Withanolide

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Group of steroid compounds

title: "Withanolide" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["steroids", "pyrones", "epoxides", "hydroxymethyl-compounds", "cyclic-ketones"] description: "Group of steroid compounds" topic_path: "general/steroids" source: "https://en.wikipedia.org/wiki/Withanolide" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Group of steroid compounds ::

::figure[src="https://upload.wikimedia.org/wikipedia/commons/6/6a/Withaferin_A.svg" caption="[[Withaferin A"] ::

::figure[src="https://upload.wikimedia.org/wikipedia/commons/a/a3/Salpichrolide_A.svg" caption="Salpichrolid A"] ::

::figure[src="https://upload.wikimedia.org/wikipedia/commons/c/c5/Nicandrenone-1.svg" caption="Nicandrenon-1"] ::

::figure[src="https://upload.wikimedia.org/wikipedia/commons/9/90/Ixocarpalactone_A.svg" caption="Ixocarpalacton A"] ::

Withanolides are a group of at least 300 naturally occurring steroids built on an ergostane skeleton. They occur as secondary metabolites primarily in genera of the Nightshade family, for example in the tomatillo.

Structurally, withanolides consist of a steroid backbone bound to a lactone or one of its derivatives; they are produced via oxidation of steroids. It remains unknown to what end withanolides are produced; they may act as a deterrent for feeding insect larvae and other herbivores.

Genera within the nightshade family that produce withanolides include: Datura, Iochroma, Lycium, Nicandra, Physalis, Salpichroa, Solanum, Mandragora, Withania, and Jaborosa. No withanolide has been discovered in Nicotiana to date.

Examples

Withaferin A, the first withanolide to be isolated, was found in winter cherry (Withania somnifera) and Acnistus arborescens.

Salpichrolides A, B and G (isolated from Salpichroa origanifolia) exhibit an inhibitory effect on the growth of larva of the Mediterranean fruit fly (Ceratitis capitata). For this reason, potential pesticide uses for the compounds are being explored.

References

References

  1. (1991). "Withanolides and related ergostane-type steroids". Natural Product Reports.
  2. (1981). "Recent Developments in Naturally Occurring Ergostane-Type Steroids. A Review". Journal of Natural Products.
  3. (November 2018). "Withanolides from the leaves of ''Datura metel'' L". [[Phytochemistry (journal).
  4. (1993). "Withanolides from ''Iochroma coccineum''". Phytochemistry.
  5. (1975). "Zwei Withanolide aus Lycium chinense". Archiv der Pharmazie.
  6. (2017). "Withanolides from Leaves of ''Nicandra physalodes''". Journal of the Brazilian Chemical Society.
  7. (July 2007). "Isolation, structures, and structure — cytotoxic activity relationships of withanolides and physalins from ''Physalis angulata''". [[Journal of Natural Products]].
  8. (December 2013). "Withanolides with phytotoxic activity from two species of the genus Salpichroa: ''S. origanifolia'' and ''S. tristis'' var. lehmannii". [[Journal of Natural Products]].
  9. (2019). "Simultaneous High-Performance Thin-Layer Chromatographic Quantification of Withaferin A and Withanolide A in ''Solanum nigrum'' L. "Black Nightshade"". Journal of Planar Chromatography: Modern TLC.
  10. (October 2010). "New withanolides from ''Mandragora officinarum'': first report of withanolides from the Genus Mandragora". [[Fitoterapia]].
  11. (December 2011). "Chlorinated Withanolides from ''Withania somnifera''". [[Phytochemistry Letters]].
  12. (2006). "Phytotoxic withanolides from ''Jaborosa rotacea''". Journal of Natural Products.
  13. (1965). "1371. Constituents of ''Withania somnifera'' Dun. Part IV. The structure of withaferin A". Journal of the Chemical Society.
  14. (1969). "Tumor inhibitors. XXXIX. Active principles of ''Acnistus arborescens''. Isolation and structural and spectral studies of withaferin a and withacnistin". The Journal of Organic Chemistry.
  15. (2004). "Lethal and Sublethal Effects of Withanolides from ''Salpichroa origanifolia'' and Analogues on ''Ceratitis capitata''". Journal of Agricultural and Food Chemistry.

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steroidspyronesepoxideshydroxymethyl-compoundscyclic-ketones