A Highly Sensitive SPE Derivatization–UHPLC–MS Approach for Quantitative Profiling of Carotenoid-Derived Dialdehydes from Vegetables

Mi, Jianing; Jia, Kun-Peng; Balakrishna, Aparna; Feng, Qitong; Al‐Babili, Salim

doi:10.1021/acs.jafc.9b01749

Cited by 13 publications

(12 citation statements)

References 29 publications

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“…This approach led to the discovery of the presumed diapocarotenoid anchorene as a novel carotenoid-derived bioactive that promotes the development of anchor roots (ANRs) (Jia et al, 2019a), a less investigated type of Arabidopsis roots, which develop from the collet region situated at the root hypocotyl junction (Lucas et al, 2011). Although it is still unclear how it is formed, anchorene (C 10 ) is a natural metabolite, as confirmed by LC-MS analysis (Jia et al, 2019a; Mi et al, 2019a), and its structure indicates that it can be produced by cleaving the (C11–C12) and (C11′–C12′) double bound from all carotenoids downstream of ζ-carotene in the carotenoid biosynthesis pathway ( Figure 5B ). In Arabidopsis , application of anchorene induces ANR formation.…”

Section: Novel Carotenoid-derived Signaling Moleculesmentioning

confidence: 97%

Apocarotenoids Involved in Plant Development and Stress Response

et al. 2019

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Carotenoids are isoprenoid pigments synthesized by all photosynthetic organisms and many heterotrophic microorganisms. They are equipped with a conjugated double-bond system that builds the basis for their role in harvesting light energy and in protecting the cell from photo-oxidation. In addition, the carotenoids polyene makes them susceptible to oxidative cleavage, yielding carbonyl products called apocarotenoids. This oxidation can be catalyzed by carotenoid cleavage dioxygenases or triggered nonenzymatically by reactive oxygen species. The group of plant apocarotenoids includes important phytohormones, such as abscisic acid and strigolactones, and signaling molecules, such as β-cyclocitral. Abscisic acid is a key regulator of plant's response to abiotic stress and is involved in different developmental processes, such as seed dormancy. Strigolactone is a main regulator of plant architecture and an important signaling molecule in the plant-rhizosphere communication. β-Cyclocitral, a volatile derived from β-carotene oxidation, mediates the response of cells to singlet oxygen stress. Besides these wellknown examples, recent research unraveled novel apocarotenoid growth regulators and suggests the presence of yet unidentified ones. In this review, we describe the biosynthesis and biological functions of established regulatory apocarotenoids and touch on the recently identified anchorene and zaxinone, with emphasis on their role in plant growth, development, and stress response.

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Section: Novel Carotenoid-derived Signaling Moleculesmentioning

confidence: 97%

Apocarotenoids Involved in Plant Development and Stress Response

et al. 2019

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“…Ion fragments appear in very low intensities, even increasing the positive collision energy (> 20eV). It has been reported that diapocarotenoids or dyaldehydes produced from the oxidative cleavage of carotenoids have a low ionization efficiency in mass spectrometry (Mi et al, 2019). In the case of BoCCD1-3 and BoCCD4-4 we found a very small peak corresponding to m/z 350 [M + 2] + and m/z 349 [M + 1] + , respectively, that was impossible to fragment (Supplementary Figure 10).…”

Section: Boccd1 and Boccd4 Enzymes Are Involved In Bixin Aldehyde Bio...mentioning

confidence: 83%

“…In all the bacterial extracts the bixin aldehyde peak (m/z 349.1) was not prominent when injected directly (Supplementary Figure 7). It is also possible that the low intensities are due to the low amount of bixin aldehyde, or its high consumption efficiency (Rubio-Moraga et al, 2008;Mi et al, 2019). Results indicate that the BoCCD1-4, BoCCD4-1, and BoCCD4-2 enzymes are capable of cleaving lycopene at 5,6/5 ,6 double bonds to produce bixin aldehyde, as BoCCD1-1 and BoCCD4-3 do.…”

Section: Boccd1 and Boccd4 Enzymes Are Involved In Bixin Aldehyde Bio...mentioning

confidence: 99%

Identifying Bixa orellana L. New Carotenoid Cleavage Dioxygenases 1 and 4 Potentially Involved in Bixin Biosynthesis

