Herbal Reference Standards - Thieme
Review689AuthorsMichael Schwarz, Bernhard Klier, Hartwig SieversAffiliationPhytoLab GmbH & Co. KG, Vestenbergsgreuth, GermanyKey words" reference substancesl" reference extractsl" phytochemical markersl" herbal medicinal productsl" dietary supplementsl" food supplementsl" quality controllAbstractUSP:USP RS:!This review describes the current definitions andregulatory requirements that apply to referencestandards that are used to analyse herbal products. It also describes and discusses the currentuse of reference substances and reference extractsin the European and United States pharmacopoeias.AbbreviationsEuropean Pharmacopoeiaherbal medicinal productIntroduction!receivedrevisedacceptedNov. 27, 2008April 9, 2009April 14, 2009BibliographyDOI 10.1055/s-0029-1185705Published online May 18, 2009Planta Med 2009; 75: 689–703 Georg Thieme Verlag KGStuttgart · New York ·ISSN 0032‑0943CorrespondenceDr. Michael SchwarzPhytoLab GmbH & Co. KGDutendorfer Str. 5–791487 VestenbergsgreuthGermanyPhone: 49 9 16 38 83 27Fax: 49 9 16 38 84 56michael.schwarz@phytolab.dewww.phytolab.comThe term “herbal products” as used throughoutthis review refers to herbal drugs, herbal preparations as well as to finished herbal medicinal products unless a different meaning is obvious fromthe context. More specific terms are used wherenecessary.Supporting information available online amedica!EP:HMP:United States PharmacopoeiaUnited States Pharmacopoeia reference standardReference standards are used to calibrate and validate the testing methods that are applied withinthe framework of quality control throughout all ofthe stages in the production and manufacture ofherbal products. The quality of these referencestandards is therefore of prime importance to thequality and associated safety and efficacy of theseproducts. As the individual constituents themselves are only rarely identified in herbal products, the analysts frequently have to rely on characteristic constituents, so-called phytochemicalmarkers. This review therefore begins by outlining the regulatory requirements that apply to theselection and use of markers. It then focuses onthe regulatory stipulations and practical requirements that apply to the establishment, characterisation, documentation and handling of the reference standards produced on the basis of these.Reference standards used to test herbal preparations and products are basically subject to thesame requirements as those used to analysechemically defined products. A few special requirements are imposed with respect to the refer-ence standards for herbal products and these arediscussed in greater detail below [1–4].Herbal medicinal products (HMP) have to meetmany statutory requirements relating to theirmanufacture, constitution, testing, storage anddistribution. Most of the pertinent specificationsand regulations describe the level of requirements and the criteria to be met in order to comply with them. This means, for example, thatthere are detailed regulations stipulating that theactive substance in an HMP must be declared andtested, as well as the way in which this must bedone. At the same time, comprehensive validationshould ensure that the applied methods provideprecise, reproducible and accurate results. The results of analytical methods are affected by numerous influential variables, such as the matrix, thereagents and materials used, as well as light, temperature and equipment, where applicable, and –last but not least – the mode of operation. In thisrespect, there are few factors that are of such fundamental importance and require such exhaustive testing and qualification as the referencestandard used. Unlike physical properties, chemical reference standards cannot be traced back toSchwarz M et al. Herbal Reference Standards Planta Med 2009; 75: 689–703This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited.Herbal Reference Standards
Reviewinternational prototypes. Their suitability as points of referencefor the determination of a characteristic, e.g., “substance XY content” ensues from a multitude of factors, which can frequentlyonly be determined by means of relative methods. This problemis exacerbated by the diversity of possible sources for one and thesame herbal reference standard. The requirement relating to theactive substance content of an HMP (accuracy of 5 %) is a hurdlethat can frequently only be met with a great deal of effort and expense. Traditional herbal combination products typically containing 3 or more herbal preparations are even more challenging.It is not unusual that the marker substances in such combinationproducts are present at a trace level only. Considering the 50 %tolerances that are usually accepted in trace analysis by way ofcontrast, the magnitude of the challenge facing guideline-compliant analysis of herbal products today becomes evident.Alarmingly, little attention is given to the quality of the standardsused in pharmacological or toxicological research, on the