Formation mechanism of an inclusion complex of lenthionine with α-cyclodextrin and enhancement of its bioavailability

1,2,3,5,6-Pentathiepane (lenthionine) is a cyclic polysulphur compound that contributes to the distinctive flavour of shiitake mushrooms (Lentinula edodes) and inhibits platelet aggregation. However, its volatile hydrophobic characteristics present a challenge for its use in food applications. In this study, lenthionine was complexed with α-cyclodextrin (α-CD) to enhance its stability and bioavailability. The inclusion ratio of lenthionine with α-CD was 1:2. The formation of a stable inclusion complex was confirmed through diffusion order spectroscopy (DOSY) and proton nuclear magnetic resonance (¹H NMR) analyses. The inclusion of lenthionine in α-CD markedly suppressed its release. In vivo experiments demonstrated that the lenthionine/α-CD inclusion complex exhibited a more rapid and pronounced inhibitory effect on platelet aggregation than lenthionine alone. These findings indicate that inclusion of lenthionine in α-CD simultaneously mitigates its flavour and enhances its bioavailability, thereby expanding its potential for application in functional foods and pharmaceuticals.