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bsequent rearrangement 52 53 the resulting mep is converted to 4 cytidine 5 diphospho 2 c methyl d erythritol cdp me in the presence of ctp using the enzyme mep cytidylyltransferase cdp me is then converted in the presence of atp to 2 phospho 4 cytidine 5 diphospho 2 c methyl d erythritol cdp me2p the conversion to cdp me2p is catalyzed by cdp me kinase next cdp me2p is converted to 2 c methyl d erythritol 2 4 cyclodiphosphate mecdp this reaction occurs when mecdp synthase catalyzes the reaction and cmp is eliminated from the cdp me2p molecule mecdp is then converted to e 4 hydroxy 3 methylbut 2 en 1 yl diphosphate hmbdp via hmbdp synthase in the presence of flavodoxin and nadph hmbdp is reduced to ipp in the presence of ferredoxin and nadph by the enzyme hmbdp reductase the last two steps involving hmbpd synthase and reductase can only occur in completely anaerobic environments ipp is then able to isomerize to dmapp via ipp isomerase 53 carotenoid biosynthetic pathway edit the conversion of phytoene to lycopene in plants and cyanobacteria left differs compared to bacteria and fungi right carotenoid biosynthesis occurs primarily in the plastids of plant cells particularly within chloroplasts and chromoplasts the biosynthetic pathway initiates with the condensation of two molecules of geranylgeranyl pyrophosphate ggpp a 20 carbon isoprenoid precursor the key steps in this pathway are as follows formation of phytoene the enzyme phytoene synthase psy catalyzes the condensation of two ggpp molecules to produce phytoene a colorless carotenoid 55 desaturation to lycopene phytoene undergoes a series of desaturation reactions facilitated by enzymes such as phytoene desaturase pds and ζ carotene isomerase z iso resulting in the formation of lycopene a red carotenoid cyclization to carotenoids lycopene is cyclized into various carotenoids including α carotene and β carotene through the action of lycopene cyclase lcy which catalyzes cyclization at the ends of the lycopene molecule 56 further modifications subsequent modifications such as hydroxylation and oxidation lead to the formation of xanthophylls e g lutein and zeaxanthin and other derivatives two ggpp molecules condense via phytoene synthase psy forming the 15 cis isomer of phytoene psy belongs to the squalene phytoene synthase family and is homologous to squalene synthase that takes part in steroid biosynthesis the subsequent conversion of phytoene into all trans lycopene depends on the organism bacteria and fungi employ a single enzyme the bacterial phytoene desaturase crti for the catalysis plants and cyanobacteria however utilize four enzymes for this process 57 the first of these enzymes is a plant type phytoene desaturase which introduces two additional double bonds into 15 cis phytoene by dehydrogenation and isomerizes two of its existing double bonds from trans to cis producing 9 15 9 tri cis ζ carotene the central double bond of this tri cis ζ carotene is isomerized by the zeta carotene isomerase z iso and the resulting 9 9 di cis ζ carotene is dehydrogenated again via a ζ carotene desaturase zds this again introduces two double bonds resulting in 7 9 7 9 tetra cis lycopene crtiso a carotenoid isomerase is needed