otherhand, in spite of the fact that the test results obtained here oftenconstitute the basis to assess the safety and efficacy of herbalproducts.Regulatory Requirements and Definitions!While the legal framework and detailed quality requirements areclearly regulated for HMP in the EU, in the USA and in many othercountries, these have not yet been defined to the same extent forfood supplements (covered by food law within the EU) or dietarysupplements in the USA (covered by the Dietary Supplementsand Health Education Act [5]), and there are good reasons forthis. However, as health-promoting functions and effects arebeing claimed to an increasing extent, it is to be expected thatquality requirements for such products be tightened up in the future. This has already taken place in the USA with the introduction of cGMP for dietary supplements in June 2007 [6]. The quality of reference standards and the pertinent documentation playan important role in this respect. In contrast to this, there are noexplicit rulings for the quality of plant-based food supplements inthe EU, apart from the general quality requirements that apply toall foodstuffs. Nevertheless, the quality aspect has been broughtup more frequently in discussion papers and drafts in recentyears; examples include the current EFSA draft guidance document for the safety assessment of botanicals and botanical preparations used in food supplements [7] and the European Commissionʼs Terms of Reference for the assessment of claims by theEFSA [8].As far as the manufacturers of drugs and medicinal products areconcerned, the guidelines drawn up by the WHO, ISO and NISTserve as guiding principles, and the monographs of such internationally acknowledged pharmacopoeias as the PharmacopoeiaEuropaea (Ph. Eur. or EP) [9] and the United States Pharmacopoeia (USP) [10] are binding within their respective geographicalscopes. There are no specific EMEA or ICH guidelines for reference standards yet. A few fundamental requirements for the establishment, documentation and use of primary and secondarystandards within the framework of manufacturing and testing active pharmaceutical ingredients (APIs) can be found in the Notefor Guidance on Good Manufacturing Practice for Active Pharmaceutical Ingredients (CPMP/ICH/4106/00) [11].The ISO Guides 30–35 of the International Organisation forStandadization are of essential importance to every manufacturer or user of reference standards [12–17]. Although theseSchwarz M et al. Herbal Reference StandardsPlanta Med 2009; 75: 689–703documents are not legally binding, they represent the generallyaccepted international state of the art and therefore constitutethe basis for the use of reference standards where no special,mandatory regulations exist. This is the case in the EuropeanPharmacopoeia and USP, for example, in which the chapters onreference standards primarily describe details and conventionsrelating to the handling of pharmacopoeial standards, whileagreeing with the requirements of the ISO Guides to a great extent regarding the technical principles." ISO Guide 30: 1992: Terms and definitions used in connectionwith reference materials." ISO Guide 31: 2000: Reference materials – contents of certificates and labels." ISO Guide 32: 1997: Calibration in analytical chemistry and useof certified reference materials." ISO Guide 33: 2000: Uses of certified reference materials." ISO Guide 34: 2000: General requirements for the competenceof reference materials producers." ISO Guide 35: 2006: Reference materials – general and statistical principles for certification.ISO Guide 30: 1992 defines a reference material as follows: “Material or substance one or more of whose property values are sufficiently homogeneous and well established to be used for thecalibration of an apparatus, the assessment of a measurementmethod, or for assigning values to materials.” At the same time, areference material can also be a defined individual substance.ISO Guide 30 defines a certified reference material (CRM) as follows: “Reference material, accompanied by a certificate, one ormore of whose property values are certified by a procedurewhich establishes its traceability to an accurate realization ofthe unit in which the property values are expressed, and forwhich each certified value is accompanied by an uncertainty at astated level of confidence.”Of formal significance is the fact that each set of rules and standards – ISO Guides and EP – contains cross-references to the other one, which means that the requirements of the ISO Guides areespecially relevant to the pharmaceutical sector, at least indirectly. This is particularly important where standards that havebeen established by the manufacturer himself, or a third party,are used for testing instead of pharmacopoeial standards. On theother hand, there are also some important deviations, as neitherthe EP nor the USP include information about the uncertainty ofthe assigned value of a reference standard with the respectivedocumentation, “since the