Strategies for Database Dereplication of Natural Products

Corley, David G.; Durley, Richard C.

doi:10.1021/np50113a002

Cited by 79 publications

(50 citation statements)

References 2 publications

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“…The use of a number of chemical databases dealing with pharmacognosy and natural product's chemistry are invaluable in understanding the therapeutic bases for any pharmacopeia (Corley and Durley, 1994). Reference to these should provide information substantiating the nature of phytochemicals of interest or others related to them.…”

Section: Chemical Dereplication and Patent Databasesmentioning

confidence: 99%

Dereplications Can Amplify The Extent And Worth Of Traditional Pharmacopeias.

Elvin‐Lewis

2011

Afr. J. Trad. Compl. Alt. Med.

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As aculturization and globalization continues, there is an urgent need to carefully record and delineate traditional pharmacopeias so that their true worth is understood and protected and any possible benefits related to their commercial development are equitably distributed. In the past most of these endeavors resulted in a list of plants with their associated uses without providing further explanations as to the extent of this knowledge within the traditional group, or if this knowledge was known elsewhere. This practice tended to generate the notion of finite exclusivity without providing proof that this was actually the case. Moreover, since the talents and methods of those conducting these initial studies varied widely, little effort was made to provide adequate information on how selective processes and preferences as well as modes of collection, preparation and use were achieved. Without these data, the potential of their clinical worth, bioreactive capacities or chemical compositions were often compromised. This frequently led to expending much time, effort and treasure on a pharmacopeia's evaluation without guidance on how these efforts could be optimized to achieve its best possible medicinal potential. This paper will review how types of dereplications and other techniques are helpful in amplifying this process. IntroductionBefore appropriate dereplications can be applied to a traditional pharmacopeia it is important to know how these data were acquired and by whom. The worth of this information is dependant upon the expertise of not only those involved in the acquisition of the data but also those that examine its worth. Nowadays to corroborate and/or exploit the medicinal value of a traditional-based pharmacopeia it is important to utilize the talents of many expert scientists. Such endeavors should be viewed as a team effort, with data evolved by one type of investigator providing insights to others along the validation process.In the past it was not unusual for medicinal plant inventories pertaining to a specific traditional pharmacopeia to be conducted by individuals who were limited in their expertise. This often generated a list of plants and/or local names associated with some, but not necessarily all of their uses. I have observed that depending on the extent of the study, this occasionally results in incomplete or erroneous information being recorded regarding the true nature of the malady or remedy or the correct identification of the plant itself. In the latter instance, when accompanying plant vouchers were not provided, or inappropriately prepared without fruit and/or flowers, misidentifications could be made in a variety of ways. Sometimes this has meant depending on local names to guide determinations without understanding if one or more disparate taxa were associated with this epithet e.g., Akan designation of "tweapea" for Garcinia afzellii and G. epunctata (Adu-tutu. et al 1979;Elvin-Lewis, 1980, Elvin-Lewis, 1982. There was also a tendency to list plants for a use without c...

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Section: Chemical Dereplication and Patent Databasesmentioning

confidence: 99%

Dereplications Can Amplify The Extent And Worth Of Traditional Pharmacopeias.

Elvin‐Lewis

2011

Afr. J. Trad. Compl. Alt. Med.

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“…Instead, mass spectrometry alone may be used to quickly "dereplicate" or identify the known compounds based on molecular mass, fragmentation patterns and elemental composition in combination with natural product database searching [35][36][37][38][39]. Commercially available natural products databases include NAPRALERT [40], Scientific & Technical information Network (STN) [41], and the Dictionary of Natural Products [42]. Since some of these databases also contain UV-vis absorbance data, it is also advantageous to use a photodiode array detector between the HPLC and mass spectrometer to obtain additional spectrometric data during LC-UV-MS dereplication [36,37].…”

Section: Encoding and Identification Of Compounds In Combinatorial LImentioning

confidence: 99%

Mass Spectrometry and Drug Discovery

Breemen

Newsome

Dahl

2010

Burger's Medicinal Chemistry and Drug Discovery

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In the twenty‐first century, medicinal chemists are producing large numbers of organic compounds through a process called combinatorial chemistry and then testing them against pharmacological targets such as enzymes or receptors using high‐throughput screening. As a result, lead compounds can emerge from drug discovery programs in a few weeks instead of several years. Although a variety of spectroscopic and chromatographic techniques are used to support drug discovery, only HPLC or UHPLC combined with mass spectrometry (LC‐MS) are compatible with virtually all drug‐like molecules. In addition to providing a universal means to characterize drug molecules based on molecular mass and structural features, mass spectrometry provides high throughput. With the development of routine LC‐MS interfaces and ionization techniques such as electrospray and atmospheric pressure chemical ionization, mass spectrometry has also become an ideal HPLC detector for the analysis of combinatorial libraries. Furthermore, a variety of mass spectrometry‐based screening assays have been developed to screen complex mixtures of compounds including natural product extracts as a means of expanding the molecular diversity of drug leads. The use of mass spectrometry in support of combinatorial library synthesis and purification is addressed as well as screening applications such as frontal affinity chromatography‐mass spectrometry, gel permeation chromatography‐LC‐MS, affinity chromatography‐mass spectrometry, and pulsed ultrafiltration mass spectrometry. Since drug development issues such as metabolic stability and the formation of reactive metabolites are now being considered during the drug discovery process, some applications of mass spectrometry to early drug development are addressed.

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“…Instead, mass spectrometry alone may be used to quickly 'dereplicate' or identify the known compounds based on molecular weight, fragmentation patterns and elemental composition in combination with natural product database searching [32][33][34][35][36]. Commercially available natural products databases include NAPRA-LERT [37], Scientific & Technical information Network (STN) [38], and the Dictionary of Natural Products [39]. Since some of these databases also contain UV/VIS absorbance data, it is also advantageous to use a photodiode array detector between the HPLC and mass spectrometer to obtain additional spectrometric data during LC-UV-MS dereplication [33,34].…”

Section: Characterization and Dereplication Of Natural Productsmentioning

confidence: 99%

Analysis and screening of combinatorial libraries using mass spectrometry

Shin

Breemen

2001

Biopharm & Drug Disp

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Mass spectrometry is a highly selective and high throughput analytical technique that is ideally suited for the identification and purity determination of large numbers of compounds prepared using combinatorial chemistry or for the dereplication of natural products. Compounds may be characterized based on molecular weight, elemental composition and structural features based on fragmentation patterns. When coupled to a separation technique such as highperformance liquid chromatography (HPLC) or capillary electrophoresis, mass spectrometric applications may be expanded to include analysis of complex mixtures. However, the slower speed of the separation step reduces the throughput of the analysis. This review concerns the application of mass spectrometry to the characterization of combinatorial libraries and the screening of library and natural product mixtures. Strategies to enhance the throughput of LC-MS are discussed including fast HPLC and parallel LC-MS. Also, mass spectrometry-based screening methods are described including frontal affinity chromatography-mass spectrometry, gel permeation chromatography LC-MS, direct electrospray mass spectrometry of receptor-ligand complexes, affinity chromatography-mass spectrometry, and pulsed ultrafiltration mass spectrometry.

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Strategies for Database Dereplication of Natural Products

Cited by 79 publications

References 2 publications

Dereplications Can Amplify The Extent And Worth Of Traditional Pharmacopeias.

Dereplications Can Amplify The Extent And Worth Of Traditional Pharmacopeias.

Mass Spectrometry and Drug Discovery

Analysis and screening of combinatorial libraries using mass spectrometry

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