et al. 2022

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Carotene cleavage dioxygenases (CCDs) are a large family of Fe2+ dependent enzymes responsible for the production of a wide variety of apocarotenoids, such as bixin. Among the natural apocarotenoids, bixin is second in economic importance. It has a red-orange color and is produced mainly in the seeds of B. orellana. The biosynthesis of bixin aldehyde from the oxidative cleavage of lycopene at 5,6/5′,6′ bonds by a CCD is considered the first step of bixin biosynthesis. Eight BoCCD (BoCCD1-1, BoCCD1-3, BoCCD1-4, CCD4-1, BoCCD4-2, BoCCD4-3 and BoCCD4-4) genes potentially involved in the first step of B. orellana bixin biosynthesis have been identified. However, the cleavage activity upon lycopene to produce bixin aldehyde has only been demonstrated for BoCCD1-1 and BoCCD4-3. Using in vivo (Escherichia coli) and in vitro approaches, we determined that the other identified BoCCDs enzymes (BoCCD1-3, BoCCD1-4, BoCCD4-1, BoCCD4-2, and BoCCD4-4) also participate in the biosynthesis of bixin aldehyde from lycopene. The LC-ESI-QTOF-MS/MS analysis showed a peak corresponding to bixin aldehyde (m/z 349.1) in pACCRT-EIB E. coli cells that express the BoCCD1 and BoCCD4 proteins, which was confirmed by in vitro enzymatic assay. Interestingly, in the in vivo assay of BoCCD1-4, BoCCD4-1, BoCCD4-2, and BoCCD4-4, bixin aldehyde was oxidized to norbixin (m/z 380.2), the second product of the bixin biosynthesis pathway. In silico analysis also showed that BoCCD1 and BoCCD4 proteins encode functional dioxygenases that can use lycopene as substrate. The production of bixin aldehyde and norbixin was corroborated based on their ion fragmentation pattern, as well as by Fourier transform infrared (FTIR) spectroscopy. This work made it possible to clarify at the same time the first and second steps of the bixin biosynthesis pathway that had not been evaluated for a long time.

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“…Furthermore, diapocarotenoids are widely present in plants (Fiorilli et al , 2019; Jia et al , 2019a; Mi et al , 2020). Examples of in planta identified diapocarotenoids are crocetin dialdehyde (C 20 ), which is the precursor of crocin (Frusciante et al , 2014), anchorene, which is a C 10 dialdehyde that regulates anchor root formation in Arabidopsis (Jia et al , 2019), and a series of diapocarotenoids with different chain lengths, which are present in tomato fruit ( Solanum lycopersicum ; Mi et al , 2019). In this study, we show that iso‐anchorene is a further diapocarotenoid that occurs in Arabidopsis and fulfills a specific biological function in inhibiting primary root growth (Figure 5).…”

Section: Discussionmentioning

confidence: 99%

“…This is due to their instability and low abundance in biological systems, which impede their detection and the elucidation of their biological function. Nevertheless, it has been shown that diapocarotenoids, like apocarotenoids, are common metabolites that occur with different chain length, stereospecificities, or structural configurations (Mi et al , 2019; Mi et al , 2020). Several plant and microbial CCDs have been shown to form diapocarotenoids in vitro (Scherzinger et al , 2006; Alder et al , 2008; Ilg et al , 2014).…”

Section: Introductionmentioning

confidence: 99%

Iso‐anchorene is an endogenous metabolite that inhibits primary root growth in Arabidopsis

Jia

Ablazov

et al. 2021

The Plant Journal

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Carotenoid-derived regulatory metabolites and hormones are generally known to arise through the oxidative cleavage of a single double bond in the carotenoid backbone, which yields mono-carbonyl products called apocarotenoids. However, the extended conjugated double bond system of these pigments predestines them also to repeated cleavage forming dialdehyde products, diapocarotenoids, which have been less investigated due to their instability and low abundance. Recently, we reported on the short diapocarotenoid anchorene as an endogenous Arabidopsis metabolite and specific signaling molecule that promotes anchor root formation. In this work, we investigated the biological activity of a synthetic isomer of anchorene, iso-anchorene, which can be derived from repeated carotenoid cleavage. We show that iso-anchorene is a growth inhibitor that specifically inhibits primary root growth by reducing cell division rates in the root apical meristem. Using auxin efflux transporter marker lines, we also show that the effect of iso-anchorene on primary root growth involves the modulation of auxin homeostasis. Moreover, by using liquid chromatography-mass spectrometry analysis, we demonstrate that iso-anchorene is a natural Arabidopsis metabolite. Chemical inhibition of carotenoid biosynthesis led to a significant decrease in the iso-anchorene level, indicating that it originates from this metabolic pathway. Taken together, our results reveal a novel carotenoid-derived regulatory metabolite with a specific biological function that affects root growth, manifesting the biological importance of diapocarotenoids.

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A Highly Sensitive SPE Derivatization–UHPLC–MS Approach for Quantitative Profiling of Carotenoid-Derived Dialdehydes from Vegetables

Cited by 13 publications

References 29 publications

Apocarotenoids Involved in Plant Development and Stress Response

Apocarotenoids Involved in Plant Development and Stress Response

Identifying Bixa orellana L. New Carotenoid Cleavage Dioxygenases 1 and 4 Potentially Involved in Bixin Biosynthesis

Iso‐anchorene is an endogenous metabolite that inhibits primary root growth in Arabidopsis

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