Hericene D

Secondary Metabolites from Hericium erinaceus and Their Anti-Inflammatory Activities.[Pubmed:35408555]

Molecules. 2022 Mar 27;27(7):2157.

Hericium erinaceus, a culinary and medicinal mushroom, is widely consumed in Asian countries. Chemical investigation on the fruiting bodies of Hericium erinaceus led to the isolation of one new ergostane-type sterol fatty acid ester, erinarol K (1); and eleven known compounds: 5alpha,8alpha -epidioxyergosta-6,22-dien-3beta-yl linoleate (2); ethyl linoleate (3); linoleic acid (4); hericene A (5); Hericene D (6); hericene E (7); ergosta-4,6,8(14),22-tetraen-3-one (8); hericenone F (9); ergosterol (10); ergosterol peroxide (11); 3beta,5alpha,6alpha,22E-ergosta-7,22-diene-3,5,6-triol 6-oleate (12). The chemical structures of the compounds were determined by 1D and 2D NMR (nuclear magnetic resonance) spectroscopy, mass spectra, etc. Anti-inflammatory effects of the isolated aromatic compounds (5-7, 9) were evaluated in terms of inhibition of pro-inflammatory mediator (TNF-alpha, IL-6 and NO) production in lipopolysaccharide (LPS)-stimulated murine RAW 264.7 macrophage cells. The results showed that compounds 5 and 9 exhibited moderate activity against TNF-alpha (IC(50): 78.50 muM and 62.46 muM), IL-6 (IC(50): 56.33 muM and 48.50 muM) and NO (IC(50): 87.31 muM and 76.16 muM) secretion. These results supply new information about the secondary metabolites of Hericium erinaceus and their anti-inflammatory effects.

Total Synthesis, Structure Revision, and Neuroprotective Effect of Hericenones C-H and Their Derivatives.[Pubmed:33492133]

J Org Chem. 2021 Feb 5;86(3):2602-2620.

The first total syntheses of hericenones C-H and "putative 3-hydroxyhericenone F" were achieved. Highlights of the synthesis include the straightforward construction of the resorcinol core and geranyl side chain, assembly of the natural product skeleton by sequential O-geranylation and a clay/zeolite-mediated O --> C rearrangement reaction, and a biomimetic cyclization to form a variety of bicyclic natural hericenones and their congeners. The structure of the "putative 3-hydroxyhericenone F" was revised as the 5-exo cyclization product (named: hericenone Z) of epoxyhericenone C through in-depth analyses of the cyclization modes in addition to NMR spectroscopic studies. To gain insights into the biological functions of geranyl-resorcinols in Hericium erinaceus, potential neuroprotective effects against endoplasmic reticulum (ER) stress-dependent cell death were evaluated systematically to clarify a fundamental structure-activity relationship. Among the compounds assayed, the linoleate-containing hericenone analogue, i.e., the regioisomer of Hericene D, was found to possess the most potent neuroprotective effect against tunicamycin and thapsigargin-induced ER stress-dependent cell death.

Characterization of alpha-glucosidase inhibitory constituents of the fruiting body of lion's mane mushroom (Hericium erinaceus).[Pubmed:32738392]

J Ethnopharmacol. 2020 Nov 15;262:113197.

ETHNOPHARMACOLOGICAL RELEVANCE: Hericium erinaceus, commonly called lion's mane mushroom, is an edible and medicinal mushroom that has been traditionally used for the treatment of metabolic disorders, gastrointestinal diseases and memory impairment. In this study, potential anti-hyperglycemic constituents were identified to support the traditional usage of H. erinaceus. MATERIALS AND METHODS: The components of H. erinaceus were purified using various column chromatography techniques. The structure of the separated compounds was determined based on spectroscopic data analysis, i.e., 1D and 2D NMR analysis. The anti-hyperglycemic activity of the isolated compounds was evaluated by measuring the inhibitory effects on alpha-glucosidase activity. Molecular docking analysis was also conducted for elucidation of alpha-glucosidase inhibitory activity of isolated compounds. RESULTS: Ten compounds including four new compounds, erinacenols A-D (1-4), were isolated from the fruiting bodies of H. erinaceus. Investigation of the anti-hyperglycemic effect of isolated compounds demonstrated that erinacenol D (4), 4-[3',7'-dimethyl-2',6'-octadienyl]-2-formyl-3-hydroxy-5-methyoxybenzylalcohol (6), hericene A (7), Hericene D (8) and hericenone D (9) strongly inhibited alpha-glucosidase activity with IC(50) values of <20 muM. The structure activity relationship suggested the importance of long side chain for alpha-glucosidase inhibitory activity. Further analysis by molecular docking demonstrated the interaction of alpha-glucosidase and isolated compounds, which supported the inhibitory activity of alpha-glucosidase. CONCLUSION: Our present study demonstrated the beneficial effect of H. erinaceus by characterization of alpha-glucosidase inhibitory compounds, including four new compounds. This approach can be valuable support for the traditional use of H. erinaceus for the treatment of diabetes and metabolic diseases, which needs to be clarified by further in-vivo study.