precision of the method and uncertainty of the value attributed to the reference standard are takeninto account when setting the limit(s) in a monograph” [9].The stipulations laid down in the EP Section 5.12 “Referencestandards” apply to reference standards throughout the area ofapplication of the European Pharmacopoeia, i.e., in the memberstates of the European Pharmacopoeia Commission (36 states atthe moment). Although the rider “This chapter is published for information” is attached to this section, it has a virtually binding effect for the pharmaceutical sector within the pharmacopoeiaʼsscope of application. Any deviations from these stipulations mustbe documented with evidence of their equivalence.According to the definition laid down in the European Pharmacopoeia: “Reference standards are shown to be suitable for their intended purpose; they are not necessarily suitable for other purposes. If a reference standard is to be used for any purpose otherthan that of which it has been established, its suitability for thenew use has to be fully demonstrated. Any value assigned to a ref-This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited.690
erence standard is valid for the intended use and not necessarilyfor other uses.”This applies in full consequence to CRS standards of the EuropeanPharmacopoeia. CRS (chemical reference substances) are only regarded as having validity with respect to the tests for which theyare specified in the pertinent monographs. The CRS standardspecified in an herbal drug monograph must therefore qualifybefore it can be used to test an extract made from the drug, forexample.Within the European Pharmacopoeiaʼs scope of application, theterm “reference standard” is used to refer to reference substances,reference preparations and reference spectra. This means thatthe reference extracts increasingly used in the testing of herbalproducts and described in certain pharmacopoeia monographsare equivalent to reference substances by definition.Reference standards that have been established under the aegisof and released by the European Pharmacopoeia Commissionare generally referred to as European Pharmacopoeia ReferenceStandards. European Pharmacopoeia Chemical Reference Substances are primary reference standards by definition (with theexception of certain antibiotics, which are calibrated in international units).A primary standard is defined as being: “A standard shown tohave suitable properties for the intended use, the demonstrationof suitability being made without comparison to an existing standard.” Secondary standards are derived by comparison with primary standards. The term working standard is used to describesecondary standards that serve as standards within the framework of routine analysis. They are derived from primary reference standards and are therefore equivalent to secondary reference standards.The terms internal and external standard do not refer to a qualitative categorisation of a reference standard, but rather to theway in which it is used.Reference standards offered by the EDQM are established andqualified within the framework of an elaborate process. This regularly includes testing in several laboratories, as well as the performance of inter-laboratory tests. As far as the testing of herbaldrugs or preparations is concerned, reference extracts may alsobe used as CRSs. It is necessary to resort to comprehensivelyqualified reference substances for the marker to be quantified inorder to qualify such reference extracts. Interestingly enough, thepertinent passage of text merely refers to these as “ well characterised samples of active constituents or markers”. This formulation fails to stipulate whether these samples refer to primarystandards, which should be the case (the problems associatedwith reference extracts are discussed below).The EDQM issues a catalogue containing the current batches of itsreference standards at regular intervals. A European Pharmacopoeia Reference Standard can be used as long as the batch is listedas a current batch in the catalogue, whereby it may only be usedunder the conditions (use immediately after opening) and for thepurpose specified in the pharmacopoeia. Theoretically, stabilitytesting of a monographed herbal drug or extract would fall within this scope. However, this is not feasible in practice as it is notpossible to plan how long the current batch will maintain its “inuse” status. As an alternative, a working standard could be derived in sufficient quantities from a CRS, based on a differentsource of the standard.United States Pharmacopoeia (USP) rulings on reference standards: The USP runs a comprehensive establishment and qualification programme for the reference standards used in the appli-cation of pharmacopoeial methods. The USPʼs rulings on reference standards are described in detail in Section 11 of the General Chapters. They differ from the rulings of the EP with respectto certain formal aspects of the establishment and qualificationprocedures. Interestingly