Chemistry: analytical and immunological testing – Heterocyclic carbon compound – Hetero-o
Reexamination Certificate
2000-05-25
2003-10-21
Warden, Jill (Department: 1743)
Chemistry: analytical and immunological testing
Heterocyclic carbon compound
Hetero-o
C536S018500, C536S128000
Reexamination Certificate
active
06635490
ABSTRACT:
FIELD OF THE INVENTION
The invention relates to methods for the rapid industrially advantageous analysis of flavonoid and steroidal glycosidic compounds in natural products. Existing methods of equivalent analytical power are cumbersome, time consuming and expensive as well as being difficult to implement in the context of the contract research laboratory. The analysis of flavonoid and steroidal glycosidic compounds in HOSTA leaves served as model system.
BACKGROUND OF THE INVENTION
Since ancient times a vast number of natural remedies of plant and animal origin has been used for medical treatment and disease prevention (Shibata, S.,
The Chemistry of Chinese Drugs,
American Journal of Chinese Medicine (1979) 7(2): 103-141). The earliest known recorded recommendation of plants use to fight cancer appeared in the Ebers papyrus of Egypt dating from 1550 BC but this document implied an existence of already highly developed knowledge from far earlier times (Hartwell, J. L., et al.,
Antineoplastic Principles in Plants: Recent Developments in the Field,
Advances in Pharmacology (1969) 1: 117-209). A fast growing body of evidence obtained in the recent years by utilization of modern scientific, experimental and clinical methods confirms the biological activity of many micro components of plants that can be utilized in prevention or treatment of a variety of chronic diseases, including cancer and cardiovascular disease (Rao, A. V., et al.,
Anticarcinogenic Effects of Saponins and Phytosterols,
American Chemical Society Symposium Series (1997) 662: 313-324; Ghai, G., et al, U.S. Pat. No. 5,955,269; Hartwell, J. L.,
Types of Anticancer Agents Isolated from Plants,
Cancer Treatment Reports (1979) 60(8): 1031-1067; Hutabarat, L. S., et al.,
Development and Validation of an Isocratic High-performance Liquid Chromatographic Method for Quantitative Determination of Phytoestrogens in Soya Bean,
Journal of Chromatography A (1998) 795: 377-382).
Recently there has been visible a prominent trend to replace the conventional medicine approach, heavily dependent on the application of surgical intervention and use of potent synthetic drugs with many detrimental side effects (and thus being perceived by the public as inadequate or even harmful), by using herbal remedies or other forms of nutraceutical supplementation. Many herbal products available on the market are advertised as cures or preventative agents for a wide range of ailments. While a number of these claims might be true, based on their traditional use in folk medicine, for many of them there is little scientific basis underlying the claims of their health benefits.
Despite the fact that scientific evaluation of medicinal plants historically has been responsible for discovery of a multitude of modern medicine, approximately only 1% of plants has been analyzed so far.
When working with medicinal plants, the main goal is to isolate and identify the bioactive constituents. The typical strategy consists of the activity-guided fractionation of the plant extracts, leading to the isolation and identification of the active components. This approach is highly limited, time-consuming and may lead to easily missing any interesting lead compounds that don't poses the tested activity (Wolfender, J., et al.,
Comparison of Liquid Chromatography/Electrospray, Atmospheric Pressure Chemical Ionization, Thermospray and Continuous-flow Fast Atom Bombardment Mass Spectrometry for the Determination of Secondary Metabolites in Crude Plant Extracts,
Journal of Mass Spectrometry and Rapid Communications in Mass Spectrometry (1995) (Special Issue): S35-S46).
The growing demand of the aging population for high quality herbal supplements offering scientifically confirmed health benefits and presented in a standardized form of known potency, purity and efficacy has created a conducive environment for facilitation of the basic research on the identification of new herbal medicines as well as requirement for development of time and cost effective, reliable quality control analytical testing procedures. The concern of healthcare government agencies for safe and efficacious herbal supplements has led to introduction of much more stringent legislation regulating the allowed medical claims and demanding from the industry presentation of analytical data proving the products purity, potency and efficacy. Thus both, the search for novel, scientifically evaluated herbal medicines and the screening, standardization and quality control of already known herbal remedies, either in the plant material or in different formulations (including extracts, tinctures, suspensions, capsules and compressed tablets) call for a development of a rapid and reliable analytical method.
The analysis of botanical material is not a trivial matter. Usually, a sample to be analyzed contains a very complex mixture of many components. Only some of them might be biologically active, while other may be toxic. Components of these complex mixtures are usually interacting amongst themselves and often work synergistically. Frequently, in many plants, dozens of species and strains of the same genus, differ substantially in content of the active ingredients. Even within the same plant, different parts often have different chemical composition. Furthermore, the presence and concentration of some substances depend greatly on the soil, location, season, time of harvest, storage conditions, handling methods, conditions and solvents used for extraction, etc. This diversity of important conditions affecting the quality of botanical remedies requires therefore implementation of stringent, well-designed and closely-monitored standard operating procedures of manufacturing to ensure consistency from batch to batch of a nutraceutical product, followed by application of an appropriate analysis to ensure consistent potency and efficacy.
The major aims of qualitative analyses in phytochemistry include monitoring of the preparative isolation and purification of phytochemicals, chemotaxonomic testing and drug identification and/or detection of adulterants (Maillard, M. P., et al.,
Use of Liquid Chromatography
-
Thermospray Mass Spectrometry in Phytochemical Analysis of Crude Plant Extracts,
Journal of Chromatography (1993) 647: 147-154; Games, D. E.,
Combined High Performance Liquid Chromatography Mass Spectrometry,
Biomedical Mass Spectrometry (1981) 8(9): 454-462).
Plant constituents often exist in the form of glycosides. These conjugates may or may not occur together with their respective aglycones. Many glycosides play an important role as drugs and dyes. Glycosides are thermally labile, polar and non-volatile compounds frequently differing in their solubility and biological activity from their respective aglycones. By changing a type and/or number of attached saccharides the physicochemical and biological properties of the glycosides can be modified (Vaccaro, W. D., et al.,
Sugar
-
Substituted
2-
Azetidinone Cholesterol Absorption Inhibitors: Enhanced Potency by Modification of the Sugar,
Bioorganic & Medicinal Chemistry Letters (1998) 8: 313-318). Among phytochemicals existing in the glycosilated form that deserve a special attention due to their wide distribution in nature and a high number of beneficial biological and medicinal properties, are saponins and flavonoid glycosides.
Saponins are glycosides that commonly occur in higher plants where they are generally found in the roots, flowers and seeds. They are biosynthesized by more than 500 species belonging to almost 100 different families (Price, K. R., et al.,
The Chemistry and Biological Significance of Saponins in Foods and Feedingstuffs,
Critical Reviews in Food Science and Nutrition (1987) 26(1): 27-135). They are also found in many marine organisms. Saponins belong to one of two groups depending on the structure of their aglycone moiety (sapogenin): the triterpine group, in which the aglycone is usually represented by oleanane, ursane or damarane skeleton, and the steroid group. The latter also includes the steroid alkaloids. The most co
Fu Kejian
Kaminski Maciej A.
Liu Jessica
Caesar Rivise Bernstein Cohen & Pokotilow Ltd.
Cole Monique T.
Noble Laboratories
Warden Jill
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