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Progress in the Chemistry of Organic Natural Products Vol. 94 pp 127–229Cite as

Withanolides and Related Steroids

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Abstract

Since the isolation of the first withanolides in the mid-1960s, over 600 new members of this group of compounds have been described, with most from genera of the plant family Solanaceae. The basic structure of withaferin A, a C28 ergostane with a modified side chain forming a δ-lactone between carbons 22 and 26, was considered for many years the basic template for the withanolides. Nowadays, a considerable number of related structures are also considered part of the withanolide class; among them are those containing γ-lactones in the side chain that have come to be at least as common as the δ-lactones. The reduced versions (γ and δ-lactols) are also known. Further structural variations include modified skeletons (including C27 compounds), aromatic rings and additional rings, which may coexist in a single plant species. Seasonal and geographical variations have also been described in the concentration levels and types of withanolides that may occur, especially in the Jaborosa and Salpichroa genera, and biogenetic relationships among those withanolides may be inferred from the structural variations detected. Withania is the parent genus of the withanolides and a special section is devoted to the new structures isolated from species in this genus. Following this, all other new structures are grouped by structural types.

Many withanolides have shown a variety of interesting biological activities ranging from antitumor, cytotoxic and potential cancer chemopreventive effects, to feeding deterrence for several insects as well as selective phytotoxicity towards monocotyledoneous and dicotyledoneous species. Trypanocidal, leishmanicidal, antibacterial, and antifungal activities have also been reported. A comprehensive description of the different activities and their significance has been included in this chapter. The final section is devoted to chemotaxonomic implications of withanolide distribution within the Solanaceae.

Overall, this chapter covers the advances in the chemistry and biology of withanolides over the last 16 years.

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Acknowledgments

We thank CONICET, Universidad de Buenos Aires and Universidad de Córdoba for financial support.

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Authors and Affiliations

  1. Departamento de Química Orgánica and UMYMFOR (CONICET-UBA), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, Buenos Aires, C1428EGA, Argentina

    Rosana I. Misico & Gerardo Burton

  2. Departamento de Química Orgánica and IMBIV (CONICET), Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, Ciencias Químicas II, Córdoba, 5000, Argentina

    Viviana E. Nicotra & Juan C. Oberti

  3. Departamento de Farmacia and IMBIV (CONICET), Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, Córdoba, 5000, Argentina

    Gloria Barboza

  4. Department of Chemistry, Carnegie Mellon University, 4400 Fifth Ave, Pittsburgh, PA, 15213, USA

    Roberto R. Gil

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  1. Rosana I. Misico
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  2. Viviana E. Nicotra
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  3. Juan C. Oberti
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  4. Gloria Barboza
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  5. Roberto R. Gil
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  6. Gerardo Burton
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Correspondence to Gerardo Burton .

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Editors and Affiliations

  1. College of Pharmacy, Div. Medicinal Chemistry &, Ohio State University, West 12th Ave. 500, Columbus, 43210, Ohio, USA

    A. Douglas Kinghorn

  2. Leonfeldner Str. 150, Linz, 4040, Austria

    Heinz Falk

  3. Graduate School of Medical Sciences, Dept. Developmental, Kyushu University, Maidashi 3-1-1, Fukuoka, 812-8582, Japan

    Junichi Kobayashi

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Misico, R.I., Nicotra, V.E., Oberti, J.C., Barboza, G., Gil, R.R., Burton, G. (2011). Withanolides and Related Steroids. In: Kinghorn, A., Falk, H., Kobayashi, J. (eds) Progress in the Chemistry of Organic Natural Products Vol. 94. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 94. Springer, Vienna. https://doi.org/10.1007/978-3-7091-0748-5_3

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