Carotenoid

DATA No : VCA1007 INFORMANT : Norihiko Misawa

NAME : b,y-Carotene

COMMON NAME	:	g-Carotene/ b,y-Carotene
SYMBOL	:
FORMULA	:	C₄₀H₅₆ MOL.WT (average) : 536.873

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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) 284, 356, 440 (shoulder), 462, 492, %III/II=41.7 [Spectrum 1010] (Ref. 1057/1103); methanol 459, 485 [Spectrum 1118] (Ref. 1055)

IR SPECTRA	:

NMR SPECTRA	:	¹H-NMR (CDCl3) (Ref. 1103)

MASS SPECTRA	:	FD-MS m/z: 536 (Ref. 1103/1105)

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=14.8 min (Ref. 1057)

SOURCE

Chloroflexus aurantiacus (Ref. 1105) and Chloroflexus aggregans (S. Takaichi) (Ref. 1106) (green filamentous bacteria)
Chlorobium (present name, Chlorobaculum) tepidum (green sulfer bacteria) (Ref. 1103)
Rhodococcus rhodochrous (Nocardioform actinomycetes) (Ref. 1111)
Erythrobacter longus (aerobic photosynthetic bacterium) (Ref. 1055)

CHEMICAL SYNTHESIS

METABOLISM

g-Carotene is the biosynthetic intermediate through cyclization reactions from lycopene to b-carotene.
A mutant of Rhodococcus rhodochrous accumulats g-karotene and 4-keto-g-karotene (Ref. 1111).
[Table 1031]

GENETIC INFORMATION

A lycopene b-monocyclase gene crtYm is isolated from a unique marine bacterium that produces myxol (Ref. 1241), and crtLm is isolated from Rhodococcus erythropolis and Deinococcus radiodurans (bacteria) (Ref. 1278).

NOTE

REFERENCES

[1055]

AUTHOR	:	Takaichi, S., Shimada, K., and Ishidsu, J.
TITLE	:	Carotenoids from the aerobic photosynthetic bacterium, Erythrobacter longus: b-Carotene and its hydroxyl derivatives
JOURNAL	:	Arch. Microbiol.
VOL	:	153 PAGE : 118 -122 (1990)

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[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)

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[1103]

AUTHOR	:	Takaichi, S., Wang, Z. Y., Umetsu, M., Nozawa, T., Shimada, K., and Madigan, M. T.
TITLE	:	New carotenoids from the thermophilic green sulfur bacterium Chlorobium tepidum: 1',2'-dihydro-gamma-carotene, 1',2'-dihydrochlorobactene, and OH-chlorobactene glucoside ester, and the carotenoid composition of different strains PubMed ID:9297463
JOURNAL	:	Arch Microbiol.
VOL	:	168 PAGE : 270-276 (1997)

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[1105]

AUTHOR	:	Takaichi, S., Tsuji, K., Matsuura, K., and Shimada, K.
TITLE	:	A monocyclic carotenoid glucoside ester is a major carotenoid in the green filamentous bacterium Chloroflexus aurantiacus
JOURNAL	:	Plant Cell Physiol.
VOL	:	36 PAGE : 773 -778 (1995)

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[1106]

AUTHOR	:	Hanada, S., Hiraishi, A., Shimada, K., and Matsuura, K.
TITLE	:	Chloroflexus aggregans sp. nov., a filamentous phototrophic bacterium which forms dense cell aggregates by active gliding movement PubMed ID:7547286
JOURNAL	:	Int J Syst Bacteriol.
VOL	:	45 PAGE : 676-681 (1995)

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[1111]

AUTHOR	:	Takaichi, S., Tamura, Y., Miyamoto, Ta., Azegami, K., Yamamoto, Y., and Ishidsu, J.
TITLE	:	Carotenogenesis pathway of novel carotenoid glucoside mycolic acid esters in Rhodococcus rhodochrous using carotenogenesis mutants and inhibitors
JOURNAL	:	Biosci. Biotechnol. Biochem.
VOL	:	63 PAGE : 2014 -2016 (1999)

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[1241]

AUTHOR	:	Teramoto, M., Takaichi, S., Inomata, Y., Ikenaga, H., and Misawa, N.
TITLE	:	Structural and functional analysis of a lycopene beta-monocyclase gene isolated from a unique marine bacterium that produces myxol PubMed ID:12804761
JOURNAL	:	FEBS Lett.
VOL	:	545 PAGE : 120-126 (2003)

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[1278]

AUTHOR	:	Tao, L., Picataggio, S., Routière, P.E., Cheng, Q.
TITLE	:	Asymmetrically acting lycopene b-cyclases (CrtLm) from non-photosynthetic bacteria
JOURNAL	:	Mol. Gen. Genomics
VOL	:	271 PAGE : 180 -188 (2004)

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