- -

Crocins with high levels of sugar conjugation contribute to the yellow colours of early-spring flowering

RiuNet: Repositorio Institucional de la Universidad Politécnica de Valencia

Compartir/Enviar a

Citas

Estadísticas

  • Estadisticas de Uso

Crocins with high levels of sugar conjugation contribute to the yellow colours of early-spring flowering

Mostrar el registro sencillo del ítem

Ficheros en el ítem

Thumbnail
Nombre: Rubio-Moraga;AHRA ...
Tamaño: 1.611Mb
Formato: PDF
Descripción: Versión editorial
Abrir
dc.contributor.author Rubio-Moraga, A. es_ES
dc.contributor.author Ahrazem, Oussama es_ES
dc.contributor.author Rambla Nebot, Jose Luis es_ES
dc.contributor.author Granell Richart, Antonio es_ES
dc.contributor.author Gómez Gómez, Lourdes es_ES
dc.date.accessioned 2014-08-28T10:59:37Z
dc.date.available 2014-08-28T10:59:37Z
dc.date.issued 2013-09
dc.identifier.issn 1932-6203
dc.identifier.uri http://hdl.handle.net/10251/39273
dc.description.abstract 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. beta-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. es_ES
dc.description.sponsorship The laboratory is supported by the Spanish Ministerio de Ciencia e Innovacion (BIO2009-07803) and participates in the IBERCAROT network (112RT0445). Dr. Ahrazem was funded by FPCYTA through the INCRECYT Programme. The funders had no role in study design, data collection and analysis, decision to publish, or preparation of the manuscript. en_EN
dc.language Inglés es_ES
dc.publisher Public Library of Science es_ES
dc.relation.ispartof PLoS ONE es_ES
dc.rights Reconocimiento (by) es_ES
dc.subject Carotenoid cleavage dioxygenase es_ES
dc.subject Boronia-megastigma nees es_ES
dc.subject Mycorrhizal roots es_ES
dc.subject Sativus stigmas es_ES
dc.subject C-27 apocarotenoids es_ES
dc.subject Gene-expression es_ES
dc.subject In-vitro es_ES
dc.subject Saffron es_ES
dc.subject Accumulation es_ES
dc.subject Crocetin es_ES
dc.title Crocins with high levels of sugar conjugation contribute to the yellow colours of early-spring flowering es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1371/journal.pone.0071946
dc.relation.projectID info:eu-repo/grantAgreement/MICINN//BIO2009-07803/ES/Glucosiltransferasas Y Glucosidasas (Cazy Enzymes) De Flavonoides Y Apocarotenoides De Crocus Sativus/ es_ES
dc.rights.accessRights Abierto es_ES
dc.contributor.affiliation Universitat Politècnica de València. Instituto Universitario Mixto de Biología Molecular y Celular de Plantas - Institut Universitari Mixt de Biologia Molecular i Cel·lular de Plantes es_ES
dc.description.bibliographicCitation Rubio-Moraga, A.; Ahrazem, O.; Rambla Nebot, JL.; Granell Richart, A.; Gómez Gómez, L. (2013). Crocins with high levels of sugar conjugation contribute to the yellow colours of early-spring flowering. PLoS ONE. 8(9):71946-71946. https://doi.org/10.1371/journal.pone.0071946 es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion http://dx.doi.org/10.1371/journal.pone.0071946 es_ES
dc.description.upvformatpinicio 71946 es_ES
dc.description.upvformatpfin 71946 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 8 es_ES
dc.description.issue 9 es_ES
dc.relation.senia 256958
dc.identifier.pmid 24058441 en_EN
dc.identifier.pmcid PMC3772802 en_EN
dc.contributor.funder Ministerio de Ciencia e Innovación es_ES
dc.contributor.funder Fundación Parque Científico Tecnológico de Albacete es_ES
dc.description.references Auldridge, M. E., McCarty, D. R., & Klee, H. J. (2006). Plant carotenoid cleavage oxygenases and their apocarotenoid products. Current Opinion in Plant Biology, 9(3), 315-321. doi:10.1016/j.pbi.2006.03.005 es_ES
