Analysis of the Enhanced Stability of R(+)-Alpha Lipoic Acid by the Complex Formation with Cyclodextrins

International Journal of Molecular Sciences

Naoko Ikuta²  Hironori Sugiyama²  Hiroshi Shimosegawa²  Rie Nakane²  Yoshiyuki Ishida¹  Yukiko Uekaji¹  Daisuke Nakata¹  Kathrin Pallauf³  Gerald Rimbach³  Keiji Terao¹ 

[1] CycloChem Bio Co., Ltd., KIBC654R 5-5-2 Minatojima-minamimachi Chuo-ku, Kobe 650-0047, Japan; E-Mails:;School of Natural Systems, College of Science and Engineering, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan; E-Mails:;Institute of Human Nutrition and Food Science, Christian Albrechts University, Kiel D-24118, Germany; E-Mails:

关键词: R(+)-alpha lipoic acid;    cyclodextrins;    particle distribution;    enhanced stability;    XRD analysis;    complex formation;   

DOI  :  10.3390/ijms14023639

来源: mdpi

【 摘 要 】

R(+)-alpha lipoic acid (RALA) is one of the cofactors for mitochondrial enzymes and, therefore, plays a central role in energy metabolism. RALA is unstable when exposed to low pH or heat, and therefore, it is difficult to use enantiopure RALA as a pharma- and nutra-ceutical. In this study, we have aimed to stabilize RALA through complex formation with cyclodextrins (CDs). α-CD, β-CD and γ-CD were used for the formation of these RALA-CD complexes. We confirmed the complex formation using differential scanning calorimetry and showed by using HPLC analysis that complexed RALA is more stable than free RALA when subjected to humidity and high temperature or acidic pH conditions. Scanning electron microscopy studies showed that the particle size and shape differed depending on the cyclodextrin used for complexation. Further, the complexes of CD and RALA showed a different particle size distribution pattern compared with that of CD itself or that of the physical mixture of RALA and CD.

【 授权许可】

CC BY   
© 2013 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland.