**1. Introduction**

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62 Using Old Solutions to New Problems - Natural Drug Discovery in the 21st Century

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Since the discovery of Electron Paramagnetic Resonance (EPR) spectroscopy in 1944 by Za‐ voisky[1], and the realization of the Nuclear Magnetic Resonance (NMR) spectroscopic sig‐ nal in the mid 1940's by Bloch and Purcell[2,3], the capabilities and applications of the technology have continued to advance at an enormous rate particularly after the implemen‐ tation of Fourier transform NMR in the mid 1960's by Ernst[4]. Magnetic Resonance (MR) spectroscopy was initially utilized to characterize the structure of matter.[1,5] Through the early to mid 1970's, the development of multidimensional (nD) methods and more powerful instruments opened the door for the detailed atomistic characterization of small molecules culminating in structural elucidation of proteins by the mid 1980's.[6] At about the same time, it was proposed that a magnetic field gradient could be applied to obtain a 3-dimen‐ sional (3D) image leading to the invention of nuclear Magnetic Resonance Imaging (MRI) with, among other capabilities, the potential to monitor the bio-distribution and bio-accu‐ mulation of molecules *in vivo*.[7] Beyond the 1980's MR technologies were mixing with other technologies and evolving to play an integral role for advancing pharmaceuticals and be‐ coming indispensable tools for drug discovery, design and diagnostics.

#### **1.1. Capabilities**

Early on it was recognized (see Ref. 8 and references therein) that MR techniques can offer a variety of unique advantages over other spectroscopic techniques such as MR is completely non-destructive and non-invasive. Thus, MR technologies can be utilized with inanimate samples or living organisms with no obvious detrimental or destructive effects. In addition, MR techniques can be applied to a variety of states of matter including solution, semi-solids,

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solids and mixtures obtaining comprehensive information of the chemical and physical properties. In addition to the typical static structural information, one can also detail dy‐ namic processes. NMR measurements provide information about dynamic processes with rates in the range from 10-2 to 10-10 sec-1. Furthermore, many nuclei possess magnetic mo‐ ments, and with the availability of more sensitive spectrometers, chemists are beginning to take greater advantage of the technique for structure/bonding information for organometal‐ lic compounds (for example see Ref. 9).

An important application, although commonly overlooked, is the accurate quantitative in‐ formation that can be obtained without the need for laborious calibrations. Under quantita‐ tive conditions and for all practical purposes with semi-solid or solution state samples, NMR spectroscopy has the unique distinction of having a uniform molar response for all nuclei of the same type *i.e*. all 1 H nuclei have the same integrated intensity and thus, a single calibrated (internal or more significantly external) standard can be used for accurate quanti‐ tation.[10] For the aforementioned reasons NMR is a valuable tool for providing atomistic structural, dynamic and quantitative information on natural products such as small mole‐ cules, metabolites, peptides, proteins, complex mixtures, and molecular assemblies such as lipid bilayers or tissues.

Nuclear MRI, on-the-other-hand, can provide 3D images of macroscopic matter, and moni‐ tor the bio-accumulation and bio-distribution of MRI tagged natural products *in vivo*. Ulti‐ mately MR technologies can be used at almost every stage along the natural product discovery pipeline – from discovery to implementation, from molecules to medicine.

#### **1.2. Scope and limitations**

MR technologies encompass a range of techniques including electron or nuclear MR spectro‐ scopy, MR time domain, and nuclear or electron MRI. Herein, this chapter focuses on the nuclear MR technologies of spectroscopy and imaging for solution and semi-solid states. We provide a general overview of techniques and methodologies applicable throughout the de‐ velopment pipeline for natural products, as well as some potential impacts the information has for product development. It is well beyond the scope of a chapter (or in fact an entire book) to be a comprehensive description of all applicable MR methodologies. Thus within each section, the reader is directed to review articles, books, *etc*.
