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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.
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.
- ^ 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.
- ^ Kirson I, Glotter E (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.
- ^ 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. Bibcode:2018PChem.155..136G. doi:10.1016/j.phytochem.2018.08.005. PMID 30121428. S2CID 52068105.
- ^ Alfonso D, Bernardinelli G, Kapetanidis I (1993). "Withanolides from Iochroma coccineum". Phytochemistry. 34 (2): 517–521. Bibcode:1993PChem..34..517A. doi:10.1016/0031-9422(93)80038-T.
- ^ Hansel R, Huang JT, 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.
- ^ Carrero D, Batista P, Souza L, Pinto F, de Vasconcelos M, Teixeira E, Canuto K, Santiago G, Silveira E, Pessoa O (2017). "Withanolides from Leaves of Nicandra physalodes". Journal of the Brazilian Chemical Society. doi:10.21577/0103-5053.20170105. ISSN 0103-5053.
- ^ 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.
- ^ 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. hdl:11336/18683. PMID 24303781.
- ^ Preet R, Gupta RC, Kaur M (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.
- ^ 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.
- ^ Tong X, Zhang H, Timmermann BN (December 2011). "Chlorinated Withanolides from Withania somnifera". Phytochemistry Letters. 4 (4): 411–4. Bibcode:2011PChL....4..411T. doi:10.1016/j.phytol.2011.04.016. PMC 3223914. PMID 22125584.
- ^ 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. hdl:11336/32933. PMID 16724841.
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