to convert the cis lycopene into an all trans lycopene in the presence of reduced fad this all trans lycopene is cyclized cyclization gives rise to carotenoid diversity which can be distinguished based on the end groups there can be either a beta ring or an epsilon ring each generated by a different enzyme lycopene beta cyclase beta lcy or lycopene epsilon cyclase epsilon lcy α carotene is produced when the all trans lycopene first undergoes reaction with epsilon lcy then a second reaction with beta lcy whereas β carotene is produced by two reactions with beta lcy α and β carotene are the most common carotenoids in the plant photosystems but they can still be further converted into xanthophylls by using beta hydrolase and epsilon hydrolase leading to a variety of xanthophylls 52 key enzymes edit several enzymes play critical roles in the carotenoid biosynthetic pathway phytoene synthase psy catalyzes the first committed step in carotenoid biosynthesis converting ggpp into phytoene 58 phytoene desaturase pds introduces double bonds into phytoene facilitating its conversion into lycopene 59 lycopene cyclase lcy responsible for the cyclization of lycopene into α carotene or β carotene 60 carotenoid hydroxylases enzymes such as lutein epoxide cyclase lut introduce hydroxyl groups into carotenoids leading to the formation of xanthophylls 61 regulation edit it is believed that both dxs and dxr are rate determining enzymes allowing them to regulate carotenoid levels 52 this was discovered in an experiment where dxs and dxr were genetically overexpressed leading to increased carotenoid expression in the resulting seedlings 52 also j protein j20 and heat shock protein 70 hsp70 chaperones are thought to be involved in post transcriptional regulation of dxs activity such that mutants with defective j20 activity exhibit reduced dxs enzyme activity while accumulating inactive dxs protein 62 regulation may also be caused by external toxins that affect enzymes and proteins required for synthesis ketoclomazone is derived from herbicides applied to soil and binds to dxp synthase 53 this inhibits dxp synthase preventing synthesis of dxp and halting the mep pathway 53 the use of this toxin leads to lower levels of carotenoids in plants grown in the contaminated soil 53 fosmidomycin an antibiotic is a competitive inhibitor of dxp reductoisomerase due to its similar structure to the enzyme 53 application of said antibiotic prevents reduction of dxp again halting the mep pathway 53 naturally occurring carotenoids edit hydrocarbons lycopersene 7 8 11 12 15 7 8 11 12 15 decahydro γ γ carotene phytofluene lycopene hexahydrolycopene 15 cis 7 8 11 12 7 8 hexahydro γ γ carotene torulene 3 4 didehydro β γ carotene α zeacarotene 7 8 dihydro ε γ carotene α carotene β carotene γ carotene δ carotene ε carotene ζ carotene alcohols alloxanthin bacterioruberin 2 2 bis 3 hydroxy 3 methylbutyl 3 4 3 4 tetradehydro 1 2 1 2 tetrahydro γ γ carotene 1 1 diol cynthiaxanthin pectenoxanthin cryptomonaxanthin 3r 3 r 7 8 7 8 tetradehydro β β carotene 3 3 diol crustaxanthin β carotene 3 4 3 4 tetrol gazaniaxanthin 3r 5 cis β γ caroten 3 ol oh chlorobactene 1 2 dihydro f γ caroten 1 ol loroxanthin β ε carotene 3 19 3 triol lutein 3r 3 r 6 r β ε carotene 3 3 diol