Hericium erinaceum, commonly called lion’s mane mushroom, is a traditional edible mushroom widely used in culinary applications and herbal medicines in East Asian countries. In this study, a new sterol, cerevisterol 6-cinnamate (
6), was isolated from the fruiting bodies of
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Hericium erinaceum, commonly called lion’s mane mushroom, is a traditional edible mushroom widely used in culinary applications and herbal medicines in East Asian countries. In this study, a new sterol, cerevisterol 6-cinnamate (
6), was isolated from the fruiting bodies of
H. erinaceum together with five aromatic compounds
1–
5 and five sterols
7–
11. The chemical structures of these compounds were elucidated using chemical and physical methods and comparison of HRESIMS,
1D-NMR (
1H,
13C, and DEPT) and 2D-NMR (COSY, HMQC, HMBC, and NOESY) spectra with previously reported data. The antioxidant and anti-osteoporotic activities of extracts and the isolated compounds
1–
11 were investigated. All compounds exhibited peroxyl radical-scavenging capacity but only compounds
1,
3, and
4 showed potent reducing capacity. Moreover, compounds
1,
2,
4, and
5 showed moderate effects on cellular antioxidant activity and inhibited the receptor activator of nuclear factor κB ligand (RANKL)-induced osteoclastic differentiation. These results suggested that
H. erinaceum could be utilized in the development of natural antioxidant and anti-osteoporotic nutraceuticals and functional foods.
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