Login Register Cart 0
Generic placeholder image

Current Pharmaceutical Design

Editor-in-Chief

ISSN (Print): 1381-6128
ISSN (Online): 1873-4286

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
General Review Article

A Review of Analytical Methods for the Determination of Hypericin in Foods, Herbal, Biological and Pharmaceutical Matrices

Author(s): Patricia Rocha de Araújo, Bruno Fonseca-Santos, Ana Carolina Kogawa*, Hérida Regina Nunes Salgado and Marlus Chorilli

Volume 26, Issue 36, 2020

Page: [4648 - 4657] Pages: 10

DOI: 10.2174/1381612826666200531145624

Price: $65

Abstract

Aims: A review of analytical methods for the determination of hypericin in foods, herbal, biological and pharmaceutical matrices.

Background: Hypericin (HYP) is a naturally-occurring pigment obtained from some plants of the genus Hypericum. Although HYP has been known for many years, it has recently attracted attention due to its varied biological properties, such as anti-inflammatory and antidepressant activity and it is also an efficient photosensitizer.

Objective: The objective of this review is to provide insights into the physicochemical properties of HYP, as well as to report the analytical methods existing in the literature and official compendia for different matrices.

Methods: The survey data were collected by Google Scholar® and Scopus® using keys terms.

Result: Analytical methods involving HYP are mainly concerned with the quality control of pharmaceutical preparations, foods, beverages, biological samples and drug delivery systems using different types of analysis methods. Some difficulties have also been identified due to the physicochemical properties of HYP. It presents great solubility in alkaline solutions, organic bases and common polar organic solvents.

Conclusion: It can be analyzed by thin layer chromatography, spectrophotometry in the ultraviolet region, but the most commonly used method is by HPLC. HYP presents monographs in the American, British and European Pharmacopoeias, however, the methods of analysis are not yet harmonized.

Keywords: Hypericin, anti-inflammatory, antidepressant, photosensitizing, HPLC, analytical methods, Hypericum.

