SUMMARY
Huperzine A is an alkaloid isolated from the Chinese plant Huperzia serrata. The absorption spectra
and electrophoretic behaviour of the compound were studied. The compound shows two absorption
maxima (lambdamax 230 and 310nm). The protonation constant was determined by spectrophotometry and
capillary zone electrophoresis (CZE) and the recommended value is pK=7.70±0.07. A CZE method
for the determination of Huperzine A in pharmaceutical tablets and serum has been developed. The
method is based on separation of the compound as a protonated species with electrophoretic
mobility determined as 50.7 x 10-9 m2V-1s-1. The optimal separation conditions were: acetate buffer
(pH 4.60; 20 mM) as a background electrolyte, separation voltage 20 kV, temperature 25 °C,
hydrodynamic injection 10 s and detection at wavelengths 230 and 310 nm. The analyses were run
in an uncoated fused-silica capillary with total length of 47.5 cm (39.0 cm to the detector) and
75 microm I.D. The detection limit was found to be 70 microg/l. The method of Huperzine A determination
was applied for analysis of various pharmaceutical products. The results were found to be in good
agreement with the declared amount. The precision of the method is ±2.30%. A method for the
determination of HupA in serum was also developed with detection limit 110 microg/l, which is
applicable for pharmacokinetics and therapeutic drug monitoring of this compound.
KEY WORDS
huperzine A; Alzheimer's disease; capillary zone electrophoresis
REFERENCES
Ashani Y, Grunwald J, Kronman C,
Velann B, Shafferman A: Role of tyrosine 337
in the binding of huperzine A to the active site
of human acetylcholinesterase. Mol Pharmacol
45:555-560, 1994.
Bai DL, Tang XC, He XC: Huperzine A, a
potential therapeutic agent for treatment of
Alzheimer's disease. Curr Med Chem 7:355-374, 2000.
Cheng DH, Ren H, Tang CC: Huperzine A, a
novel promising acetylcholinesterase inhibitor.
Neuroreport 8:97-101, 1996.
Cummings JL, Cole G: Alzheimer disease.
J Am Med Assoc 287:2335-2338, 2002.
Emre M: Switching cholinesterase inhibitors in
patients with Alzheimer's disease. Int J Clin
Pract, Suppl. 127:64-72, 2002.
Grunwald J, Raveh L, Doctor BP, Sahani Y:
Huperzine A as a pretreatment candidate drug
against nerve agent toxicity. Life Sci 54:991-997, 1994.
Havel J, Janos J: Evaluation of capillary zone
electrophoresis equilibrium data using the
CELET program. J Chromatogr A 786:321-331, 1997.
Kukull WA, Bowen JD: Dementia
epidemiology. Med Clin North Am 86:573-590, 2002.
Lallement G, Baille V, Baubichon D,
Carpentier P, Collombet JM, Filliat P, Foquin A, Four E, Masqueliez C, Testylier G,
Tonduli L, Dorandeu F: Review of the value of
huperzine as pretreatment of organophosphate
poisoning. Neurotoxicology 23:1-5, 2002.
Lawrence AD, Sahakian BJ: The cognitive
psychopharmacology of Alzheimer's disease:
focus on cholinergic systems. Neurochem Res
23:787-794, 1998.
Leggett DJ (ed.): Computational Methods for
Determination of Formation Constants, Plenum
Press, New York, 1985.
Malovana S, Gajdosova D, Benedik J, Havel J:
Determination of esmolol in serum by capillary
zone electrophoresis and its monitoring in course
of heart surgery. J Chromatogr B, 760:37-43, 2001.
Mazurek AA: Treatment of Alzheimer's disease.
N Engl J Med 342:821, 2000.
McKinney M, Miller JH, Yamada F,
Tuckmantel W, Kozikowski AP: Potencies and
stereoselectivities of enantiomers of huperzine A
for inhibition of rat cortical acetylcholinesterase.
Eur J Pharmacol 203:303-305, 1991.
Patocka J: Muze stara cinska droga pomoci
pacientum s Alzheimerovou chorobou?
Psychiatrie 3:23-24, 1999.
Poirier J: Evidence that the clinical effects of
cholinesterase inhibitors are related to potency
and targeting of action. Int J Clin Pract,
Suppl. 127:6-19, 2002.
Qian BC, Wang M, Zhou ZF, Chen K,
Zhou RR, Chen GS: Pharmacokinetics of
tablet huperzine A in six volunteers. Acta
Pharmacolog Sinica 16:396-398, 1995.
Skolnick AA: Old Chinese herbal medicine used
for fever yields possible new Alzheimer disease
therapy. J Amer Med Assoc 277:776, 1997.
Tonduli LS, Testylier G, Masqueliez C,
Lallement G, Monmaur P: Effects of Huperzine
used as pre-treatment against soman-induced
seizures. Neurotoxicology 22:29-37, 2001.
Ved HS, Koenig ML, Dave JR, Doktor BP:
Huperzine A, a potential therapeutic agent for
dementia, reduces neuronal cell death caused by
glutamate. Neuroreport 8:963-968, 1997.
Yuan SQ, Wei TT: Studies on the alkaloids of
Huperzia serrata (Thunb.) Trev. [Article in
Chinese]. Yao Xue Xue Bao 23:516-520, 1988.
|
CITED
Tsioupi DA, Nicolaou IN, Moore L, Kapnissi-Christodoulou CP. Chiral separation of Huperzine A using CE - Method validation and application in pharmaceutical formulations. Electrophoresis. 33: 516-522, 2012.
