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Structure Database (LMSD)

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Common Name

Capsorubin

Systematic Name

(3S,5R,3'S,5'R)-3,3'-Dihydroxy-kappa,kappa-carotene-6,6'-dione

Synonyms

LM ID

LMPR01070048

Formula

C₄₀H₅₆O₄

Exact Mass

Calculate m/z

600.41786

Status

Curated

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Classification

Biological Context

Capsorubin is a carotenoid that has been found in C. annuum and has diverse biological activities.^1,2,3 It inhibits lipid peroxidation induced by 2,2’-azobis(2,4-dimethyl valeronitrile) (AMVN) in vitro when used at a concentration of 167 µM.¹ Capsorubin (1 µM) decreases UVB-induced formation of DNA strand breaks and apoptosis in isolated human dermal fibroblasts.² It also inhibits Epstein-Barr virus early antigen (EBV-EA) activation induced by phorbol 12-myristate 13-acetate (TPA), a marker of tumor formation, in Raji cells.

This information has been provided by Cayman Chemical

References

1. Maoka, T., Goto, Y., Isobe, K., et al. Antioxidative activity of capsorubin and related compounds from paprika (Capsicum annuum). J. Oleo Sci. 50(8), 663-665 (2001).

2. Fernández-García, E., Carvajal-Lérida, I., and Pérez-Gálvez, A. Carotenoids exclusively synthesized in red pepper (capsanthin and capsorubin) protect human dermal fibroblasts against UVB induced DNA damage. Photochem. Photobiol. Sci. 15(9), 1204-1211 (2016).

3. Maoka, T., Mochida, K., Kozuka, M., et al. Cancer chemopreventive activity of carotenoids in the fruits of red paprika Capsicum annuum L. Cancer Lett. 172(2), 103-109 (2001).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Capsicum annuum (#4072)

Magnoliopsida (#3398)

Carotenoids and related compounds. Part IX. The structures of capsanthin and capsorubin,
J Chem Soc, 1961

DOI: 10.1039/JR9610004019

String Representations

InChiKey (Click to copy)

GVOIABOMXKDDGU-YUURSNASSA-N

InChi (Click to copy)

InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-23-35(43)39(9)27-33(41)25-37(39,5)6)15-11-12-16-30(2)18-14-20-32(4)22-24-36(44)40(10)28-34(42)26-38(40,7)8/h11-24,33-34,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t33-,34-,39-,40-/m0/s1

SMILES (Click to copy)

C(/C([C@]1(C)C[C@@H](O)CC1(C)C)=O)=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C([C@]1(C)C[C@@H](O)CC1(C)C)=O