their time investment and fruitful suggestions that remarkably improved the final version of manuscript. Publisher Copyright: © 2021 Elsevier Ltd

PY - 2021/7

Y1 - 2021/7

N2 - Here we describe the structure elucidation and quantification of six glucosinolates (GSLs) from the roots of the desert plant Ochradenus baccatus, Delile 1813 (family Resedaceae; order Brassicales). The structure elucidation was established on the corresponding enzymatically desulfated derivatives of the native GSLs of the plant. Among these GSLs we describe the previously undescribed 2″-O-(α-L-arabinopyranosyloxy)benzylglucosinolate (1a), for which we propose the name glucoochradenin. The other five glucosinolates (2a-6a) were (2S)-2-hydroxy-2-phenylethylglucosinolate (2a; glucobarbarin), 2″-O-(α-L-rhamnopyranosyloxy)benzylglucosinolate (3a), benzylglucosinolate (4a; glucotropaeolin), indol-3-ylmethylglucosinolate (5a; glucobrassicin) and phenethylglucosinolate (6a; gluconasturtiin), all elucidated as their desulfo-derivatives, 2b-6b respectively). Structures were elucidated by MS and 1D and 2D-NMR techniques, the identity of the arabinose verified by ion chromatography, and the absolute configuration of the sugar units determined by hydrolysis, coupling to cysteine methyl-ester and phenyl isothiocyanate followed by HPLC-MS analysis of the resulted diastereomers. Response factors were generated for desulfo-2″-O-(α-L-arabinopyranosyloxy)benzylglucosinolate and for desulfo-2″-O-(α-L-rhamnopyranosyloxy)benzylglucosinolate and all six GSLs were quantified, indicating that the root of O. baccatus is rich in GSLs (Avg. 61.3 ± 10.0 μmol/g DW and up to 337.2 μmol/g DW).

AB - Here we describe the structure elucidation and quantification of six glucosinolates (GSLs) from the roots of the desert plant Ochradenus baccatus, Delile 1813 (family Resedaceae; order Brassicales). The structure elucidation was established on the corresponding enzymatically desulfated derivatives of the native GSLs of the plant. Among these GSLs we describe the previously undescribed 2″-O-(α-L-arabinopyranosyloxy)benzylglucosinolate (1a), for which we propose the name glucoochradenin. The other five glucosinolates (2a-6a) were (2S)-2-hydroxy-2-phenylethylglucosinolate (2a; glucobarbarin), 2″-O-(α-L-rhamnopyranosyloxy)benzylglucosinolate (3a), benzylglucosinolate (4a; glucotropaeolin), indol-3-ylmethylglucosinolate (5a; glucobrassicin) and phenethylglucosinolate (6a; gluconasturtiin), all elucidated as their desulfo-derivatives, 2b-6b respectively). Structures were elucidated by MS and 1D and 2D-NMR techniques, the identity of the arabinose verified by ion chromatography, and the absolute configuration of the sugar units determined by hydrolysis, coupling to cysteine methyl-ester and phenyl isothiocyanate followed by HPLC-MS analysis of the resulted diastereomers. Response factors were generated for desulfo-2″-O-(α-L-arabinopyranosyloxy)benzylglucosinolate and for desulfo-2″-O-(α-L-rhamnopyranosyloxy)benzylglucosinolate and all six GSLs were quantified, indicating that the root of O. baccatus is rich in GSLs (Avg. 61.3 ± 10.0 μmol/g DW and up to 337.2 μmol/g DW).

KW - Aromatic glucosinolates

KW - Desert plants

KW - Glycosylated glucosinolates

KW - NMR

KW - Ochradenus baccatus (Resedaceae)

KW - Quantitative variation

KW - Response factors

KW - Root

KW - Structure elucidation

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U2 - 10.1016/j.phytochem.2021.112760

DO - 10.1016/j.phytochem.2021.112760

M3 - Article

AN - SCOPUS:85103717828

SN - 0031-9422

VL - 187

JO - Phytochemistry

JF - Phytochemistry

M1 - 112760

ER -

Investigation of glucosinolates in the desert plant Ochradenus baccatus (Brassicales: Resedaceae). Unveiling glucoochradenin, a new arabinosylated glucosinolate

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

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