Hericenones and erinacines: stimulators of nerve growth factor (NGF) biosynthesis in Hericium erinaceus

Alberto A, Rosanna C, Gianluca N, Orso VP. 1995. Secondary mold metabolites: part 46. hericenes A-C and erinapyrone C: new metabolites produced by the fungus Hericium erinaceum. J Nat Prod. 57: 602–606.

Allen SJ, Dawbarn D. 2006. Clinical relevance of the neurotrophins and their receptors. Clin Sci. (Lond.) 110: 175–191.

Ayer WA, Homast T, Nakashima TT, Ward DE. 1978. Metabolites of bird’s nest fungi. Part 10. Carbon-13 nuclear magnetic resonance studies on the cyathins. Can J Chem. 56: 2197–2199.

Furukawa Y, Furukawa S, Ikeda F, Satoyoshi K. 1986. Aliphatic side chain of catecholamine potentiates the stimulatory effect of the catechol part on the synthesis of nerve growth factor. FEBS Lett. 208: 258–262.

Kawagishi H, Ando M, Mizuno T. 1990. Hericenone A and B as cytotoxic principles from the mushroom Hericium erinaceum. Tetrahedron Lett. 31: 373–376.

Kawagishi H, Ando M, Sakamoto H, Yoshida S, Ojima F, Ishiguro Y, Ukai N, Furukawa S. 1991. Hericenones C, D and E, stimulators of nerve growth factor (NGF)-synthesis from the mushroom Hericium erinaceum. Tetrahadron Lett. 32: 4561–4564.

Kawagishi H, Ando M, Shinba K, Sakamoto H, Yoshida S, Ojima F, Ishiguro Y, Ukai N, Furukawa S. 1993. Chromans, hericenones F, G and H from the mushroom Hericium erinaceum. Phytochemistry 32: 175–178.

Kawagishi H, Shimada A, Shirai R, Okamoto K, Ojima F, Sakamoto H, Ishiguro Y, Furukawa S. 1994. Erinacines A, B and C, strong stimulators of nerve growth factor (NGF)-synthesis, from the mycelia of Hericium erinaceum. Tetrahedron Lett. 35: 1569–1572.

Kawagishi H, Simada A, Shizuki K, Mori H, Sakamoto H, Furukawa S. 1996a. Erinacine D. A Stimulator of NGF-synthesis from the mycelia of Hericium erinaceum. Heterocycl Commun. 2: 51–54.

Kawagishi H, Simada A, Shizuki K, Mori H, Sakamoto H, Furukawa S. 1996b. Erinacines E, F, and G, stimulators of nerve growth factor (NGF)-synthesis, from the mycelia of Hericium erinaceum. Tetrahedron Lett. 41: 7399–7402.

Kawagishi H, Masui A, Tokuyama S, Nakamura T. 2006. Erinacines J and K from the mycelia of Hericium erinaceum. Tetrahadron 62: 8463–8466.

Kenmoku H, Sassa T, Kato N. 2000. Isolation of erinacine P, a new parental metabolite of cyathane-xylosides, from Hericium erinaceum and its biomimetic conversion into erinacines A and B. Tetrahedron Lett. 41: 4389–4393.

Kenmoku H, Kato N, Shimada M, Omoto M, Mori A, Mituhashi W, Sassa T. 2001. Isolation of (–)-cyatha-3,12-diene, a common biosynthetic intermediate of cyathane diterpenoids, from an erinacine-producing basidiomycete, Hericium erinaceum. Tetrahedron Lett. 42: 7439–7422.

Kenmoku H, Shimai T, Toyomasu T, Kato N, Sassa T. 2002. Erinacine Q, a new erinacine from Hericium erinaceum, and its biosynthetic route to erinacine C in the basidiomycete. Biosci Biotechnol Biochem. 66: 571–575.

Kenmoku H, Tanaka K, Okada K, Kato N, Sassa T. 2004. Erinacol (cyatha-3,12-dien-14β-ol) and 11-O-acetylcyathin A₃, new cyathane metabolites from an erinacine Q-producing Hericium erinaceum. Biosci Biotechnol Biochem. 68: 1786–1789.

Kimura Y, Nishibe M, Nakajima H, Hamasaki T, Shimada A, Tsuneda A, Shigematsu N. 1991. Hericerin, a new pollen growth inhibitor from the mushroom Hericium erinaceum. Agric Biol Chem. 55: 2673–2674.

Kita T, Takaya Y, Oshima Y. 1998. Scabronines B, C, D, E and F, novel diterpenoids showing stimulating activity of nerve growth factor synthesis, from the mushroom Sarcodon scabrosus. Tetrahedron 54: 11877–11886.

