Granadaene

Granadaene is the trivial name of a non-isoprenoid polyene that constitutes the red pigment characteristic of Streptococcus agalactiae (group B streptococcus).

Granadaene
Names
IUPAC name
(2S)-5-Amino-2-[[(2E,4E,6E,8E,10E,12E,14E,16E,18E,20E,22E,24E)-27-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoctacosa-2,4,6,8,10,12,14,16,18,20,22,24-dodecaenoyl]amino]pentanoic acid
Identifiers
3D model (JSmol)
Properties
C39H52N2O8
Molar mass 676.851 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Characteristics

Granadaene contains a conjugated system made up of a linear chain of 12 conjugated double bonds which is conntected to the amino acid ornithine at one end and the sugar rhamnose at the other.[1][2] Granadaene is dark red, odorless, insoluble in water, methanol, ethanol, diethyl ether, acetone, hexane, dimethyl sulfoxide (DMSO), acetonitrile, tetrahydrofuran, chloroform, and in most solvents, it is soluble in DMSO–0.1% trifluoroacetic acid (TFA).[1] Granadaene, can be extracted from cultures of S.agalactiae in granada broth (granada medium without agar) with 0.1 M potassium hydroxide (KOH) and purified by size-exclusion chromatography on Sephadex LH using DMSO–0.1%TFA.[1]

Streptococcus agalactiae in granada broth
Ultraviolet/visible spectrum of granadaene, in DMSO+TFA
Proposed metabolic pathway for granadaene biosynthesis

The ultraviolet-visible absorption spectrum of the granadaene (in DMSO/TFA) is almost identical to that of a carotene with a similar conjugated system of double bonds (e.g. alpha-carotene), that is why the GBS pigment was considered to be a carotene for many years.[3]

Biological relevance

Granadaene is an organic compound produced by S.agalactiae. It is the product of a metabolic pathway similar to that of biosynthesis of fatty acids. The enzymes necessary for the biosynthesis of granadaene in GBS are coded by a gene cluster of 12 genes, the cyl operon, and a pathway for the pigment biosynthesis requiring all the genes of the cyl operon has been proposed.[4][4][5] Like the biosynthesis of the pigment, the hemolytic activity requires also in GBS the 12 genes of the cyl operon.[6][7] The pigment is localized, in GBS, in the cell membrane,[3] where it could play a role in membrane stabilization, similarly to the role of carotenes in other bacterial membranes.[8] It has also been proposed that granadaene is indeed the hemolysin of S.agalactiae, and because the GBS hemolysin is a broad-spectrum cytolysin able to destroy many eukaryotic cells, it is considered an important virulence factor for GBS.[4][5][9]

Production of the red pigment granadaene is a phenotypic trait specific to β-hemolytic GBS, and because of that, detection of red colonies from clinical samples, when cultivated on granada medium, allows the straightforward identification of GBS.[10][11]

In addition to S.agalactiae the presence of granadaene has been reported in Propionibacterium jensenii, where it can cause defects such as red spots in some cheeses.[12] Probably granadaene is also present in other Propionibacterium sp. such as P.thoenii and P.rubrum.[5][12]

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References
  1. Rosa-Fraile M, Rodríguez-Granger J, Haidour-Benamin A, Cuerva JM, Sampedro A (2006). "Granadaene: Proposed Structure of the Group B Streptococcus Polyenic Pigment". Appl Environ Microbiol. 72 (9): 6367–6370. doi:10.1128/aem.00756-06. PMC 1563658. PMID 16957264.
  2. Paradas M, Jurado R, Haidour A, Rodríguez Granger J, Sampedro Martínez A, de la Rosa Fraile M, Robles R, Justicia J, Cuerva JM (2012). "Clarifying the structure of granadaene: Total synthesis of related analogue - granadaene and confirmation of its absolute stereochemistry". Bioorg Med Chem. 20 (22): 6655–6661. doi:10.1016/j.bmc.2012.09.017. PMID 23043725.
  3. Merrit K, Jacobs NJ (1978). "Characterization and Incidence of Pigment Production by Human Clinical Group B Streptococci". J Clin Microbiol. 8 (1): 105–107. PMC 275130. PMID 353069.
  4. Whidbey C, Harrell MI, Burnside K, Ngo L, Becraft AK, Iyer LM, Aravind L, Hitti J, Waldorf KM, Rajagopal L (2013). "A hemolytic pigment of Group B Streptococcus allows bacterial penetration of human placenta". J Exp Med. 210 (6): 1265–1281. doi:10.1084/jem.20122753. PMC 3674703. PMID 23712433.
  5. Rosa-Fraile M, Dramsi S, Spellerberg B (2014). "Group B streptococcal haemolysin and pigment, a tale of twins" (PDF). FEMS Microbiol. Rev. 38 (5): 932–946. doi:10.1111/1574-6976.12071. PMC 4315905. PMID 24617549.
  6. Spellerberg B, Pohl B, Haase G, Martin S, Weber-Heynemann J, Lütticken R (1999). "Identification of genetic determinants for the hemolytic activity of Streptococcus agalactiae by ISS1 transposition". J. Bacteriol. 181 (10): 3212–3219. PMC 93778. PMID 10322024.
  7. Spellerberg B, Martin S, Brandt C, Lütticken R (2000). "The cyl genes of Streptococcus agalactiae are involved in the production of pigment". FEMS Microbiol. Lett. 188 (2): 125–128. doi:10.1111/j.1574-6968.2000.tb09182.x. PMID 10913694.
  8. Taylor RF. (1984). "Bacterial triterpenoids". Microbiol. Rev. 48 (3): 181–198. PMC 373008. PMID 6387426.
  9. Whidbey C, Vornhagen J, Gendrin C, Boldenow E, Samson JM, Doering K, Ngo L, Ezekwe EA Jr, Gundlach JH, Elovitz MA, Liggitt D, Duncan JA, Adams Waldorf KM, Rajagopal L (2015). "A streptococcal lipid toxin induces membrane permeabilization and pyroptosis leading to fetal injury". EMBO Mol. Med. 7 (4): 488–505. doi:10.15252/emmm.201404883. PMC 4403049. PMID 25750210.
  10. Rosa-Fraile M, Rodriguez-Granger J, Cueto-Lopez M, Sampedro A, Biel Gaye E, Haro M, Andreu A (1999). "Use of Granada Medium To Detect Group B Streptococcal Colonization in Pregnant Women" (PDF). J Clin Microbiol. 37: 2674–2677.
  11. Verani JR, McGee L, Schrag SJ (2010). "Prevention of perinatal group B streptococcal disease: revised guidelines from CDC, 2010" (PDF). MMWR Recomm Rep. 59(RR-10): 1–32.
  12. Vanberg C, Lutnaes BF, Langsrud T, Nees IF, Holo H (2007). "Propionibacterium jensenii produces the polyene pigment granadaene and has hemolytic properties similar to those of Streptococcus agalactiae". Appl Environ Microbiol. 73 (17): 5501–5506. doi:10.1128/AEM.00545-07. PMC 2042088. PMID 17630313.
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