{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,9]],"date-time":"2026-09-09T01:08:20Z","timestamp":1788916100682,"version":"build-2803163510"},"reference-count":45,"publisher":"Oxford University Press (OUP)","issue":"4","license":[{"start":{"date-parts":[[2021,1,25]],"date-time":"2021-01-25T00:00:00Z","timestamp":1611532800000},"content-version":"vor","delay-in-days":3261,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2012,4,2]]},"abstract":"<jats:title>Abstract<\/jats:title>\n               <jats:p>Amygdalin is a cyanogenic diglucoside and constitutes the bitter component in bitter almond (Prunus dulcis). Amygdalin concentration increases in the course of fruit formation. The monoglucoside prunasin is the precursor of amygdalin. Prunasin may be degraded to hydrogen cyanide, glucose, and benzaldehyde by the action of the \u03b2-glucosidase prunasin hydrolase (PH) and mandelonitirile lyase or be glucosylated to form amygdalin. The tissue and cellular localization of PHs was determined during fruit development in two sweet and two bitter almond cultivars using a specific antibody toward PHs. Confocal studies on sections of tegument, nucellus, endosperm, and embryo showed that the localization of the PH proteins is dependent on the stage of fruit development, shifting between apoplast and symplast in opposite patterns in sweet and bitter cultivars. Two different PH genes, Ph691 and Ph692, have been identified in a sweet and a bitter almond cultivar. Both cDNAs are 86% identical on the nucleotide level, and their encoded proteins are 79% identical to each other. In addition, Ph691 and Ph692 display 92% and 86% nucleotide identity to Ph1 from black cherry (Prunus serotina). Both proteins were predicted to contain an amino-terminal signal peptide, with the size of 26 amino acid residues for PH691 and 22 residues for PH692. The PH activity and the localization of the respective proteins in vivo differ between cultivars. This implies that there might be different concentrations of prunasin available in the seed for amygdalin synthesis and that these differences may determine whether the mature almond develops into bitter or sweet.<\/jats:p>","DOI":"10.1104\/pp.111.192021","type":"journal-article","created":{"date-parts":[[2012,2,22]],"date-time":"2012-02-22T03:22:55Z","timestamp":1329880975000},"page":"1916-1932","source":"Crossref","is-referenced-by-count":49,"title":["Prunasin Hydrolases during Fruit Development in Sweet and Bitter Almonds\n\u00a0\n\u00a0\n\u00a0"],"prefix":"10.1093","volume":"158","author":[{"given":"Raquel","family":"S\u00e1nchez-P\u00e9rez","sequence":"first","affiliation":[{"name":"Department of Plant Breeding, Centro de Edafolog\u00eda y Biolog\u00eda Aplicada del Segura-Consejo Superior de Investigaciones Cient\u00edficas, E\u201330100 Espinardo, Murcia, Spain (R.S.-P., F.D.); Plant Biochemistry Laboratory, Faculty of Science, University of Copenhagen, 1871 Frederiksberg C, Copenhagen, Denmark (R.S.-P., B.L.M., K.J.); Department of Bioimaging, Campus Universitario de Espinardo, 30100 Murcia,"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fara S\u00e1ez","family":"Belmonte","sequence":"additional","affiliation":[{"name":"Department of Plant Breeding, Centro de Edafolog\u00eda y Biolog\u00eda Aplicada del Segura-Consejo Superior de Investigaciones Cient\u00edficas, E\u201330100 Espinardo, Murcia, Spain (R.S.-P., F.D.); Plant Biochemistry Laboratory, Faculty of Science, University of Copenhagen, 1871 Frederiksberg C, Copenhagen, Denmark (R.S.-P., B.L.M., K.J.); Department of Bioimaging, Campus Universitario de Espinardo, 30100 Murcia,"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jonas","family":"Borch","sequence":"additional","affiliation":[{"name":"Department of Plant Breeding, Centro de Edafolog\u00eda y Biolog\u00eda Aplicada del Segura-Consejo Superior de Investigaciones Cient\u00edficas, E\u201330100 Espinardo, Murcia, Spain (R.S.