Chemistry:Erinacine

Erinacines are natural substances isolated from the mycelium of Hericium erinaceus (lion's mane mushroom). They belong to the group of cyathin diterpenoids (erinacines A–K, P, Q, S, U) and are subjects of pharmacological research, which largely focuses on the benefits of erinacine on the brain. All erinacines are able to readily cross the blood–brain barrier in vivo, which largely influences the bioavailability of the compounds in the brain.

Erinacine A

Erinacine A, isolated from the cultured mycelia of Hericium erinaceus, the main representative of this compounds group, has an enhancing effect on nerve growth factor synthesis in vitro. It also increases the levels of catecholamines in the central nervous system of rats. . Erinacine A has been observed to lead to the activation of antioxidant pathways including the transcription factor Nrf2.

Stimulator of nerve growth factor (NGF) synthesis in vitro((250.1 ± 36.2) pg/mL at 1.0 mmol/L),weak cytotoxicity against PC12 cells (IC50: 73.7 μmol/L),Anti‐methicillin-resistant Staphylococcus aureus (MRSA) activity

Erinacine A has also been prepared by total synthesis.

Erinacine B

Stimulator of NGF synthesis in vitro((129.7 ± 6.5) pg/mL at 1.0 mmol/L)

Erinacine C

Erinacine C has also been observed to activate the transcription factor Nrf2 and has been observed to play a role in neurogenesis and neuroplasticity.

Stimulator of NGF synthesis in vitro((299.1 ± 59.6) pg/mL at 1.0 mmol/L)

Erinacine D

Stimulators of NGF synthesis(amount of NGF: 141.5 pg/mL at 1.67 mmol/L)

Erinacine E

Erinacine E is a kappa opioid receptor agonist.

Stimulators of NGF synthesis by astrocytes(amount of NGF: (105.0 ± 5.2) pg/mL at 5.0 mmol/L)

Erinacine F

Stimulators of NGF synthesis by astrocytes(amount of NGF: (175.0 ± 52.0) pg/mL at 5.0 mmol/L)

Erinacine G

Stimulators of NGF synthesis by astrocytes

Erinacine H

Obvious NGF stimulating activity, 33.3 g/mL, five times more NGF (31.5 pg/mL)

Erinacine I

No stimulatory activity of NGF synthesis in astrocytes

Erinacine J

Inactive against MRSA

Erinacine K

Anti-MRSA activity(500 μmol/L)

Erinacine L

Erinacine L is the only xyloside-cyathane diterpene currently found to contain a hemiacetal group. EL with hemiacetal group has excellent neurotrophic and anti-neuroinflammatory activities, suggesting that the hemiacetal moiety may be an essential pharmacophore for the treatment of neurodegenerative diseases.

Erinacine P

Significant neurotrophic effects(2.5single bond10 μmol/L, at 10 μmol/L: percentage of neurite-bearing cells: 48.3 %)

Erinacine S

Erinacine S has been shown to reduce neuropathic pain in vivo and can increase myelination in vivo.

Elevated levels of insulin-degrading enzymes(2.395 g/kg BW (H. erinaceus mycelial extract equivalent to 50 mg/kg BW) the male Sprague-Dawley rats of pharmacokinetics: 15.13 %)

Erinacine T

Promotion of PC12 cells differentiation and axonal growth (2.5single bond10 mol/L, at 10 μmol/L: percentage of neurite-bearing cells: 43.7 %)

Erinacine U

Promote the neurite growth of PC12 cells (2.5single bond10 μmol/L, at 10 μmol/L: percentage of neurite-bearing cells: 76.31 %

Erinacine V

Promote the neurite growth of PC12 cells (2.5single bond10 μmol/L, at 10 μmol/L: percentage of neurite-bearing cells: 65.3 %)

Erinacines Z1,Z2

Z1- Promote PC12 cell differentiation and neurite growth(potent cytotoxicity against HL-60 cell lines: IC50: 8.9 μmol/L)

Z2- Promote PC12 cell differentiation and neurite growth(potent cytotoxicity against HL-60 cell lines: IC50: 0.5 μmol/)

References

A, B, C, D, E, F, G, I, J, K, L, P, Q1, R, S, T, U, V, Z1, Z2 Qi, Jianzhao; Wu, Jing; Kang, Shijie; Gao, Jingming; Hirokazu, Kawagishi; Liu, Hongwei; Liu, Chengwei (August 2024). "The chemical structures, biosynthesis, and biological activities of secondary metabolites from the culinary-medicinal mushrooms of the genus Hericium: a review". Chinese Journal of Natural Medicines 22 (8): 676–698. doi:10.1016/S1875-5364(24)60590-X. ISSN 1875-5364. https://linkinghub.elsevier.com/retrieve/pii/S187553642460590X. Retrieved 2026-01-30. 