Lee EW, Shizuki K, Hosokawa S, Suzuki M, Suganuma H, Inakuma T, Kawagishi H. 2000. Two novel diterpenoids, erinacines H and I from the mycelia of Hericium erinaceum. Biosci Biotechnol Biochem. 64: 2402–2405.

Ma BJ, Zhou Y, Li LZ, Li HM, Gao ZM, Ruan Y. 2008. A new cyathane-xyloside from the mycelia of Hericium erinaceum. Z Naturforsch. 63b; 1241–1242.

Marcotullio MC, Pagiott R, Maltese F, Obara Y, Hoshino T, Nakahata N, Curini M. 2006. Neurite outgrowth activity of cyathane diterpenes from Sarcodon cyrneus, cyrneines A and B. Planta Med. 72: 819–823.

Marcotullio MC, Pagiotti R, Maltese F, Oball-Mond Mwankie GN, Hoshino T, Obara Y, Nakahata N. 2007. Cyathane diterpenes from Sarcodon cyrneus and evaluation of their activities of neuritegenesis and nerve growth factor production. Bioorg Med Chem. 15: 2878–2882.

Mizuno T. 1999. Bioactive substances in Hericium erinaceus (Bull.: Fr.) Pers. and its medicinal utilization. Int J Med Mushrooms 1: 105–119.

Mori K, Obara Y, Hirota M, Azumi Y, Kinnugasa S, Inatomi S, Nakahata N. 2008. Nerve growth factor-inducing activity of Hericium erinaceus in 1321N1 human astrocytoma cells. Biol Pharm Bull. 9: 1727–1732.

Obara Y, Nakahata N. 2002. The signaling pathway of neurotropic factor. Drug News Perspect. 15: 290–298.

Obara Y, Nakahata N, Kita T, Takaya Y, Kobayashi H, Oshima Y. 1999. Stimulation of neurotrophic factor secretion from 1321N1 human astrocytoma cells by novel diterpenoids, scabronines A and G. Eur J Pharmacol. 370: 79–84.

Obara Y, Hoshino T, Marcotullio MC, Pagiotti R, Nakahata N. 2007. A novel cyathane diterpene, cyrneine A, induces neurite outgrowth in a Rac1-dependent mechanism in PC12 cells. Life Sci. 80: 1669–1677.

Ohta T, Kita T, Kobayashi N, Obara Y, Nakahata N, Takaya Y, Oshima Y. 1998. Scabronine A, a novel diterpenoid having potent inductive activity of the nerve growth factor synthesis, isolated from the mushroom Sarcodon scabrosus. Tetrahedron Lett. 39: 6229–6232.

Saito T, Aoki F, Hirai H, Inagaki T, Matsunaga Y, Sakakibara T, Sakemi S, Suzuki Y, Watanabe S, Suga O, Sujaku T, Smogowicz AA, Truesdell SJ, Wong JW, Nagahisa A, Kojima Y, and Kojima N. 1998. Erinacine E as a kappa opioid receptor agonist and its new analogs from a basidiomycete, Hericium ramosum. J Antibiot. 51: 983–990.

Shimbo M, Kawagishi H, Yokogoshi H. 2005. Erinacine A increases catecholamine and nerve growth factor content in the central nervous system of rats. Nutr Res. 25: 617–623.

Takano M, Umino A, Nakad M. 2004. Synthetic studies on cyathins: enantioselective total synthesis of (+)-allocyathin B₂, Org Lett. 26: 4897–4900.

Takei N, Tsukui H, Hatanaka H. 1989. Intracellular storage and evoked release of acetylcholine from postnatal rat basal forebrain cholinergic neurons in culture with nerve growth factor. J Neurochem. 53: 1405–1410.

Trost BM, Dong L, Schroeder GM. 2005. Total synthesis of (+)-allocyathin B₂. J Am Chem Soc. 127: 2844–2845.

Ueda K, Tsujimori M, Kodani S, Chiba A, Kubo M, Masuno K, Sekiya A, Nagai K, Kawagishi H. 2008. An endoplasmic reticulum (ER) stress-suppressive compounds and its analogues from the mushroom Hericium erinaceum. Bioorg Med Chem. 16: 9467–9470.

Wright DL, Whitehead CR. 2000. Recent progress on the synthesis of cyathane type diterpenes. Org Prep Proc Int. 32: 307–331.

Yaoita Y, Danbara K, Kikuchi M. 2005. Two new aromatic compounds from Hericium erinaceum (Bull.:Fr.) Pers. Chem Pharm Bull. 53: 1202–1203.