-P., F.D.); Plant Biochemistry Laboratory, Faculty of Science, University of Copenhagen, 1871 Frederiksberg C, Copenhagen, Denmark (R.S.-P., B.L.M., K.J.); Department of Bioimaging, Campus Universitario de Espinardo, 30100 Murcia,"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Federico","family":"Dicenta","sequence":"additional","affiliation":[{"name":"Department of Plant Breeding, Centro de Edafolog\u00eda y Biolog\u00eda Aplicada del Segura-Consejo Superior de Investigaciones Cient\u00edficas, E\u201330100 Espinardo, Murcia, Spain (R.S.-P., F.D.); Plant Biochemistry Laboratory, Faculty of Science, University of Copenhagen, 1871 Frederiksberg C, Copenhagen, Denmark (R.S.-P., B.L.M., K.J.); Department of Bioimaging, Campus Universitario de Espinardo, 30100 Murcia,"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Birger Lindberg","family":"M\u00f8ller","sequence":"additional","affiliation":[{"name":"Department of Plant Breeding, Centro de Edafolog\u00eda y Biolog\u00eda Aplicada del Segura-Consejo Superior de Investigaciones Cient\u00edficas, E\u201330100 Espinardo, Murcia, Spain (R.S.-P., F.D.); Plant Biochemistry Laboratory, Faculty of Science, University of Copenhagen, 1871 Frederiksberg C, Copenhagen, Denmark (R.S.-P., B.L.M., K.J.); Department of Bioimaging, Campus Universitario de Espinardo, 30100 Murcia,"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kirsten","family":"J\u00f8rgensen","sequence":"additional","affiliation":[{"name":"Department of Plant Breeding, Centro de Edafolog\u00eda y Biolog\u00eda Aplicada del Segura-Consejo Superior de Investigaciones Cient\u00edficas, E\u201330100 Espinardo, Murcia, Spain (R.S.-P., F.D.); Plant Biochemistry Laboratory, Faculty of Science, University of Copenhagen, 1871 Frederiksberg C, Copenhagen, Denmark (R.S.-P., B.L.M., K.J.); Department of Bioimaging, Campus Universitario de Espinardo, 30100 Murcia,"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"286","published-online":{"date-parts":[[2012,2,21]]},"reference":[{"key":"2021041909373799800_b1","doi-asserted-by":"crossref","first-page":"1750","DOI":"10.1104\/pp.010334","article-title":"Different myrosinase and idioblast distribution in Arabidopsis and Brassica napus","volume":"127","author":"Andr\u00e9asson","year":"2001","journal-title":"Plant Physiol"},{"key":"2021041909373799800_b2","author":"Arr\u00e1zola","year":"2002"},{"key":"2021041909373799800_b3","doi-asserted-by":"crossref","first-page":"331","DOI":"10.1104\/pp.39.3.331","article-title":"Biosynthesis of prunasin, the cyanogenic glucoside of peach","volume":"39","author":"Ben-Yehoshua","year":"1964","journal-title":"Plant Physiol"},{"key":"2021041909373799800_b4","doi-asserted-by":"crossref","first-page":"433","DOI":"10.1146\/annurev.pp.31.060180.002245","article-title":"Cyanogenic compounds","volume":"31","author":"Conn","year":"1980","journal-title":"Annu Rev Plant Physiol"},{"key":"2021041909373799800_b5","doi-asserted-by":"crossref","first-page":"2149","DOI":"10.1021\/jf0113070","article-title":"Relationship between cyanogenic compounds in kernels, leaves, and roots of sweet and bitter kernelled almonds","volume":"50","author":"Dicenta","year":"2002","journal-title":"J Agric Food Chem"},{"key":"2021041909373799800_b6","doi-asserted-by":"crossref","first-page":"1153","DOI":"10.21273\/HORTSCI.35.6.1153","article-title":"Cultivar pollinizer does not affect almond flavor","volume":"35","author":"Dicenta","year":"2000","journal-title":"HortScience"},{"key":"2021041909373799800_b7","doi-asserted-by":"crossref","first-page":"1364","DOI":"10.1021\/jf030061r","article-title":"Anatomy and cell wall polysaccharides of almond (Prunus dulcis D. A. Webb) seeds","volume":"52","author":"Dourado","year":"2004","journal-title":"J Agric Food Chem"},{"key":"2021041909373799800_b8","doi-asserted-by":"crossref","first-page":"236","DOI":"10.1071\/FP07275","article-title":"A seed coat cyanohydrin glucosyltransferase is associated with bitterness in almond (Prunus