Improvement of Antifungal Activity of 10-Undecyn-1-ol by Inclusion Complexation with Cyclodextrin Derivatives

• Published in: Journal of agricultural and food chemistry 2008-05, Vol.56 (10), p.3699-3705
• Main Authors: Neoh, Tze Loon, Tanimoto, Takahiro, Ikefuji, Shuichi, Yoshii, Hidefumi, Furuta, Takeshi
• Format: Article
• Language: English
• Subjects: 10-undecyn-1-ol; antifungal activity; Biological and medical sciences; Crop and Animal Protection Chemistry; Cyclodextrin derivative; Cyclodextrins - chemistry; Cyclodextrins - pharmacology; Drug Stability; Fatty Alcohols - analysis; Food industries; Fundamental and applied biological sciences. Psychology; Fungicides, Industrial - chemistry; Fungicides, Industrial - pharmacology; inclusion complex; Mycelium - drug effects; Mycelium - growth & development; Rosellinia necatix; Solubility; Structure-Activity Relationship; Xylariales - drug effects; Xylariales - growth & development
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf0731898

The inclusion complexation behavior between 10-undecyn-1-ol and cyclodextrin (CD) derivatives, namely, randomly methylated β-CD (RM-β-CD) and hydroxypropyl-β-CD (HP-β-CD), was studied in terms of solubility improvement, apparent stability constant, and the inclusion ratios of the resultant inclusion complexes. The aqueous solubility of 10-undecyn-1-ol was greatly improved through complexation with the CD derivatives. RM-β-CD is comparatively more efficient in solubilizing 10-undecyn-1-ol with an apparent stability constant outstripping that of HP-β-CD by about an order of magnitude. Comparative in vitro evaluations of the growth inhibition effects of inclusion complex solutions toward Rosellinia necatrix, a phytopathogenic fungus, were performed. In comparison with the positive control, appreciable improvements of the antifungal activity of 10-undecyn-1-ol through the addition of CD derivatives were observed visually. The improvement was evaluated in terms of area covered by the mycelia of Rosellinia necatrix and their growth rate. RM-β-CD was proven to be more effective compared to HP-β-CD with regard to the reduction of both fungal mycelium-covered area and growth rate constant, presumably owing to greater solubility enhancement by RM-β-CD and thus the bioavailability of 10-undecyn-1-ol. Inclusion complexation of 10-undecyn-1-ol with CD derivatives suggests a potential means for production of an environmentally friendly 10-undecyn-1-ol-based fungicide to counteract R. necatrix.