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Uncovering Hericenones from the Fruiting Bodies of Hericium erinaceus through Interdisciplinary Collaboration

Uncovering Hericenones from the Fruiting Bodies of Hericium erinaceus through Interdisciplinary Collaboration

Hericium erinaceus is an edible and medicinal mushroom. Previously, we found hericenones C-H from the fruiting bodies and erinacines A-I from the mycelia of the fungus. These compounds stimulated nerve growth factor (NGF) synthesis both in vitro and in vivo; some have been suggested to be effective in the prevention and treatment of dementia. Recently, the total synthesis of hericenones C-H and their derivatives has been reported by us. We considered that the chemical synthetic route would also be reasonable as a biosynthetic pathway of the compounds. Based on the hypothesis, we investigated the endogenous existence of synthetic intermediates and products of the chemical synthesis in the fruiting bodies. The n-hexane soluble part of the fruiting bodies of H. erinaceus was fractionated, and all the fractions were subjected to product ion scan and multiple reaction monitoring (MRM) analysis by LC-MS/MS and compared to the authentic synthesized compounds. The analysis proved the endogenous existence of not only byproducts and intermediate produced in the synthetic study but also the dehydrated form of hericenone Z or the chromane derivative. Eventually, the dehydrated form was elucidated to be (Z)-form of the dehydrated hericenone Z by cooperation of synthesis and analysis, and a plausible biosynthetic pathway was proposed. This research approach will be useful not only for discovering new natural products and elucidating their biosynthetic pathways, but also for analyzing extremely trace components contained in organisms in nature.

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