lycoxanthin γ γ caroten 16 ol rhodopin 1 2 dihydro γ γ caroten l ol rhodopinol a k a warmingol 13 cis 1 2 dihydro γ γ carotene 1 20 diol saproxanthin 3 4 didehydro 1 2 dihydro β γ carotene 3 1 diol zeaxanthin glycosides oscillaxanthin 2 2 bis β l rhamnopyranosyloxy 3 4 3 4 tetradehydro 1 2 1 2 tetrahydro γ γ carotene 1 1 diol phleixanthophyll 1 β d glucopyranosyloxy 3 4 didehydro 1 2 dihydro β γ caroten 2 ol ethers rhodovibrin 1 methoxy 3 4 didehydro 1 2 1 2 tetrahydro γ γ caroten 1 ol spheroidene 1 methoxy 3 4 didehydro 1 2 7 8 tetrahydro γ γ carotene epoxides diadinoxanthin 5 6 epoxy 7 8 didehydro 5 6 dihydro carotene 3 3 diol luteoxanthin 5 6 5 8 diepoxy 5 6 5 8 tetrahydro β β carotene 3 3 diol mutatoxanthin citroxanthin zeaxanthin furanoxide 5 8 epoxy 5 8 dihydro β β carotene 3 3 diol neochrome 5 8 epoxy 6 7 didehydro 5 6 5 8 tetrahydro β β carotene 3 5 3 triol foliachrome trollichrome vaucheriaxanthin 5 6 epoxy 6 7 didehydro 5 6 5 6 tetrahydro β β carotene 3 5 19 3 tetrol aldehydes rhodopinal warmingone 13 cis 1 hydroxy 1 2 dihydro γ γ caroten 20 al torularhodinaldehyde 3 4 didehydro β γ caroten 16 al acids and acid esters torularhodin 3 4 didehydro β γ caroten 16 oic acid torularhodin methyl ester methyl 3 4 didehydro β γ caroten 16 oate ketones astacene astaxanthin canthaxanthin 63 a k a aphanicin chlorellaxanthin β β carotene 4 4 dione capsanthin 3r 3 s 5 r 3 3 dihydroxy β κ caroten 6 one capsorubin 3s 5r 3 s 5 r 3 3 dihydroxy κ κ carotene 6 6 dione cryptocapsin 3 r 5 r 3 hydroxy β κ caroten 6 one 2 2 diketospirilloxanthin 1 1 dimethoxy 3 4 3 4 tetradehydro 1 2 1 2 tetrahydro γ γ carotene 2 2 dione echinenone β β caroten 4 one 3 hydroxyechinenone flexixanthin 3 1 dihydroxy 3 4 didehydro 1 2 dihydro β γ caroten 4 one 3 oh canthaxanthin a k a adonirubin a k a phoenicoxanthin 3 hydroxy β β carotene 4 4 dione hydroxyspheriodenone 1 hydroxy 1 methoxy 3 4 didehydro 1 2 1 2 7 8 hexahydro γ γ caroten 2 one okenone 1 methoxy 1 2 dihydro c γ caroten 4 one pectenolone 3 3 dihydroxy 7 8 didehydro β β caroten 4 one phoeniconone a k a dehydroadonirubin 3 hydroxy 2 3 didehydro β β carotene 4 4 dione phoenicopterone β ε caroten 4 one rubixanthone 3 hydroxy β γ caroten 4 one siphonaxanthin 3 19 3 trihydroxy 7 8 dihydro β ε caroten 8 one esters of alcohols astacein 3 3 bispalmitoyloxy 2 3 2 3 tetradehydro β β carotene 4 4 dione or 3 3 dihydroxy 2 3 2 3 tetradehydro β β carotene 4 4 dione dipalmitate fucoxanthin 3 acetoxy 5 6 epoxy 3 5 dihydroxy 6 7 didehydro 5 6 7 8 5 6 hexahydro β β caroten 8 one isofucoxanthin 3 acetoxy 3 5 5 trihydroxy 6 7 didehydro 5 8 5 6 tetrahydro β β caroten 8 one physalien siphonein 3 3 dihydroxy 19 lauroyloxy 7 8 dihydro β ε caroten 8 one or 3 19 3 trihydroxy 7 8 dihydro β ε caroten 8 one 19 laurate apocarotenoids β apo 2 carotenal 3 4 didehydro 2 apo b caroten 2 al apo 2 lycopenal apo 6 lycopenal 6 apo y caroten 6 al azafrinaldehyde 5 6 dihydroxy 5 6 dihydro 10 apo β caroten 10 al bixin 6 methyl hydrogen 9 cis 6 6 diapocarotene 6 6 dioate citranaxanthin 5 6 dihydro 5 apo β caroten 6 one or 5 6 dihydro 5 apo 18 nor β caroten 6 one or 6 methyl 6 apo β caroten 6 one crocetin 8 8 diapo 8 8 carotenedioic acid crocetinsemialdehyde 8 oxo 8 8 diapo 8 carotenoic acid crocin digentiobiosyl 8 8 diapo 8 8 carotenedioate