The interaction of cyclodextrins (CDs) with L-alpha-dipalmitoyl phopsatidyl choline (DPPC), L-alpha-distearoyl phosphatidyl choline (DSPC), and L-alpha-dimyristoyl phosphatidyl choline (DMPC) unilamellar liposomes was investigated by the leakage of carboxylfluorescein (CF) entrapped in the inner aqueous phase of liposomes, at 25 degrees C (DPPC and DSPC liposomes) and at 5 degrees C (DMPC liposomes). The efficiency of CDs for CF leakage was remarkable in the order of heptakis (2,6-di-O-methyl)-beta-CD (DOM-beta-CD) > alpha-CD > heptakis (2,3,6-tri-O-methy)-beta-CD (TOM-beta-CD) from DPPC liposomes, in the order of DOM-beta-CD > TOM-beta-CD > alpha-CD from DSPC liposomes and in the order of alpha-CD > DOM-beta-CD > TOM-beta-CD from DMPC liposomes. The other CDs used in the present studies, beta-CD, 2-hydroxylpropyl beta-CD, and gamma-CD scarcely induced the CF leakage from above the three liposomes. From the profiles of % CF leakage, together with measurements of differential scanning calorimetry, it was found that hydrophobic DOM-beta-CD penetrates the matrix of the liposomes to interact with them as well as TOM-beta-CD, and that less hydrophobic alpha-CD exists at the surface of the membrane to interact with the liposomes. Further, it was found that the interaction of CDs with liposomes changes depending not only on the length of fatty acid chain of phospholipid (condensation force and hydrophobicity) but also the hydrophobicity and the cavity size of CD.

The interaction of cyclodextrins (CDs) with dipalmitoylphosphatidylcholine (DPPC) liposomes has been studied using differential scanning calorimetry (DSC). The phase transition temperature and the enthalpy change due to the gel-to-liquid crystalline phase transition of the liposomes were measured in the presence of alpha-CD, beta-CD, gamma-CD, heptakis (2,6-di-O-methyl)-beta-CD (DOM-beta-CD), heptakis (2,3,6-tri-O-methyl)-beta-CD (TOM-beta-CD) and 2-hydroxylpropyl beta-CD, respectively. The effects on the change of enthalpy of the transition temperature were remarkable in the order of DOM-beta-CD > alpha-CD > TOM-beta-CD. The residual CDs caused scarcely detectable changes in the enthalpy changes and the transition temperatures. In order to clarify the DSC curves in the presence of the CDs mentioned above, the type of interactions which occurred between CDs and DPPC liposomes were studied. Consequently, it was found that DOM-beta-CD forms a soluble complex and alpha-CD forms an insoluble complex with DPPC liposomes, whereas only a slight amount of TOM-beta-CD was suggested to penetrate the matrix of the liposomes.

The sesquiterpene lactones cynaropicrin and cnicin are isolated from artichoke (Cynara scolymus) and blessed thistle (Cnicus benedictus), respectively. These natural products exhibit several biological activities, including inhibitory activity against Trypanosoma brucei, which causes human African trypanosomiasis (HAT; sleeping sickness). The present study describes a novel ionic liquid-assisted plant extraction and isolation method for cynaropicrin and cnicin using centrifugation and decantation techniques. The results showed that the extraction yield of cynaropicrin and cnicin using 1-ethyl-3-methylimidazolium methylphosphonate ([C 2 mim][(MeO)(H)PO 2 ])/acetone (1:1) was 1.9 and 1.4 times higher than that obtained using only acetone, respectively. The proposed extraction and isolation method will enable the acquisition of other natural products from medicinal plants.

The polymethoxyflavonoids nobiletin and tangeretin are isolated from peels of shekwasha (Citrus depressa Hayata) and ponkan (Citrus reticulata Blanco). These natural products possess biological activities, including anticancer and anti-inflammation properties. This report describes an efficient method for the extraction and isolation of nobiletin and tangeretin from citrus peels using 1-ethyl-3-methylimidazolium methylphosphonate ([C 2 mim][(MeO)(H)PO 2 ]) and centrifugation/decantation. The results showed that the extraction yield of nobiletin and tangeretin using [C 2 mim][(MeO)(H)PO 2 ]/organic solvent (1:1 w/w) was 1.4 to 1.6 times higher than that using organic solvent. This extraction method is expected to be applicable for obtaining other organic compounds from natural sources.