Abstract
Skimmianine (1), a newly discovered strong acetylcholinesterase (AChE) inhibitor, along with nine weakly or no active compounds, toddalolactone (2), dictamnine (3), γ-fagarine (4), magnolone (5), (−)-(S)-edulinine (6), zanthodioline (7), edulitine (8), 5,6,7-trimethoxycoumarin (9), and haplopine (10) have been isolated from Zanthoxylum nitidum (Z. nitidum). Skimmianine (1) inhibited 50% of AChE activity at the concentrations of 8.6 ± 0.7 μg/ml when the IC50 value of Physostigmine as a standard was 0.013 ± 0.002 μg/ml. Antiacetylcholinesterase activity of skimmianine (1) was also supported by TLC bioautographic assay. The structure activity relationship on the anti-acetylcholinesterase activity of the quinoline moiety is also discussed in this article.
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Ambrozin ARP, Mafezoli J, Vieira PC, Fernandes JB, da Silva M, Ellena JA, de Albuquerque S (2005) New pyrone and quinoline alkaloid from Almeidea rubra and their trypanocidal activity. J Braz Chem Soc 16:434–439
Boyd DR, Sharma ND, Barr SA, Carroll JG, Mackerracher D, Malone JF (2000) Synthesis and absolute stereochemistry assignment of enantiopure dihydrofuro- and dihydropyrano-quinoline alkaloids. J Chem Soc Perkin 1(1):3397–3405
Carpinella MC, Andrione DG, Ruiz G, Palacios SM (2010) Screening for acetylcholinesterase inhibitory activity in plant extracts from Argentina. Phytother Res 24:259–263
Chakravarty AK, Sarkar T, Masuda K, Shiojima K (1999) Carbazole alkaloids from roots of Glycosmis arborea. Phytochemistry 50:1263–1266
Chaturvedula VSP, Schilling JK, Miller JS, Andriantsiferana R, Rasamison VE, Kingston DGI (2003) New cytotoxic alkaloids from the wood of Vepris punctata from the Madagascar rainforest. J Nat Prod 66:532–534
Chen IS, Tsai IW, Teng CM, Chen JJ, Chang YL, Ko FN, Lu MC, Pezzuto JM (1997) Pyranoquinoline alkaloids from Zanthoxylum simulans. Phytochemistry 46:525–529
Chen KS, Chang YL, Teng CM, Chen CF, Wu YC (2000) Furoquinolines with antiplatelet aggregation activity from leaves of Melicope confusa. Planta Med 66:80–81
Cheng JT (1986) Effect of skimmianine on animal behavior. Arch Int Pharmacodyn Ther 281:35–43
Ellman GL, Courtney KD, Andres V, Featherstone RM (1961) A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 7:88–95
Fang SD, Wang LK, Hecht SM (1993) Inhibitors of DNA topoisomerase-I isolated from the roots of Zanthoxylum-nitidum. J Org Chem 58:5025–5027
Houghton PJ, Ren YH, Howes MJ (2006) Acetylcholinesterase inhibitors from plants and fungi. Nat Prod Rep 23:181–199
Hu J, Xu XK, Liu RH, Zhang C, Li HL, Liang MJ, Zhang WD (2006a) Study on lignans constituents of Zanthoxylum nitidum. Pharmaceut Care Res 6:51–53
Hu J, Zhang WD, Liu RH, Zhang C, Shen YH, Li HL, Liang MJ, Xu XK (2006b) Benzophenanthridine alkaloids from Zanthoxylum nitidum (Roxb.) DC, and their analgesic and anti-inflammatory activities. Chem Biodivers 3:990–995
Imai F, Itoh K, Kishibuchi N, Kinoshita T, Sankawa U (1989) Constituents of the root bark of Murraya-paniculata collected in Indonesia. Chem Pharm Bull 37:119–123