« Previous Next »
[1]
Wolkenstein K, Gross JH, Falk H, Schöler HF. Preservation of hypericin and related polycyclic quinone pigments in fossil crinoids. Proc Biol Sci 2006; 273(1585): 451-6.
[http://dx.doi.org/10.1098/rspb.2005.3358 ] [PMID: 16615212]
[2]
Falk H. From the photosensitizer hypericin to the photoreceptor stentorin- the chemistry of phenanthroperylene quinones. Angew Chem Int Ed Engl 1999; 38(21): 3116-36.
[http://dx.doi.org/10.1002/(SICI)1521-3773(19991102)38:21<3116::AID-ANIE3116>3.0.CO;2-S ] [PMID: 10556884]
[3]
Avato P. A Survey on the Hypericum genus: Secondary metabolites and bioactivity. In: Atta ur R ed, Studies in Natural Products Chemistry: Elsevier . 2005; pp. 603-34.
[4]
Sirvent TM, Krasnoff SB, Gibson DM. Induction of hypericins and hyperforins in Hypericum perforatum in response to damage by herbivores. J Chem Ecol 2003; 29(12): 2667-81.
[http://dx.doi.org/10.1023/B:JOEC.0000008011.77213.64 ] [PMID: 14969354]
[5]
Giese AC. Hypericism. Photochemical and photobiological reviews. London: Plenum Press 1980; pp. 229-56.
[http://dx.doi.org/10.1007/978-1-4684-3641-9_6]
[6]
Hölzl J, Petersen M. Chemical constituents of Hypericum spp Hypericum: The genus Hypericum. London: CRC Press 2003; pp. 77-93.
[7]
Crockett SL, Robson NK. Taxonomy and chemotaxonomy of the genus Hypericum. Med Aromat Plant Sci Biotechnol 2011; 5(Special Issue 1): 1-13.
[PMID: 22662019]
[8]
Bisset NG. Hypericin Herba. In Herbal drugs and phytopharmaceuticals: A handbook for practice on a scientific basis. London: CRC Press 1994; pp. 305-8.
[9]
Butterweck V, Schmidt MSt. John’s wort: role of active compounds for its mechanism of action and efficacy. Wien Med Wochenschr 2007; 157(13-14): 356-61.
[http://dx.doi.org/10.1007/s10354-007-0440-8 ] [PMID: 17704987]
[10]
Schempp CM, Lüdtke R, Winghofer B, Simon JC. Effect of topical application of Hypericum perforatum extract (St. John’s wort) on skin sensitivity to solar simulated radiation. Photodermatol Photoimmunol Photomed 2000; 16(3): 125-8.
[http://dx.doi.org/10.1034/j.1600-0781.2000.d01-18.x ] [PMID: 10885442]
[11]
Hostettmann K, Wolfender J-L. Phytochemistry. St John’s wort and its active principles in depression and anxiety. Berlin: Birkhäuser Basel 2005; pp. 5-20.
[12]
Walt H. Nature’s gift to photodynamic medicine. Herbal medicines: Development and validation of plant-derived medicines for human health. Boca Raton: CRC Press 2012; pp. 279-82.
[13]
Van de Putte M, Ni Y, De Witte PA. Exploration of the mechanism underlying the tumor necrosis avidity of hypericin. Oncol Rep 2008; 19(4): 921-6.
[http://dx.doi.org/10.3892/or.19.4.921 ] [PMID: 18357376]
[14]
Bernal C, Ribeiro AO, Andrade GP, Perussi JR. Photodynamic efficiency of hypericin compared with chlorin and hematoporphyrin derivatives in HEp-2 and Vero epithelial cell lines. Photodiagn Photodyn Ther 2015; 12(2): 176-85.
[http://dx.doi.org/10.1016/j.pdpdt.2015.04.003 ] [PMID: 25910552]
[15]
Freeman D, Frolow F, Kapinus E, et al. Acidic properties of hypericin and its octahydroxy analogue in the ground and excited states. J Chem Soc Chem Commun 1994; 891-2.
[http://dx.doi.org/10.1039/c39940000891]
[16]
Vollmer JJ, Rosenson J. Chemistry of St. John’s Wort: Hypericin and Hyperforin. J Chem Educ 2004; 81: 1450.
[http://dx.doi.org/10.1021/ed081p1450]
[17]
Kapinus EI, Falk H, Tran HTN. Spectroscopic investigation of the molecular structure of hypericin and its salts. |Monatshefte für Chemie/ Chemical Monthly 1999; 130: 623-35.
[http://dx.doi.org/10.1007/PL00010243]
[18]
Lavie G, Mazur Y, Lavie D, Meruelo D. The chemical and biological properties of hypericin-a compound with a broad spectrum of biological activities. Med Res Rev 1995; 15(2): 111-9.
[http://dx.doi.org/10.1002/med.2610150203 ] [PMID: 7739292]
[19]
Leonhartsberger JG, Falk H. The protonation and deprotonation equilibria of hypericin revisited. Monatshefte für Chemie / Chemical Monthly 2002; 133: 167-72.
[20]
Etzlstorfer C, Falk H, Mayr E, Schwarzinger S. Concerning the acidity and hydrogen bonding of hydroxyphenanthroperylene quinones like fringelite D, hypericin, and stentorin. Monatshefte für Chemie / Chemical Monthly 1996; 127: 1229-37.
[21]
Gai F, Fehr MJ, Petrich JW. Ultrafast excited-state processes in the antiviral agent hypericin. J Am Chem Soc 1993; 115: 3384-5.
[http://dx.doi.org/10.1021/ja00061a069]
[22]
Fehr MJ, McCloskey MA, Petrich JW. Light-induced acidification by the antiviral agent hypericin. J Am Chem Soc 1995; 117: 1833-6.
[http://dx.doi.org/10.1021/ja00111a024]
[23]
Kubin A, Loew HG, Burner U, Jessner G, Kolbabek H, Wierrani F. How to make hypericin water-soluble. Pharmazie 2008; 63(4): 263-9.
[PMID: 18468384]
[24]
Falk H, Meyer J. On the homo- and heteroassociation of hypericin. Monatshefte für Chemie / Chemical Monthly 1994; 125 : 753-62.
[25]
Li T, Yang S, Liu W, et al. Preparation and characterization of nanoscale complex liposomes containing medium-chain fatty acids and vitamin C. Int J Food Prop 2015; 18: 113-24.
[http://dx.doi.org/10.1080/10942912.2012.685683]
[26]
Roslaniec M, Weitman H, Freeman D, Mazur Y, Ehrenberg B. Liposome binding constants and singlet oxygen quantum yields of hypericin, tetrahydroxy helianthrone and their derivatives: studies in organic solutions and in liposomes. J Photochem Photobiol B 2000; 57(2-3): 149-58.
[http://dx.doi.org/10.1016/S1011-1344(00)00090-7 ] [PMID: 11154081]
[27]
Skalkos D, Tatsis E, Gerothanassis IP, Troganis A. Towards a consensus structure of hypericin in solution: Direct evidence for a single tautomer and different ionization states in protic and nonprotic solvents by the use of variable temperature gradient 1H NMR. Tetrahedron 2002; 58: 4925-9.
[http://dx.doi.org/10.1016/S0040-4020(02)00419-2]
[28]
Siddiqui MR, AlOthman ZA, Rahman N. Analytical techniques in pharmaceutical analysis: A review. Arab J Chem 2017; 10: S1409-21.
[http://dx.doi.org/10.1016/j.arabjc.2013.04.016]
[29]
Kamal A, Ahmad FJ, Ahmad S, Saleem K. A validated HPLC method for the quantification of hypericin in hypericum perforatum. Asian J Chem 2012; 24: 4689-92.
[30]
Head CS, Luu Q, Sercarz J, Saxton R. Photodynamic therapy and tumor imaging of hypericin-treated squamous cell carcinoma. World J Surg Oncol 2006; 4: 87.
[http://dx.doi.org/10.1186/1477-7819-4-87 ] [PMID: 17147827]
[31]
Wynn JL, Cotton TM. Spectroscopic properties of hypericin in solutions and at surfaces. J Phys Chem 1995; 99: 4317-23.
[http://dx.doi.org/10.1021/j100012a063]
[32]
Castano AP, Demidova TN, Hamblin MR. Mechanisms in photodynamic therapy: Part one-photosensitizers, photochemistry and cellular localization. Photodiagn Photodyn Ther 2004; 1(4): 279-93.
[http://dx.doi.org/10.1016/S1572-1000(05)00007-4 ] [PMID: 25048432]
[33]
Lakowicz JR. Fluorescence sensing principles of fluorescence spectroscopy. Boston, MA: Springer 2006.
[http://dx.doi.org/10.1007/978-0-387-46312-4]
[34]
Cott JMSt. John’s Wort (Hypericum perforatum). New York: Marcel Dekker 2005.
[35]
Gîtea D, Şipoş M, Mircea T, Paşca B. The analysis of alcoholic extracts of Hypericum species by UV/VIS spectrophotometry. An Univ Oradea Fasc Biol 2010; 17: 111-5.
[36]
Anyzewska M, Kowalczuk A, Łozak A, Jabłczyńska R, Fijałek Z. Determination of total hypericins in St. John’s wort and herbal medicinal products. Acta Pol Pharm 2010; 67(6): 586-92.
[PMID: 21229872]
[37]
Chandrasekera DH, Welham KJ, Ashton D, Middleton R, Heinrich M. Quantitative analysis of the major constituents of St John’s wort with HPLC-ESI-MS. J Pharm Pharmacol 2005; 57(12): 1645-52.
[http://dx.doi.org/10.1211/jpp.57.12.0015 ] [PMID: 16354409]
[38]
Tatsis EC, Exarchou V, Troganis AN, Gerothanassis IP. 1H NMR determination of hypericin and pseudohypericin in complex natural mixtures by the use of strongly deshielded OH groups. Anal Chim Acta 2008; 607(2): 219-26.
[http://dx.doi.org/10.1016/j.aca.2007.11.040 ] [PMID: 18190811]
[39]
Li Y, Zhang J, Wang B, Shen Y, Ouahab A. Co-delivery of siRNA and hypericin into cancer cells by hyaluronic acid modified PLGA-PEI nanoparticles. Drug Dev Ind Pharm 2016; 42(5): 737-46.
[http://dx.doi.org/10.3109/03639045.2015.1091469 ] [PMID: 26472259]
[40]
Zhang W, Gong X, Cai Y, et al. Investigation of water-soluble inclusion complex of hypericin with β-cyclodextrin polymer. Carbohydr Polym 2013; 95(1): 366-70.
[http://dx.doi.org/10.1016/j.carbpol.2013.03.020 ] [PMID: 23618281]
[41]
Knox JP, Dodge AD. Isolation and activity of the photodynamic pigment hypericin. Plant Cell Environ 1985; 8: 19-25.
[http://dx.doi.org/10.1111/j.1365-3040.1985.tb01204.x]
[42]
Cakir A, Mavi A, Yildirim A, Duru ME, Harmandar M, Kazaz C. Isolation and characterization of antioxidant phenolic compounds from the aerial parts of Hypericum hyssopifolium L. by activity-guided fractionation. J Ethnopharmacol 2003; 87(1): 73-83.
[http://dx.doi.org/10.1016/S0378-8741(03)00112-0 ] [PMID: 12787957]
[43]
Beat M. Herbal medicinal products of St John’s wort Manufacturing and quality control Hypericum: The genus Hypericum. London: Taylor & Francis 2003; pp. 106-36.
[44]
Lotz A, Habermehl P, Spangenberg B. A new and highly sensitive TLC method to measure hypericin using chemiluminescence. J Liq Chromatogr Relat Technol 2017; 40: 287-91.
[http://dx.doi.org/10.1080/10826076.2017.1298030]
[45]
Kartnig T, Go¨bel I. Determination of hypericin and pseudohypericin by thin-layer chromatography-densitometry. J Chromatogr A 1992; 609: 423-6.
[http://dx.doi.org/10.1016/0021-9673(92)80192-W]
[46]
Jensen AG, Hansen SH. Separation of hypericins and hyperforins in extracts of Hypericum perforatum L. using non-aqueous capillary electrophoresis with reversed electro-osmotic flow. J Pharm Biomed Anal 2002; 27(1-2): 167-76.
[http://dx.doi.org/10.1016/S0731-7085(01)00548-9 ] [PMID: 11682223]
[47]
Huck CW, Abel G, Popp M, Bonn GK. Comparative analysis of naphthodianthrone and phloroglucine derivatives in St. John’s Wort extracts by near infrared spectroscopy, high-performance liquid chromatography and capillary electrophoresis. Anal Chim Acta 2006; 580(2): 223-30.
[http://dx.doi.org/10.1016/j.aca.2006.07.062 ] [PMID: 17723777]
[48]
Brolis M, Gabetta B, Fuzzati N, Pace R, Panzeri F, Peterlongo F. Identification by high-performance liquid chromatography-diode array detection-mass spectrometry and quantification by high-performance liquid chromatography-UV absorbance detection of active constituents of Hypericum perforatum. J Chromatogr A 1998; 825: 9-16.
