Everything about Curcumin totally explained
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Curcumin is the principal curcuminoid of the Indian curry spice
turmeric, the other two
curcuminoids being
demethoxycurcumin and
Bis-demethoxycurcumin. The curcuminoids are
polyphenols and are responsible for the yellow color of
turmeric. Curcumin can exist in at least two
tautomeric forms,
keto and
enol. The enol form is more energetically stable in the solid phase and in solution. It is also
hepatoprotective.
Curcumin can be used for boron quantification in the so-called curcumin method. It reacts with
boric acid forming a red colored compound, known as
rosocyanine.
Since curcumin is brightly colored, it may be used as a
food coloring. As a
food additive, its
E number is
E100.
Chemistry
Curcumin incorporates several functional groups. The aromatic ring systems, which are
polyphenols are connected by two α,β-unsaturated
carbonyl groups. The two carbonyl groups form a
diketone. The diketone form stable
enols or are easily deprotonated and form enolates, while the α,β-unsaturated carbonyl is a good
Michael acceptor and undergoes
nucleophilic addition.
Potential medical uses
Curcumin is known for its
antitumor,
antioxidant,
antiarthritic,
anti-amyloid and
anti-inflammatory properties. Anti-inflammatory properties may be due to inhibition of
eicosanoid biosynthesis. In addition it may be effective in treating
malaria, prevention of
cervical cancer, and may interefere with the replication of the
HIV virus. In HIV, it appears to act by interfering with
P300/CREB-binding protein (CBP).
A 2008 study at
Michigan State University showed that low concentrations of curcumin interfere with
Herpes simplex virus-1 (HSV-1) replication. The same study showed that curcumin inhibited the recruitment of
RNA polymerase II to viral DNA, thus inhibiting the
transcription of the viral DNA.
Curcumin acts as a free radical scavenger and antioxidant, inhibiting
lipid peroxidation and oxidative DNA damage. Curcuminoids induce
glutathione S-transferase and are potent inhibitors of
cytochrome P450.
For the last few decades, extensive work has been done to establish the biological activities and pharmacological actions of curcumin. Its anticancer effects stem from its ability to induce
apoptosis in cancer cells without cytotoxic effects on healthy cells. Curcumin can interfere with the activity of the transcription factor
NF-κB, which has been linked to a number of inflammatory diseases such as
cancer. Indeed, when 0.2% curcumin is added to diet given to rats or mice previously given a carcinogen, it significantly reduces colon carcinogenesis (Data from sixteen scientific articles reported in the
Chemoprevention Database
). A 2007 report indicates that curcumin may suppress
MDM2, an
oncogene involved in mechanisms of
malignant tumor formation.
A 2004 UCLA-Veterans Affairs study involving genetically altered mice suggests that curcumin might inhibit the accumulation of destructive beta-amyloid in the brains of
Alzheimer's disease patients and also break up existing plaques associated with the disease.
There is also circumstantial evidence that curcumin improves mental functions; a survey of 1010 Asian people who ate
yellow curry and were between the ages of 60 and 93 showed that those who ate the sauce "once every six months" or more had higher
MMSE results than those who did not. From a scientific standpoint, though, this doesn't show whether the curry caused it, or people who had healthy habits also tended to eat the curry, or some completely different relationship.
Numerous studies have demonstrated that curcumin, amongst only a few other things such as high impact exercise, learning, bright light, and antidepressant usage, has a positive affect on neurogenesis in the
hippocampus and concentrations of
Brain-derived neurotrophic factor (BDNF), both of which reductions in are associated with stress, depression, and anxiety. et al.
Little curcumin, when eaten, is absorbed 2 to 10 grams of curcumin alone resulted in undetectable to very low serum levels. Curcumin is unstable in the gut, and the traces that pass through the GI tract rapidly degrades or is conjugated through
glucuronidation. Co-supplementation with 20 mg of
piperine (extracted from black pepper) significantly increased the absorption of curcumin by 2000% in a study funded by a prominent manufacturer of piperine) has been synthesized which has the potential to bypass many of the shortcomings associated with free curcumin, such as poor solubility and poor systemic bioavailability. Nanocurcumin particles have a size of less than 100 nanometers on average, and demonstrate comparable to superior efficacy compared to free curcumin in human cancer cell line models. At this point no supplements are available on the market in this form.
Risks and Side Effects
Kawanishi et al. (2005) of NCBI remarked that curcumin, like many antioxidants, can be a "double-edged sword" where in the test tube, anti-cancer and antioxidant effects may be seen in addition to pro-oxidant effects. Carcinogenic effects are inferred from interference with the
p53 tumor suppressor pathway, an important factor in human
colon cancer. Carcinogenic and
LD50 tests in mice and rats, however, have failed to establish a relationship between tumorogenesis and administration of curcumin in turmeric
oleoresin at >98% concentrations.
This may prove curcumin medicinally useful as it helps activate
p53. When a cell is inhibited by cancer the concentrations of p53 increase, helping cells defend against cancer mechanisms. But it may also suppress p53 levels, preventing cells from initiating defensive mechanisms, a response seen only in certain diseases .
Clinical studies in humans with high doses (>2-12 grams) curcumin supplementation have shown some subjects reporting diarrhea and nausea, however curcumin has also been indicated for these conditions as well.
Curcumin Analogs:
S. Mishra et al. have synthesized various conjugates of curcumin. And it was found that curcumin bioconjugates containing glycine, alanine, and/or piperic acid were found to show improved antimicrobial properties over curcumin, suggesting increased cellular uptake or reduced metabolism of these bioconjugates resulting in increased concentration inside the infected cells. Study of pro- and anti-oxidant properties of different bioconjugates of curcumin and testing their apoptotic potential on tumor cells. Various curcumin based natural antimalarial agent’s viz. pyrazole, isoxazole, substituted pyrazole and Knoevenagel condensates of curcumin have been designed and synthesized. It was found that some of the curcumin analogs showed better activity (in nanomolar range) as compared to the parent molecule against malarial parasite; P. falciparum.
Further Information
Get more info on 'Curcumin'.
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