dulcis) kernels","volume":"35","author":"Franks","year":"2008","journal-title":"Funct Plant Biol"},{"key":"2021041909373799800_b9","doi-asserted-by":"crossref","first-page":"28","DOI":"10.1104\/pp.94.1.28","article-title":"Pattern of the cyanide-potential in developing fruits","volume":"94","author":"Frehner","year":"1990","journal-title":"Plant Physiol"},{"key":"2021041909373799800_b10","doi-asserted-by":"crossref","first-page":"795","DOI":"10.1016\/S0168-9452(00)00423-4","article-title":"Purification and characterisation of a \u03b2-glucosidase abundantly expressed in ripe sweet cherry (Prunus avium L.) fruit","volume":"160","author":"Gerardi","year":"2001","journal-title":"Plant Sci"},{"key":"2021041909373799800_b11","doi-asserted-by":"crossref","first-page":"1552","DOI":"10.1104\/pp.90.4.1552","article-title":"Biosynthesis of the cyanogenic glucoside dhurrin in seedlings of Sorghum bicolor (L.) Moench and partial purification of the enzyme system involved","volume":"90","author":"Halkier","year":"1989","journal-title":"Plant Physiol"},{"key":"2021041909373799800_b12","doi-asserted-by":"crossref","first-page":"313","DOI":"10.1093\/oxfordjournals.aob.a085922","article-title":"Development of the almond nut (Prunus dulcis (Mill.) D.A. Webb): anatomy and chemical composition of fruit parts from anthesis to maturity","volume":"46","author":"Hawker","year":"1980","journal-title":"Ann Bot (Lond)"},{"key":"2021041909373799800_b13","doi-asserted-by":"crossref","first-page":"390","DOI":"10.1093\/genetics\/8.4.390","article-title":"The factor for bitterness in the sweet almond","volume":"8","author":"Heppner","year":"1923","journal-title":"Genetics"},{"key":"2021041909373799800_b14","doi-asserted-by":"crossref","first-page":"18848","DOI":"10.1073\/pnas.0709315104","article-title":"Evolution of heteromeric nitrilase complexes in Poaceae with new functions in nitrile metabolism","volume":"104","author":"Jenrich","year":"2007","journal-title":"Proc Natl Acad Sci USA"},{"key":"2021041909373799800_b15","doi-asserted-by":"crossref","first-page":"222","DOI":"10.1104\/pp.110.160754","article-title":"Release of hormones from conjugates: chloroplast expression of \u03b2-glucosidase results in elevated phytohormone levels associated with significant increase in biomass and protection from aphids or whiteflies conferred by sucrose esters","volume":"155","author":"Jin","year":"2011","journal-title":"Plant Physiol"},{"key":"2021041909373799800_b16","doi-asserted-by":"crossref","first-page":"35483","DOI":"10.1074\/jbc.274.50.35483","article-title":"The UDP-glucose:p-hydroxymandelonitrile-O-glucosyltransferase that catalyzes the last step in synthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor: isolation, cloning, heterologous expression, and substrate specificity","volume":"274","author":"Jones","year":"1999","journal-title":"J Biol Chem"},{"key":"2021041909373799800_b17","doi-asserted-by":"crossref","first-page":"1034","DOI":"10.1007\/s001220050988","article-title":"Construction of a saturated linkage map for Prunus using an almond \u00d7 peach F2 progeny","volume":"97","author":"Joobeur","year":"1998","journal-title":"Theor Appl Genet"},{"key":"2021041909373799800_b18","author":"Kester","year":"1975"},{"key":"2021041909373799800_b19","doi-asserted-by":"crossref","first-page":"4225","DOI":"10.1093\/jxb\/erm279","article-title":"Maize nitrilases have a dual role in auxin homeostasis and \u03b2-cyanoalanine hydrolysis","volume":"58","author":"Kriechbaumer","year":"2007","journal-title":"J Exp Bot"},{"key":"2021041909373799800_b20","first-page":"82","article-title":"Fruit and seed development in almond in relation to flowering and ripening dates for fresh market supply","volume":"62","author":"Mart\u00ednez-G\u00f3mez","year":"2008","journal-title":"J Am Pomol Soc"},{"key":"2021041909373799800_b21","first-page":"254","article-title":"Bitterness of kernels of almond \u00d7 peach hybrids and their parents","volume":"59","author":"McCarty","year":"1952","journal-title":"Proc