HuperzineA
Agent in Chinese herbal medicine; used in treatment of dementia; potential for use in Alzheimer's disease. purified from Huperzia serrata (Thunb.) Trev [syn. Lycopodium serratum Thunb.(Qian ceng ta). The natural (-)-huperzine A is 38 fold more potent than its enantiomer (+)-huperzine A. Also low binding to the N-methyl-D-aspartate (NMDA) receptors. || In 1960, Wiesner and co-workers isolated an alkaloid from Huperzia selago, which named as selagine (Valenta et al. 1960, Yoshimura et al 1960). The structure of selagine was determined with minor mistakes. The double bond in C ring was misplaced and configuration of the exocyclic double bond was wrong. In 1986, Liu et al. reported ()-huperzine A from Huperzia serrata (Thunb.). Until 1989, Chinese and Canadian scientists cooperatively found the identity of selagine with huperzine A, therefore, the chemical structure of selagine was corrected. Occurs in stem and leaves of Lycopodium selago L. (Muszynski 1948 Quart. J. Pharm. Pharmacol. 21, 34) The powdered plant had been used as insecticide in Poland and proposed as a substitute for pilocarpine and eserine in glaucoma (miratyn-Ernestowa 1948 Klinika Oczna 18, 437)
General
Type : Derivative of Huperzine, Natural, Alkaloid
Chemical_Nomenclature : (5R,9R,11E)-5-amino-11-ethylidene-5,6.9,10-tetrahydro-7-methyl-5,9-methanocycloocteno[b]pyridin-2(1H)-one || selagine (5R,9R,11E)-5-amino-11-ethylidene-5,6.9,10-tetrahydro-7-methyl-5,9-methanocycloocteno[b]pyridin-2(1H)-one
Canonical SMILES : CC=C1C2CC3=C(C1(CC(=C2)C)N)C=CC(=O)N3 || Selagine CC=C1C2CC3=C(C1(CC(=C2)C)N)C=CC(=O)N3
InChI : InChI=1S\/C15H18N2O\/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10\/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)\/b11-3-\/t10-,15+\/m0\/s1 || Selagine InChI=1S\/C15H18N2O\/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10\/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)\/b11-3+\/t10-,15+\/m0\/s1
InChIKey : ZRJBHWIHUMBLCN-SEQYCRGISA-N || Selagine ZRJBHWIHUMBLCN-YQEJDHNASA-N
Other name(s) : Fordine || Huperzine || Huperzine A || Huperzine-A || (-)-huperzine A || CHEMBANK164 || C-117 || 103735-86-0 || HUP || Selagine || Isomer of Selagine || Isomer of HuperzineA
MW : 242.3
Formula : C15H18N2O
CAS_number : 102518-79-6
PubChem : 854026, 907504, Selagine 907504
UniChem : ZRJBHWIHUMBLCN-SEQYCRGISA-N, Selagine ZRJBHWIHUMBLCN-YQEJDHNASA-N
Wikipedia : Huperzine
Target
Families : HuperzineA ligand of proteins in family
ACHE
Protein :
torca-ACHE
human-ACHE
References (27)
| Title : Advances in the structural modification of Alzheimer's disease drug - Huperzine A - Zhu_2024_Bioorg.Chem_154_108012 |
| Author(s) : Zhu X , Xu JB , Gao F , Wan LX |
| Ref : Bioorg Chem , 154 :108012 , 2024 |
| Abstract : |
| PubMedSearch : Zhu_2024_Bioorg.Chem_154_108012 |
| PubMedID: 39637486 |
| Title : Huperzine alkaloids: forty years of total syntheses - Cheng_2023_Nat.Prod.Rep__ |
