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Chemistry and Biology of Cinchona Alkaloids

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Natural Products

Abstract

Cinchona alkaloids comprising quinine, quinidine, cinchonidine, and cinchonine as the major members constitute a unique class of quinoline alkaloids with tremendous impact on human civilization. The odyssey of Cinchona alkaloids began with the discovery of their antimalarial properties followed by the very successful application in stereochemistry and in asymmetric synthesis. Currently, the portfolio of applications of Cinchona alkaloids is much broader, involving chiral stationary phases for enantioselective chromatography, novel biological activities, and several useful transformation converting them into other modular and chiral building blocks, such as, for example, quincorine or quincoridine. Current pressure on a more intense exploration of sustainable products and easy access to diverse molecular architectures make Cinchona alkaloids of primary importance for synthetic catalytic and medicinal chemistry.

The aim of this chapter, which covers almost 300 references, is to summarize all aspects of Cinchona alkaloids chemistry and biology with the special emphasis on new developments.

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Abbreviations

AZT:

Azidothymidine

Bz:

Benzoil

Et:

Ethyl

HPLC:

High-performance liquid chromatography

HPTLC:

High-performance thin layer chromatography

IC50 :

Half maximal inhibitory concentration

LC-MS:

Liquid chromatography-mass spectrometry

NADPH:

Nicotinamide adenine dinucleotide phosphate

NMR:

Nuclear magnetic resonance

Me:

Methyl

Ms:

Mesyl (methanesulfonyl)

P:

Protection group

Ph:

Phenyl

TLC:

Thin layer chromatography

tBu:

tert-Butyl

X:

Halogen

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Acknowledgment

Research support from Ministry of Science and Higher Education (Grant No. N N 204 178340) is gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, Adam Mickiewicz University, Ul. Grunwaldzka 6, 60-780, Poznań, Poland

    Dr. Karol Michał Kacprzak

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  1. Dr. Karol Michał Kacprzak
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Correspondence to Karol Michał Kacprzak .

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  1. Botany Department, M.L. Sukhadia University, Durga Nursery Road, Udaipur, 313001, Rajasthan, India

    Kishan Gopal Ramawat

  2. Institute of Vine and Wine Sciences, Biological-Active Plant Substances Study, University of Bordeaux, 210 Chemin de Leysotte CS 50008, Villenave d'Ornon, 33882, France

    Jean-Michel Mérillon

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Kacprzak, K.M. (2013). Chemistry and Biology of Cinchona Alkaloids. In: Ramawat, K., Mérillon, JM. (eds) Natural Products. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-22144-6_22

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