Am Soc Hortic Sci"},{"key":"2021041909373799800_b22","doi-asserted-by":"crossref","first-page":"19619","DOI":"10.1073\/pnas.0707368104","article-title":"Phloem loading in Verbascum phoeniceum L. depends on the synthesis of raffinose-family oligosaccharides","volume":"104","author":"McCaskill","year":"2007","journal-title":"Proc Natl Acad Sci USA"},{"key":"2021041909373799800_b23","first-page":"1072","article-title":"Sur la biogen\u00e8se du glucoside cyanog\u00e9n\u00e9tique des feuilles de laurier-cerise (Prunus lauro-cerasus)","volume":"253","author":"Mentzer","year":"1961","journal-title":"C R Acad Sci (Paris)"},{"key":"2021041909373799800_b24","doi-asserted-by":"crossref","first-page":"295","DOI":"10.1007\/BF02772805","article-title":"Chromosomal walking of flanking regions from short known sequences in GC-rich plant genomic DNA","volume":"21","author":"Michiels","year":"2003","journal-title":"Plant Mol Biol Rep"},{"key":"2021041909373799800_b25","author":"M\u00f8ller","year":"1991"},{"key":"2021041909373799800_b26","doi-asserted-by":"crossref","first-page":"88","DOI":"10.1016\/j.phytochem.2007.06.033","article-title":"Metabolon formation in dhurrin biosynthesis","volume":"69","author":"Nielsen","year":"2008","journal-title":"Phytochemistry"},{"key":"2021041909373799800_b27","doi-asserted-by":"crossref","first-page":"2616","DOI":"10.1074\/jbc.M007890200","article-title":"The Arabidopsis thaliana isogene NIT4 and its orthologs in tobacco encode beta-cyano-L-alanine hydratase\/nitrilase","volume":"276","author":"Piotrowski","year":"2001","journal-title":"J Biol Chem"},{"key":"2021041909373799800_b28","doi-asserted-by":"crossref","first-page":"111","DOI":"10.1007\/s11103-005-6217-9","article-title":"Cyanide metabolism in higher plants: cyanoalanine hydratase is a NIT4 homolog","volume":"61","author":"Piotrowski","year":"2006","journal-title":"Plant Mol Biol"},{"key":"2021041909373799800_b29","doi-asserted-by":"crossref","first-page":"401","DOI":"10.1104\/pp.94.2.401","article-title":"Cyanogenesis in plants","volume":"94","author":"Poulton","year":"1990","journal-title":"Plant Physiol"},{"key":"2021041909373799800_b30","doi-asserted-by":"crossref","first-page":"29","DOI":"10.1104\/pp.104.1.29","article-title":"Tissue level compartmentation of (R)-amygdalin and amygdalin hydrolase prevents large-scale cyanogenesis in undamaged Prunus seeds","volume":"104","author":"Poulton","year":"1994","journal-title":"Plant Physiol"},{"key":"2021041909373799800_b31","doi-asserted-by":"crossref","first-page":"663","DOI":"10.1021\/ac026117i","article-title":"Stop and go extraction tips for matrix-assisted laser desorption\/ionization, nanoelectrospray, and LC\/MS sample pretreatment in proteomics","volume":"75","author":"Rappsilber","year":"2003","journal-title":"Anal Chem"},{"key":"2021041909373799800_b32","doi-asserted-by":"crossref","first-page":"310","DOI":"10.1111\/j.1439-0523.2007.01329.x","article-title":"Mapping major genes and quantitative trait loci controlling agronomic traits in almond","volume":"126","author":"S\u00e1nchez-P\u00e9rez","year":"2007","journal-title":"Plant Breed"},{"key":"2021041909373799800_b33","doi-asserted-by":"crossref","first-page":"237","DOI":"10.1007\/s11295-009-0244-7","article-title":"Molecular markers for bitterness in almond","volume":"6","author":"S\u00e1nchez-P\u00e9rez","year":"2010","journal-title":"Tree Genet Genomes"},{"key":"2021041909373799800_b34","doi-asserted-by":"crossref","first-page":"894","DOI":"10.1111\/j.1365-313X.2009.03997.x","article-title":"Tissue and cellular localization of individual \u03b2-glycosidases using a substrate-specific sugar reducing assay","volume":"60","author":"S\u00e1nchez-P\u00e9rez","year":"2009","journal-title":"Plant J"},{"key":"2021041909373799800_b35","doi-asserted-by":"crossref","first-page":"1040","DOI":"10.1104\/pp.107.112979","article-title":"Bitterness in almonds","volume":"146","author":"S\u00e1nchez-P\u00e9rez","year":"2008","journal-title":"Plant