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Zeta-carotene cis isomers as products and substrates in the plant poly-cis carotenoid biosynthetic pathway to lycopene
The plant carotenoid biosynthetic pathway to cyclic carotenes proceeds via carotene precursors in cis configuration. Involvement of individual isomers was elucidated by genetic complementation of desaturations and in vitro reactions of the corresponding enzyme. Determination of substrate and product...
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| Published in: | Planta 2005-03, Vol.220 (5), p.785-793 |
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| Language: | English |
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| creator | Breitenbach, J Sandmann, G |
| description | The plant carotenoid biosynthetic pathway to cyclic carotenes proceeds via carotene precursors in cis configuration. Involvement of individual isomers was elucidated by genetic complementation of desaturations and in vitro reactions of the corresponding enzyme. Determination of substrate and product specificity of phytoene and ζ-carotene desaturase revealed that 15-cisphytoene is converted to 9,15,9′-tricis-ζ-carotene with 15,9′-dicis-phytofluene as intermediate by the first desaturase. Prior to a subsequent conversion by ζ-carotene desaturase, the 15-cis double bond of 9,15,9′-tricis-ζ-carotene has to be (photo)isomerized to all-trans. Then, the resulting 9,9′-dicis-ζ-carotene is utilized by ζ-carotene desaturase via 7,9,9′-tricis-neurosporene to 7,9,7′,9′-tetracis-lycopene. Other ζ-carotene isomers that are assumed to be spontaneous isomerization products were not converted, except for the asymmetric 9-cis-ζ-carotene. This isomer is desaturated only to 7,9-dicis-neurosporene resembling a dead-end of the pathway. Prolycopene, the product of the desaturation reactions, is finally isomerized by a specific isomerase to all-trans-lycopene, which is a prerequisite for cyclization to β-carotene. The 5-cislycopene and the 9-cis-and 13-cis-β-carotene isomers detected in leaves are thought to originate independently from cis precursors by non-enzymatic isomerization of their all-trans forms. |
| doi_str_mv | 10.1007/s00425-004-1395-2 |
| format | article |
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Involvement of individual isomers was elucidated by genetic complementation of desaturations and in vitro reactions of the corresponding enzyme. Determination of substrate and product specificity of phytoene and ζ-carotene desaturase revealed that 15-cisphytoene is converted to 9,15,9′-tricis-ζ-carotene with 15,9′-dicis-phytofluene as intermediate by the first desaturase. Prior to a subsequent conversion by ζ-carotene desaturase, the 15-cis double bond of 9,15,9′-tricis-ζ-carotene has to be (photo)isomerized to all-trans. Then, the resulting 9,9′-dicis-ζ-carotene is utilized by ζ-carotene desaturase via 7,9,9′-tricis-neurosporene to 7,9,7′,9′-tetracis-lycopene. Other ζ-carotene isomers that are assumed to be spontaneous isomerization products were not converted, except for the asymmetric 9-cis-ζ-carotene. This isomer is desaturated only to 7,9-dicis-neurosporene resembling a dead-end of the pathway. Prolycopene, the product of the desaturation reactions, is finally isomerized by a specific isomerase to all-trans-lycopene, which is a prerequisite for cyclization to β-carotene. The 5-cislycopene and the 9-cis-and 13-cis-β-carotene isomers detected in leaves are thought to originate independently from cis precursors by non-enzymatic isomerization of their all-trans forms.</description><identifier>ISSN: 0032-0935</identifier><identifier>EISSN: 1432-2048</identifier><identifier>DOI: 10.1007/s00425-004-1395-2</identifier><identifier>PMID: 15503129</identifier><identifier>CODEN: PLANAB</identifier><language>eng</language><publisher>Berlin: Springer-Verlag</publisher><subject>Agronomy. Soil science and plant productions ; beta Carotene - metabolism ; Biochemical pathways ; Biological and medical sciences ; biosynthesis ; Capsicum - enzymology ; Capsicum annuum ; carotene 7,8-desaturase ; carotenes ; Carotenoids ; Carotenoids - biosynthesis ; Carotenoids - chemistry ; Carotenoids - metabolism ; Chemical desaturation ; Economic plant physiology ; enzyme activity ; Enzymes ; Fruit - enzymology ; Fundamental and applied biological sciences. Psychology ; Isomerism ; Isomerization ; Isomers ; lycopene ; Lycopersicon esculentum - enzymology ; Molecular Structure ; Nutrition. Photosynthesis. Respiration. Metabolism ; Oxidoreductases - metabolism ; phytoene desaturase ; plant biochemistry ; Plant Leaves - enzymology ; Plants ; Plasmids ; Reaction products ; Substrate Specificity ; zeta Carotene - chemistry ; zeta Carotene - metabolism</subject><ispartof>Planta, 