dc.description.references AKIYAMA, K. (2007). Chemical Identification and Functional Analysis of Apocarotenoids Involved in the Development of Arbuscular Mycorrhizal Symbiosis. Bioscience, Biotechnology, and Biochemistry, 71(6), 1405-1414. doi:10.1271/bbb.70023 es_ES
dc.description.references Lendzemo, V. W., Kuyper, T. W., Matusova, R., Bouwmeester, H. J., & Ast, A. V. (2007). Colonization by Arbuscular Mycorrhizal Fungi of Sorghum Leads to Reduced Germination and Subsequent Attachment and Emergence ofStriga hermonthica. Plant Signaling & Behavior, 2(1), 58-62. doi:10.4161/psb.2.1.3884 es_ES
dc.description.references Gomez-Roldan, V., Fermas, S., Brewer, P. B., Puech-Pagès, V., Dun, E. A., Pillot, J.-P., … Rochange, S. F. (2008). Strigolactone inhibition of shoot branching. Nature, 455(7210), 189-194. doi:10.1038/nature07271 es_ES
dc.description.references Umehara, M., Hanada, A., Yoshida, S., Akiyama, K., Arite, T., Takeda-Kamiya, N., … Yamaguchi, S. (2008). Inhibition of shoot branching by new terpenoid plant hormones. Nature, 455(7210), 195-200. doi:10.1038/nature07272 es_ES
dc.description.references Jella, P., Rouseff, R., Goodner, K., & Widmer, W. (1998). Determination of Key Flavor Components in Methylene Chloride Extracts from Processed Grapefruit Juice. Journal of Agricultural and Food Chemistry, 46(1), 242-247. doi:10.1021/jf9702149 es_ES
dc.description.references Pfander, H., & Schurtenberger, H. (1982). Biosynthesis of C20-carotenoids in Crocus sativus. Phytochemistry, 21(5), 1039-1042. doi:10.1016/s0031-9422(00)82412-7 es_ES
dc.description.references Bathaie, S. Z., & Mousavi, S. Z. (2010). New Applications and Mechanisms of Action of Saffron and its Important Ingredients. Critical Reviews in Food Science and Nutrition, 50(8), 761-786. doi:10.1080/10408390902773003 es_ES
dc.description.references Abdullaev, F. I., & Espinosa-Aguirre, J. J. (2004). Biomedical properties of saffron and its potential use in cancer therapy and chemoprevention trials. Cancer Detection and Prevention, 28(6), 426-432. doi:10.1016/j.cdp.2004.09.002 es_ES
dc.description.references Zhang Z, Wang CZ, Wen XD, Shoyama Y, Yuan CS (2013) Role of saffron and its constituents on cancer chemoprevention. Pharm Biol. es_ES
dc.description.references Schmidt, M., Betti, G., & Hensel, A. (2007). Saffron in phytotherapy: Pharmacology and clinical uses. Wiener Medizinische Wochenschrift, 157(13-14), 315-319. doi:10.1007/s10354-007-0428-4 es_ES
dc.description.references Howes, M.-J. R., & Perry, E. (2011). The Role of Phytochemicals in the Treatment and Prevention of Dementia. Drugs & Aging, 28(6), 439-468. doi:10.2165/11591310-000000000-00000 es_ES
dc.description.references Castillo, R., Fernández, J.-A., & Gómez-Gómez, L. (2005). Implications of Carotenoid Biosynthetic Genes in Apocarotenoid Formation during the Stigma Development of Crocus sativus and Its Closer Relatives. Plant Physiology, 139(2), 674-689. doi:10.1104/pp.105.067827 es_ES
dc.description.references Moraga, Á. R., Rambla, J. L., Ahrazem, O., Granell, A., & Gómez-Gómez, L. (2009). Metabolite and target transcript analyses during Crocus sativus stigma development. Phytochemistry, 70(8), 1009-1016. doi:10.1016/j.phytochem.2009.04.022 es_ES
dc.description.references Rubio-Moraga, A., Trapero, A., Ahrazem, O., & Gómez-Gómez, L. (2010). Crocins transport in Crocus sativus: The long road from a senescent stigma to a newborn corm. Phytochemistry, 71(13), 1506-1513. doi:10.1016/j.phytochem.2010.05.026 es_ES
dc.description.references Moraga, A. R., Nohales, P. F., P�rez, J. A. F., & G�mez-G�mez, L. (2004). Glucosylation of the saffron apocarotenoid crocetin by a glucosyltransferase isolated from Crocus sativus stigmas. Planta, 219(6), 955-966. doi:10.1007/s00425-004-1299-1 es_ES