enough, the USP does not distinguishbetween primary and secondary standards; neither of theseterms are used. The categories of standards used by the USP areUSP Reference Standards (USP RS) and so-called Authentic Substances (USP AS).USP Reference Standards are standards that have been established in accordance with an extensive protocol and released foruse within the framework of monographs or general methods bythe USP Reference Substances Expert Committee. The USP already attaches great importance to the qualification of the sourcematerial for a reference standard batch. The currently releasedreference standard batches are listed on the USP web site (www.usp.org) with the pertinent batch numbers, whereby a distinction is made between current lots and previous lots. A current lotmay be used for as long as it remains listed on the web site. If abatch falls into the previous lot category, it is given a “valid usedate”. The user assumes responsibility for ensuring that he always uses a current lot or a previous lot which is still within the“valid use date”. Like the EP CRSs, the user does not receive a certificate of analysis although the label provides comprehensive information concerning the quality.Selection of Markers for Herbal Medicinal Products!Unlike chemically defined products, the constituents responsiblefor the therapeutic activity and efficacy of most herbal productsare only known to a certain extent, if at all. This is the reason whythe active substance in an HMP (or food/dietary supplement) isalways the herbal preparation in its entirety and complexity,e.g., an extract or a plant powder. The use of suitable referencestandards for herbal products is therefore preceded by the selection of constituents that are suitable for control purposes, socalled markers. Regulatory stipulations for the selection ofmarkers for herbal medicinal products can be found in variousguidance documents issued by the EMEA Herbal Medicinal Product Committee (HMPC) and the FDA. These essentially consist ofthe following documents:" Guideline on quality of herbal medicinal products/traditionalherbal medicinal products (CPMP/QWP/2819/00 Rev 1) [18]." Guideline on specifications: test procedures and acceptancecriteria for herbal substances, herbal preparations and herbalmedicinal products/traditional herbal medicinal products(CPMP/QWP/2820/00 Rev 1) [19].These stipulations include the following: “In the case of herbalsubstances with constituents of known therapeutic activity, assays of their content (with the test procedures) are required ”and “ where constituents of known therapeutic activity are notknown, assays of marker substances (with the test procedures)are required. The choice of markers should be justified.”And for herbal preparations: “A quantitative determination (assay) of markers or of substances with known therapeutic activityis also required. The content should be indicated with the lowestpossible tolerance (the narrowest possible tolerance with bothupper and lower limits stated). The test methods should be described in detail.”Schwarz M et al. Herbal Reference Standards Planta Med 2009; 75: 689–703691This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited.Review
ReviewThese requirements apply analogously to finished products.Markers are defined as follows: “Markers are chemically definedconstituents of a herbal substance which are of interest for control purposes independent of whether they have any therapeuticactivity or not. Markers may serve to calculate the quantity ofherbal substance(s) or herbal preparation(s) in the finished product if that marker has been quantitatively determined in theherbal substance(s) or herbal preparation(s) when the startingmaterials were tested. There are two categories of markers: Active markers are constituents or groups of constituents whichare generally accepted to contribute to the therapeutic activity.Analytical markers are constituents or groups of constituentsthat serve for analytical purposes.”Comparable requirements are stipulated in the FDAʼs “Guidancefor Industry – Botanical Drug Products” [20].While markers for many herbal drugs and drug preparations aredefined in the pertinent monographs of the European Pharmacopoeia (or other acknowledged pharmacopoeias, e.g., USP, BP, PF,etc.), markers for herbal drug preparations that have not beenmonographed can often only be selected in the course of developing the product or method. As far as extracts are concerned,the categories in accordance with the EP “Extracts” monographplay an important role:Standardised extracts are adjusted within an acceptable tolerance to a given content of constituents with known therapeuticactivity.Quantified extracts are adjusted to a defined range of constituents.Other extracts are essentially defined by their production process.Suitable markers must first be selected and established, particularly where constituents responsible for or contributing to thetherapeutic activity are unknown. Important criteria