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Myxoxanthophyll

Myxoxanthophyll
Names
IUPAC name
(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
Other names
Myxoxanthophyll, myxol-2' fucoside
Identifiers
3D model (JSmol)
UNII
  • InChI=MUCOHWBULSBLLZ-GVZUTNEGSA-N
  • 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
Properties
C46H66O7
Molar mass 731.012 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Myxoxanthophyll is a carotenoid glycoside pigment present (usually as rhamnosides) in the photosynthetic apparatus of cyanobacteria.[1] It is named after the word "Myxophyceae", a former term for cyanobacteria.[2] As a monocyclic xanthophyll, it has a yellowish color. It is required for normal cell wall structure and thylakoid organization in the cyanobacterium Synechocystis.[3] The pigment is unusual because it is glycosylated on the 2'-OH rather than the 1'-OH position of the molecule.[2] Myxoxanthophyll was first isolated from Oscillatoria rubenscens in 1936.[4]

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.[2]

References

  1. ^ "myxoxanthophyll: definition of myxoxanthophyll in Oxford dictionary (American English) (US)". Oxford Dictionaries. Oxford University Press. 2015. Archived from the original on September 24, 2015. Retrieved 1 September 2015.
  2. ^ a b c Graham JE, Bryant DA (2009). "The biosynthetic pathway for myxol-2' fucoside (myxoxanthophyll) in the cyanobacterium Synechococcus sp. strain PCC 7002". J Bacteriol. 191 (10): 3292–300. doi:10.1128/JB.00050-09. PMC 2687168. PMID 19304845.
  3. ^ Mohamed HE, van de Meene AM, Roberson RW, Vermaas WF (2005). "Myxoxanthophyll is required for normal cell wall structure and thylakoid organization in the cyanobacterium Synechocystis sp. strain PCC 6803". J. Bacteriol. 187 (20): 6883–92. doi:10.1128/JB.187.20.6883-6892.2005. PMC 1251633. PMID 16199557.
  4. ^ Engel JA, Jerlhag E, Svensson L, Smith RG, Egecioglu E (2015). "Blockade of growth hormone secretagogue receptor 1A signaling by JMV 2959 attenuates the NMDAR antagonist, phencyclidine-induced impairments in prepulse inhibition". Psychopharmacology. 232 (23): 4285–4292. doi:10.1007/s00213-015-4054-3. PMC 4613889. PMID 26319159.
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