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Carotenoid


DATA No : VCA0046 INFORMANT : Masayoshi Ito

NAME : (3S,5R,3'S,5'R)-3,3'-Dihydroxy-k,k-carotene-6,6'-dione

COMMON NAME: Capsorubin
SYMBOL:
FORMULA: C40H56O4 MOL.WT (average) : 600.870


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BIOLOGICAL ACTIVITY
Singlet oxygen quenching activity (Ref. 0441)
Anti-tumore promoting effect (Ref. 1095)
Anti-oxidative activity (Ref. 1096)
Suppressing efect of generation of nitric oxide (Ref. 1097)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:214-216degC (Ref. 0140)
216-217degC (Ref. 0141)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (nm) (E 1%1cm): hexane 297 (310), 423sh (845), 445 (1528), 471 (2218), 505 (1985) (Ref. 0140); benzene 303 (284), 435sh (746), 445 (1528), 461 (1303), 487 (1838), 521 (1635) (Ref. 0140/0141>

IR SPECTRA:nmax(KBr)/cm-1: 3464s (OH), 1669s (conj. C=O), 1588s, 1556s (conj. C=C), 1055s, 983s (Ref. 0140/0141)

NMR SPECTRA:1H-NMR d(400 MHz, CDCl3): 0.84 (6H, s, 16,16'-Me), 1.21 (6H, s, 17,17'-Me), 1.37 (6H, s, 18,18'-Me), 1.48 (2H, dd, J 14.5, 4, 4b,4'b-H), 1.71 (2H, dd, J 13.5, 4, 2b,2'b-H), 1.96 (6H, s, 19,19'-Me), 1.99 (6H, s, 20,20'-Me), 2.00 (2H, dd, J 13.5, 7, 2a,2'a-H), 2.96 (2H, dd, J 14.5, 8.5, 4a,4'a-H), 4.51 (2H, m, 3,3'-H), 6.36 (2H, m, 14,14'-H), 6.45 (2H, d, J 15, 7,7'-H), 6.52 (2H, d, J 14.5, 12,12'-H), 6.55 (2H, d, J 11, 10,10'-H), 6.64 (2H, dd, J 14.7, 11, 11,11'-H), 6.69 (2H, m, 15,15'-H), 7.32 (2H, d, J 15, 7,7'-H) (Ref. 0140)
13C-NMR d(100.6 MHz, CDCl3): 12.88 (C19,19',20,20'), 21.37, 25.15, 25.93 (C16,16',17,17',18,18'), 44.02 (C1,1'), 45.44 (C4,4'), 51.02 (C2,2'), 59.03 (C6,6'), 70.42 (C3,3'), 121.23 (C7,7'), 124.67 (C11,11'), 146.76 (C8,8'), 202.87 (C6,6') (Ref. 0140/0061)

MASS SPECTRA:m/z: 600 (10, M), 494 (9), 445 (5), 221 (10), 145 (16), 127 (48), 109 (100), 106 (15), 105 (15), 91 (28), 83 (46) (Ref. 0140/0141)

OTHER SPECTRA:CD in dioxane: De 374 (-3.13), 366sh (-2.94), 358sh (-2.64), 339sh (-1.30), 331sh (-0.91), 301 (+6.14), 290sh (+4.10), 268sh (+0.11), 258sh (-1.00), 252 (-1.47), 249 (-1.41), 239sh (-1.13), 224sh (+0.61) (Ref. 0140/0141)
CHROMATOGRAM DATA
TLC [Kieselgel F254 (Merck); CHCl3-acetone 9:1) Rf = 0.15 (Ref. 0140)
HPLC (columun: Chromsil C18 6mm end-capped, detection at 450nm, eluent 12% (v/v) H2O in MeOH (A), MeOH (B), 50% (v/v) acetone in MeOH (C). The gradient program was 100% A, 8min, to 80% A/20% B in 8 min, to 50% A/50% B in 8min, to 100% B in 7 min, 100% B, 2min, to 100% C in 6min, 100% C, 5min (linear steps), The flow rate was 1.5 mL/min. capsanthin 3,6-epoxide tR=16 min, capsanthin tR=17min, cryptpcapsin tR=32 min. (Ref. 0506)
HPLC (columun: Sheriosorb ODS 2, 250X4mm i.d. 5 mm, flow rate 1.5ml/min, detection 450nm, solvent system (A) hexane-EtOAc-EtOH-acetone (96:3:2:2); (B) light petrolum ether -acetone-diethylamine (10:4:1); (C) CH2Cl2-EtOAc (4:1), solvent A, B, C gradient, gradient program in text, capsorubin tR=3.49, capsanthin tR=6.35 min, capsanthin tR=17min, cryptpcapsin tR=11.85 min. (Ref. 0507)
SOURCE
Capsicum annuum (red paprika) (Ref. 0142)
CHEMICAL SYNTHESIS
Aldol condensation between crocetindialdehyde and [(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]methylketone with sodium hydride as a base provided capsorbin. (Ref. 0019/0140)
METABOLISM
Zeaxanthin a_right violaxanthin a_right capsorubin in Capsicum annuum (Ref. 0515) in Caosicum annuum chrmoplastes (Ref. 0514)
Changes in carotenoid composition and content during ripening of selective cultivars for paprika (Capsicum annuum) production (Ref. 1271).
GENETIC INFORMATION
The capsanthin-capsorubin synthase (CCS) gene was isolated from Capsicum annuum (red pepper) in 1994 (Ref. 1023). It is considered that capsorubin is synthesized from violaxanthin by CCS.
NOTE

