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An Update of Erythrinan Alkaloids and Their Pharmacological Activities

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Progress in the Chemistry of Organic Natural Products 107

Part of the book series: Progress in the Chemistry of Organic Natural Products ((POGRCHEM,volume 107))

Abstract

The period of the past 5 years has witnessed a remarkable increase in all of the number, structural variety, and complexity of erythrinan alkaloids reported. This structural diversity seems to be most pronounced in the alkaloids reported from the two species Erythrina arborescens and Erythrina variegata. Between them, work-up of these taxa yielded new polymeric (dimeric and trimeric) erythrinan alkaloids, a first example in one case where a normal 6,5,6,6-membered indoloisoquinoline spirocylic core has rearranged to a spiro-fused 6,5,7,6-skeleton. Furthermore, erythrinan alkaloids with a fifth ring containing a 2H-imidazole functionality were also reported for the first time, together with some new structures having an unusual substitution and with functionalities at positions C-3 and C-7 of the erythrinan core. This contribution has included 40 more erythrinan alkaloids that are either new or were omitted in the most recent major reviews on the same topic, leading to a total of 154 known erythrinan alkaloids to date. There are a few cases where the structures of the new alkaloids are contestable due to insufficient data having been obtained on isolation. To facilitate easier reference and identification, all structures having a common core have been placed in the same table or figure in this chapter.

The reported pharmacological activities of the new and known erythrinan alkaloids documented have shown a considerable bias towards central nervous system and related activities. Other prominent activities that have been reported are antifeedant, insecticidal, cytotoxic, antiprotozoal, anti-inflammatory, antioxidant, antifungal, and antiviral effects. Erythrinan alkaloids generally seem to lack antibacterial activity. Several new polymeric alkaloids were found to lack cytotoxicity against a number of human cancer cell lines, although two of them showed moderate aphicidal activity and one exhibited weak to moderate acetylcholinesterase inhibition. The biological activity of erythrinan alkaloids seems to be influenced by basic substructural requirements, such as a conjugated diene (Δ1,2, Δ6,7) system and is modulated by the presence (or absence) of other groups in rings A, B, C, and D of the erythrinan core. The erythrinan core may provide potential leads to structures that eventually may be useful therapeutically.

In recent years, a number of stereoselective chemical synthesis methods have been applied towards the erythinan alkaloids, and these are described in this contribution.

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Acknowledgments

I wish to thank Mr. J. O. Ombito for kindly sending me some of the references cited herein while he was in Germany. Messrs Japhet Omollo Ombito, Sampson Dominic Umoh, and Nayang Kgakatsi are thanked for reading through the draft of the manuscript.

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  1. Department of Chemistry, University of Botswana, Gaborone, Botswana

    Runner R. T. Majinda

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Editors and Affiliations

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

    A. Douglas Kinghorn

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

    Heinz Falk

  3. UCL School of Pharmacy, University College London, Research, London, UK

    Simon Gibbons

  4. Grad. 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 Univ. for Nationalities, Wuhan, China

    Ji-Kai Liu

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Majinda, R.R.T. (2018). An Update of Erythrinan Alkaloids and Their Pharmacological Activities. In: Kinghorn, A., Falk, H., Gibbons, S., Kobayashi, J., Asakawa, Y., Liu, JK. (eds) Progress in the Chemistry of Organic Natural Products 107. Progress in the Chemistry of Organic Natural Products, vol 107. Springer, Cham. https://doi.org/10.1007/978-3-319-93506-5_2

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