[http://dx.doi.org/10.1016/S0021-9673(98)00697-9]
[49]
Agapouda A, Booker A, Kiss T, Hohmann J, Heinrich M, Csupor D. Quality control of Hypericum perforatum L. analytical challenges and recent progress. J Pharm Pharmacol 2017; 71(S1)
[http://dx.doi.org/10.1111/jphp.12711 ] [PMID: 28266019]
[50]
Draves AH, Walker SE. Determination of hypericin and pseudohypericin in pharmaceutical preparations by liquid chromatography with fluorescence detection. J Chromatogr B Biomed Sci Appl 2000; 749(1): 57-66.
[http://dx.doi.org/10.1016/S0378-4347(00)00383-2 ] [PMID: 11129079]
[51]
Unterweger H, Subatzus D, Tietze R, et al. Hypericin-bearing magnetic iron oxide nanoparticles for selective drug delivery in photodynamic therapy. Int J Nanomedicine 2015; 10: 6985-96.
[http://dx.doi.org/10.2147/IJN.S92336 ] [PMID: 26648714]
[52]
Kirakosyan A, Hayashi H, Inoue K, Charchoglyan A, Vardapetyan H. Stimulation of the production of hypericins by mannan in Hypericum perforatum shoot cultures. Phytochemistry 2000; 53(3): 345-8.
[http://dx.doi.org/10.1016/S0031-9422(99)00496-3 ] [PMID: 10703055]
[53]
Piovan A, Filippini R, Caniato R, Borsarini A, Bini Maleci L, Cappelletti EM. Detection of hypericins in the “red glands” of Hypericum elodes by ESI-MS/MS. Phytochemistry 2004; 65(4): 411-4.
[http://dx.doi.org/10.1016/j.phytochem.2003.11.003 ] [PMID: 14759533]
[54]
Sakavitsi M-E, Christodoulou M-I, Tchoumtchoua J, et al. Comparative HPLC-DAD and UHPLC-ESI(-)-HRMS & MS/MS profiling of Hypericum species and correlation with necrotic cell-death activity in human leukemic cells. Phytochem Lett 2017; 20: 481-90.
[http://dx.doi.org/10.1016/j.phytol.2017.05.003]
[55]
Koyu H, Haznedaroglu MZ. Investigation of impact of storage conditions on Hypericum perforatum L. dried total extract. Yao Wu Shi Pin Fen Xi 2015; 23(3): 545-51.
[http://dx.doi.org/10.1016/j.jfda.2015.04.002 ] [PMID: 28911714]
[56]
Li W, Fitzloff JF. High performance liquid chromatographic analysis of St. John’s wort with photodiode array detection. J Chromatogr B Biomed Sci Appl 2001; 765(1): 99-105.
[http://dx.doi.org/10.1016/S0378-4347(01)00404-2 ] [PMID: 11817315]
[57]
Kerb R, Brockmöller J, Staffeldt B, Ploch M, Roots I. Single-dose and steady-state pharmacokinetics of hypericin and pseudohypericin. Antimicrob Agents Chemother 1996; 40(9): 2087-93.
[http://dx.doi.org/10.1128/AAC.40.9.2087 ] [PMID: 8878586]
[58]
Liebes L, Mazur Y, Freeman D, et al. A method for the quantitation of hypericin, an antiviral agent, in biological fluids by high-performance liquid chromatography. Anal Biochem 1991; 195(1): 77-85.
[http://dx.doi.org/10.1016/0003-2697(91)90298-8 ] [PMID: 1888019]
[59]
Brockmöller J, Reum T, Bauer S, Kerb R, Hübner W-D, Roots I. Hypericin and pseudohypericin: pharmacokinetics and effects on photosensitivity in humans. Pharmacopsychiatry 1997; 30(Suppl. 2): 94-101.
[http://dx.doi.org/10.1055/s-2007-979527 ] [PMID: 9342768]
[60]
Fox E, Murphy RF, McCully CL, Adamson PC. Plasma pharmacokinetics and cerebrospinal fluid penetration of hypericin in nonhuman primates. Cancer Chemother Pharmacol 2001; 47(1): 41-4.
[http://dx.doi.org/10.1007/s002800000188 ] [PMID: 11221960]
[61]
Schulz HU, Schürer M, Bässler D, Weiser D. Investigation of the bioavailability of hypericin, pseudohypericin, hyperforin and the flavonoids quercetin and isorhamnetin following single and multiple oral dosing of a hypericum extract containing tablet. Arzneimittelforschung 2005; 55(1): 15-22.
