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.
Withanolides are a group of at least 300 naturally occurring steroids built on an ergostane skeleton. They occur as secondary metabolites primarily in...
Solanaceae. It is the first member of the withanolide class of ergostane type product to be discovered. Withanolides are a group of naturally occurring C28-...
was first described in 1848. In addition to the known withanolide D {1}, three new withanolides have been isolated from Iochroma fuchsioides. "Iochroma...
withanolides, a group of triterpene lactones that include withaferin A, alkaloids, steroidal lactones, tropine, and cuscohygrine. Forty withanolides,...
group of the steroidal lactones known as withanolides. The nicandrenones, like certain other types of withanolide, have insecticidal properties. 30 years...
the chemical compound in the plant that inhibits bacteria growth to be withanolide. The whole plant showed bacteria inhibiting properties but extracts from...
compounds called withanolides. Many of the withanolides isolated from Jaborosa have been dubbed jaborosalactones. Some withanolides are phytotoxic, having...
diagnoses, the unpleasant side effects lasting several days. A variety of withanolides and hydroxycinnamic acid amides have been isolated from Iochroma species...
Rf; Vazquez, Ar; Martínez, M; Maldonado, E (Jul 2006), "Labdanes and withanolides from Physalis coztomatl.", Journal of Natural Products, 69 (7): 1029–33...
giftige Stoffe' (the plant contains narcotic poisons). The plant contains withanolides, including cytotoxic withaphysalins. An alkaloid, acnistine is also sometimes...
"Anti-proliferative bioactivity against HT-29 colon cancer cells of a withanolides-rich extract from golden berry (Physalis peruviana L.) calyx investigated...
and animals. The most important of these are the heavily derivatised withanolides. However simpler forms do exist, such as the sterane campestane (24R-methylcholestane)...
Withania somnifera, commonly known as Ashwagandha, and the team identified Withanolide, Withaferin A and Withanone as the three steroidal contents of the plant...