» Articles » PMID: 19304845

The Biosynthetic Pathway for Myxol-2' Fucoside (myxoxanthophyll) in the Cyanobacterium Synechococcus Sp. Strain PCC 7002

Overview
Journal J Bacteriol
Specialty Microbiology
Date 2009 Mar 24
PMID 19304845
Citations 32
Authors
Affiliations
Soon will be listed here.
Abstract

Synechococcus sp. strain PCC 7002 produces a variety of carotenoids, which comprise predominantly dicylic beta-carotene and two dicyclic xanthophylls, zeaxanthin and synechoxanthin. However, this cyanobacterium also produces a monocyclic myxoxanthophyll, which was identified as myxol-2' fucoside. Compared to the carotenoid glycosides produced by diverse microorganisms, cyanobacterial myxoxanthophyll and closely related compounds are unusual because they are glycosylated on the 2'-OH rather than on the 1'-OH position of the psi end of the molecule. In this study, the genes encoding two enzymes that modify the psi end of myxoxanthophyll in Synechococcus sp. strain PCC 7002 were identified. Mutational and biochemical studies showed that open reading frame SynPCC7002_A2032, renamed cruF, encodes a 1',2'-hydroxylase [corrected] and that open reading frame SynPCC7002_A2031, renamed cruG, encodes a 2'-O-glycosyltransferase. The enzymatic activity of CruF was verified by chemical characterization of the carotenoid products synthesized when cruF was expressed in a lycopene-producing strain of Escherichia coli. Database searches showed that homologs of cruF and cruG occur in the genomes of all sequenced cyanobacterial strains that are known to produce myxol or the acylic xanthophyll oscillaxanthin. The genomes of many other bacteria that produce hydroxylated carotenoids but do not contain crtC homologs also contain cruF orthologs. Based upon observable intermediates, a complete biosynthetic pathway for myxoxanthophyll is proposed. This study expands the suite of enzymes available for metabolic engineering of carotenoid biosynthetic pathways for biotechnological applications.

Citing Articles

Product Speculation from Carotenogenic Gene Cluster of Genome, and Identification of Myxol and Functional Analysis of Each Gene.

Nakazawa K, Mineo D, Harayama T, Yoshizawa S, Takaichi S, Sugiyama K Genes (Basel). 2025; 16(2).

PMID: 40004531 PMC: 11855829. DOI: 10.3390/genes16020202.


Distribution, Biosynthesis, and Function of Carotenoids in Oxygenic Phototrophic Algae.

Takaichi S Mar Drugs. 2025; 23(2).

PMID: 39997186 PMC: 11857680. DOI: 10.3390/md23020062.


Isolation, Identification and Pigment Analysis of Novel Cyanobacterial Strains from Thermal Springs.

Sandybayeva S, Kossalbayev B, Zayadan B, Kopecky J, Kakimova A, Bolatkhan K Plants (Basel). 2024; 13(21).

PMID: 39519869 PMC: 11547633. DOI: 10.3390/plants13212951.


Research progress on the pharmacological activity, biosynthetic pathways, and biosynthesis of crocins.

Hua Z, Liu N, Yan X Beilstein J Org Chem. 2024; 20:741-752.

PMID: 38633914 PMC: 11022409. DOI: 10.3762/bjoc.20.68.


Genes and Pathway Reactions Related to Carotenoid Biosynthesis in Purple Bacteria.

Sandmann G Biology (Basel). 2023; 12(10).

PMID: 37887056 PMC: 10604819. DOI: 10.3390/biology12101346.


References
1.
Dembitsky V . Astonishing diversity of natural surfactants: 3. Carotenoid glycosides and isoprenoid glycolipids. Lipids. 2005; 40(6):535-57. DOI: 10.1007/s11745-005-1415-z. View

2.
Lutnaes B, Oren A, Liaaen-Jensen S . New C(40)-carotenoid acyl glycoside as principal carotenoid in Salinibacter ruber, an extremely halophilic eubacterium. J Nat Prod. 2002; 65(9):1340-3. DOI: 10.1021/np020125c. View

3.
Mochimaru M, Masukawa H, Maoka T, Mohamed H, Vermaas W, Takaichi S . Substrate specificities and availability of fucosyltransferase and beta-carotene hydroxylase for myxol 2'-fucoside synthesis in Anabaena sp. strain PCC 7120 compared with Synechocystis sp. strain PCC 6803. J Bacteriol. 2008; 190(20):6726-33. PMC: 2566191. DOI: 10.1128/JB.01881-07. View

4.
Takaichi S, Maoka T, Masamoto K . Myxoxanthophyll in Synechocystis sp. PCC 6803 is myxol 2'-dimethyl-fucoside, (3R,2'S)-myxol 2'-(2,4-di-O-methyl-alpha-L-fucoside), not rhamnoside. Plant Cell Physiol. 2001; 42(7):756-62. DOI: 10.1093/pcp/pce098. View

5.
Maresca J, Graham J, Bryant D . The biochemical basis for structural diversity in the carotenoids of chlorophototrophic bacteria. Photosynth Res. 2008; 97(2):121-40. DOI: 10.1007/s11120-008-9312-3. View