Erinacine E as a kappa opioid receptor agonist and its new analogs from a basidiomycete, Hericium ramosum

Journal of Antibiotics

Volumn 51, Issue 11, 1998, Pages 983-990

  Saito, Toshiyuki ^a   Aoki, Fukumatsu ^a   Hirai, Hideo ^a   Inagaki, Taisuke ^a   Matsunaga, Yasue ^a   Sakakibara, Tatsuo ^a   Sakemi, Shinichi ^a   Suzuki, Yumiko ^a   Watanabe, Shuzo ^a   Suga, Osamu ^b   Sujaku, Tetsujo ^b   Smogowicz, Adam A ^b   Truesdell, Susan J ^b   Wong, John W ^b   Nagahisa, Atsushi ^b   Kojima, Yasuhiro ^a   Kojima, Nakao ^a  

^a Nat Prod and Lead Discov Lab   (Japan)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ERINACINE E; KAPPA OPIATE RECEPTOR AGONIST; UNCLASSIFIED DRUG;

ARTICLE; BASIDIOMYCETES; BIOTRANSFORMATION; FERMENTATION; HERICIUM RAMOSUM; MUSCLE TWITCH; PRIORITY JOURNAL; RABBIT; STRUCTURE ACTIVITY RELATION; VAS DEFERENS;

HERICIUM RAMOSUM;

EID: 0000020716     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.7164/antibiotics.51.983     Document Type: Article

References (28)