requiredfor this have been proposed in the recent HMPC “Reflection Paperon Markers used for Quantitative and Qualitative Analysis ofHerbal Medicinal Products and Traditional Herbal MedicinalProducts” (EMEA/HMPC/253 629/2007) [21]:" Characteristic for the herbal drug;" Constancy of presence in the herbal drug/preparation;" Chemically defined;" Analysable with routine analytical equipment;" Adequate content in herbal drug and herbal drug preparationfor the development of a valid, reproducible quantitative method;" Stability.tal importance for herbal products in particular, for the reasonsmentioned in the introduction. The purely phytochemicalscreening procedures used to locate characteristic secondarysubstances by combining TLC, HPLC or GC with various classicaldetection methods (e.g., chromogenic reagents, UV‑VIS, FID,etc.) in the past are now being used alongside more specificmethods, such as GC‑MS, LC‑MS/MS or LC‑NMR. These methodsoffer a very rapid means of characterising or even identifying secondary substances in complex fractions or complete extractswithout isolating the substances concerned beforehand. Theytherefore offer a means of identifying minor components, as well,which could only be determined in very time-consuming processes using larger quantities of plant material until just a fewyears ago. Constituents that contribute towards therapeutic activity can also be selected and characterised or identified on ananalytical scale by means of bioassay-guided fractionation. In thiscontext, the development of informative natural substance spectral libraries is becoming increasingly important. Nowadays, numerous spectral libraries are available for different measuringtechniques, whereby LC‑MS libraries play a major role in theidentification of natural substances. This approach enables a highlevel of dereplication for the isolation and structural determination of natural substances on a preparative scale. The informational value of an automated comparison with spectral librariesis fundamentally subject to certain restrictions. The signal patterns and intensities of mass spectra depend on analysis conditions and matrix effects in some respects, even if the ionisationtechnique is the same. This can give rise to false positive or falsenegative assignments or exclusions, particularly where large,pooled spectral databases are concerned. Nevertheless LC‑MSscreening is primarily used for selection of suitable markers. Asa rule, fully documented structural determination with subsequent establishment of a reference substance is achieved by carrying out off-line measurements on appropriately large quantities of the substance and a comprehensive comparison with published reference values for different measuring techniques (UV,IR, NMR, MS, etc.).Examples of commercially and/or publicly accessible spectral databases with high-quality data are as follows:" NIST/EPA/NIH (NIST 08) Mass Spectral Library [22];" Spectral Database for Organic Compounds SDBS [23].Requirements for the Characterisation of PrimaryStandards!While these criteria define the framework for selection, characterisation and use of marker substances for herbal medicinalproducts, there are currently no corresponding sets of rules forplant-based foodstuffs, such as functional food and food supplements. However, principles existing for markers of herbal medicinal products could be applied analogously where appropriate.Techniques for the Selection, Identification andCharacterisation of Marker Substances in HerbalPreparations!A highly developed set of analytical methods and instruments arecurrently available for the selection and identification of characteristic markers in herbal preparations. Although this is not intended as a subject for detailed discussion in this article, it has vi-Schwarz M et al. Herbal Reference StandardsPlanta Med 2009; 75: 689–703IdentificationThe analytical characterisation of primary reference substances issubject to the most stringent requirements. The identity of a primary reference substance is verified through characterisation byappropriate chemical attributes such as structural formula, empirical formula and molecular weight are (also refer to Section5.12 of the European Pharmacopoeia). Nuclear magnetic resonance (NMR) spectroscopy performs a central role in identitytesting as the structure of the reference substance can be determined by measuring and interpreting 1D- and 2D‑NMR spectrawithout the need for comparison with reference spectra. Apartfrom the usual 1H- and 13C‑NMR spectra, which generally sufficefor structural determination, 14/15 N-, 17O- and 31P‑NMR spectramay be measured and interpreted for verification or validationof specific structural elements containing heteroatoms. AlthoughX‑ray structural analysis also offers a suitable alternative for in-This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited.692
