Chapter 13
A Method for Extraction and LC-MS-Based Identification
of Carotenoid-Derived Dialdehydes in Plants
Jianing Mi, Kun-Peng Jia, Aparna Balakrishna, and Salim Al-Babili
Abstract
We developed a chemical derivatization based ultra-high performance liquid chromatography-hybrid
quadrupole-Orbitrap mass spectrometer (UHPLC-Q-Orbitrap MS) analytical method to identify
low-abundant and instable carotenoid-derived dialdehydes (DIALs, diapocarotenoids) from plants. Application of this method enhances the MS response signal of DIALs, enabling the detection of diapocarotenoids, which is crucial for understanding the function of these compounds and for elucidating the
carotenoid oxidative metabolic pathway in plants.
Key words Carotenoid-derived dialdehydes, Apocarotenoids, Diapocarotenoids, Chemical derivatization, Arabidopsis, UHPLC-MS
1 Introduction
Carotenoids are a large class of mostly C 40 terpenoids characterized
by an extended conjugated double bond system that enables them
to absorb light in the blue-green (450–550 nm) range of the visible
spectrum and to contribute to plant light-harvesting via extending
the range of light absorption of the photosynthetic apparatus
beyond that of chlorophyll [1–9]. In addition, carotenoids are
indispensable photoprotective pigments that prevent destructive
oxidation processes by quenching both singlet and triplet state
chlorophylls [10–15]. Furthermore, carotenoids are important
determinants of the fluidity of plastid membranes and are accumulated in flowers and fruits to attract animals for pollination and seed
dispersal [9, 16, 17]. Carotenoid-derived metabolites also exert
important biologic functions. Thus, the class of carotenoidderivatives includes hormones, such as abscisic acid and strigolactone, [18–25], retinoids, that is, retinal, retinol (vitamin A), and
retinoic acid [26–28], the fungal pheromone trisporic acid
[29, 30], the stress signaling molecule β-cyclocitral [31–33], the
Manuel Rodrı ´guez-Concepcio ´ n and Ralf Welsch (eds.), Plant and Food Carotenoids: Methods and Protocols,
Methods in Molecular Biology, vol. 2083, https://doi.org/10.1007/978-1-4939-9952-1_13,
© Springer Science+Business Media, LLC, part of Springer Nature 2020
177
A Method for Extraction and LC-MS-Based Identification
of Carotenoid-Derived Dialdehydes in Plants
Jianing Mi, Kun-Peng Jia, Aparna Balakrishna, and Salim Al-Babili
Abstract
We developed a chemical derivatization based ultra-high performance liquid chromatography-hybrid
quadrupole-Orbitrap mass spectrometer (UHPLC-Q-Orbitrap MS) analytical method to identify
low-abundant and instable carotenoid-derived dialdehydes (DIALs, diapocarotenoids) from plants. Application of this method enhances the MS response signal of DIALs, enabling the detection of diapocarotenoids, which is crucial for understanding the function of these compounds and for elucidating the
carotenoid oxidative metabolic pathway in plants.
Key words Carotenoid-derived dialdehydes, Apocarotenoids, Diapocarotenoids, Chemical derivatization, Arabidopsis, UHPLC-MS
1 Introduction
Carotenoids are a large class of mostly C 40 terpenoids characterized
by an extended conjugated double bond system that enables them
to absorb light in the blue-green (450–550 nm) range of the visible
spectrum and to contribute to plant light-harvesting via extending
the range of light absorption of the photosynthetic apparatus
beyond that of chlorophyll [1–9]. In addition, carotenoids are
indispensable photoprotective pigments that prevent destructive
oxidation processes by quenching both singlet and triplet state
chlorophylls [10–15]. Furthermore, carotenoids are important
determinants of the fluidity of plastid membranes and are accumulated in flowers and fruits to attract animals for pollination and seed
dispersal [9, 16, 17]. Carotenoid-derived metabolites also exert
important biologic functions. Thus, the class of carotenoidderivatives includes hormones, such as abscisic acid and strigolactone, [18–25], retinoids, that is, retinal, retinol (vitamin A), and
retinoic acid [26–28], the fungal pheromone trisporic acid
[29, 30], the stress signaling molecule β-cyclocitral [31–33], the
Manuel Rodrı ´guez-Concepcio ´ n and Ralf Welsch (eds.), Plant and Food Carotenoids: Methods and Protocols,
Methods in Molecular Biology, vol. 2083, https://doi.org/10.1007/978-1-4939-9952-1_13,
© Springer Science+Business Media, LLC, part of Springer Nature 2020
177