[PMID: 15727160]
[62]
Butterweck V, Liefländer-Wulf U, Winterhoff H, Nahrstedt A. Plasma levels of hypericin in presence of procyanidin B2 and hyperoside: a pharmacokinetic study in rats. Planta Med 2003; 69(3): 189-92.
[http://dx.doi.org/10.1055/s-2003-38495 ] [PMID: 12677519]
[63]
Chi JD, Franklin M. Determination of hypericin in plasma by high-performance liquid chromatography. J Chromatogr B Biomed Sci Appl 1999; 724(1): 195-8.
[http://dx.doi.org/10.1016/S0378-4347(98)00572-6 ] [PMID: 10202973]
[64]
Uzdensky A, Iani V, Ma L-W, Moan J. On hypericin application in fluorescence diagnosis and cancer treatment: Pharmacokinetics and photosensitizing efficiency in nude mice bearing WiDr carcinoma. Med Laser Appl 2006; 21: 271-6.
[http://dx.doi.org/10.1016/j.mla.2006.05.005]
[65]
Borghi-Pangoni FB, Junqueira MV, Silva LL, Bruschi ML. HPLC method for determination of hypericin contained in polymeric system: Analysis of the regression significance, lack of fit, and applicability. Lat Am J Pharm 2016; 35: 2125-31.
[66]
Fadel M, Kassab K, Youssef T. Photodynamic efficacy of hypericin targeted by two delivery techniques to hepatocellular carcinoma cells. Lasers Med Sci 2010; 25(5): 675-83.
[http://dx.doi.org/10.1007/s10103-010-0787-8 ] [PMID: 20393766]
[67]
Lopera AA, Montoya A, Vélez ID, Robledo SM, Garcia CP. Synthesis of calcium phosphate nanostructures by combustion in solution as a potential encapsulant system of drugs with photodynamic properties for the treatment of cutaneous leishmaniasis. Photodiagn Photodyn Ther 2018; 21: 138-46.
[http://dx.doi.org/10.1016/j.pdpdt.2017.11.017 ] [PMID: 29198762]
[68]
Penjweini R, Deville S, D’Olieslaeger L, Berden M, Ameloot M, Ethirajan A. Intracellular localization and dynamics of Hypericin loaded PLLA nanocarriers by image correlation spectroscopy. Journal of controlled release. Official J Controlled Release Society 2015; 218: 82-93.
[http://dx.doi.org/10.1016/j.jconrel.2015.09.064]
[69]
Karioti A, Bilia AR. Hypericins as potential leads for new therapeutics. Int J Mol Sci 2010; 11(2): 562-94.
[http://dx.doi.org/10.3390/ijms11020562 ] [PMID: 20386655]
[70]
Shah AK, Avery BA, Wyandt CM. Content analysis and stability evaluation of selected commercial preparations of St. John’s wort. Drug Dev Ind Pharm 2005; 31(9): 907-16.
[http://dx.doi.org/10.1080/03639040500272066 ] [PMID: 16306003]
[71]
Draves AH, Walker SE. Analysis of the hypericin and pseudohypericin content of commercially available St John’s Wort preparations. Can J Clin Pharmacol 2003; 10(3): 114-8.
[PMID: 14506510]
[72]
Wang X, Mi J, Dong Y, Yang J. Optimization of extraction process of hypericin from St. John’s Wort by central composite design-response surface methodology. J Chem Pharm Res 2014; 6: 1667-75.
[73]
Huck-Pezzei VA, Bittner LK, Pallua JD, et al. A chromatographic and spectroscopic analytical platform for the characterization of St John’s wort extract adulterations. Anal Methods 2013; 5: 616-28.
[http://dx.doi.org/10.1039/C2AY26030A]
[74]
Sirvent T, Gibson DM. Rapid isocratic HPLC analysis of hypericins. J Liq Chromatogr Relat Technol 2000; 23: 251-9.
[http://dx.doi.org/10.1081/JLC-100101449]
[75]
Ayan AK, Çirak C. Hypericin and Pseudohypericin Contents in Some Hypericum. Species Growing in Turkey. Pharm Biol 2008; 46: 288-91.
[http://dx.doi.org/10.1080/13880200701741211]
[76]