J, K Kawagishi, Hirokazu; Masui, Ayano; Tokuyama, Shinji; Nakamura, Tomoyuki (September 2006). "Erinacines J and K from the mycelia of Hericium erinaceum". Tetrahedron 62 (36): 8463–8466. doi:10.1016/j.tet.2006.06.091. ISSN 0040-4020. Bibcode: 2006Tetra..62.8463K. https://linkinghub.elsevier.com/retrieve/pii/S0040402006010362. Retrieved 2026-01-30. 

Spangenberg, E. T.; Moneypenny, A.; Bozzo, G. G.; Perreault, M. L. (2025-06-23). "Unveiling the role of erinacines in the neuroprotective effects of Hericium erinaceus: a systematic review in preclinical models". Frontiers in Pharmacology 16. doi:10.3389/fphar.2025.1582081. ISSN 1663-9812. 

L Wei, Jing; Li, Jia-yao; Feng, Xi-long; Zhang, Yilin; Hu, Xuansheng; Hui, Heping; Xue, Xiaodong; Qi, Jianzhao (2023-08-31). "Unprecedented Neoverrucosane and Cyathane Diterpenoids with Anti-Neuroinflammatory Activity from Cultures of the Culinary-Medicinal Mushroom Hericium erinaceus". Molecules 28 (17): 6380. doi:10.3390/molecules28176380. ISSN 1420-3049. PMID 37687209. 

Z1, Z2 Rupcic, Zeljka; Rascher, Monique; Kanaki, Sae; Köster, Reinhard; Stadler, Marc; Wittstein, Kathrin (2018-03-06). "Two New Cyathane Diterpenoids from Mycelial Cultures of the Medicinal Mushroom Hericium erinaceus and the Rare Species, Hericium flagellum". International Journal of Molecular Sciences 19 (3): 740. doi:10.3390/ijms19030740. ISSN 1422-0067. PMID 29509661. Bibcode: 2018IJMSc..19..740R. 

A-C, Za, Zb, Zc, T, P, Q, X, W, Y Ma, Ke; Zhang, Yuting; Guo, Cui; Yang, Yanlong; Han, Junjie; Yu, Bo; Yin, Wenbing; Liu, Hongwei (2021-09-01). "Reconstitution of biosynthetic pathway for mushroom-derived cyathane diterpenes in yeast and generation of new "non-natural" analogues". Acta Pharmaceutica Sinica B 11 (9): 2945–2956. doi:10.1016/j.apsb.2021.04.014. ISSN 2211-3835. PMID 34589407. 

S Chen, Chien-Chih; Tzeng, Tsai-Teng; Chen, Chin-Chu; Ni, Ching-Li; Lee, Li-Ya; Chen, Wan-Ping; Shiao, Young-Ji; Shen, Chien-Chang (2016-02-26). "Erinacine S, a Rare Sesterterpene from the Mycelia of Hericium erinaceus". Journal of Natural Products 79 (2): 438–441. doi:10.1021/acs.jnatprod.5b00474. ISSN 1520-6025 0163-3864, 1520-6025. PMID 26807743. Bibcode: 2016JNAtP..79..438C. https://pubs.acs.org/doi/10.1021/acs.jnatprod.5b00474. Retrieved 2026-01-30. 

A-I, P, Q, J, K, R, S, T, U, V, Z1, Z2 Qiu, Yue; Lin, Genglan; Liu, Weiming; Zhang, Fuming; Linhardt, Robert J.; Wang, Xingli; Zhang, Anqiang (July 2024). "Bioactive compounds in Hericium erinaceus and their biological properties: a review". Food Science and Human Wellness 13 (4): 1825–1844. doi:10.26599/FSHW.2022.9250152. ISSN 2213-4530 2097-0765, 2213-4530. https://www.sciopen.com/article/10.26599/FSHW.2022.9250152. Retrieved 2026-01-30. 

A, B, C, D, E, F, G, I, J, K, L, P, Q1, R, S, T, U, V, Z1, Z2 Qi, Jianzhao; Wu, Jing; Kang, Shijie; Gao, Jingming; Hirokazu, Kawagishi; Liu, Hongwei; Liu, Chengwei (August 2024). "The chemical structures, biosynthesis, and biological activities of secondary metabolites from the culinary-medicinal mushrooms of the genus Hericium: a review". Chinese Journal of Natural Medicines 22 (8): 676–698. doi:10.1016/S1875-5364(24)60590-X. ISSN 1875-5364. https://linkinghub.elsevier.com/retrieve/pii/S187553642460590X. Retrieved 2026-01-30. 

Further reading

• "Erinacine Q, a new erinacine from Hericium erinaceum, and its biosynthetic route to erinacine C in the basidiomycete". Bioscience, Biotechnology, and Biochemistry 66 (3): 571–5. March 2002. doi:10.1271/bbb.66.571. PMID 12005051. Bibcode: 2002BsBtB..66..571K.