Changes in Some Carotenoids and Apocarotenoids during Flower Development in Boronia megastigma (Nees)

Cooper, Chris M.; Davies, Noel W.; Menary, RC

doi:10.1021/jf802610p

Cited by 22 publications

(9 citation statements)

References 36 publications

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“…For instance, the petals of Eschscholzia californica (Papaveraceae) accumulate crocetin among other carotenoids [48] and those of Crocosmia (Iridaceae) accumulate crocin [49]. Various apocarotenoids such as β-ionone, 10′-apocaroten-10′-oic acid, and hydroxy 10′-apocaroten- 10′-oic acid are found in the petals of Boronia megastigma [50].…”

Section: Discussionmentioning

confidence: 99%

Crocins with High Levels of Sugar Conjugation Contribute to the Yellow Colours of Early-Spring Flowering Crocus Tepals

et al. 2013

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Crocus sativus is the source of saffron spice, the processed stigma which accumulates glucosylated apocarotenoids known as crocins. Crocins are found in the stigmas of other Crocuses, determining the colourations observed from pale yellow to dark red. By contrast, tepals in Crocus species display a wider diversity of colours which range from purple, blue, yellow to white. In this study, we investigated whether the contribution of crocins to colour extends from stigmas to the tepals of yellow Crocus species. Tepals from seven species were analysed by UPLC-PDA and ESI-Q-TOF-MS/MS revealing for the first time the presence of highly glucosylated crocins in this tissue. β-carotene was found to be the precursor of these crocins and some of them were found to contain rhamnose, never before reported. When crocin profiles from tepals were compared with those from stigmas, clear differences were found, including the presence of new apocarotenoids in stigmas. Furthermore, each species showed a characteristic profile which was not correlated with the phylogenetic relationship among species. While gene expression analysis in tepals of genes involved in carotenoid metabolism showed that phytoene synthase was a key enzyme in apocarotenoid biosynthesis in tepals. Expression of a crocetin glucosyltransferase, previously identified in saffron, was detected in all the samples. The presence of crocins in tepals is compatible with the role of chromophores to attract pollinators. The identification of tepals as new sources of crocins is of special interest given their wide range of applications in medicine, cosmetics and colouring industries.

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Section: Discussionmentioning

confidence: 99%

Crocins with High Levels of Sugar Conjugation Contribute to the Yellow Colours of Early-Spring Flowering Crocus Tepals

et al. 2013

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“…In plants, they play key roles in reproduction, defense, and architecture [50]. 3-OH-β-Apo-10’-carotenoic acid has been identified in Boronia megastigma (Nees) during flower development, indicating cleavage of xanthophylls and oxidation of cleavage products [51, 52]. In animals, a number of studies have identified a broad array of apocarotenoids and apolycopenoids with potential biological activities [7, 18, 20, 53, 54].…”

Section: Discussionmentioning

confidence: 99%

Enzymatic formation of apo-carotenoids from the xanthophyll carotenoids lutein, zeaxanthin and β-cryptoxanthin by ferret carotene-9′,10′-monooxygenase

Mein

Dolnikowski

Ernst

et al. 2011

Archives of Biochemistry and Biophysics

122

106

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Xanthophyll carotenoids, such as lutein, zeaxanthin and β-cryptoxanthin, may provide potential health benefits against chronic and degenerative diseases. Investigating pathways of xanthophyll metabolism are important to understanding their biological functions. Carotene-15,15'-monooxygenase (CMO1) has been shown to be involved in vitamin A formation, while recent studies suggest that carotene-9',10'-monooxygenase (CMO2) may have a broader substrate specificity than previously recognized. In this in vitro study, we investigated baculovirusgenerated recombinant ferret CMO2 cleavage activity towards the carotenoid substrates zeaxanthin, lutein and β-cryptoxanthin. Utilizing HPLC, LC-MS and GC-MS, we identified both volatile and non-volatile apocarotenoid products including 3-OH-β-ionone, 3-OH-α-ionone, β-ionone, 3-OH-α-apo-10'-carotenal, 3-OH-β-apo-10'-carotenal, and β-apo-10'-carotenal, indicating cleavage at both the 9,10 and 9',10' carbon-carbon double bond. Enzyme kinetic analysis indicated the xanthophylls zeaxanthin and lutein are preferentially cleaved over β-cryptoxanthin, indicating a key role of CMO2 in non-provitamin A carotenoid metabolism. Furthermore, incubation of 3-OH-β-apo-10'-carotenal with CMO2 lysate resulted in the formation of 3-OH-β-ionone. In the presence of NAD + , in vitro incubation of 3-OH-β-apo-10'-carotenal with ferret hepatic homogenates formed 3-OH-β-apo-10'-carotenoic acid. Since apo-carotenoids serve as important signaling molecules in a variety of biological processes, enzymatic cleavage of xanthophylls by mammalian CMO2 represents a new avenue of research regarding vertebrate carotenoid metabolism and biological function.

