Total Synthesis of Isohericerinol A and Its Analogues to Access Their Potential Neurotrophic Effects

Abstract

The secondary metabolites from Hericium erinaceus are well-known to have neurotrophic and neuroprotective effects. Isohericerinol A (1), isolated by our colleagues from its fruiting parts has a strong ability to increase the nerve growth factor secretion in C6 glioma cells. The current work describes the total synthesis of 1 and its regioisomer 5 in a few steps. We present two different approaches to 1 and a regiodivergent approach for both 1 and 5 by utilizing easily accessible feedstocks. Interestingly, the natural product 1, regioisomer 5, and their intermediates exhibited potent neurotrophic activity in in vitro experimental systems. Thus, these synthetic strategies provide access to a systematic structure–activity relationship study of natural product 1.

Multiple Metabolites Derived from Mushrooms and Their Beneficial Effect on Alzheimer’s Diseases

“…Additionally, there have been reports on the ability of other mushroom alkaloids, such as ganocochlearine A, infractopicrin, and 10-hydroxy-infractopicrin, to alleviate NDs [ 221 , 222 ]. Because of the neuroprotective potential of these compounds, the synthesis of isohericerinol, dictyoquinazol, and related derivatives has been continuously explored [ 223 , 224 ]. However, mushrooms remain the main sources of these compounds, and it is particularly important to explore their neuroprotective mechanisms in vivo.…”