The Arabidopsis DWARF27 gene encodes an all-trans-/9-cis-β-carotene isomerase and is induced by auxin, abscisic acid and phosphate deficiency

Abuauf, Haneen W.; Haider, Imran; Jia, Kun-Peng; Ablazov, Abdugaffor; Mi, Jianing; Blilou, Ikram; Al‐Babili, Salim

doi:10.1016/j.plantsci.2018.06.024

Cited by 61 publications

(85 citation statements)

References 77 publications

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“…SLs are synthesized through a pathway that involves a 9- cis /all- trans -β-carotene isomerase DWARF27 (D27) and CAROTENOID CLEAVAGE DIOXYGENASE 7 (CCD7) and CCD8. These three enzymes are plastid-localized and conduct the steps converting all- trans -β-carotene into the key intermediate carlactone (CL) (Alder et al., 2012; Bruno et al., 2016, 2017; Bruno and Al-Babili, 2016; Abuauf et al., 2018). CL is then exported into the cytosol where cytochrome P450 (711 clade; homologs of the Arabidopsis thaliana ) MORE AUXILLARY GROWTH 1 (MAX1) homologs and other enzymes convert it into SLs (Abe et al., 2014; Zhang et al., 2014; Al-Babili and Bouwmeester, 2015; Brewer et al., 2016).…”

Section: Introductionmentioning

confidence: 99%

Methylation at the C-3′ in D-Ring of Strigolactone Analogs Reduces Biological Activity in Root Parasitic Plants and Rice

et al. 2019

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Strigolactones (SLs) regulate plant development and induce seed germination in obligate root parasitic weeds, e.g. Striga spp. Because organic synthesis of natural SLs is laborious, there is a large need for easy-to-synthesize and efficient analogs. Here, we investigated the effect of a structural modification of the D-ring, a conserved structural element in SLs. We synthesized and investigated the activity of two analogs, MP13 and MP26, which differ from previously published AR8 and AR36 only in the absence of methylation at C-3′. The de-methylated MP13 and MP26 were much more efficient in regulating plant development and inducing Striga seed germination, compared with AR8. Hydrolysis assays performed with purified Striga SL receptor and docking of AR8 and MP13 to the corresponding active site confirmed and explained the higher activity. Field trials performed in a naturally Striga -infested African farmer’s field unraveled MP13 as a promising candidate for combating Striga by inducing germination in host’s absence. Our findings demonstrate that methylation of the C-3′ in D-ring in SL analogs has a negative impact on their activity and identify MP13 and, particularly, MP26 as potent SL analogs with simple structures, which can be employed to control Striga , a major threat to global food security.

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Section: Introductionmentioning

confidence: 99%

Methylation at the C-3′ in D-Ring of Strigolactone Analogs Reduces Biological Activity in Root Parasitic Plants and Rice

et al. 2019

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“…Instead, 9CBC is present in humans with preferred accumulation in organs, while less abundant in the serum [23] and moderately abundant in the human food chain, and may represent the nutritionally-relevant provitamin A5/X (present data and [24][25][26]). 9CBC originates mainly from plant-based metabolism [27] or from food processing of ATBC [25,28]. As mice are not an optimal model to study carotenoid nutri-kinetics [29] we speculate that in humans a more important and nutritional-relevant precursor function of 9CBC is more likely.…”

Section: Discussionmentioning

confidence: 99%

Vitamin A5/X, a new food to lipid hormone concept for a nutritional ligand to control RXR-mediated signaling

Krężel

Rivas

Szklenar³

et al. 2020

Preprint

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Background: Vitamin A is a family of derivatives synthesized from carotenoids acquired from the diet and can be converted in animals to bioactive forms essential for life. The vitamin A1 (all-trans-retinol / ATROL) and provitamin A1 (all-trans-β,β-carotene / ATBC) are precursors of all-trans-retinoic acid acting as a ligand for the retinoic acid receptors. The contribution of ATROL and ATBC to formation of 9-cis-13,14-dihydroretinoic acid (9CDHRA), the only endogenous retinoid acting as retinoid X receptor ligand remains unknown. Methods: Novel and well know retinoids and carotenoids were synthesized via organic chemical synthesis. Further, novel and well know retinoids / carotenoids were administered to in vitro oligodendrocyte cell culture and to in vivo oral supplemented mice with following HPLC-MS / UV-Vis based metabolomic evaluation of these administered retinoids / carotenoids. In addition, working memory analyses were performed in a mouse study. Results: In this study, we show that ATROL and ATBC are at best only weak and non-selective precursors of 9CDHRA. Instead, we identify 9-cis-13,14-dihydroretinol (9CDHROL) and 9-cis-13,14-dihydro-β,β-carotene (9CDHBC) as novel direct nutritional precursors of 9CDHRA, which are present endogenously in humans and the human food chain matrix. We also propose that the endogenous carotenoid 9-cis-β,β-carotene (9CBC) can also act as weak, indirect precursor of 9CDHRA via hydrogenation to 9CDHBC and further metabolism to 9CDHROL and/or 9CDHRA.Conclusion: In summary, since classical vitamin A1 is not an efficient 9CDHRA precursor, we conclude that this group of molecules constitutes as a new class of vitamin or a new independent member of the vitamin A family, named “Vitamin A5/X”.

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“…2) [144]. The stereospecific CCD7 cleaves 9-cis-β-carotene provided by the carotene isomerase DWARF27 at the (C9'-C10') double bound to produce 9-cis-β-apo-10'-carotenal and β-ionone [144][145][146][147]. In the next step, 9-cis-β-apo-10'-carotenal is converted by CCD8 into carlactone [144].…”

Section: Carotenoid Cleavagementioning

confidence: 99%

Carotenoid biofortification in crop plants: citius, altius, fortius

Zheng

Giuliano

Al‐Babili

2020

Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biolog

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The Arabidopsis DWARF27 gene encodes an all-trans-/9-cis-β-carotene isomerase and is induced by auxin, abscisic acid and phosphate deficiency

Cited by 61 publications

References 77 publications

Methylation at the C-3′ in D-Ring of Strigolactone Analogs Reduces Biological Activity in Root Parasitic Plants and Rice

Methylation at the C-3′ in D-Ring of Strigolactone Analogs Reduces Biological Activity in Root Parasitic Plants and Rice

Vitamin A5/X, a new food to lipid hormone concept for a nutritional ligand to control RXR-mediated signaling

Carotenoid biofortification in crop plants: citius, altius, fortius

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