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“…The Xowers of this small shrub native to southwestern Australia are collected for their Xavor and fragrance based on various C 13 apocarotenoid constituents (Cooper et al 2003). A palmitic ester of a C 27 3-hydroxy-10Ј-apocaroten-10Јoic acid and other C 27 apocarotenoids have been tentatively identiWed recently from this system (Cooper et al 2009). Based on C 27 identiWcation in rose petals, such a two-step sequential cleavage mechanism has been proposed for C 13 scent and aroma compound biogenesis many years ago (Eugster and Märki-Fischer 1991), but this mechanistic proposal has never been substantiated by enzymatic data and fell into oblivion in the wake of many studies showing dual 9-10 and 9Ј-10Ј cleavage activity of recombinant CCD1 proteins on various C 40 carotenoids in vitro.…”

Section: Role Of Ccd1 In Mycorrhizal Roots and Beyondmentioning

confidence: 99%

Apocarotenoids: hormones, mycorrhizal metabolites and aroma volatiles

Walter

Floß

Strack

2010

Planta

216

191

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Apocarotenoids are tailored from carotenoids by oxidative enzymes [carotenoid cleavage oxygenases (CCOs)], cleaving specific double bonds of the polyene chain. The cleavage products can act as hormones, signaling compounds, chromophores and scent/aroma constituents. Recent advances were the identification of strigolactones as apocarotenoids and the description of their novel role as shoot branching inhibitor hormones. Strigolactones are also involved in plant signaling to both harmful (parasitic weeds) and beneficial [arbuscular mycorrhizal (AM) fungi] rhizosphere residents. This review describes the progress in the characterization of CCOs, termed CCDs and NCEDs, in plants. It highlights the importance of sequential cleavage reactions of C(40) carotenoid precursors, the apocarotenoid cleavage oxygenase (ACO) nature of several CCOs and the topic of compartmentation. Work on the biosynthesis of abundant C(13) cyclohexenone and C(14) mycorradicin apocarotenoids in mycorrhizal roots has revealed a new role of CCD1 as an ACO of C(27) apocarotenoid intermediates, following their predicted export from plastid to cytosol. Manipulation of the AM-induced apocarotenoid pathway further suggests novel roles of C(13) apocarotenoids in controlling arbuscule turnover in the AM symbiosis. CCD7 has been established as a biosynthetic crosspoint, controlling both strigolactone and AM-induced C(13) apocarotenoid biosynthesis. Interdependence of the two apocarotenoid pathways may thus play a role in AM-mediated reduction of parasitic weed infestations. Potential scenarios of C(13) scent/aroma volatile biogenesis are discussed, including the novel mechanism revealed from mycorrhizal roots. The recent progress in apocarotenoid research opens up new perspectives for fundamental work, but has also great application potential for the horticulture, food and fragrance industries.

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Changes in Some Carotenoids and Apocarotenoids during Flower Development in Boronia megastigma (Nees)

Cited by 22 publications

References 36 publications

Crocins with High Levels of Sugar Conjugation Contribute to the Yellow Colours of Early-Spring Flowering Crocus Tepals

Crocins with High Levels of Sugar Conjugation Contribute to the Yellow Colours of Early-Spring Flowering Crocus Tepals

Enzymatic formation of apo-carotenoids from the xanthophyll carotenoids lutein, zeaxanthin and β-cryptoxanthin by ferret carotene-9′,10′-monooxygenase

Apocarotenoids: hormones, mycorrhizal metabolites and aroma volatiles

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