1. PASTERNAK, G. W.: The opiate receptors. Human Press, Clifton, NJ, 1988
2. PERT, C. B. & S. H. SNYDER: Opiate receptor: demonstration in nervous tissue. Science 179: 1011-1014, 1973
3. MARTIN, W. R.; C. G. EADES, J. A. THOMPSON, R. E. HUPPLER & P. E. GILBERT: The effects of morphine- and nalorphine-like drugs in the nondependent and morphine-dependent chronic spinal dog. J. Pharmacol. Exp. Ther. 197: 517-532, 1976
4. LORD, J. A. H.; A. A. WATERFIELD, J. HUGHES & H. W. KOSTERLITZ: Endogenous opioid peptides: multiple agonists and receptors. Nature 267: 495-499, 1977
5. WOOD, P. L.; S. E. CHARLESON, D. LANE & R. L. HUDGIN: Multiple opiate receptors: Differential binding of μ, κ and δ agonists. Neuropharmacol. 20: 1215-1220, 1981
6. MANSOUR, A.; H. KHACHATURIAN, M. E. LEWIS, H. AKIL & S. J. WATSON: Autoradiographic differentiation of mu, delta, and kappa opioid receptors in the rat forebrain and midbrain. J. Neurosci. 7: 2445-2464, 1987
7. KIEFFER, B. L.; K. BEFORT, C. GAVERIAUX-RUFF & C. G. HIRTH: The δ-opioid receptor: Isolation of a cDNA by expression cloning and pharmacological characterization. Proc. Natl. Acad. Sci. USA 89: 12048-12052, 1992
8. EVANS, C. J.; D. E. KEITH Jr, H. MORRISON, K. MAGENDZO & R. H. EDWARDS: Cloning of a delta opioid receptor by functional expression. Science 258: 1952-1955, 1992
9. CHEN, Y.; A. MESTEK, J. LIU, J. A. HURLEY & L. YU: Molecular cloning and functional expression of a μ-opioid receptor from rat brain. Mol. Pharmacol. 44: 8-12, 1993
10. FUKUDA, K.; S. KATO, K. MORI, M. NISHI & H. TAKESHIMA: Primary structures and expression from cDNAs of rat opioid receptor δ- and μ-subtypes. FEBS Lett. 327: 311-314, 1993
11. WANG, J. B.; Y. IMAI, C. M. EPPLER, P. GREGOR, C. E. SPIVAK & G. R. UHL: μ opiate receptor: cDNA cloning and expression. Proc. Natl. Acad. Sci. USA 90: 10230-10234, 1993
12. YASUDA, K.; K. RAYNOR, H. KONG, C. D. BREDER, J. TAKEDA, T. REISINE & G. I. BELL: Cloning and functional comparison of κ and δ opioid receptors from mouse brain. Proc. Natl. Acad. Sci. USA 90: 6736-6740, 1993
13. NISHI, M.; H. TAKESHIMA, K. FUKUDA, S. KATO & K. MORI: cDNA cloning and pharmacological characterization of an opioid receptor with high affinities for κ-subtype-selective ligands. FEBS Lett. 330: 77-80, 1993
14. MINAMI, M.; T. TOYA, Y. KATAO, K. MAEKAWA, S. NAKAMURA, T. ONOGI, S. KANEKO & M. SATOH: Cloning and expression of a cDNA for the rat κ-opioid receptor. FEBS Lett. 329: 291-295, 1993
15. MENG, F.; G.-X. XIE, R. C. THOMPSON, A. MANSOUR, A. GOLDSTEIN, S. J. WATSON & H. AKIL: Cloning and pharmacological characterization of a rat κ opioid receptor. Proc. Natl. Acad. Sci. USA 90:9954-9958, 1993
16. PASTERNAK, G. W.; S. R. CHILDERS & S. H. SNYDER: Opiate analgesia: evidence for mediation by a subpopulation of opiate receptors. Science 208: 514-516, 1980
17. CHAILLET, P.; A. COULAUD, J.-M. ZAJAC, M.-C. FOURNIE-ZALUSKI, J. COSTENTIN & B. P. ROQUES: The μ rather than the δ subtype of opioid receptors appears to be involved in enkephalin-induced analgesia. Eur. J. Pharmacol. 101: 83-90, 1984
18. STEIN, C.; M. J. MILLAN, T. S. SHIPPENBERG, K. PETER & A. HERZ: Peripheral opioid receptors mediating antinociception in inflammation. Evidence for involvement of mu, delta and kappa receptors. J. Pharmacol. Exp. Ther. 248: 1269-1275, 1989
19. KAWAGISHI, H.; A. SHIMADA, S. HOSOKAWA, H. MORI, H. SAKAMOTO, Y. ISHIGURO, S. SAKEMI, J. BORDNER, N. KOJIMA & S. FURUKAWA: Erinacines E, F, and G, stimulators of nerve growth factor (NGF)-synthesis, from the mycelia of Hericium erinaceum. Tetrahedron Lett. 37: 7399-7402, 1996
20. KAWAGISHI, H.; A. SIMADA, R. SHIRAI, K. OKAMOTO, F. OJIMA, H. SAKAMOTO, Y. ISHIGURO & S. FURUKAWA: Erinacines A, B and C, strong stimulators of nerve growth factor (NGF)-synthesis, from the mycelia of Hericium erinaceum. Tetrahedron Lett. 35: 1569-1572, 1994
21. KAWAGISHI, H.; A. SHIMADA, K. SHIZUKI, H. MORI, K. OKAMOTO, H. SAKAMOTO & S. FURUKAWA: Erinacine D, a stimulator of NGF-synthesis, from the mycelia of Hericium erinaceum. Heterocycl. Commun. 2: 51-54, 1996
22. HECHT, H.-J.; G. HÖFLE, W. STEGLICH, T. ANKE & F. OBERWINKER: Striatin A. B, and C: novel diterpenoid antibiotics from Cyathus striants; X-ray crystal structure of striatin A. J. Chem. Soc. Chem. Commun. 665-666, 1978
23. OKA, T.; N. NEGISHI, M. SUDA, T. MATSUMIYA, T. INAZU & M. UEKI: Rabbit vas deferens: a specific bioassay for opioid κ-receptor agonists. Eur. J. Pharmacol. 73: 235-236, 1980
24. PORTOGHESE, P. S.; A. W. LIPKOWSKI & A. E. TAKEMORI: Bimorphinans as highly selective, potent κ opioid receptor antagonists. J. Med. Chem. 30: 238-239, 1987
25. PORTOGHESE, P. S.; A. W. LIPKOWSKI & A. E. TAKEMORI: Binaltorphimine and nor-binaltorphimine, a potent and selective κ-opioid receptor antagonists. Life Science 40: 1287-1292, 1987
26. TAKEMORI, A. E.; B. Y. HO, J. S. NAESETH & P. S. PORTOGHESE: Nor-binaltorphimine, a highly selective kappa-opioid antagonists in analgesic and receptor binding assays. J. Pharmacol. Exp. Ther. 246: 255-258, 1988
27. HALL, D. & D. E. STUNTZ: Pileate hydnaceae of the puget sound area. I. White-spored genera: Auriscalpium, Hericium, Dentinum and Phellodon. Mycologia 63: 1099-1128, 1971
28. SMITH, R. V. & J. P. ROSAZZA: Microbial models of mammalian metabolism. J. Pharm. Sci. 64: 1737-1759, 1975