Lahiri DK, Farlow MR, Greig NH, Sambamurti K (2002) Current drug targets for alzheimer’s disease treatment. Drug Dev Res 56:267–281
Li X, Tang HZ, Gou XJ, Tu J (2008) Study on chemical constituents of the root of Dictamnus dasycarpus. Zhong Yao Cai 31:1816–1819
Munoz-Torrero D, Camps P (2006) Dimeric and hybrid anti-alzheimer drug candidates. Curr Med Chem 13:399–422
Pang YP, Quiram P, Jelacic T, Hong F, Brimijoin S (1996) Highly potent, selective, and low cost bis-tetrahydroaminacrine inhibitors of acetylcholinesterase—steps toward novel drugs for treating alzheimer’s disease. J Biol Chem 271:23646–23649
Rahman AU, Khalid A, Sultana N, Ghayur MN, Mesaik MA, Khan MR, Gilani AH, Choudhary I (2006) New natural cholinesterase inhibiting and calcium channel blocking quinoline alkaloids. J Enzyme Inhib Med Chem 21:703–710
Snider BB, Wu XX (2006) Synthesis of (+)-myrtopsine, (+)-7,8-dimethoxymyrtopsine, and related 2,3-dihydro-3-hydroxy-2-(1-hydroxy-1-methylethyl) benzofuran natural products. Heterocycles 70:279–294
Tang J, Zhu W, Tu ZB (1995) Study on chemical constituents of the stem of Zanthoxylum dissitum. Zhong Cao Yao 26:563–565
Wan H-C, Hu D-Y, Liu H-C (2005) Clinical observation of toothpaste containing Zanthoxylum nitidum extract on dental plaque and gingivitis. Zhongguo Zhong Xi Yi Jie He Za Zhi 25:1024–1026
Wang B-L, Liu H-G, Yang B, Qin S-H (2007) Anticancer activity of nitidine chloride from Zanthoxylum nitidum (Roxb.) DC. On multidrug resistant KBV200 cells in vitro. Chin J Pharmacol Toxicol 21:512–515
Yang GH, Chen DF (2008) Alkaloids from the roots of Zanthoxylum nitidum and their antiviral and antifungal effects. Chem Biodivers 5:1718–1722
Yang CH, Cheng MJ, Lee SJZ, Yang CWZ, Chang HS, Chen IS (2008) Secondary metabolites and cytotoxic activities from the stem bark of Zanthoxylum nitidum. Planta Med 74:1046
Yang ZD, Zhang X, Duan DZ, Song ZW, Yang MJ, Li S (2009) Modified tlc bioautographic method for screening acetylcholinesterase inhibitors from plant extracts. J Sep Sci 32:3257–3259
Ye JH, Zhou YL, Huang ZH (1989) Study on the chemical-constituents of Alstonia-mairei. Acta Chimi Sin 47:1012–1016
Yu HJ, Chen CC, Shieh BJ (1998) Two new constituents from the leaves of Magnolia coco. J Nat Prod 61:1017–1019
Zeng XY, Chen XF, He XQ, Hong GX (1982) Studies on the antispasmodic and analgesic actions of crystal-8 isolated from Zanthoxylum nitidum (Roxb.) DC. Yao Xue Xue Bao 17:253–258
Zheng XL, Xing FW (2009) Ethnobotanical study on medicinal plants around mt.Yinggeling, Hainan Island, China. J Ethnopharmacol 124:197–210
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This study is supported by the National Natural Science Foundation of China (no. 20802031) and the Excellent Young Teachers Program of Lanzhou University of Technology (no. Q200904).
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Yang, Zd., Zhang, Db., Ren, J. et al. Skimmianine, a furoquinoline alkaloid from Zanthoxylum nitidum as a potential acetylcholinesterase inhibitor. Med Chem Res 21, 722–725 (2012). https://doi.org/10.1007/s00044-011-9581-9
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DOI: https://doi.org/10.1007/s00044-011-9581-9