| Author(s) : Cheng B , Song L , Chen F |
| Ref : Nat Prod Rep , : , 2023 |
| Abstract : |
| PubMedSearch : Cheng_2023_Nat.Prod.Rep__ |
| PubMedID: 37818549 |
| Title : Structures of human acetylcholinesterase in complex with pharmacologically important ligands - Cheung_2012_J.Med.Chem_55_10282 |
| Author(s) : Cheung J , Rudolph MJ , Burshteyn F , Cassidy MS , Gary EN , Love J , Franklin MC , Height JJ |
| Ref : Journal of Medicinal Chemistry , 55 :10282 , 2012 |
| Abstract : |
| PubMedSearch : Cheung_2012_J.Med.Chem_55_10282 |
| PubMedID: 23035744 |
| Gene_locus related to this paper: human-ACHE |
| Title : Improving effects of huperzine A on spatial working memory in aged monkeys and young adult monkeys with experimental cognitive impairment - Ye_1999_J.Pharmacol.Exp.Ther_288_814 |
| Author(s) : Ye JW , Cai JX , Wang LM , Tang XC |
| Ref : Journal of Pharmacology & Experimental Therapeutics , 288 :814 , 1999 |
| Abstract : |
| PubMedSearch : Ye_1999_J.Pharmacol.Exp.Ther_288_814 |
| PubMedID: 9918593 |
| Title : Synthesis and acetylcholinesterase inhibitory activity of (+\/-)-14- fluorohuperzine A - Zeng_1998_Bioorg.Med.Chem.Lett_8_1661 |
| Author(s) : Zeng F , Jiang H , Tang X , Chen K , Ji R |
| Ref : Bioorganic & Medicinal Chemistry Lett , 8 :1661 , 1998 |
| Abstract : |
| PubMedSearch : Zeng_1998_Bioorg.Med.Chem.Lett_8_1661 |
| PubMedID: 9873409 |
| Title : Huperzine A--an interesting anticholinesterase compound from the Chinese herbal medicine - Patocka_1998_Acta.Medica_41_155 |
| Author(s) : Patocka J |
| Ref : Acta Medica , 41 :155 , 1998 |
| Abstract : |
| PubMedSearch : Patocka_1998_Acta.Medica_41_155 |
| PubMedID: 9951045 |
| Title : Synthesis and evaluation of tacrine-huperzine A hybrids as acetylcholinesterase inhibitors of potential interest for the treatment of Alzheimer's disease - Badia_1998_Bioorg.Med.Chem_6_427 |
| Author(s) : Badia A , Banos JE , Camps P , Contreras J , Gorbig DM , Munoz-Torrero D , Simon M , Vivas NM |
| Ref : Bioorganic & Medicinal Chemistry , 6 :427 , 1998 |
| Abstract : |
| PubMedSearch : Badia_1998_Bioorg.Med.Chem_6_427 |
| PubMedID: 9597187 |
| Title : Nonequilibrium analysis alters the mechanistic interpretation of inhibition of acetylcholinesterase by peripheral site ligands - Szegletes_1998_Biochemistry_37_4206 |
| Author(s) : Szegletes T , Mallender WD , Rosenberry TL |
| Ref : Biochemistry , 37 :4206 , 1998 |
| Abstract : |
| PubMedSearch : Szegletes_1998_Biochemistry_37_4206 |
| PubMedID: 9521743 |
| Title : Comparative studies of huperzine A, E2020, and tacrine on behavior and cholinesterase activities - Cheng_1998_Pharmacol.Biochem.Behav_60_377 |
| Author(s) : Cheng DH , Tang XC |
| Ref : Pharmacol Biochem Behav , 60 :377 , 1998 |
| Abstract : |
| PubMedSearch : Cheng_1998_Pharmacol.Biochem.Behav_60_377 |
| PubMedID: 9632220 |
| Title : Inhibition of cholinesterase-associated aryl acylamidase activity by anticholinesterase agents: focus on drugs potentially effective in Alzheimer's disease - Costagli_1998_Biochem.Pharmacol_55_1733 |
