Biological evaluation of curcumin and related diarylheptanoids.
Nine derivatives of three natural diarylheptanoids, curcumin, demethoxycurcumin and bisdemethoxycurcumin, were prepared. Their antioxidant, free radical scavenging, nitric oxide (NO) inhibitory and cytotoxic activities were evaluated and compared with those of the respective natural compounds. Curcumin (1), demethoxycurcumin (2), demethyldemethoxy-curcumin (C3), diacetyldemethoxycurcumin (AC2) and triacetyldemethylcurcumin (AC5) exhibited higher antioxidant activity than quercetin while products from demethylation of 1 and 2 exhibited higher free radical scavenging activity. Compounds AC2 and AC5 were found to be most active in inhibiting breast cancer cells (MCF-7) proliferation with IC50 values of 6.7 and 3.6 microM, respectively. The activity of AC2 is almost doubled and of AC5 almost tripled as compared to curcumin. Their selectivity towards different cell lines is also more noticeable. Compounds AC2 and AC5 also showed increased activity against a human prostate cancer cell line (DU-145) and non-small lung cancer cell line (NCI-H460) with IC50 values of 20.4, 16.3 and 18.3, 10.7 microM, respectively.
Abas
Faridah
F
Laboratory of Natural Products, Institute of Bioscience, University Putra Malaysia, 43400 Serdang, Selangor, Malaysia.
Hui
Lim Siang
LS
Ahmad
Syahida
S
Stanslas
Johnson
J
Israf
D A
DA
Shaari
Khozirah
K
Lajis
Nordin H
NH
D000975:Antioxidants / Q000302:isolation & purification / Q000494:pharmacology; D002845:Chromatography; D002855:Chromatography, Thin Layer; D003474:Curcumin / Q000737:chemistry / Q000302:isolation & purification*; D036381:Diarylheptanoids / Q000737:chemistry / Q000302:isolation & purification*; D016166:Free Radical Scavengers; D015394:Molecular Structure; D011794:Quercetin / Q000737:chemistry / Q000302:isolation & purification
D000975:Antioxidants; D036381:Diarylheptanoids; D016166:Free Radical Scavengers; D011794:Quercetin; D003474:Curcumin