Affiliation:
1. Department of Oils, Oleochemicals and Surfactants Technology, Institute of Chemical Technology, Nathalal Parekh Marg,
Matunga (East), Mumbai- 400 019, India
Abstract
Abstract:
Curcumin with medicinal value should possess good bioavailability and stability. Unfortunately,
the bioavailability of curcumin is less, and its stability depends on the medium. After intake
of curcumin, it undergoes metabolism to form metabolites, which are bioactive and show better bioavailability
than curcumin. Hence, the disadvantages of curcumin can be overcome by the formation
of its synthetic derivative. In this review paper, the derivatives of curcumin, namely tetrahydrocurcumin,
hexahydrocurcumin, octahydrocurcumin, deketene curcumin, and dimethoxycurcumin are
discussed. The diketo group, diene moiety, and ortho-methoxy phenolic groups present in curcumin
influence its properties. Curcumin undergoes degradation in alkaline and non-polar mediums, mainly
because of its property to exhibit keto-enol tautomerism, which is further enhanced due to the presence
of diene moiety and ortho-methoxy phenolic groups. If the keto-enol tautomerism is inhibited
by its derivatization, then its stability is improved. This is especially true in the case of hexahydrocurcumin,
octahydrocurcumin, and deketene curcumin, which do not possess an active methylene
group. Although tetrahydrocurcumin undergoes keto-enol tautomerism, the degradation of enol tautomer
is prevented due to the absence of diene moiety. The activities of curcumin are medium dependent,
whereas the activities of hydrogenated derivatives of curcumin and deketene curcumin are
medium independent. Dimethoxycurcumin exhibits keto-enol tautomerism and can undergo degradation
in alkaline and non-polar mediums at a faster rate than curcumin. The reason is that the strong
activating hydroxyl groups in curcumin are replaced by a stronger activating methoxy group in dimethoxycurcumin.
On the other hand, in acidic and polar mediums, the rate of beneficial activities
of dimethoxycurcumin is more than curcumin. Also, the bioavailability of the above-mentioned derivatives
of curcumin is more than curcumin.
Publisher
Bentham Science Publishers Ltd.
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