Paulke A, Schubert-Zsilavecz M, Wurglics M. Determination of hypericin and pseudohypericin from Hypericum perforatum in rat brain after oral administration. Monatshefte für Chemie - Chemical Monthly 2008; 139: 489-94.
[http://dx.doi.org/10.1007/s00706-007-0792-1]
[77]
Bauer S, Störmer E, Graubaum HJ, Roots I. Determination of hyperforin, hypericin, and pseudohypericin in human plasma using high-performance liquid chromatography analysis with fluorescence and ultraviolet detection. J Chromatogr B Biomed Sci Appl 2001; 765(1): 29-35.
[http://dx.doi.org/10.1016/S0378-4347(01)00390-5 ] [PMID: 11817306]
[78]
Micali G, Lanuzza F, Currò P. High-performance liquid chromatographic determination of the biologically active principle hypericin in phytotherapeutic vegetable extracts and alcoholic beverages. J Chromatogr A 1996; 731(1-2): 336-9.
[http://dx.doi.org/10.1016/0021-9673(95)01222-2 ] [PMID: 8646329]
[79]
Tateo F, Martello S, Lubian E, Bononi M. Hypericin and hypericin-like substances: Analytical problems. Developments in Food Science 1998; pp. 143-57.
[80]
Borghi-Pangoni FB, Junqueira MV, de Souza Ferreira SB, et al. Preparation and characterization of bioadhesive system containing hypericin for local photodynamic therapy. Photodiagn Photodyn Ther 2017; 19: 284-97.
[http://dx.doi.org/10.1016/j.pdpdt.2017.06.016 ] [PMID: 28669792]
[81]
Zeisser-Labouèbe M, Lange N, Gurny R, Delie F. Hypericin-loaded nanoparticles for the photodynamic treatment of ovarian cancer. Int J Pharm 2006; 326(1-2): 174-81.
[http://dx.doi.org/10.1016/j.ijpharm.2006.07.012 ] [PMID: 16930882]
[82]
Ernst ESt. John’s Wort, an anti-depressant? A systematic, criteria-based review. Phytomedicine: Int J Phytotherapy Phytopharmacol 1995; 2: 67-71.
[83]
Laakmann G, Schüle C, Baghai T, Kieser MSt. John’s wort in mild to moderate depression: the relevance of hyperforin for the clinical efficacy. Pharmacopsychiatry 1998; 31(Suppl. 1): 54-9.
[http://dx.doi.org/10.1055/s-2007-979346 ] [PMID: 9684948]
[84]
Linde K, Ramirez G, Mulrow CD, Pauls A, Weidenhammer W, Melchart D. St John’s wort for depression--an overview and meta-analysis of randomised clinical trials. BMJ 1996; 313(7052): 253-8.
[http://dx.doi.org/10.1136/bmj.313.7052.253 ] [PMID: 8704532]
[85]
Booker A, Agapouda A, Frommenwiler DA, Scotti F, Reich E, Heinrich M. St John's wort (Hypericum perforatum) products - an assessment of their authenticity and quality. Phytomedicine: International J Phytotherapy Phytopharmacol 2017.
[http://dx.doi.org/10.1016/j.phymed.2017.12.012]
[86]
Folashade O, Omoregie H, Ochogu P. Standardization of herbal medicines-A review. Int J Biodivers Conserv 2012; 4: 101-12.
[87]
Calixto JB. Efficacy, safety, quality control, marketing and regulatory guidelines for herbal medicines (phytotherapeutic agents). Braz J Med Biol Res 2000; 33(2): 179-89.
[http://dx.doi.org/10.1590/S0100-879X2000000200004 ] [PMID: 10657057]
[88]
Mosihuzzaman M, Choudhary MI. Protocols on safety, efficacy, standardization, and documentation of herbal medicine (IUPAC Technical Report). Pure and Applied Chemistry 2008 ; 2195.
[89]
Pharmacopeia US. United States Pharmacopeia. 39th ed. Baltimore: United Book Press 2015.
[90]
BP British Pharmacopoeia. . London: The Stationey Office 2011.
[91]
EP. European Pharmacopoeia.. 7th ed Strasbourg: European Directorate for the Quality of Medicines and HealthCare. 2010.

Rights & Permissions Print Cite
Article Metrics
13
© 2024 Bentham Science Publishers | Privacy Policy