| Author(s) : Costagli C , Galli A |
| Ref : Biochemical Pharmacology , 55 :1733 , 1998 |
| Abstract : |
| PubMedSearch : Costagli_1998_Biochem.Pharmacol_55_1733 |
| PubMedID: 9634011 |
| Title : Reversal of scopolamine-induced deficits in radial maze performance by (-)-huperzine A: comparison with E2020 and tacrine - Wang_1998_Eur.J.Pharmacol_349_137 |
| Author(s) : Wang T , Tang XC |
| Ref : European Journal of Pharmacology , 349 :137 , 1998 |
| Abstract : |
| PubMedSearch : Wang_1998_Eur.J.Pharmacol_349_137 |
| PubMedID: 9671090 |
| Title : Structure of acetylcholinesterase complexed with the nootropic alkaloid, (-)-huperzine A - Raves_1997_Nat.Struct.Biol_4_57 |
| Author(s) : Raves ML , Harel M , Pang YP , Silman I , Kozikowski AP , Sussman JL |
| Ref : Nat Struct Biol , 4 :57 , 1997 |
| Abstract : |
| PubMedSearch : Raves_1997_Nat.Struct.Biol_4_57 |
| PubMedID: 8989325 |
| Gene_locus related to this paper: torca-ACHE |
| Title : Huperzine A, a novel promising acetylcholinesterase inhibitor - Cheng_1996_Neuroreport_8_97 |
| Author(s) : Cheng DH , Ren H , Tang XC |
| Ref : Neuroreport , 8 :97 , 1996 |
| Abstract : |
| PubMedSearch : Cheng_1996_Neuroreport_8_97 |
| PubMedID: 9051760 |
| Title : Effects of isovanihuperzine A on cholinesterase and scopolamine-induced memory impairment - Xiong_1995_Zhongguo.Yao.Li.Xue.Bao_16_21 |
| Author(s) : Xiong ZQ , Tang XC , Lin JL , Zhu DY |
| Ref : Acta Pharmacol Sin , 16 :21 , 1995 |
| Abstract : |
| PubMedSearch : Xiong_1995_Zhongguo.Yao.Li.Xue.Bao_16_21 |
| PubMedID: 7771190 |
| Title : Synthesis and evaluation of 5-amino-5,6,7,8-tetrahydroquinolinones as potential agents for the treatment of Alzheimer's disease - Fink_1995_J.Med.Chem_38_3645 |
| Author(s) : Fink DM , Bores GM , Effland RC , Huger FP , Kurys BE , Rush DK , Selk DE |
| Ref : Journal of Medicinal Chemistry , 38 :3645 , 1995 |
| Abstract : |
| PubMedSearch : Fink_1995_J.Med.Chem_38_3645 |
| PubMedID: 7658452 |
| Title : Identification of amino acid residues involved in the binding of Huperzine A to cholinesterases - Saxena_1994_Protein.Sci_3_1770 |
| Author(s) : Saxena A , Qian N , Kovach IM , Kozikowski AP , Pang YP , Vellom DC , Radic Z , Quinn DM , Taylor P , Doctor BP |
| Ref : Protein Science , 3 :1770 , 1994 |
| Abstract : |
| PubMedSearch : Saxena_1994_Protein.Sci_3_1770 |
| PubMedID: 7849595 |
| Title : Comparison of the effects of natural and synthetic huperzine-A on rat brain cholinergic function in vitro and in vivo - Tang_1994_J.Ethnopharmacol_44_147 |
| Author(s) : Tang XC , Kindel GH , Kozikowski AP , Hanin I |
| Ref : J Ethnopharmacol , 44 :147 , 1994 |
| Abstract : |
| PubMedSearch : Tang_1994_J.Ethnopharmacol_44_147 |
| PubMedID: 7898122 |
| Title : Prediction of the binding sites of huperzine A in acetylcholinesterase by docking studies - Pang_1994_J.Comput.Aided.Mol.Des_8_669 |
