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

References

• Alberto , A , Rosanna , C , Gianluca , N and 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 .
   Google Scholar
• Allen , SJ and Dawbarn , D. 2006 . Clinical relevance of the neurotrophins and their receptors . Clin Sci. (Lond.) , 110 : 175 – 191 .
   PubMed Web of Science ®Google Scholar
• Ayer , WA , Homast , T , Nakashima , TT and 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 .
   Google Scholar
• Furukawa , Y , Furukawa , S , Ikeda , F and 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 .
   PubMed Web of Science ®Google Scholar
• Kawagishi , H , Ando , M and Mizuno , T. 1990 . Hericenone A and B as cytotoxic principles from the mushroom Hericium erinaceum . Tetrahedron Lett. , 31 : 373 – 376 .
   Web of Science ®Google Scholar
• Kawagishi , H , Ando , M , Sakamoto , H , Yoshida , S , Ojima , F , Ishiguro , Y , Ukai , N and 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 .
   Web of Science ®Google Scholar
• Kawagishi , H , Ando , M , Shinba , K , Sakamoto , H , Yoshida , S , Ojima , F , Ishiguro , Y , Ukai , N and Furukawa , S. 1993 . Chromans, hericenones F, G and H from the mushroom Hericium erinaceum . Phytochemistry , 32 : 175 – 178 .
   Google Scholar
• Kawagishi , H , Shimada , A , Shirai , R , Okamoto , K , Ojima , F , Sakamoto , H , Ishiguro , Y and 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 .
   Web of Science ®Google Scholar
• Kawagishi , H , Kojima , F and Okamoto , K. 1995 . JP 7070168 .
   Google Scholar
• Kawagishi , H , Simada , A , Shizuki , K , Mori , H , Sakamoto , H and Furukawa , S. 1996a . Erinacine D. A Stimulator of NGF-synthesis from the mycelia of Hericium erinaceum . Heterocycl Commun. , 2 : 51 – 54 .
   Web of Science ®Google Scholar
• Kawagishi , H , Simada , A , Shizuki , K , Mori , H , Sakamoto , H and 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 .
   Google Scholar
• Kawagishi , H , Masui , A , Tokuyama , S and Nakamura , T. 2006 . Erinacines J and K from the mycelia of Hericium erinaceum . Tetrahadron , 62 : 8463 – 8466 .
   Google Scholar
• Kenmoku , H , Sassa , T and 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 .
   Google Scholar
• Kenmoku , H , Kato , N , Shimada , M , Omoto , M , Mori , A , Mituhashi , W and 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 .
   Google Scholar
• Kenmoku , H , Shimai , T , Toyomasu , T , Kato , N and 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 .
   PubMed Web of Science ®Google Scholar
• Kenmoku , H , Tanaka , K , Okada , K , Kato , N and 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 .
   PubMed Web of Science ®Google Scholar
• Kimura , Y , Nishibe , M , Nakajima , H , Hamasaki , T , Shimada , A , Tsuneda , A and Shigematsu , N. 1991 . Hericerin, a new pollen growth inhibitor from the mushroom Hericium erinaceum . Agric Biol Chem. , 55 : 2673 – 2674 .
   Web of Science ®Google Scholar
• Kita , T , Takaya , Y and 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 .
   Web of Science ®Google Scholar
• Lee , EW , Shizuki , K , Hosokawa , S , Suzuki , M , Suganuma , H , Inakuma , T and Kawagishi , H. 2000 . Two novel diterpenoids, erinacines H and I from the mycelia of Hericium erinaceum . Biosci Biotechnol Biochem. , 64 : 2402 – 2405 .
   PubMed Web of Science ®Google Scholar
• Ma , BJ , Zhou , Y , Li , LZ , Li , HM , Gao , ZM and Ruan , Y. 2008 . A new cyathane-xyloside from the mycelia of Hericium erinaceum . Z Naturforsch. , 63b : 1241 – 1242 .
   Google Scholar
• Marcotullio , MC , Pagiott , R , Maltese , F , Obara , Y , Hoshino , T , Nakahata , N and Curini , M. 2006 . Neurite outgrowth activity of cyathane diterpenes from Sarcodon cyrneus, cyrneines A and B . Planta Med. , 72 : 819 – 823 .
   PubMed Web of Science ®Google Scholar
• Marcotullio , MC , Pagiotti , R , Maltese , F , Oball-Mond Mwankie , GN , Hoshino , T , Obara , Y and 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 .
   PubMed Web of Science ®Google Scholar
• Mizuno , T. 1999 . Bioactive substances in Hericium erinaceus (Bull.: Fr.) Pers. and its medicinal utilization . Int J Med Mushrooms , 1 : 105 – 119 .
   Google Scholar
• Mori , K , Obara , Y , Hirota , M , Azumi , Y , Kinnugasa , S , Inatomi , S and Nakahata , N. 2008 . Nerve growth factor-inducing activity of Hericium erinaceus in 1321N1 human astrocytoma cells . Biol Pharm Bull. , 9 : 1727 – 1732 .
   Google Scholar
• Obara , Y and Nakahata , N. 2002 . The signaling pathway of neurotropic factor . Drug News Perspect. , 15 : 290 – 298 .
   PubMedGoogle Scholar
• Obara , Y , Nakahata , N , Kita , T , Takaya , Y , Kobayashi , H and 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 .
   PubMedGoogle Scholar
• Obara , Y , Hoshino , T , Marcotullio , MC , Pagiotti , R and 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 .
   PubMed Web of Science ®Google Scholar
• Ohta , T , Kita , T , Kobayashi , N , Obara , Y , Nakahata , N , Takaya , Y and 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 .
   Google Scholar
• 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 .
   PubMed Web of Science ®Google Scholar
• Shimada , A , Kawagishi , H and Furukawa , A. 1996 . JP 8073486 .
   Google Scholar
• Shimbo , M , Kawagishi , H and Yokogoshi , H. 2005 . Erinacine A increases catecholamine and nerve growth factor content in the central nervous system of rats . Nutr Res. , 25 : 617 – 623 .
   Google Scholar
• Takano , M , Umino , A and Nakad , M. 2004 . Synthetic studies on cyathins: enantioselective total synthesis of (+)-allocyathin B2 . Org Lett. , 26 : 4897 – 4900 .
   Google Scholar
• Takei , N , Tsukui , H and 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 .
   PubMedGoogle Scholar
• Trost , BM , Dong , L and Schroeder , GM. 2005 . Total synthesis of (+)-allocyathin B2 . J Am Chem Soc. , 127 : 2844 – 2845 .
   PubMedGoogle Scholar
• Ueda , K , Tsujimori , M , Kodani , S , Chiba , A , Kubo , M , Masuno , K , Sekiya , A , Nagai , K and Kawagishi , H. 2008 . An endoplasmic reticulum (ER) stress-suppressive compounds and its analogues from the mushroom Hericium erinaceum . Bioorg Med Chem. , 16 : 9467 – 9470 .
   PubMed Web of Science ®Google Scholar
• Wright , DL and Whitehead , CR. 2000 . Recent progress on the synthesis of cyathane type diterpenes . Org Prep Proc Int. , 32 : 307 – 331 .
   Web of Science ®Google Scholar
• Yaoita , Y , Danbara , K and Kikuchi , M. 2005 . Two new aromatic compounds from Hericium erinaceum (Bull.:Fr.) Pers . Chem Pharm Bull. , 53 : 1202 – 1203 .
   PubMed Web of Science ®Google Scholar