Encapsulation of isohexenylnaphthazarins in cyclodextrins.
Naturally occurring isohexenylnaphthazarins (IHN), such as Alkannin, Shikonin (A/S) and their derivatives, are potent pharmaceutical substances with a wide spectrum of biological activity. In the present study, inclusion complexes of alkannin and shikonin commercial samples and IHN derivatives in the form of an oily extract of Alkanna tinctoria roots were formed with beta-cyclodextrin (CD) and beta-HPCD. These complexes were investigated to evaluate the effect of complexation on their aqueous solubility, decoloration, and also the percentage of polymeric A/S and IHN derivatives enclosed in the CDs cavity, since these decrease the active monomeric IHN. Both beta-CD and beta-HPCD increased the aqueous solubility of A/S and IHN derivatives and thus inclusion complexes can be used as drug delivery systems for A/S in both internal (capsules, tablets) and external hydrophilic pharmaceutical and cosmetic preparations (creams, gels, sprays) with enhanced bioavailability. The inclusion complexes formed had a pale purple colour, contributing to the partial decoloration of the A/S and thus of the fi nal pharmaceutical preparations. Finally, CDs selectively included more monomeric and less polymeric IHN, compared with the initial each time sample that is encapsulated; thus inclusion complexes may present enhanced biological activity.
Assimopoulou
A N
AN
Organic Chemistry Laboratory, Department of Chemical Engineering, Aristotle University of Thessaloniki, 541 24 Thessaloniki, Greece.
Papageorgiou
V P
VP
D000073738:2-Hydroxypropyl-beta-cyclodextrin; D001682:Biological Availability; D002214:Capsules / Q000737:chemistry*; D002626:Chemistry, Pharmaceutical; D003505:Cyclodextrins / Q000737:chemistry*; D004304:Dosage Forms; D004337:Drug Carriers; D008854:Microscopy, Electron; D009285:Naphthoquinones / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry; D012995:Solubility; D047392:beta-Cyclodextrins / Q000737:chemistry
D002214:Capsules; D003505:Cyclodextrins; D004304:Dosage Forms; D004337:Drug Carriers; D009285:Naphthoquinones; D010936:Plant Extracts; D047392:beta-Cyclodextrins; C024720:isohexenylnaphthazarin; C018204:alkannin; D000073738:2-Hydroxypropyl-beta-cyclodextrin; C016101:shikonin; C031215:betadex