| Author(s) : Pang YP , Kozikowski AP |
| Ref : J Comput Aided Mol Des , 8 :669 , 1994 |
| Abstract : |
| PubMedSearch : Pang_1994_J.Comput.Aided.Mol.Des_8_669 |
| PubMedID: 7738603 |
| Title : Role of tyrosine 337 in the binding of huperzine A to the active site of human acetylcholinesterase - Ashani_1994_Mol.Pharmacol_45_555 |
| Author(s) : Ashani Y , Grunwald J , Kronman C , Velan B , Shafferman A |
| Ref : Molecular Pharmacology , 45 :555 , 1994 |
| Abstract : |
| PubMedSearch : Ashani_1994_Mol.Pharmacol_45_555 |
| PubMedID: 8145739 |
| Gene_locus related to this paper: human-ACHE |
| Title : Natural and synthetic Huperzine A: effect on cholinergic function in vitro and in vivo - Hanin_1993_Ann.N.Y.Acad.Sci_695_304 |
| Author(s) : Hanin I , Tang XC , Kindel GL , Kozikowski AP |
| Ref : Annals of the New York Academy of Sciences , 695 :304 , 1993 |
| Abstract : |
| PubMedSearch : Hanin_1993_Ann.N.Y.Acad.Sci_695_304 |
| PubMedID: 8239300 |
| Title : Mechanism of inhibition of cholinesterases by huperzine A - Ashani_1992_Biochem.Biophys.Res.Commun_184_719 |
| Author(s) : Ashani Y , Peggins JO, 3rd , Doctor BP |
| Ref : Biochemical & Biophysical Research Communications , 184 :719 , 1992 |
| Abstract : |
| PubMedSearch : Ashani_1992_Biochem.Biophys.Res.Commun_184_719 |
| PubMedID: 1575745 |
| Title : Huperzine A--a potent acetylcholinesterase inhibitor of use in the treatment of Alzheimer's disease - Geib_1991_Acta.Crystallogr_C824 |
| Author(s) : Geib SJ , Tuckmantel W , Kozikowski AP |
| Ref : Acta Crystallographica , C47 pt4 :824 , 1991 |
| Abstract : |
| PubMedSearch : Geib_1991_Acta.Crystallogr_C824 |
| PubMedID: 1863425 |
| Title : Development of natural products as drugs acting on central nervous system - Zhu_1991_Mem.Inst.Oswaldo.Cruz_86_173 |
| Author(s) : Zhu XZ |
| Ref : Mem Inst Oswaldo Cruz , 86 Suppl 2 :173 , 1991 |
| Abstract : |
| PubMedSearch : Zhu_1991_Mem.Inst.Oswaldo.Cruz_86_173 |
| PubMedID: 1841995 |
| Title : The structures of huperzine A and B, two new alkaloids exhibiting marked anticholinesterase activity - Liu_1986_Can.J.Chem_64_837 |
| Author(s) : Liu J-S , Zhu Y-L , Yu C-M , Zhou Y-Z , Han Y-Y , Wu F-W , Qi B-F |
| Ref : Canadian Journal of Chemistry , 64 :837 , 1986 |
| Abstract : |
| PubMedSearch : Liu_1986_Can.J.Chem_64_837 |
| PubMedID: |
| Title : Structure of Selagine - |
| Author(s) : Valenta Z , Yoshimura H , Rogers EF , Ternbah M , Wiesner K |
| Ref : Tetrahedron Letters , 10 :26 , 1960 |
| PubMedID: |
| Title : A rigorous proof of the selegaine structure - Yoshimura_1960_Tetrahedron.Lett_1_14 |
| Author(s) : Yoshimura H , Valenta Z , Wiesner K |
| Ref : Tetrahedron Letters , 1 :14 , 1960 |
| Abstract : |
| PubMedSearch : Yoshimura_1960_Tetrahedron.Lett_1_14 |
| PubMedID: |
| Title : The alkaloids of clubmosses. - |
| Author(s) : Muszynski J |
| Ref : Quart J Pharm Pharmacol , 21 :34 , 1948 |
| PubMedID: 18863097 |