REFERENCES
[0019]
AUTHOR:Pfander,H. and Bartels,B. (1996) Carotenoids Volume 2: Synthesis Chapter 3: Carotenoid Synthesis Part III: Synthesis of Cyclic Carotenoids (Britton,G.,Liaaen-Jensen,S., and Pfander,H., eds), pp161-200, Birkhäuser Verlag,Basel,Boston,Berlin
TITLE:
JOURNAL:
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[0061]
AUTHOR:Moss,G.P.
TITLE:Carbon-13 NMR spectra of carotenoids
JOURNAL:Pure Appl. Chem.
VOL:2047 PAGE : 97 -102 (1976)
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[0140]
AUTHOR:Rüttimann,A.,Englert,G.,Mayer,H.,Moss,G.P., and Weedon,B.C.L.
TITLE:Synthese von optisch aktiven, natürlichen Carotinoiden und strukturell verwandten Naturprodukten. X. Synthese von (3R,3'S,5'R)-Capsanthin, (3S,5R,3'S,5'R)-Capsorbin, (3'S,5'R)-Kryptocapsin und einigen verwandten Verbindungen. Ein neuer Zugang zu optisch aktiven Fünfring-Carotinoidbausteinen durch Hydroborierung
JOURNAL:Helv. Chim. Acta
VOL:66 PAGE : 1939 -1960 (1983)
[TOP]

[0141]
AUTHOR:Bowden,R.D.,Cooper,R.D.G.,Harris,C.H.,Moss,G.P.,Weedon,B.C.L., and Jackman,L.M.
TITLE:Carotenoids and Related Compounds. Part 37. Stereochemistry and Synthesis of Capsorubin
JOURNAL:J. Chem. Soc., Perkin Trans. 1
VOL: PAGE : 1465 -1474 (1983)
[TOP]

[0441]
AUTHOR:Hirayama, O., Nakamura, K., Hamada, S., and Kobayasi, Y.
TITLE:Singlet oxygen quenching ability of naturally occurring carotenoids PubMed ID:8152349
JOURNAL:Lipids.
VOL:29 PAGE : 149-150 (1994)
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[0506]
AUTHOR:Deli,J.,Matus,Z., and Toth,G.
TITLE:Carotenoid Composition in the Fruits of Capsicum annuum Cv. Szentesi Kosszarvu during Ripening
JOURNAL:J. Agric. Food Chem.
VOL:44 PAGE : 711 -716 (1996)
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[0507]
AUTHOR:Minguenz-Mosquera,M.I., and Hornero-Mendez,D.
TITLE:Separation and Quantification of the Carotenoid Pigments in Red Peppers (Capsicum annuum L.), Paprika, and Oleoresin by Reversed-Phase HPLC
JOURNAL:J. Agric. Food Chem.
VOL:41 PAGE : 1616 -1620 (1993)
[TOP]

[0514]
AUTHOR:Camara,B.
TITLE:Carotenogenic enzymes from Capsicum chromoplasts
JOURNAL:Pure Appl. Chem.
VOL:57 PAGE : 675 -677 (1985)
[TOP]

[0515]
AUTHOR:Camara,B.
TITLE:Biosynthesis of keto-carotenoids in Capsicum annuum fruits
JOURNAL:FEBS Lett.
VOL:118 PAGE : 315 -318 (1980)
[TOP]

[1023]
AUTHOR:Bouvier, F., Hugueney, P., d'Harlingue, A., Kuntz, M., and Camara, B.
TITLE:Xanthophyll biosynthesis in chromoplasts: isolation and molecular cloning of an enzyme catalyzing the conversion of 5,6-epoxycarotenoid into ketocarotenoid PubMed ID:7920703
JOURNAL:Plant J.
VOL:6 PAGE : 45-54 (1994)
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[1095]
AUTHOR:Maoka, T., Mochida, K., Kozuka, M., Ito, Y., Fujiwara, Y., Hashimoto, K., Enjo, F., Ogata, M., Nobukuni, Y., Tokuda, H., et al.
TITLE:Cancer chemopreventive activity of carotenoids in the fruits of red paprika Capsicum annuum L PubMed ID:11566483
JOURNAL:Cancer Lett.
VOL:172 PAGE : 103-109 (2001)
[TOP]

[1096]
AUTHOR:Maoka, T., Goto, Y., Isobe, K., Fujiwara, Y., Hashimoto, K. and Mochida, K.
TITLE:Antioxidative activity of capsorubin and related compounds from paprika (Capsicum annuum)
JOURNAL:J. Oleo Science
VOL:50 PAGE : 663 -665 (2001)
[TOP]

[1097]
AUTHOR:Murakami, A., Nakashima, M., Koshiba, T., Maoka, T., Nishino, H., Yano, M., Sumida, T., Kim, O. K., Koshimizu, K., and Ohigashi, H.
TITLE:Modifying effects of carotenoids on superoxide and nitric oxide generation from stimulated leukocytes PubMed ID:10737715
JOURNAL:Cancer Lett.
VOL:149 PAGE : 115-123 (2000)
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[1271]
AUTHOR:Hornero-Mendez, D., Costa-Garcia, J., and Minguez-Mosquera, M. I.
TITLE:Characterization of carotenoid high-producing Capsicum annuum cultivars selected for paprika production PubMed ID:12236703
JOURNAL:J Agric Food Chem.
VOL:50 PAGE : 5711-5716 (2002)
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