Physiol"},{"key":"2021041909373799800_b36","doi-asserted-by":"crossref","first-page":"61","DOI":"10.17660\/ActaHortic.1994.375.3","article-title":"Translocation of cyanogenic glucosides in cassava","volume":"375","author":"Selmar","year":"1994","journal-title":"Acta Hortic"},{"key":"2021041909373799800_b37","doi-asserted-by":"crossref","first-page":"791","DOI":"10.1093\/gbe\/evq058","article-title":"Connections between alternative transcription and alternative splicing in mammals","volume":"2","author":"Shabalina","year":"2010","journal-title":"Genome Biol Evol"},{"key":"2021041909373799800_b38","doi-asserted-by":"crossref","first-page":"2856","DOI":"10.1038\/nprot.2006.468","article-title":"In-gel digestion for mass spectrometric characterization of proteins and proteomes","volume":"1","author":"Shevchenko","year":"2006","journal-title":"Nat Protoc"},{"key":"2021041909373799800_b39","doi-asserted-by":"crossref","first-page":"388","DOI":"10.1007\/s004250050414","article-title":"Molecular cloning of the cDNA coding for the (R)-(+)-mandelonitrile lyase of Prunus amygdalus: temporal and spatial expression patterns in flowers and mature seeds","volume":"206","author":"Suelves","year":"1998","journal-title":"Planta"},{"key":"2021041909373799800_b40","doi-asserted-by":"crossref","first-page":"291","DOI":"10.1104\/pp.100.1.291","article-title":"Tissue and subcellular localization of enzymes catabolizing (R)-amygdalin in mature Prunus serotina seeds","volume":"100","author":"Swain","year":"1992","journal-title":"Plant Physiol"},{"key":"2021041909373799800_b41","doi-asserted-by":"crossref","first-page":"1285","DOI":"10.1104\/pp.106.4.1285","article-title":"Immunocytochemical localization of prunasin hydrolase and mandelonitrile lyase in stems and leaves of Prunus serotina","volume":"106","author":"Swain","year":"1994","journal-title":"Plant Physiol"},{"key":"2021041909373799800_b42","doi-asserted-by":"crossref","first-page":"437","DOI":"10.1104\/pp.106.2.437","article-title":"Utilization of amygdalin during seedling development of Prunus serotina","volume":"106","author":"Swain","year":"1994","journal-title":"Plant Physiol"},{"key":"2021041909373799800_b43","first-page":"325","article-title":"Chilling requirements in almond. in Spanish","volume":"11","author":"Tabuenca","year":"1972","journal-title":"Anal Estacion Exp Aula Dei"},{"key":"2021041909373799800_b44","doi-asserted-by":"crossref","first-page":"462","DOI":"10.1080\/14620316.2008.11512407","article-title":"Characterizing the flavor phenotypes of almond (Prunus dulcis Mill.) kernels","volume":"83","author":"Wirthensohn","year":"2008","journal-title":"J Hortic Sci Biotechnol"},{"key":"2021041909373799800_b45","doi-asserted-by":"crossref","first-page":"1252","DOI":"10.1104\/pp.010863","article-title":"Investigation of the microheterogeneity and aglycone specificity-conferring residues of black cherry prunasin hydrolases","volume":"129","author":"Zhou","year":"2002","journal-title":"Plant Physiol"}],"container-title":["Plant Physiology"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/academic.oup.com\/plphys\/article-pdf\/158\/4\/1916\/37157253\/plphys_v158_4_1916.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"http:\/\/academic.oup.com\/plphys\/article-pdf\/158\/4\/1916\/37157253\/plphys_v158_4_1916.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2021,4,19]],"date-time":"2021-04-19T22:02:14Z","timestamp":1618869734000},"score":1,"resource":{"primary":{"URL":"https:\/\/academic.oup.com\/plphys\/article\/158\/4\/1916\/6109325"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,2,21]]},"references-count":45,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2012,2,21]]},"published-print":{"date-parts":[[2012,4,2]]}},"URL":"https:\/\/doi.org\/10.1104\/pp.111.192021","relation":{},"ISSN":["1532-2548"],"issn-type":[{"value":"1532-2548","type":"electronic"}],"subject":[],"published-other":{"date-parts":[[2012,4,1]]},"published":{"date-parts":[[2012,2,21]]}}}