Carotenoids and related compounds. Part XXI. Structure of neoxanthin (foliaxanthin)

Cholnoky, L. v.; Györgyfy, K.; Rónai, A.; Szabolcs, J.; Tóth, Gy.; Galasko, Gail; Mallams, Alan K.; Waight, E. S.; Weedon, B. C. L.

doi:10.1039/j39690001256

Cited by 44 publications

(20 citation statements)

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“…There has been some confusion about the stereochemistry of neoxanthin. Cholnoky et al (2) reported that the initial isolation of neoxanthin had probably been that of 9'-cisneoxanthin, due to treatments used to saponify Chl. They reported that the all-trans isomer predominated if saponification was deleted.…”

Section: Discussionmentioning

confidence: 99%

“…The identities of violaxanthin, neoxanthin, and antheraxanthin were confirmed by their spectral shifts after the addition of acid (5). The identities of 9'-cis-neoxanthin and 9-cis-violaxanthin were confirmed by their optical rotatory dispersion and circular dichroism spectra recorded with Cary 60 and 14 recording spectrophotometers, respectively (1,2,18 (12), except that an 8 m SPB-1 fused silica capillary column was used.…”

Section: Materials and Methods Plant Materialsmentioning

confidence: 99%

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Violaxanthin Is an Abscisic Acid Precursor in Water-Stressed Dark-Grown Bean Leaves

Walton²

1990

Plant Physiol.

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The leaves of dark-grown bean (Phaseolus vulgaris L.) seedlings accumulate considerably lower quantities of xanthophylls and carotenes than do leaves of light-grown seedlings, but they synthesize at least comparable amounts of abscisic acid (ABA) and its metabolites when water stressed. We observed a 1:1 relationship on a molar basis between the reduction in levels of violaxanthin, 9'-cis-neoxanthin, and 9-cis-violaxanthin and the accumulation of ABA, phaseic acid, and dihydrophaseic acid, when leaves from dark-grown plants were (10,12,15,20 one atom of 180 into the carboxyl group of ABA. One explanation for these latter results is that a preformed xanthophyll was cleaved by a dioxygenase to form an aldehyde that was converted to ABA by dehydrogenases. Li and Walton (12) suggested that at least a portion of ABA was derived from violaxanthin in water-stressed bean leaves based on studies in which the violaxanthin epoxide oxygens were labeled in situ with 180 via the xanthophyll cycle.One of the difficulties in demonstrating a precursor role for a major leaf xanthophyll is that these compounds are present at high levels in green leaves compared with the levels to which ABA and its metabolites accumulate even under water stress. Small differences in xanthophyll levels between leaf samples, either real or due to experimental error, can obscure any reductions that might result from ABA synthesis. Resynthesis of the precursors could also mask any reductions. Gamble and Mullet (7) stressed dark-grown fluridone-treated barley leaves which contained considerably lower xanthophyll levels than were present in untreated green leaves. They observed that ABA production was still 25% of normal, even when xanthophyll levels had been reduced by 99%. They also reported that violaxanthin, neoxanthin, and antheraxanthin levels were reduced during the stress period. Their results were confounded, however, by the fact that xanthophyll levels were also reduced, albeit to a lesser extent, when leaves were detached but not stressed. Thus, they were unable to conclude what the stoichiometry was between xanthophyll reduction and total ABA synthesis. We report on the results we have obtained with bean leaves stressed after detachment from dark-grown bean seedlings. In this system, only leaves that have been stressed show significant changes in xanthophyll content, the levels of ABA produced are at least comparable to those in light-grown plants, and the total amount of ABA produced is closely matched by reductions in the levels of several xanthophylls. These results enable us to draw inferences about the origin of ABA. MATERIALS AND METHODS Plant MaterialsPhaseolus vulgaris L. cv Blue Lake seeds were surfacesterilized with a 10% Clorox solution for 30 min and then imbibed in sterile water for 7 h. The seeds were planted in flats in a soil:vermiculite mixture (1:1) and grown in complete darkness at about 23°C for 8 or 9 d. Unless otherwise indicated, plants were sprayed with fluridone (13 mg L-') twice daily from d 4 to the end o...

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Section: Discussionmentioning

confidence: 99%

Section: Materials and Methods Plant Materialsmentioning

confidence: 99%

Violaxanthin Is an Abscisic Acid Precursor in Water-Stressed Dark-Grown Bean Leaves

Walton²

1990

Plant Physiol.

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“…On the other hand, experiments with radiochemically purified 14 C-Neo have revealed its transformation into Viol, Lut, and Car [3]. Demonstration of the allene structure of Neo [8] has made it possible to verify the transformation of epoxyxanthophylls and their furanoid derivatives into structurally simpler Xan upon treatment with LiAlH 4 . In particular, it has been shown that Neo furanoid is converted without disrupting the carbon backbone into Zea identical to Zea isolated from Physalis ; Viol, into Zea; and epoxy-β -Car, into Car [8,9].…”

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Redox Transformation of 14C-Neoxanthin in Animal and Plant Tissues

2005

Dokl Biochem Biophys

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“…So schrieben ChoInoky rt a/. [7] bei der Isolierung von Neoxanthinen aus Ahornblattern'): 'it was found that neoxanthin X (heute als (all-E)-Neoxanthin bezeichnet) constitutes the principal isomer from maple leaves, provided that the customary alkaline hydrolysis step is omitted in the isolation procedure'. In eine ahnliche Richtung zielt auch die Bemerkung von Khachik et al [8] [I 11.…”

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“…In der Literatur sind quantitative UV/VIS-Spektren von (9'Z)-Neoxanthin (6) kaum zu finden. Eine Ausnahme bildet das von Cholnoky et al [7] aus Ahornblattern isolierte Praparat. Zum Vergleich isolierten wir nun auch ein kristallines Priiparat aus grunem Gras.…”

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(6R,9′Z)‐Neoxanthin: Synthese, Schmelzverhalten, Spektren und Konformationsberechnungen

Baumeler

Zerbe

Kunz

et al. 1994

Helvetica Chimica Acta

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The synthesis of pure and crystalline (9'Z)-neoxanthin (6) is described. MnO, Oxidation of (9Z)-C15-alcohol 7 at room temperature produces a mixture 8/9 of (92)-and (9E)-aldehydes. Predominant formation of the required (9Z)-aldehyde 8 is achieved by performing the oxidation at -10". Condensation of 8 with the mono-Li salt of the symmetrical C,,-diphosphonate 10 gave the (9Z)-C,,-monophosphonate 11. The Wittig-Horner condensation of 10 with the allenic C,,-aldehyde lb, under selected conditions allows the preparation of pure and crystalline (9'Z)-15,15'-didehydroneoxanthin (12) and, after subsequent semireduction, of crystalline (1 52,9'Z)-neoxanthin (13). Thermal isomerisation of a AcOEt solution of 13 at 95" yields preferentially (9'Z

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Carotenoids and related compounds. Part XXI. Structure of neoxanthin (foliaxanthin)

Cited by 44 publications

References 1 publication

Violaxanthin Is an Abscisic Acid Precursor in Water-Stressed Dark-Grown Bean Leaves

Violaxanthin Is an Abscisic Acid Precursor in Water-Stressed Dark-Grown Bean Leaves

Redox Transformation of 14C-Neoxanthin in Animal and Plant Tissues

(6R,9′Z)‐Neoxanthin: Synthese, Schmelzverhalten, Spektren und Konformationsberechnungen

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