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Carotenoid


DATA No : VCA1050 INFORMANT : Norihiko Misawa

NAME : 7,8-Dihydro-4,4'-diapo-y,y-carotene

COMMON NAME: 4,4'-Diaponeurosporene
SYMBOL:
FORMULA: C30H42 MOL.WT (average) : 402.654


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (nm): acetonitrile/methanol/THF (58:35:7) 267, 331, 416, 439, 468, %III/II=95
[Spectrum 1016] (Ref. 1057/1069); HPLC eluent 416, 438, 468 (Ref. 1117); methanol
[Spectrum 1132] ; petroleum (390), 412, 436, 466; ethanol (391), 414, 438, 467.5 (Ref. 1364); petroleum (390), 412, 435, 465 (Ref. 1368)

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:FD-MS m/z: 402 (Ref. 1069); LC/MS m/z: 403 [M+H]+ (Ref. 1117); (Ref. 1368)

OTHER SPECTRA:
CHROMATOGRAM DATA
HPLC (column; Novapak C18 (Waters) 8 X 100 mm: eluelnt; acetonitrile/methanol/THF 58:35:7: flow 2.0 ml/min) Rt=5.9 min (Ref. 1057/1069)
SOURCE
Major carotenoid of Heliobacillus mobilis, Heliophilum fasciatum, Hebacterium chlorum, Heliobacteirum modesticaldum, Heliobacterium gestii (heliobacteria) (Ref. 1069); and alkaliphilic heliobacteria, Heliorestis daurensis and Heliorestis baculata, produces 4,4'-diaponeurosporen and OH-diaponeurosporene glucoside esters (Ref. 1270).
Staphylococcus aureus Newman (Ref. 1092), Staphylococcus aureus 209P (1% of total) (Ref. 1364), Streptococcus faecium UNH 564P (13% of total) (Ref. 1363), and Staphylococcus carnosus, Lactobacillus plantarum, Enterococcus mundtii, Enterococcus sulfureus (Ref. 1117).
CHEMICAL SYNTHESIS

METABOLISM
Characteristics of CrtN from Staphylococcus aureus; membrane protein, 52 kDa single peptide, substrate specificity, FAD-dependent and diphenylamine inhibition (Ref. 1128/1129).
An Escherichia coli transformant carrying the S. aureus crtM and crtN genes produces 4,4'-diaponeurosporene (Ref. 1092/1215).
The symmetrical carbon skeleton is reduced from biosynthetic labelling studies in Streptococcus faecium UNH 564P (Ref. 1363/1369).
GENETIC INFORMATION
A 4,4'-diapophytoene desaturase gene (crtN), which mediates the desaturation reactions from 4,4'-diapophytoene (dehydrosqualene) to 4,4'-diaponeurosporene, has been cloned from Staphylococcus aureus (Ref. 1092). Another crtN gene has also been found in Heliobacillus mobilis based on the sequence similarity (Ref. 1070).
NOTE

REFERENCES
[1057]
AUTHOR:Takaichi, S.
TITLE:Characterization of carotenes in a combination of a C18 HPLC column with isocratic elution and absorption spectra with a photodiode-array detector
JOURNAL:Photosynth. Res.
VOL:65 PAGE : 93 -99 (2000)
[TOP]

[1069]
AUTHOR:Takaichi, S., Inoue, K., Akaike, M., Kobayashi, M., Oh-oka, H., and Madigan, M. T.
TITLE:The major carotenoid in all known species of heliobacteria is the C30 carotenoid 4,4'-diaponeurosporene, not neurosporene PubMed ID:9297464
JOURNAL:Arch Microbiol.
VOL:168 PAGE : 277-281 (1997)
[TOP]

[1070]
AUTHOR:Xiong, J., Inoue, K., and Bauer, C. E.
TITLE:Tracking molecular evolution of photosynthesis by characterization of a major photosynthesis gene cluster from Heliobacillus mobilis PubMed ID:9843979
JOURNAL:Proc Natl Acad Sci U S A.
VOL:95 PAGE : 14851-14856 (1998)
[TOP]

[1092]
AUTHOR:Wieland, B., Feil, C., Gloria-Maercker, E., Thumm, G., Lechner, M., Bravo, J. M., Poralla, K., and Gotz, F.
TITLE:Genetic and biochemical analyses of the biosynthesis of the yellow carotenoid 4,4'-diaponeurosporene of Staphylococcus aureus PubMed ID:8002598
JOURNAL:J Bacteriol.
VOL:176 PAGE : 7719-7726 (1994)
[TOP]

[1117]
AUTHOR:Breithaupt, D.E., Schwack, W., Wolf, G., and Hammes, W.P.
TITLE:Characterization of the triterpenoid 4,4'-diaponeurosporene and its isomers in food-associated bacteria
JOURNAL:Eur. Food Res. Technol.
VOL:213 PAGE : 231 -233 (2001)
[TOP]

[1128]
AUTHOR:Raisig, A., and Sandmann, G.
TITLE:Functional properties of diapophytoene and related desaturases of C(30) and C(40) carotenoid biosynthetic pathways PubMed ID:11566453
JOURNAL:Biochim Biophys Acta.
VOL:1533 PAGE : 164-170 (2001)
[TOP]

[1129]
AUTHOR:Raisig, A., and Sandmann, G.
TITLE:4,4'-diapophytoene desaturase: catalytic properties of an enzyme from the C(30) carotenoid pathway of Staphylococcus aureus PubMed ID:10498735
JOURNAL:J Bacteriol.
VOL:181 PAGE : 6184-6187 (1999)
[TOP]

[1215]
AUTHOR:Umeno, D., Tobias, A. V., and Arnold, F. H.
TITLE:Evolution of the C30 carotenoid synthase CrtM for function in a C40 pathway PubMed ID:12426357
JOURNAL:J Bacteriol.
VOL:184 PAGE : 6690-6699 (2002)
[TOP]

[1270]
AUTHOR:Takaichi, S., Oh-Oka, H., Maoka, T., Jung, D. O., and Madigan, M. T.
TITLE:Novel carotenoid glucoside esters from alkaliphilic heliobacteria PubMed ID:12560987
JOURNAL:Arch Microbiol.
VOL:179 PAGE : 95-100 (2003)
[TOP]

[1363]
AUTHOR:Davies, B.H., Taylor, R.F.
TITLE:The biosynthesis of triterpenoid carotenoids in Streptococcus faecium UNH 564P PubMed ID:7116207
JOURNAL:Can. J. Biochem.
VOL:60 PAGE : 684 -692 (1982)
[TOP]

[1364]
AUTHOR:Taylor, R.F., Davies, B.H.
TITLE:The triterpenoid carotenoids and related terpenoids in Staphylococcus aureus 209P PubMed ID:6627101
JOURNAL:Can. J. Biochem. Cell Biol.
VOL:61 PAGE : 892 -905 (1983)
[TOP]

[1368]
AUTHOR:Taylor, R.F., Davies, B.H.
TITLE:Triterpenoid carotenoids and related lipids: The triterpenoid carotenes of Streptococcus faecium UNH 564P PubMed ID:4212486
JOURNAL:Biochem. J.
VOL:139 PAGE : 751 -760 (1974)
[TOP]

[1369]
AUTHOR:Taylor, R.F., Davies, B.H.
TITLE:A cell-free system from Streptococcus fecium for studies on the biosynthesis of triterpenoid carotenoids PubMed ID:6749265
JOURNAL:Can. J. Biochem.
VOL:60 PAGE : 675 -683 (1982)
[TOP]

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