2005-03, Vol.220 (5), p.785-793</ispartof><rights>Springer-Verlag 2004</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.jstor.org/stable/pdf/23388831$$EPDF$$P50$$Gjstor$$H</linktopdf><linktohtml>$$Uhttps://www.jstor.org/stable/23388831$$EHTML$$P50$$Gjstor$$H</linktohtml><link.rule.ids>315,783,787,27936,27937,58566,58799</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16585637$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15503129$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Breitenbach, J</creatorcontrib><creatorcontrib>Sandmann, G</creatorcontrib><title>Zeta-carotene cis isomers as products and substrates in the plant poly-cis carotenoid biosynthetic pathway to lycopene</title><title>Planta</title><addtitle>Planta</addtitle><description>The plant carotenoid biosynthetic pathway to cyclic carotenes proceeds via carotene precursors in cis configuration. Involvement of individual isomers was elucidated by genetic complementation of desaturations and in vitro reactions of the corresponding enzyme. Determination of substrate and product specificity of phytoene and ζ-carotene desaturase revealed that 15-cisphytoene is converted to 9,15,9′-tricis-ζ-carotene with 15,9′-dicis-phytofluene as intermediate by the first desaturase. Prior to a subsequent conversion by ζ-carotene desaturase, the 15-cis double bond of 9,15,9′-tricis-ζ-carotene has to be (photo)isomerized to all-trans. Then, the resulting 9,9′-dicis-ζ-carotene is utilized by ζ-carotene desaturase via 7,9,9′-tricis-neurosporene to 7,9,7′,9′-tetracis-lycopene. Other ζ-carotene isomers that are assumed to be spontaneous isomerization products were not converted, except for the asymmetric 9-cis-ζ-carotene. This isomer is desaturated only to 7,9-dicis-neurosporene resembling a dead-end of the pathway. Prolycopene, the product of the desaturation reactions, is finally isomerized by a specific isomerase to all-trans-lycopene, which is a prerequisite for cyclization to β-carotene. The 5-cislycopene and the 9-cis-and 13-cis-β-carotene isomers detected in leaves are thought to originate independently from cis precursors by non-enzymatic isomerization of their all-trans forms.</description><subject>Agronomy. Soil science and plant productions</subject><subject>beta Carotene - metabolism</subject><subject>Biochemical pathways</subject><subject>Biological and medical sciences</subject><subject>biosynthesis</subject><subject>Capsicum - enzymology</subject><subject>Capsicum annuum</subject><subject>carotene 7,8-desaturase</subject><subject>carotenes</subject><subject>Carotenoids</subject><subject>Carotenoids - biosynthesis</subject><subject>Carotenoids - chemistry</subject><subject>Carotenoids - metabolism</subject><subject>Chemical desaturation</subject><subject>Economic plant physiology</subject><subject>enzyme activity</subject><subject>Enzymes</subject><subject>Fruit - enzymology</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Isomerism</subject><subject>Isomerization</subject><subject>Isomers</subject><subject>lycopene</subject><subject>Lycopersicon esculentum - enzymology</subject><subject>Molecular Structure</subject><subject>Nutrition. Photosynthesis. Respiration. Metabolism</subject><subject>Oxidoreductases - metabolism</subject><subject>phytoene desaturase</subject><subject>plant biochemistry</subject><subject>Plant Leaves - enzymology</subject><subject>Plants</subject><subject>Plasmids</subject><subject>Reaction products</subject><subject>Substrate Specificity</subject><subject>zeta Carotene - chemistry</subject><subject>zeta Carotene - metabolism</subject><issn>0032-0935</issn><issn>1432-2048</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNpFkEtv1TAQhS1ERS-FH8AC8AZ2hvErdpZVxaNSpS5KN2yiie3QVLlxsB1Q_j2-uhfYjI90vjkzY0JecfjAAczHDKCEZrUyLlvNxBOy40oKJkDZp2QHUDW0Up-T5zk_AlTTmGfknGsNkot2R359DwWZwxRLmAN1Y6ZjjvuQMsVMlxT96krVs6d57XNJWEJFZloeAl0mnAtd4rSxQ-MpJY6e9mPM21yZMjq6YHn4jRstkU6bi0sd9IKcDTjl8PL0XpD7z5--XX1lN7dfrq8ub9ggrC6Mg_Iu9B6Vtj1vjG_QKu-dOmiDxvS6hWpoGwzXEoUNoRUiGOEG6ZteXpD3x9x6yc815NLtx-zCVBcPcc1dY5SVjTIVfHMC134ffLekcY9p6_7-VAXenQDMDqch4Vxv_s_VHXQjD0Gvj9xjLjH984WU1lrJq__26A8YO_yRasb9nQAugUMjJDTyD-9GjPo</recordid><startdate>20050301</startdate><enddate>20050301</enddate><creator>Breitenbach, J</creator><creator>Sandmann, G</creator><general>Springer-Verlag</general><general>Springer</general><scope>FBQ</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20050301</creationdate><title>Zeta-carotene cis isomers as products and substrates in the plant poly-cis carotenoid biosynthetic pathway to lycopene</title><author>Breitenbach, J ; Sandmann, G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-f285t-104dcebda458b167d6a84ddc4167d7a77b590b1658e7153a28ee922e72cf3d6b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Agronomy. Soil