PMID- 10418962
OWN - NLM
STAT- MEDLINE
DCOM- 19990804
LR  - 20220405
IS  - 0009-2797 (Print)
IS  - 0009-2797 (Linking)
VI  - 121
IP  - 2
DP  - 1999 Jul 1
TI  - Pro-oxidant, anti-oxidant and cleavage activities on DNA of curcumin and its 
      derivatives demethoxycurcumin and bisdemethoxycurcumin.
PG  - 161-75
AB  - Curcumin, a naturally occurring phytochemical responsible for the colour of 
      turmeric shows a wide range of pharmacological properties including antioxidant, 
      anti-inflammatory and anti-cancer effects. We have earlier shown that curcumin in 
      the presence of Cu(II) causes strand cleavage in DNA through generation of 
      reactive oxygen species, particularly the hydroxyl radical. Thus, curcumin shows 
      both antioxidant as well as pro-oxidant effects. In order to understand the 
      chemical basis of various biological properties of curcumin, we have studied the 
      structure-activity relationship between curcumin and its two naturally occurring 
      derivatives namely demethoxycurcumin (dmC) and bisdemethoxycurcumin (bdmC). 
      Curcumin was found to be the most effective in the DNA cleavage reaction and a 
      reducer of Cu(II) followed by dmC and bdmC. The rate of formation of hydroxyl 
      radicals by the three curcuminoids also showed a similar pattern. The relative 
      antioxidant activity was examined by studying the effect of these curcuminoids on 
      cleavage of plasmid DNA by Fe(II)-EDTA system (hydroxyl radicals) and the 
      generation of singlet oxygen by riboflavin. The results indicate that curcumin is 
      considerably more active both as an antioxidant as well as an oxidative DNA 
      cleaving agent. The DNA cleavage activity is the consequence of binding of Cu(II) 
      to various sites on the curcumin molecule. Based on the present results, we 
      propose three binding sites for Cu(II). Two of the sites are provided by the 
      phenolic and methoxy groups on the two benzene rings and the third site is due to 
      the presence of 1,3-diketone system between the rings. Furthermore, both the 
      antioxidant as well as pro-oxidant effects of curcuminoids are determined by the 
      same structural moieties.
FAU - Ahsan, H
AU  - Ahsan H
AD  - Department of Biochemistry, Faculty of Life Sciences, Aligarh Muslim University, 
      India.
FAU - Parveen, N
AU  - Parveen N
FAU - Khan, N U
AU  - Khan NU
FAU - Hadi, S M
AU  - Hadi SM
LA  - eng
PT  - Journal Article
PL  - Ireland
TA  - Chem Biol Interact
JT  - Chemico-biological interactions
JID - 0227276
RN  - 0 (Antioxidants)
RN  - 0 (Coumaric Acids)
RN  - 0 (DNA, Superhelical)
RN  - 0 (DNA, Viral)
RN  - 0 (Diarylheptanoids)
RN  - 2EFO1BP34R (bisdemethoxycurcumin)
RN  - 3352-57-6 (Hydroxyl Radical)
RN  - 789U1901C5 (Copper)
RN  - IT942ZTH98 (Curcumin)
RN  - S88TT14065 (Oxygen)
RN  - W2F8059T80 (demethoxycurcumin)
SB  - IM
MH  - Animals
MH  - Antioxidants/chemistry/*pharmacology
MH  - Cattle
MH  - Copper/chemistry/metabolism
MH  - Coumaric Acids/chemistry/*pharmacology
MH  - Curcumin/*analogs & derivatives/chemistry/*pharmacology
MH  - DNA, Superhelical/*drug effects/metabolism
MH  - DNA, Viral/drug effects/metabolism
MH  - Diarylheptanoids
MH  - Electrophoresis, Agar Gel
MH  - Hydroxyl Radical/metabolism
MH  - Oxidation-Reduction
MH  - Oxygen/metabolism
MH  - Plasmids/genetics
MH  - Structure-Activity Relationship
EDAT- 1999/07/27 00:00
MHDA- 1999/07/27 00:01
CRDT- 1999/07/27 00:00
PHST- 1999/07/27 00:00 [pubmed]
PHST- 1999/07/27 00:01 [medline]
PHST- 1999/07/27 00:00 [entrez]
AID - S0009-2797(99)00096-4 [pii]
AID - 10.1016/s0009-2797(99)00096-4 [doi]
PST - ppublish
SO  - Chem Biol Interact. 1999 Jul 1;121(2):161-75. doi: 10.1016/s0009-2797(99)00096-4.