Pawlat J, Stryczewska HD, Ebihara K. Sterilization Techniques for Soil Remediation and Agriculture Based on Ozone and AOP. J Adv Oxid Technol. 13: 138-145, 2010.
Hutalle-Schmelzer KML, Zwirnmann E, Kruger A, Grossart HP. Enrichment and cultivation of pelagic bacteria from a humic lake using phenol and humic matter additions. FEMS Microbiol Ecol. 72: 58-73, 2010.
Sun ZG, Zhao Y, Gao HY, Hu GX. Removal of SO2 from Flue Gas by Sodium Humate Solution. Energy Fuels. 24: 1013-1019, 2010.
Ozturk E, Ocak N, Coskun I, Turhan S, Erener G. Effects of humic substances supplementation provided through drinking water on performance, carcass traits and meat quality of broilers. J Anim Physiol Anim Nutr. 94: 78-85, 2010.
Lee E, Lee H, Jung W, Park S, Yang D, Lee K. Influences of humic acids and photoreactivation on the disinfection of Escherichia coli by a high-power pulsed UV irradiation. Korean J Chem Eng. 26: 1301-1307, 2009.
Margon A, Pastrello A, Mosetti D, Cantone P, Leita L. Interaction between Diclofenac and Soil Humic Acids. Soil Sedim Contam. 18: 489-496, 2009.
Leita L, Margon A, Pastrello A, Arcon I, Contin M, Mosetti D. Soil humic acids may favour the persistence of hexavalent chromium in soil. Environ Pollut. 157: 1862-1866, 2009.
Stenson AC. Fourier transform ion cyclotron resonance mass spectral characterization of metal-humic binding. Rapid Commun Mass Spectrom. 23: 465-476, 2009.
Habib E, Leon F, Dauer JD, Hill RA, Carvalho P, Cutler HG, Cutler SJ. Mycophenolic Derivatives from Eupenicillium parvum. J Nat Prod. 71: 1915-1918, 2008.
Kucerik J, Bakajova B, Pekar M. Antioxidant effect of lignite humic acids and its salts on the thermo-oxidative stability/degradation of polyvinyl alcohol blends. Environ Chem Lett. 6:.241-245, 2008.
Bourlinos AB, Stassinopoulos A, Anglos D, Zboril R, Karakassides M, Giannelis EP. Surface functionalized carbogenic quantum dots. Small. 4: 455-458, 2008.
Nimptsch J, Pflugmacher S. Decomposing leaf litter: The effect of allochthonous degradation products on the antioxidant fitness and photosynthesis of Vesicularia dubyana. Ecotoxicol Environ Saf. 69: 541-545, 2008.
Stenson AC. Reversed-phase chromatography fractionation tailored to mass spectral characterization of humic substances. Environ Sci Technol. 42: 2060-2065, 2008.
Stottmeister U. Environmental remediation with humic substance system. Chem unserer Zeit. 42: 24-41, 2008.
Pawlat J, Ihara S. Removal of color caused by various chemical compounds using electrical discharges in a Foaming column. Plasma Processes Polym. 4: 753-759, 2007.
Saparpakorn P, Kim JH, Hannongbua S. Investigation on the binding of polycyclic aromatic hydrocarbons with soil organic matter: A theoretical approach. Molecules. 12: 703-715, 2007.
Yee MM, Miyajima T, Takisawa N. Thermodynamic studies of dodecylpyridinium ion binding to humic acid and effect of solution parameters on their binding. Colloids Surf A. 295: 61-66, 2007.
Karthik A, Subramanian GS, Musmade P, Ranjithkumar A, Surulivelrajan M, Udupa N. Stability-indicating HPTLC determination of rivastigmine in the bulk drug and in pharmaceutical dosage forms. J Planar Chromatogr - Mod TLC. 20: 457-461, 2007.
Ben Hameda A, Taborsky P, Pena-Mendez EM, Havel J. Matrix-assisted laser desorption/ionization mass spectrometry (MALDI TOF MS) study of Huperzine A, a natural anti-Alzheimer's disease product, its derivatization and its detection by highly sensitive laser induced fluorescence (LIF). Talanta. 72: 780-784, 2007.
Rodrigues AL, Nogueira R, Janknecht P, Brito AG. Monitoring natural organic matter in surface water by UV spectroscopy: Effects of calcium, magnesium and pH value. Proceedings of the Second IASTED International Conference on Advanced Technology in the Environmental Field, pp. 54-56, 2006.
Arcon I, Pastrello A, Catalano L, De Nobili M, Cantone P, Leita L. Interaction between Fe-cyanide complex and humic acids. Environ Chem Lett. 4: 191-194, 2006.
Senta A, Horvat AJM, Mijatovic I. Trihalomethane formation potential in the surface and ground water near Jakusevec landfill (Croatia): Impact of dissolved organic matter molecular size. Fresenius Environ Bull. 15: 1447-1454, 2006.
Pena-Mendez EM, Gajdosova D, Novotna K, Prosek P, Havel J. Mass spectrometry of humic substances of different origin including those from Antarctica - A comparative study. Talanta. 67: 880-890, 2005.
Srinivasu MK, Rao BM, Reddy BSS, Kumar PR, Chandrasekhar KB, Mohakhud PK. A validated chiral liquid chromatographic method for the enantiomeric separation of Rivastigmine hydrogen tartarate, a cholinesterase inhibitor. J Pharm Biomed Anal. 38: 320-325, 2005.
Ben Hameda A, Elosta S, Havel J. Optimization of the capillary zone electrophoresis method for Huperzine A determination using experimental design and artificial neural networks. J Chromatogr A. 1084: 7-12, 2005.
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