Withanolide

Withanolides are a group of at least 300 naturally occurring steroids built on an ergostane skeleton.[1][2] They occur as secondary metabolites primarily in genera of the Nightshade family, for example in the tomatillo.

Withaferin A
Salpichrolid A
Nicandrenon-1
Ixocarpalacton A

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,[3] Iochroma,[4] Lycium,[5] Nicandra,[6] Physalis,[7] Salpichroa,[8] Solanum,[9] Mandragora,[10] Withania,[11] and Jaborosa.[12] 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)[13] and Acnistus arborescens.[14]

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.[15]

References
  1. Glotter, E. (1991). "Withanolides and related ergostane-type steroids". Natural Product Reports. 8 (4): 415–440. doi:10.1039/np9910800415. ISSN 0265-0568. PMID 1787922.
  2. Kirson, Isaac; Glotter, Erwin (1981). "Recent Developments in Naturally Occurring Ergostane-Type Steroids. A Review". Journal of Natural Products. 44 (6): 633–647. doi:10.1021/np50018a001. ISSN 0163-3864.
  3. Guo R, Liu Y, Xu ZP, Xia YG, Yang BY, Kuang HX (November 2018). "Withanolides from the leaves of Datura metel L". Phytochemistry. 155: 136–146. doi:10.1016/j.phytochem.2018.08.005. PMID 30121428. S2CID 52068105.
  4. Alfonso, D.; Bernardinelli, G.; Kapetanidis, I. (1993). "Withanolides from Iochroma coccineum". Phytochemistry. 34 (2): 517–521. doi:10.1016/0031-9422(93)80038-T.
  5. Hansel, R.; Huang, J. T.; Rosenberg, D. (1975). "Zwei Withanolide aus Lycium chinense". Archiv der Pharmazie. 308 (8): 653–4. doi:10.1002/ardp.19753080814. ISSN 0365-6233. PMID 1190992. S2CID 83568459.
  6. Carrero, Diego; Batista, Pedro; Souza, Luciana; Pinto, Francisco; de Vasconcelos, Mayron; Teixeira, Edson; Canuto, Kirley; Santiago, Gilvandete; Silveira, Edilberto; Pessoa, Otília (2017). "Withanolides from Leaves of Nicandra physalodes". Journal of the Brazilian Chemical Society. doi:10.21577/0103-5053.20170105. ISSN 0103-5053.
  7. Damu AG, Kuo PC, Su CR, Kuo TH, Chen TH, Bastow KF, Lee KH, Wu TS (July 2007). "Isolation, structures, and structure — cytotoxic activity relationships of withanolides and physalins from Physalis angulata". Journal of Natural Products. 70 (7): 1146–52. doi:10.1021/np0701374. PMID 17580910.
  8. Nicotra VE, Basso AV, Ramacciotti NS, Misico RI (December 2013). "Withanolides with phytotoxic activity from two species of the genus Salpichroa: S. origanifolia and S. tristis var. lehmannii". Journal of Natural Products. 76 (12): 2219–25. doi:10.1021/np400559p. PMID 24303781.
  9. Preet, Raman; Gupta, Raghbir Chand; Kaur, Manjot (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. 32 (4): 339–342. doi:10.1556/1006.2019.32.4.10. ISSN 0933-4173. S2CID 199075587.
  10. Suleiman RK, Zarga MA, Sabri SS (October 2010). "New withanolides from Mandragora officinarum: first report of withanolides from the Genus Mandragora". Fitoterapia. 81 (7): 864–8. doi:10.1016/j.fitote.2010.05.013. PMID 20580923.
  11. Tong X, Zhang H, Timmermann BN (December 2011). "Chlorinated Withanolides from Withania somnifera". Phytochemistry Letters. 4 (4): 411–4. doi:10.1016/j.phytol.2011.04.016. PMC 3223914. PMID 22125584.
  12. Nicotra VE, Ramacciotti NS, Gil RR, Oberti JC, Feresin GE, Guerrero CA, Baggio RF, Garland MT, Burton G (2006). "Phytotoxic withanolides from Jaborosa rotacea". Journal of Natural Products. 69 (5): 783–9. doi:10.1021/np0600090. PMID 16724841.
  13. Lavie, D.; Glotter, E.; Shvo, Y. (1965). "1371. Constituents of Withania somnifera Dun. Part IV. The structure of withaferin A". Journal of the Chemical Society: 7517. doi:10.1039/JR9650007517.
  14. Kupchan, S. Morris; Anderson, Wayne Keith; Bollinger, Pietro; Doskotch, Raymond W.; Smith, Roger M.; Saenz-Renauld, Jose A.; Schnoes, Heinrich K.; Burlingame, Alma L.; Smith, Dennis H. (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. 34 (12): 3858–66. doi:10.1021/jo01264a027. PMID 5357526.
  15. Bado, S.; Mareggiani, G.; Amiano, N.; Burton, G.; Veleiro, A. S. (2004). "Lethal and Sublethal Effects of Withanolides from Salpichroa origanifolia and Analogues on Ceratitis capitata". Journal of Agricultural and Food Chemistry. 52 (10): 2875–8. doi:10.1021/jf035508a. hdl:11336/88183. PMID 15137828.
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