1H and 13C NMR spectra of cis and trans phytoene isomers

Granger, Pierre; Maudinas, Bernard; Herber, R.; Villoutreix, J

doi:10.1016/0022-2364(73)90233-3

Cited by 12 publications

(7 citation statements)

References 5 publications

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“…Carbon chemical shifts were H-C (14, 14′) 120.00, H-C (15, 15′) 123.18. Chemical shifts values assigned were in accordance with the literature [18,23,24]. 2D-HSCQ NMR spectra of the alga biomass are shown in Figure 8b,c.…”

Section: Nmr Analysis Of Phytoene Extracts From D Salinasupporting

confidence: 83%

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Stereoisomers of Colourless Carotenoids from the Marine Microalga Dunaliella salina

Mazzucchi

Harvey

2020

Molecules

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Carotenoids comprise a diverse range of naturally occurring stereoisomers, which differ in their physico-chemical properties. Their biosynthesis begins with phytoene, which is a rarity among carotenoids because it is colourless. Phytoene is sought after as a skin protectant against harmful UV range B (290–320 nm) and C (100–290 nm) light, and as a natural skin-whitening agent and is synthesized from geranylgeranyl diphosphate. Geranylgeranyl diphosphate is catalysed by phytoene synthase and phytoene desaturase to phytoene and phytofluene, respectively. The subsequent steps involve desaturation, isomerisation and cyclisation reactions to form α- and β-carotene stereoisomers, via all-trans lycopene. The marine microalga Dunaliella salina is the richest source of β-carotene, but it can accumulate phytoene and phytofluene as well. In the present study, different analytical tools including High-Performance Liquid Chromatography (HPLC), Ultra-Performance Convergence Chromatography (UPC2-MS) and Nuclear Magnetic Resonance (NMR) were used to characterize and quantify the phytoene isomeric configurations in D. salina in order to explore both the feasibility of D. salina as a cell factory for phytoene production and to gain new insight into the carotenoid synthesis pathway in D. salina. D. salina, similar to tomato, produced predominantly 15-cis phytoene isomer (>98%) and a trace amount of all-trans phytoene (<2%). High light stress, red light stress, or use of a phytoene desaturase inhibitor or a mitotic disrupter herbicide led to the accumulation of 15-cis phytoene but not all-trans phytoene. 9-cis phytoene was not detected in any of the extracts of D. salina biomass. Our main findings suggest that 15-cis phytoene is the most abundant isomer in D. salina and that it is subject to a series of isomerisation and desaturation reactions to form all-trans and 9-cis β-carotene.

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Section: Nmr Analysis Of Phytoene Extracts From D Salinasupporting

confidence: 83%

“…NMR analysis is necessary to discriminate at a structural level between different isomers. The values of specific chemical shifts for the cisand transisomeric forms of phytoene have been assigned in previous studies [18,23,24].…”

Section: Introductionmentioning

confidence: 99%

Stereoisomers of Colourless Carotenoids from the Marine Microalga Dunaliella salina

Mazzucchi

Harvey

2020

Molecules

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“…1 H and 13 C NMR assignments of phytoene and phytofluene are reported in classical works [102,103]. A methodology for the rapid NMR identification of tomato carotenoids, including (15Z)-phytoene, involving a CDCl3 extraction procedure and high-resolution multidimensional NMR techniques using a cryogenic probe is described [104].…”

Section: Nuclear Magnetic Resonancementioning

confidence: 99%

A comprehensive review on the colorless carotenoids phytoene and phytofluene

Meléndez-Martínez

Benítez-González

Stinco

2015

Archives of Biochemistry and Biophysics

154

112

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“…ORF-B, ORF-C, and ORF-F were newly designated genes crtX, crtY, and crtZ, respectively. (9). No phytoene was detected in E. coli(pCAR-A) and E. coli(pCAR-E).…”

Section: Resultsmentioning

confidence: 95%

Elucidation of the Erwinia uredovora carotenoid biosynthetic pathway by functional analysis of gene products expressed in Escherichia coli

et al. 1990

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functions as a precursor of vitamin A in mammals (G. A. J. Pitt, in I. Osler, H. Gutmonn, and U. Solms, ed., Carotenoids-1971Carotenoids- , 1971). The enzymes and genes which mediate the biosynthesis of cyclic carotenoids such as 13-carotene are virtually unknown. We have elucidated for the first time the pathway for biosynthesis of these carotenoids at the level of enzyme-catalyzed reactions, using bacterial carotenoid biosynthesis genes. These genes were cloned from a phytopathogenic bacterium, Erwinia uredevora 20D3 (ATCC 19321)

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1H and 13C NMR spectra of cis and trans phytoene isomers

Cited by 12 publications

References 5 publications

Stereoisomers of Colourless Carotenoids from the Marine Microalga Dunaliella salina

Stereoisomers of Colourless Carotenoids from the Marine Microalga Dunaliella salina

A comprehensive review on the colorless carotenoids phytoene and phytofluene

Elucidation of the Erwinia uredovora carotenoid biosynthetic pathway by functional analysis of gene products expressed in Escherichia coli

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