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Chemical Compound Review:

Cnicin [(1R,2S,10R)-8- (hydroxymethyl)-4-methyl- 13...

Synonyms: AG-E-72503, CTK8F8750, 24394-09-0

Meepagala, K.M. et al., Bruno, M. et al., Bachelier, A. et al., Barrero, A.F. et al.

Meepagala, Osbrink, Sturtz, Lax, Barrero, Oltra, Morales, Alvarez, Rodríguez-García,

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High impact information on C09362

Aerial parts of Centaurea napifolia furnished the sesquiterpene lactones cnicin, 4'-acetoxycnicin, melitensin, dehydromelitensin, two known esters of dehydromelitensin, lappaol and a lappaol isomer, and a 1,2-diacylated glucose [1].
Judging from the structure-activity relationships, we conclude that the unsaturated ester side chain of cynaropicrin and cnicin is of particular importance for the inhibition of MurA [2].
Biomimetic cyclization of cnicin to malacitanolide, a cytotoxic eudesmanolide from Centaurea malacitana [3].

Analytical, diagnostic and therapeutic context of C09362

Among the natural products tested, vulgarone B (isolated from Artemisia douglasiana Besser), apiol (isolated from Ligusticum hultenii (Fern.) Calder & Taylor) and cnicin (isolated from Centaurea maculosa Lam.) exhibited significantly higher mortalities than in untreated controls in laboratory bioassay [4].

References

Sesquiterpene lactones and other constituents of Centaurea napifolia. Bruno, M., Fazio, C., Paternostro, M.P., Díaz, J.G., Herz, W. Planta Med. (1995) [Pubmed]
Sesquiterpene lactones are potent and irreversible inhibitors of the antibacterial target enzyme MurA. Bachelier, A., Mayer, R., Klein, C.D. Bioorg. Med. Chem. Lett. (2006) [Pubmed]
Biomimetic cyclization of cnicin to malacitanolide, a cytotoxic eudesmanolide from Centaurea malacitana. Barrero, A.F., Oltra, J.E., Morales, V., Alvarez, M., Rodríguez-García, I. J. Nat. Prod. (1997) [Pubmed]
Plant-derived natural products exhibiting activity against formosan subterranean termites (Coptotermes formosanus). Meepagala, K.M., Osbrink, W., Sturtz, G., Lax, A. Pest Manag. Sci. (2006) [Pubmed]

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