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New Techniques of Structure Elucidation for Sesquiterpenes

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Progress in the Chemistry of Organic Natural Products 114

Part of the book series: Progress in the Chemistry of Organic Natural Products ((POGRCHEM,volume 114))

Abstract

The most significant new techniques that have been used in the twenty-first century for the structure elucidation of sesquiterpenes and some derivatives are reviewed in this chapter. A distinctive feature of these methodologies is the combination of accurate experimental measurements with theoretical data obtained by molecular modeling calculations that allow to visualize, understand, and quantify many structural characteristics. This has been the case for NMR spectroscopy, which has expanded its potential for solving complex structural problems by means of comparison with quantum mechanical molecular models. Ab initio and density functional theory calculations of chemical shifts, coupling constants, and residual chemical shift anisotropies have played important roles in the solution of many structures of sesquiterpenes. The assignments of their absolute configurations by evaluation of calculated and experimental chiroptical properties as electronic and vibrational circular dichroism are also reviewed. This chapter also includes the use of X-ray diffraction analysis with emphasis on calculations of the Flack and Hooft parameters, which are applicable to all molecules that crystallize in non-centrosymmetric space groups. The accurate molecular models of sesquiterpenes, validated by concordance with their experimental properties, are nowadays essential for the interpretation of the effects of these natural products on biological systems.

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Acknowledgements

We are grateful to Conacyt-Mexico for financial support through grant CB 241053 and for a postdoctoral fellowship awarded to J.C.P.N. The authors wish to thank Dr. J. Martín Torres-Valencia, Universidad Autónoma del Estado de Hidalgo, Pachuca, Hidalgo, Mexico for kindly providing the plant photographs.

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  1. Department of Chemistry, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Avenida Instituto Politécnico Nacional 2508, Mexico City, 07360, Mexico

    Julio C. Pardo-Novoa & Carlos M. Cerda-García-Rojas

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  1. Julio C. Pardo-Novoa
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  2. Carlos M. Cerda-García-Rojas
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Correspondence to Carlos M. Cerda-García-Rojas .

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Editors and Affiliations

  1. College of Pharmacy, Ohio State University, Columbus, OH, USA

    A. Douglas Kinghorn

  2. Institute of Organic Chemistry, Johannes Kepler University, Linz, Oberösterreich, Austria

    Heinz Falk

  3. School of Pharmacy, University of East Anglia, NORWICH, UK

    Simon Gibbons

  4. Graduate School of Pharmaceutical Science, Hokkaido University, Fukuoka, Japan

    Jun'ichi Kobayashi

  5. Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima, Japan

    Yoshinori Asakawa

  6. School of Pharmaceutical Sciences, South Central University for Nationalities, Wuhan, China

    Ji-Kai Liu

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Pardo-Novoa, J.C., Cerda-García-Rojas, C.M. (2021). New Techniques of Structure Elucidation for Sesquiterpenes. In: Kinghorn, A.D., Falk, H., Gibbons, S., Kobayashi, J., Asakawa, Y., Liu, JK. (eds) Progress in the Chemistry of Organic Natural Products 114. Progress in the Chemistry of Organic Natural Products, vol 114. Springer, Cham. https://doi.org/10.1007/978-3-030-59444-2_3

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