hopkinsiaxanthin 3 hydroxy 7 8 didehydro 7 8 dihydro 7 apo b carotene 4 8 dione or 3 hydroxy 8 methyl 7 8 didehydro 8 apo b carotene 4 8 dione methyl apo 6 lycopenoate methyl 6 apo y caroten 6 oate paracentrone 3 5 dihydroxy 6 7 didehydro 5 6 7 8 tetrahydro 7 apo b caroten 8 one or 3 5 dihydroxy 8 methyl 6 7 didehydro 5 6 dihydro 8 apo b caroten 8 one sintaxanthin 7 8 dihydro 7 apo b caroten 8 one or 8 methyl 8 apo b caroten 8 one nor and seco carotenoids actinioerythrin 3 3 bisacyloxy 2 2 dinor b b carotene 4 4 dione β carotenone 5 6 5 6 diseco b b carotene 5 6 5 6 tetrone peridinin 3 acetoxy 5 6 epoxy 3 5 dihydroxy 6 7 didehydro 5 6 5 6 tetrahydro 12 13 20 trinor b b caroten 19 11 olide pyrrhoxanthininol 5 6 epoxy 3 3 dihydroxy 7 8 didehydro 5 6 dihydro 12 13 20 trinor b b caroten 19 11 olide semi α carotenone 5 6 seco b e carotene 5 6 dione semi β carotenone 5 6 seco b b carotene 5 6 dione or 5 6 seco b b carotene 5 6 dione triphasiaxanthin 3 hydroxysemi b carotenone 3 hydroxy 5 6 seco b b carotene 5 6 dione or 3 hydroxy 5 6 seco b b carotene 5 6 dione retro carotenoids and retro apo carotenoids eschscholtzxanthin 4 5 didehydro 4 5 retro b b carotene 3 3 diol eschscholtzxanthone 3 hydroxy 4 5 didehydro 4 5 retro b b caroten 3 one rhodoxanthin 4 5 didehydro 4 5 retro b b carotene 3 3 dione tangeraxanthin 3 hydroxy 5 methyl 4 5 retro 5 apo b caroten 5 one or 3 hydroxy 4 5 retro 5 apo b caroten 5 one higher carotenoids nonaprenoxanthin 2 4 hydroxy 3 methyl 2 butenyl 7 8 11 12 tetrahydro e y carotene decaprenoxanthin 2 2 bis 4 hydroxy 3 methyl 2 butenyl e e carotene c p 450 2 4 hydroxy 3 hydroxymethyl 2 butenyl 2 3 methyl 2 butenyl b b carotene c p 473 2 4 hydroxy 3 methyl 2 butenyl 2 3 methyl 2 butenyl 3 4 didehydro l 2 dihydro β γ caroten 1 ol bacterioruberin 2 2 bis 3 hydroxy 3 methylbutyl 3 4 3 4 tetradehydro 1 2 1 2 tetrahydro γ γ carotene 1 1 diol see also edit carotenoid complex list of phytochemicals in food crt genetics gene cluster responsible for the biosynthesis of carotenoids e number e100 e199 colours phytochemistry references edit 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 carotenoids micronutrient information center linus pauling institute oregon state university 2026 retrieved 23 july 2026 nelson david l cox michael m 2005 principles of biochemistry 4th ed new york w h freeman isbn 0 7167 4339 6 yabuzaki junko 2017 01 01 carotenoids database structures chemical fingerprints and distribution among organisms database 2017 1 doi 10 1093 database bax004 pmc 5574413 pmid 28365725 armstrong ga hearst je 1996 carotenoids 2 genetics and molecular biology of carotenoid pigment biosynthesis faseb j 10 2 228 37 doi 10 1096 fasebj 10 2 8641556 pmid 8641556 s2cid 22385652 1 2 bernstein p s li b vachali p p gorusupudi a shyam r henriksen b s nolan j m 2015 lutein zeaxanthin and meso zeaxanthin the basic and clinical science underlying carotenoid based nutritional interventions against ocular disease progress in retinal and eye research 50 34 66 doi 10 1016 j preteyeres 2015 10 003 pmc 4698241 pmid 26541886 maresca julia a romberger steven p bryant donald a 2008 05 28 isorenieratene biosynthesis in green sulfur 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liang gillbro tomas 1995 11 01 solvent ...