myxoxanthophyll

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| ImageFile = File:Myxoxanthophyll.svg

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| IUPACName = (3S,4R,5S)-2-[(4E,6E,8E,10E,12E,14E,16E,18E,20E,22E,24E)-2-hydroxy-25-(4-hydroxy-2,6,6-trimethylcyclohexen-1-yl)-2,6,10,14,19,23-hexamethylpentacosa-4,6,8,10,12,14,16,18,20,22,24-undecaen-3-yl]oxy-6-methyloxane-3,4,5-triol

| OtherNames = Myxoxanthophyll, myxol-2' fucoside

| Section1 = {{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 863126-98-1

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| UNII = 2D9J09M91C

| PubChem = 44237205

| SMILES = C/C(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C=C(C)/C=C/[C@@H](O[C@@H]1O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]1O)C(C)(C)O)/C=C/C2=C(C)C[C@@H](O)CC2(C)C

| InChI = MUCOHWBULSBLLZ-GVZUTNEGSA-N

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| Section2 = {{Chembox Properties

| Formula = C46H66O7

| MolarMass = 731.012 g/mol

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Myxoxanthophyll is a carotenoid glycoside pigment present (usually as rhamnosides) in the photosynthetic apparatus of cyanobacteria.{{cite web |url=http://www.oxforddictionaries.com/us/definition/american_english/myxoxanthophyll |archive-url=https://web.archive.org/web/20150924140944/http://www.oxforddictionaries.com/us/definition/american_english/myxoxanthophyll |url-status=dead |archive-date=September 24, 2015 |title=myxoxanthophyll: definition of myxoxanthophyll in Oxford dictionary (American English) (US) |website=Oxford Dictionaries |date=2015 |publisher=Oxford University Press |access-date=1 September 2015}} It is named after the word "Myxophyceae", a former term for cyanobacteria. As a monocyclic xanthophyll, it has a yellowish color. It is required for normal cell wall structure and thylakoid organization in the cyanobacterium Synechocystis.{{cite journal |vauthors=Mohamed HE, van de Meene AM, Roberson RW, Vermaas WF |title=Myxoxanthophyll is required for normal cell wall structure and thylakoid organization in the cyanobacterium Synechocystis sp. strain PCC 6803 |journal=J. Bacteriol. |volume=187 |issue=20 |pages=6883–92 |year=2005 |pmid=16199557 |pmc=1251633 |doi=10.1128/JB.187.20.6883-6892.2005 }} The pigment is unusual because it is glycosylated on the 2'-OH rather than the 1'-OH position of the molecule.{{cite journal|vauthors=Graham JE, Bryant DA | title=The biosynthetic pathway for myxol-2' fucoside (myxoxanthophyll) in the cyanobacterium Synechococcus sp. strain PCC 7002. | journal=J Bacteriol | year= 2009 | volume= 191 | issue= 10 | pages= 3292–300 | pmid=19304845 | doi=10.1128/JB.00050-09 | pmc=2687168 }} Myxoxanthophyll was first isolated from Oscillatoria rubenscens in 1936.{{cite journal|vauthors=Engel JA, Jerlhag E, Svensson L, Smith RG, Egecioglu E | title=Blockade of growth hormone secretagogue receptor 1A signaling by JMV 2959 attenuates the NMDAR antagonist, phencyclidine-induced impairments in prepulse inhibition. | journal=Psychopharmacology | year= 2015 | volume=232 | issue=23 | pages=4285–4292 | pmid=26319159 | doi=10.1007/s00213-015-4054-3 | pmc=4613889}}

Synthesis

The bright red pigment lycopene is the acyclic precursor of all carotenoids in cyanobacteria. In myxoxanthophyll synthesis, lycopene is enzymatically converted to 1-hydroxylycoprene, then to intermediates 1'-hydroxy-y-carotene, plectaniaxanthin, and myxol. Finally, the hydroxyl group in myxol is glycosylated at the 2' position to form myxoxanthophyll.

References

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