Curcumin derivatives

Chen X, Hasuma T, Yano Y, Yoshimata T, Morishima Y, Wang Y, Otani S. 1997. Inhibition of farnesyl protein transferase by monoterpene, curcumin derivatives and gallotannin. Anticancer Res 17 2555-2564. 

Shim JS, Lee J, Park HJ, Park SJ, Kwon HJ. 2004. A new curcumin derivative, HBC, interferes with the cell cycle progression of colon cancer cells via antagonization of the Ca2 + /calmodulin function. Chem Biol 11 1455-1463. 

Tong QS, Zheng LD, Lu P, Jiang FC, Chen FM, Zeng FQ, Wang L, Dong JH. 2006. Apoptosis-inducing effects of curcumin derivatives in human bladder cancer cells. 

Dutta S, Murugkar A, Gandhe N, Padhye S. 2001. Enhanced antioxidant activities of metal conjugates of curcumin derivatives. Met Based Drugs 8 183-188. 

S. Curcumin Derived from Turmeric (Curcuma longa) ... 

Another synthesis of curcumin from acetyl acetone and vanillin was reported earlier by Pabon (1964), which gave an 80% yield of curcumin. Starting with other related aldehydes, curcumin derivatives and related compounds are also obtained. The synthesis by this method has been used recently in biosynthetic studies (Roughley and Whiting, 1973). 

Reactive oxygen species inhibitors consisting of curcumin derivatives, (IV), were prepared by Pandol (4) and are used in treating inflammation disorders associated with pancreatitis. 

Gorman AA, Hamblett VS, Srinivasan VS, Wood PD. (1994) Curcumin derived transients A pulsed laser and pulse radiolysis study. Photo chem Photobiol 59 389-398. 

Curcumin, as well as compounds 40-43 were also isolated from C. xanthorrhiza by Uehara et a/. (29), who obtained from this source also two new compounds, the optically active diol (5,5)-45 and the racemic diketoalcohol 46. While formation of 45 can be envisaged by reduction of hexahydrocurcumin, racemic 46 might have been the result of addition of water onto the double bond of curcumin. Masuda and his coworkers reported in 1992 the isolation of an unsymmetrical curcumin derivative, 5-methoxycurcumin (47) from C. xanthorrhiza (40). 

Table 1. Curcumin derivatives tested in an anti-inflammatory bioassay [13]...

Curcumin Derived from Turmerie (Curcuma longa) a Spiee for All Seasons... 

The transcription of HIV-1 provims is regulated by both cellttlar and viral factors. Various pieces of evidence suggest that Tat protein secreted by HlVl-irrfected cells may have additional activity in the pathogenesis of AIDS because of its ability to also be taken up by noninfected cells. Barthelemy et al. " showed that curcumin used at 10 to lOOnAT inhibited Tat transactivation of HlVl-LTR lacZ by 70 to 80% in HeLa cells. To develop more efficient curcumin derivatives, the researchers synthesized and tested in the same experimental system the inhibitory activity of reduced curcumin (Cl), which lacks the spatial stracture of curcumin allyl-curcumin (C2), which possesses a condensed allyl derivative on curcumin that plays the role of metal chelator and tocopherylcurcumin (C3), whose stmctural alterations enhance the antioxidant activity of the molecule. Results obtained with the Cl, C2, and C3 curcumin derivatives showed a significant inhibition (70 to 85%) of Tat transactivation. Despite the fact that tocopheryl-curcumin (C3) failed to scavenge 0 , this curcumin derivative exhibited the most activity 70% inhibition was obtained at InM, while only 35% inhibition was obtained with the curcumin. 

Barthelemy, S., Vergnes, L., Moynier, M., Guyot, D., Labidalle, S., and Bahraoui, E., Curcumin and curcumin derivatives inhibit Tat-mediated transactivation of type 1 human immunodeficiency virus long terminal repeat. Res. Virol, 149 (1), 43-52,1998. 

Kumar, A.P., Garcia, G.E., Ghosh, R., Rajnarayanan, R.V., Alworth, W.L., and Slaga, T.J., 4-Hydroxy-3-methoxybenzoic acid methyl ester a curcumin derivative targets Akt/NF kappa B cell survival signaling pathway potential for prostate cancer management. Neoplasia, 5 (3), 255-266, 2003. 

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