dc.description.references Harpke, D., Meng, S., Rutten, T., Kerndorff, H., & Blattner, F. R. (2013). Phylogeny of Crocus (Iridaceae) based on one chloroplast and two nuclear loci: Ancient hybridization and chromosome number evolution. Molecular Phylogenetics and Evolution, 66(3), 617-627. doi:10.1016/j.ympev.2012.10.007 es_ES
dc.description.references Mathew B (1982) The crocus - A revision of the Genus crocus; Batsford B, editor. London. es_ES
dc.description.references Nørbæk, R., Nielsen, K., & Kondo, T. (2002). Anthocyanins from flowers of Cichorium intybus. Phytochemistry, 60(4), 357-359. doi:10.1016/s0031-9422(02)00055-9 es_ES
dc.description.references Zhu, C., Bai, C., Sanahuja, G., Yuan, D., Farré, G., Naqvi, S., … Christou, P. (2010). The regulation of carotenoid pigmentation in flowers. Archives of Biochemistry and Biophysics, 504(1), 132-141. doi:10.1016/j.abb.2010.07.028 es_ES
dc.description.references OHMIYA, A. (2011). Diversity of Carotenoid Composition in Flower Petals. Japan Agricultural Research Quarterly: JARQ, 45(2), 163-171. doi:10.6090/jarq.45.163 es_ES
dc.description.references KISHIMOTO, S., MAOKA, T., SUMITOMO, K., & OHMIYA, A. (2005). Analysis of Carotenoid Composition in Petals of Calendula (Calendula officinalisL.). Bioscience, Biotechnology, and Biochemistry, 69(11), 2122-2128. doi:10.1271/bbb.69.2122 es_ES
dc.description.references Ohmiya, A., Kishimoto, S., Aida, R., Yoshioka, S., & Sumitomo, K. (2006). Carotenoid Cleavage Dioxygenase (CmCCD4a) Contributes to White Color Formation in Chrysanthemum Petals. Plant Physiology, 142(3), 1193-1201. doi:10.1104/pp.106.087130 es_ES
dc.description.references Ohmiya, A., Sumitomo, K., & Aida, R. (2009). «Yellow Jimba»: Suppression of Carotenoid Cleavage Dioxygenase (CmCCD4a) Expression Turns White Chrysanthemum Petals Yellow. Journal of the Japanese Society for Horticultural Science, 78(4), 450-455. doi:10.2503/jjshs1.78.450 es_ES
dc.description.references Brandi, F., Bar, E., Mourgues, F., Horváth, G., Turcsi, E., Giuliano, G., … Rosati, C. (2011). Study of «Redhaven» peach and its white-fleshed mutant suggests a key role of CCD4 carotenoid dioxygenase in carotenoid and norisoprenoid volatile metabolism. BMC Plant Biology, 11(1), 24. doi:10.1186/1471-2229-11-24 es_ES
dc.description.references Campbell, R., Ducreux, L. J. M., Morris, W. L., Morris, J. A., Suttle, J. C., Ramsay, G., … Taylor, M. A. (2010). The Metabolic and Developmental Roles of Carotenoid Cleavage Dioxygenase4 from Potato. Plant Physiology, 154(2), 656-664. doi:10.1104/pp.110.158733 es_ES
dc.description.references Ahrazem, O., Rubio-Moraga, A., Lopez, R. C., & Gomez-Gomez, L. (2009). The expression of a chromoplast-specific lycopene beta cyclase gene is involved in the high production of saffron’s apocarotenoid precursors. Journal of Experimental Botany, 61(1), 105-119. doi:10.1093/jxb/erp283 es_ES
dc.description.references Ahrazem, O., Rubio-Moraga, A., Trapero, A., & Gomez-Gomez, L. (2011). Developmental and stress regulation of gene expression for a 9-cis-epoxycarotenoid dioxygenase, CstNCED, isolated from Crocus sativus stigmas. Journal of Experimental Botany, 63(2), 681-694. doi:10.1093/jxb/err293 es_ES
dc.description.references Moraga, Á., Mozos, A., Ahrazem, O., & Gómez-Gómez, L. (2009). Cloning and characterization of a glucosyltransferase from Crocus sativus stigmas involved in flavonoid glucosylation. BMC Plant Biology, 9(1), 109. doi:10.1186/1471-2229-9-109 es_ES
