Curcuminoids



Curcumin [1]
IUPAC name (1E,6E)-1,7-bis(4-hydroxy-
3-methoxyphenyl)-1,6-
heptadiene-3,5-dione
Other names curcumin
diferuloylmethane
C.I. 75300
Natural Yellow 3
Identifiers
CAS number 458-37-7
SMILES Oc1ccc(cc1OC)/C=C/C(=O)CC(=O)/C= C/c2ccc(O)c(OC)c2
Properties
Molecular formula C21H20O6
Molar mass 368.38 g/mol
Appearance Bright Yellow
to Orange powder
Melting point

183°C

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references
Demethoxycurcumin [1]
IUPAC name 1,6-Heptadiene-3,5-dione,
1-(4-hydroxy-3-methoxyphenyl)
-7-(4-hydroxyphenyl)
Other names 4-hydroxycinnamoyl(feroyl)
methane, curcumin II, BHCFM
Identifiers
CAS number 24939-17-1
SMILES C(=C\C(CC(\C=C\c1ccc(cc1)O)=O)=O)\c1cc(c(cc1)O)OC
Properties
Molecular formula C20H18O5
Molar mass 338.35 g/mol
Appearance Yellow powder
Melting point

172 º C

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references
Bisdemethoxycurcumin [1]
IUPAC name (1E,6E)-1,7-bis(4-hydroxy
phenyl)hepta-1,6-diene-
3,5-dione
Other names Bis(4-hydroxycinnamoyl)methane, BHCMT
Identifiers
CAS number 24939-16-0
SMILES C(=C\C(CC(\C=C\c1ccc(cc1)O)=O)=O)\c1ccc(cc1)O
Properties
Molecular formula C19H16O4
Molar mass 308.33 g/mol
Appearance Yellow powder
Melting point

222 º C

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Curcuminoids are yellow color. Many substituents on the phenyl groups.[3] Now there is an increasing demand for demethoxycurcumin and (curcuminoids) because of their recently discovered biological activity.[4]

Cyclodextrins

Curcurminoids form a more stable complex with solutions which contain covalent bonds are synthesized between the cyclodextrins and the curcuminoids so they are easily released from the complex.[3]

Micelles and nanoparticles

A drug design with curcuminoids in complex with solvent where the headgroups of the micelles interact with the solvent. Curcuminoids as loaded microemulsion technique. The loading capacity, the mean particle size and size distribution are all factors that have to be considered when the effects of curcuminoids in different strength are observed because it could variate.[3] The advantages of SLN are the possibilities of controlled drug release and drug targeting, protection of incorporated compound against chemical degradation, no biotoxicity of the carrier, avoidance of organic solvent and no problems with respect to large scale production.[3] In vitro studies show a prolonged release of curcuminoids from the nanoparticle preparate up to 12 hours and the curcuminoids maintained their physical and chemical stability after 6 months of storage in the absence of formulation of curcuminoids in SLN.[3]

SLN in cosmetics

SLN preparate has been developed for cosmetics where the curcuminoids are used in cream base. But there are some stability issues which have not been overcome yet, further studies need to be done to find a suitable formulation which can be carried out in order to prolong the stability of the curcuminoids. Nevertheless there have been improvements in formulation of some stable model cream preparations with SLN curcuminoids.[3] It is suggested that most of the curcuminoids are incorporated at the SLN surface where they are diffused into the cream matrix until a steady state is reached. At this state the curcuminoids go from the cream to the dissolution medium. A possible burst release in creams containing curcuminoids have been reported where the curcuminoids are rapidly released in a sufficient amount from the cream into the skin and is followed by a controlled release.[3] When SNL are prepared by microemulsion at a temperature with the range of 70-75scan they had a spherical shape and smooth surface.[3] It has been reported that increasing the lipid content over 5-10%(w/w) increased the mean particle size and broader size distribution in most common cases. That range should there for be ideal concentration for formulation of the SNL.[3]

Incorporation of SLN

Incorporation is one thing that needs to be considered in formulation of SNL. Concentration of the lipid, adsorb all the surfactant and co-surfactant molecules, and a formation of curcuminoids solution micelles will be created. This will then increase the water solubility of the curcuminoids and they could partition from the SNL into the micelles that were formed during a wash procedure. This will reduce the final incorporation efficacy on the surface of the SLN.[3]

Anti-oxidant activity

The curcumin derivatives demethoxycurcumin and bisdemethoxycurcumin have, like curcurmin itself been tested for their hydroxyl radicals. It was concluded that the derivatives of curcumin are good in trapping the 2,2-diphenyl-1-picryhydrazyl(DPPH) radical as efficiently as curcumin which is a well known antioxidant.[4]

Anti-inflammatory activity

lipophilic and there for provide a better skin penetration which could be good for that kind of drug preparation.[4]

Carcinogenesis activity

Studies suggest that the bioavailability of curcumin and possibly its derivatives is greatest in the colon. The tissue in the gastrointestinal tract seems to be more exposed predominantly to apoptosis than curcumin. It is possible that the difference in apoptosis in vitro is connected to the degradation of the two chemicals and/or their stability.[3]

References

  1. ^ a b c Separation and determination of the physico-chemical characteristics of curcumin, demethoxycurcumin and bisdemethoxycurcumin. Author(s): L. Péret-Almeida, A.P.F. Cherubino, R.J. Alves, L. Dufossé and M.B.A. Glória. Source: Food Research International. Volume 38, Issues 8-9, October-November 2005, Pages 1039-1044. [1]
  2. ^ a b Studies on curcumin and curcuminoids XXXI. Symmetric and asymmetric curcuminoids: Stability, activity and complexation with cyclodextrin. Author(s): Tomren MA (Tomren, M. A.), Masson M (Masson, M.), Loftsson T (Loftsson, T.), Tonnesen HH (Tonnesen, H. Hjorth). Source: INTERNATIONAL JOURNAL OF PHARMACEUTICS 338 (1-2): 27-34 JUN 29 2007[2]
  3. ^ a b c d e f g h i j k l Formulation and characterization of curcuminoids loaded solid lipid nanoparticles. Author(s): Tiyaboonchai W (Tiyaboonchai, Waree), Tunpradit W (Tunpradit, Watcharaphorn), Plianbangchang P (Plianbangchang, Pinyupa). Source: INTERNATIONAL JOURNAL OF PHARMACEUTICS 337 (1-2): 299-306 JUN 7 2007[3]
  4. ^ a b c d e f g h i j Antioxidant activities of curcumin, demethoxycurcumin and bisdemethoxycurcumin. Author(s): Jayaprakasha GK, Rao LJ, Sakariah KK Source: FOOD CHEMISTRY 98 (4): 720-724 2006[4]
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Curcuminoids". A list of authors is available in Wikipedia.