dependent determination of the molecular structure, this technique is in less widespread use and requires the substance to becrystallised. Information about the molecular weight of the reference substance can be obtained by recording mass spectra andthe measurement of high-resolution spectra may enable conclusions to be drawn regarding the empirical formula. Substancetypical fragmentation patterns emerge according to the ionisation technique used, which enable interpretations relating to theunderlying structural units and the presence of certain substituents. Complete determination of the structure is seldom possibleby means of mass spectrometry alone, however, which meansthat the method can only be used to verify the identity of a primary standard in conjunction with other methods. The same applies analogously to UV and IR spectra. Although conclusions maybe drawn from both types of spectra regarding certain structuredetermining properties, with IR spectra demonstrating a substance-specific fingerprint region in addition to this, neither ofthem ever provide sufficient information to deduce and verifythe complete structure. These spectra must always be eithercompared with a spectra library or combined with other identitytests. Apart from the methods mentioned above, the meltingpoint can also be determined, but this may be subject to severefluctuations depending on the last solvent used and the crystalstructure. It may be necessary to determine the optical rotationvalue and/or record CD spectra for compounds with chiralcentres. While identity testing by means of TLC requires a reference standard for comparison, performance of an elemental analysis may also prove helpful in confirming the elemental composition. Deviations from the composition or mass differences as anticipated on the basis of mass and NMR spectra may indicate possible impurities, such as water, residual solvents or inorganicconstituents.Purity testingChromatographic methods: A combination of various analyticalprocedures is also required to determine the purity of a primaryreference substance. Organic impurities in the reference substance are determined by means of a selective separating procedure – usually chromatographic (HPLC or GC) or electrophoretic(CE) – combined with a suitable detection technique. Attentionmust be given to ensuring that certain impurities are not left unaccounted for by the selected separating technique, e.g., non-volatile impurities in the event of gas chromatography or unchargedmolecules where CE is used. UV or diode array detectors are primarily used with HPLC methods as they represent detectiontechnologies that are fairly universal, as well as sensitive. Thechromatograms or electropherograms are usually evaluated according to the area normalisation method, i.e., an area percentageevaluation is carried out on all of the signals recorded in a chromatogram or electropherogram while allowing for the blank value. The nature of this method of evaluation is such that it is susceptible to a methodical error as it presupposes that all detectedcompounds have identical response factors. To eliminate this error, all of the impurities in the substance must first be known oridentified and must then be quantified exactly with the help of aspecific primary reference standard. The effort and expense involved in completely isolating and identifying potential impurities is unaffordable for natural substances because of the complex compositions of herbal drugs and, if at all, this approachmay only be considered for synthetic chemical compounds, witheducts and synthesis by-products known and available in sufficient quantities. The nature of the area normalisation (100 %)method is such that the purer the reference substance, the smaller the error. In addition to this, the error is reduced to a minimumif one assumes that mostly impurities, which are closely relatedin terms of structure and therefore have similar UV spectra andresponse factors, are co-extracted in the course of isolating thereference substance. UV detection is particularly suitable for application of the area normalisation method because related compounds usually have similar UV response factors that are not dimensions apart from that of the reference substance, which couldbe the case for electrochemical detection or detection by massspectrometry. The suitable detection wavelength must be selected after recording the UV spectra of the reference substanceand any secondary peaks. Where possible, the wavelength shouldbe an absorption maximum that includes all of the chromatogram or electropherogram signals. Many natural substances(e.g., saponins) lack a pronounced UV chromophore and theirUV spectra merely show a steeply declining shoulder around200 nm. Nevertheless, detection
Apr 09, 2009 · EP: European Pharmacopoeia HMP: herbal medicinal product USP: United States Pharmacopoeia USP RS: United States Pharmacopoeia refer-ence standard The term “herbal products” as used throughout this reviewreferstoherbal drugs, herbal prepara-tionsaswellas tofinishedherbal medicinal prod-uct
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