dc.description.references Tarantilis, P. A., Tsoupras, G., & Polissiou, M. (1995). Determination of saffron (Crocus sativus L.) components in crude plant extract using high-performance liquid chromatography-UV-visible photodiode-array detection-mass spectrometry. Journal of Chromatography A, 699(1-2), 107-118. doi:10.1016/0021-9673(95)00044-n es_ES
dc.description.references Walter, M. H., Fester, T., & Strack, D. (2000). Arbuscular mycorrhizal fungi induce the non-mevalonate methylerythritol phosphate pathway of isoprenoid biosynthesis correlated with accumulation of the «yellow pigment» and other apocarotenoids. The Plant Journal, 21(6), 571-578. doi:10.1046/j.1365-313x.2000.00708.x es_ES
dc.description.references Gómez-Miranda, B., Rupérez, P., & Leal, J. A. (1981). Changes in chemical composition during germination ofbotrytis cinerea sclerotia. Current Microbiology, 6(4), 243-246. doi:10.1007/bf01566981 es_ES
dc.description.references Cooper, C. M., Davies, N. W., & Menary, R. C. (2003). C-27 Apocarotenoids in the Flowers ofBoronia megastigma(Nees). Journal of Agricultural and Food Chemistry, 51(8), 2384-2389. doi:10.1021/jf026007c es_ES
dc.description.references Floss, D. S., Schliemann, W., Schmidt, J., Strack, D., & Walter, M. H. (2008). RNA Interference-Mediated Repression of MtCCD1 in Mycorrhizal Roots of Medicago truncatula Causes Accumulation of C27 Apocarotenoids, Shedding Light on the Functional Role of CCD1. Plant Physiology, 148(3), 1267-1282. doi:10.1104/pp.108.125062 es_ES
dc.description.references Fester, T., Schmidt, D., Lohse, S., Walter, M., Giuliano, G., Bramley, P., … Strack, D. (2002). Stimulation of carotenoid metabolism in arbuscular mycorrhizal roots. Planta, 216(1), 148-154. doi:10.1007/s00425-002-0917-z es_ES
dc.description.references Klingner, A., Bothe, H., Wray, V., & Marner, F.-J. (1995). Identification of a yellow pigment formed in maize roots upon mycorrhizal colonization. Phytochemistry, 38(1), 53-55. doi:10.1016/0031-9422(94)00538-5 es_ES
dc.description.references Rychener, M., Bigler, P., & Pfander, H. (1984). Isolierung und Strukturaufkl�rung von Neapolitanose (O-?-D-Glucopyranosyl-(1?2)-O-[?-D-glucopyranosyl-(1?6)]-(D-glucose), einem neuen Trisaccharid aus den Stempeln von Gartenkrokussen (Crocus neapolitanus var.). Helvetica Chimica Acta, 67(2), 386-391. doi:10.1002/hlca.19840670205 es_ES
dc.description.references Lu, S., Van Eck, J., Zhou, X., Lopez, A. B., O’Halloran, D. M., Cosman, K. M., … Li, L. (2006). The Cauliflower Or Gene Encodes a DnaJ Cysteine-Rich Domain-Containing Protein That Mediates High Levels of β-Carotene Accumulation. The Plant Cell, 18(12), 3594-3605. doi:10.1105/tpc.106.046417 es_ES
dc.description.references Rubio, A., Rambla, J. L., Santaella, M., Gómez, M. D., Orzaez, D., Granell, A., & Gómez-Gómez, L. (2008). Cytosolic and Plastoglobule-targeted Carotenoid Dioxygenases fromCrocus sativusAre Both Involved in β-Ionone Release. Journal of Biological Chemistry, 283(36), 24816-24825. doi:10.1074/jbc.m804000200 es_ES
dc.description.references Dufresne, C., Cormier, F., & Dorion, S. (1997). In VitroFormation of Crocetin Glucosyl Esters byCrocus sativusCallus Extract. Planta Medica, 63(02), 150-153. doi:10.1055/s-2006-957633 es_ES
dc.description.references Wakelin, A. M., Lister, C. E., & Conner, A. J. (2003). Inheritance and Biochemistry of Pollen Pigmentation in California Poppy (Eschscholzia californica Cham.). International Journal of Plant Sciences, 164(6), 867-875. doi:10.1086/378825 es_ES
dc.description.references Cooper, C. M., Davies, N. W., & Menary, R. C. (2009). Changes in Some Carotenoids and Apocarotenoids during Flower Development in Boronia megastigma (Nees). Journal of Agricultural and Food Chemistry, 57(4), 1513-1520. doi:10.1021/jf802610p es_ES
