Withanolide Explained

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.

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]

Notes and References

  1. Glotter. E.. Withanolides and related ergostane-type steroids. Natural Product Reports. 8. 4. 1991. 415–440. 0265-0568. 10.1039/np9910800415. 1787922.
  2. Kirson. Isaac. Glotter. Erwin. Recent Developments in Naturally Occurring Ergostane-Type Steroids. A Review. Journal of Natural Products. 44. 6. 1981. 633–647. 0163-3864. 10.1021/np50018a001.
  3. Guo R, Liu Y, Xu ZP, Xia YG, Yang BY, Kuang HX . Withanolides from the leaves of Datura metel L . . 155 . 136–146 . November 2018 . 30121428 . 10.1016/j.phytochem.2018.08.005 . 2018PChem.155..136G . 52068105 .
  4. Alfonso . D. . Bernardinelli . G. . Kapetanidis . I. . Withanolides from Iochroma coccineum . Phytochemistry . 34 . 2 . 517–521 . 1993 . 10.1016/0031-9422(93)80038-T . 1993PChem..34..517A .
  5. Hansel. R.. Huang. J. T.. Rosenberg. D.. Zwei Withanolide aus Lycium chinense. Archiv der Pharmazie. 308. 8. 1975. 653–4. 0365-6233. 10.1002/ardp.19753080814. 1190992. 83568459.
  6. Carrero. Diego. Batista. Pedro. Souza. Luciana. Pinto. Francisco. de Vasconcelos. Mayron. Teixeira. Edson. Canuto. Kirley. Santiago. Gilvandete. Silveira. Edilberto. Pessoa. Otília. Withanolides from Leaves of Nicandra physalodes. Journal of the Brazilian Chemical Society. 2017. 0103-5053. 10.21577/0103-5053.20170105. free.
  7. Damu AG, Kuo PC, Su CR, Kuo TH, Chen TH, Bastow KF, Lee KH, Wu TS . Isolation, structures, and structure — cytotoxic activity relationships of withanolides and physalins from Physalis angulata . . 70 . 7 . 1146–52 . July 2007 . 17580910 . 10.1021/np0701374 .
  8. Nicotra VE, Basso AV, Ramacciotti NS, Misico RI . Withanolides with phytotoxic activity from two species of the genus Salpichroa: S. origanifolia and S. tristis var. lehmannii . . 76 . 12 . 2219–25 . December 2013 . 24303781 . 10.1021/np400559p . 11336/18683 . free .
  9. Preet. Raman. Gupta. Raghbir Chand. Kaur. Manjot. 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. 2019. 339–342. 0933-4173. 10.1556/1006.2019.32.4.10. 199075587.
  10. Suleiman RK, Zarga MA, Sabri SS . New withanolides from Mandragora officinarum: first report of withanolides from the Genus Mandragora . . 81 . 7 . 864–8 . October 2010 . 20580923 . 10.1016/j.fitote.2010.05.013 .
  11. Tong X, Zhang H, Timmermann BN . Chlorinated Withanolides from Withania somnifera . . 4 . 4 . 411–4 . December 2011 . 22125584 . 3223914 . 10.1016/j.phytol.2011.04.016 . 2011PChL....4..411T .
  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 . 10.1021/np0600090 . 16724841. 11336/32933 . free .
  13. 10.1039/JR9650007517 . 1371. Constituents of Withania somnifera Dun. Part IV. The structure of withaferin A . 1965 . Lavie . D. . Glotter . E. . Shvo . Y. . Journal of the Chemical Society . 7517–7531 .
  14. 10.1021/jo01264a027 . Tumor inhibitors. XXXIX. Active principles of Acnistus arborescens. Isolation and structural and spectral studies of withaferin a and withacnistin . 1969 . 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. . The Journal of Organic Chemistry . 34 . 12 . 3858–66 . 5357526 .
  15. Bado . S. . Mareggiani . G. . Amiano . N. . Burton . G. . Veleiro . A. S. . Lethal and Sublethal Effects of Withanolides from Salpichroa origanifolia and Analogues on Ceratitis capitata . Journal of Agricultural and Food Chemistry . 2004 . 52 . 10 . 2875–8 . 10.1021/jf035508a . 15137828 . 11336/88183 . free .

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