science and plant productions</topic><topic>beta Carotene - metabolism</topic><topic>Biochemical pathways</topic><topic>Biological and medical sciences</topic><topic>biosynthesis</topic><topic>Capsicum - enzymology</topic><topic>Capsicum annuum</topic><topic>carotene 7,8-desaturase</topic><topic>carotenes</topic><topic>Carotenoids</topic><topic>Carotenoids - biosynthesis</topic><topic>Carotenoids - chemistry</topic><topic>Carotenoids - metabolism</topic><topic>Chemical desaturation</topic><topic>Economic plant physiology</topic><topic>enzyme activity</topic><topic>Enzymes</topic><topic>Fruit - enzymology</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Isomerism</topic><topic>Isomerization</topic><topic>Isomers</topic><topic>lycopene</topic><topic>Lycopersicon esculentum - enzymology</topic><topic>Molecular Structure</topic><topic>Nutrition. Photosynthesis. Respiration. Metabolism</topic><topic>Oxidoreductases - metabolism</topic><topic>phytoene desaturase</topic><topic>plant biochemistry</topic><topic>Plant Leaves - enzymology</topic><topic>Plants</topic><topic>Plasmids</topic><topic>Reaction products</topic><topic>Substrate Specificity</topic><topic>zeta Carotene - chemistry</topic><topic>zeta Carotene - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Breitenbach, J</creatorcontrib><creatorcontrib>Sandmann, G</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Planta</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Breitenbach, J</au><au>Sandmann, G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Zeta-carotene cis isomers as products and substrates in the plant poly-cis carotenoid biosynthetic pathway to lycopene</atitle><jtitle>Planta</jtitle><addtitle>Planta</addtitle><date>2005-03-01</date><risdate>2005</risdate><volume>220</volume><issue>5</issue><spage>785</spage><epage>793</epage><pages>785-793</pages><issn>0032-0935</issn><eissn>1432-2048</eissn><coden>PLANAB</coden><abstract>The plant carotenoid biosynthetic pathway to cyclic carotenes proceeds via carotene precursors in cis configuration. Involvement of individual isomers was elucidated by genetic complementation of desaturations and in vitro reactions of the corresponding enzyme. Determination of substrate and product specificity of phytoene and ζ-carotene desaturase revealed that 15-cisphytoene is converted to 9,15,9′-tricis-ζ-carotene with 15,9′-dicis-phytofluene as intermediate by the first desaturase. Prior to a subsequent conversion by ζ-carotene desaturase, the 15-cis double bond of 9,15,9′-tricis-ζ-carotene has to be (photo)isomerized to all-trans. Then, the resulting 9,9′-dicis-ζ-carotene is utilized by ζ-carotene desaturase via 7,9,9′-tricis-neurosporene to 7,9,7′,9′-tetracis-lycopene. Other ζ-carotene isomers that are assumed to be spontaneous isomerization products were not converted, except for the asymmetric 9-cis-ζ-carotene. This isomer is desaturated only to 7,9-dicis-neurosporene resembling a dead-end of the pathway. Prolycopene, the product of the desaturation reactions, is finally isomerized by a specific isomerase to all-trans-lycopene, which is a prerequisite for cyclization to β-carotene. The 5-cislycopene and the 9-cis-and 13-cis-β-carotene isomers detected in leaves are thought to originate independently from cis precursors by non-enzymatic isomerization of their all-trans forms.</abstract><cop>Berlin</cop><pub>Springer-Verlag</pub><pmid>15503129</pmid><doi>10.1007/s00425-004-1395-2</doi><tpages>9</tpages></addata></record> |
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| ispartof | Planta, 2005-03, Vol.220 (5), p.785-793 |
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| source | JSTOR Archival Journals and Primary Sources Collection【Remote access available】; Springer Link |
| subjects | Agronomy. Soil science and plant productions beta Carotene - metabolism Biochemical pathways Biological and medical sciences biosynthesis Capsicum - enzymology Capsicum annuum carotene 7,8-desaturase carotenes Carotenoids Carotenoids - biosynthesis Carotenoids - chemistry Carotenoids - metabolism Chemical desaturation Economic plant physiology enzyme activity Enzymes Fruit - enzymology Fundamental and applied biological sciences. Psychology Isomerism Isomerization Isomers lycopene Lycopersicon esculentum - enzymology Molecular Structure Nutrition. Photosynthesis. Respiration. Metabolism Oxidoreductases - metabolism phytoene desaturase plant biochemistry Plant Leaves - enzymology Plants Plasmids Reaction products Substrate Specificity zeta Carotene - chemistry zeta Carotene - metabolism |
| title | Zeta-carotene cis isomers as products and substrates in the plant poly-cis carotenoid biosynthetic pathway to lycopene |
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