dc.description.references Pfister, S., Meyer, P., Steck, A., & Pfander, H. (1996). Isolation and Structure Elucidation of Carotenoid−Glycosyl Esters in Gardenia Fruits (Gardenia jasminoidesEllis) and Saffron (CrocussativusLinne). Journal of Agricultural and Food Chemistry, 44(9), 2612-2615. doi:10.1021/jf950713e es_ES
dc.description.references Dufresne, C., Cormier, F., Dorion, S., Niggli, U. A., Pfister, S., & Pfander, H. (1999). Glycosylation of encapsulated crocetin by a Crocus sativus L. cell culture. Enzyme and Microbial Technology, 24(8-9), 453-462. doi:10.1016/s0141-0229(98)00143-4 es_ES
dc.description.references Lundmark, M., Hurry, V., & Lapointe, L. (2009). Low temperature maximizes growth of Crocus vernus (L.) Hill via changes in carbon partitioning and corm development. Journal of Experimental Botany, 60(7), 2203-2213. doi:10.1093/jxb/erp103 es_ES
dc.description.references Schliemann, W., Schmidt, J., Nimtz, M., Wray, V., Fester, T., & Strack, D. (2006). Accumulation of apocarotenoids in mycorrhizal roots of Ornithogalum umbellatum. Phytochemistry, 67(12), 1196-1205. doi:10.1016/j.phytochem.2006.05.005 es_ES
dc.description.references Gómez-Gómez L, Moraga-Rubio A, Ahrazem O (2010) Understanding Carotenoid Metabolism in Saffron Stigmas: Unravelling Aroma and Colour Formation. In: Teixeira da Silva JA, editor. Functional Plant Science adn Biotechnology United Kingdon: GLOBAL SCIENCE BOOKS. pp.56–63. es_ES
dc.description.references Schwartz, S. H., Qin, X., & Zeevaart, J. A. D. (2001). Characterization of a Novel Carotenoid Cleavage Dioxygenase from Plants. Journal of Biological Chemistry, 276(27), 25208-25211. doi:10.1074/jbc.m102146200 es_ES
dc.description.references Ilg, A., Yu, Q., Schaub, P., Beyer, P., & Al-Babili, S. (2010). Overexpression of the rice carotenoid cleavage dioxygenase 1 gene in Golden Rice endosperm suggests apocarotenoids as substrates in planta. Planta, 232(3), 691-699. doi:10.1007/s00425-010-1205-y es_ES
dc.description.references Almeida, E. R. A., & Cerdá-Olmedo, E. (2008). Gene expression in the regulation of carotene biosynthesis in Phycomyces. Current Genetics, 53(3), 129-137. doi:10.1007/s00294-007-0170-x es_ES
dc.description.references Kachanovsky, D. E., Filler, S., Isaacson, T., & Hirschberg, J. (2012). Epistasis in tomato color mutations involves regulation of phytoene synthase 1 expression by cis-carotenoids. Proceedings of the National Academy of Sciences, 109(46), 19021-19026. doi:10.1073/pnas.1214808109 es_ES
dc.description.references Walter, M. H., Floss, D. S., & Strack, D. (2010). Apocarotenoids: hormones, mycorrhizal metabolites and aroma volatiles. Planta, 232(1), 1-17. doi:10.1007/s00425-010-1156-3 es_ES
dc.description.references GIACCIO, M. (2004). Crocetin from Saffron: An Active Component of an Ancient Spice. Critical Reviews in Food Science and Nutrition, 44(3), 155-172. doi:10.1080/10408690490441433 es_ES
dc.description.references Hosseinzadeh, H., & Nassiri-Asl, M. (2012). Avicenna’s (Ibn Sina) the Canon of Medicine and Saffron (Crocus sativus): A Review. Phytotherapy Research, 27(4), 475-483. doi:10.1002/ptr.4784 es_ES
dc.description.references Ochiai, T., Shimeno, H., Mishima, K., Iwasaki, K., Fujiwara, M., Tanaka, H., … Soeda, S. (2007). Protective effects of carotenoids from saffron on neuronal injury in vitro and in vivo. Biochimica et Biophysica Acta (BBA) - General Subjects, 1770(4), 578-584. doi:10.1016/j.bbagen.2006.11.012 es_ES


Este ítem aparece en la(s) siguiente(s) colección(ones)

Mostrar el registro sencillo del ítem