# Withanolide

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Withanolide
> Markdown URL: https://mediated.wiki/source/Withanolide.md
> Source: https://en.wikipedia.org/wiki/Withanolide
> Source revision: 1296258136
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Short description|Group of steroid compounds}}
{{cs1 config|name-list-style=vanc}}
[[File:Withaferin A.svg|thumb|[Withaferin A](/source/Withaferin_A)]]
thumb|Salpichrolid A
thumb|Nicandrenon-1
thumb|Ixocarpalacton A
'''Withanolides''' are a group of at least 300 naturally occurring [steroids](/source/steroids) built on an [ergostane](/source/ergostane) skeleton.<ref name="Glotter1991">{{cite journal|last1=Glotter|first1=E.|title=Withanolides and related ergostane-type steroids|journal=Natural Product Reports|volume=8|issue=4|year=1991|pages=415–440|issn=0265-0568|doi=10.1039/np9910800415|pmid=1787922}}</ref><ref name="KirsonGlotter1981">{{cite journal|last1=Kirson|first1=Isaac|last2=Glotter|first2=Erwin|title=Recent Developments in Naturally Occurring Ergostane-Type Steroids. A Review|journal=Journal of Natural Products|volume=44|issue=6|year=1981|pages=633–647|issn=0163-3864|doi=10.1021/np50018a001}}</ref> They occur as [secondary metabolite](/source/secondary_metabolite)s primarily in [genera](/source/Genus) of the [Nightshade family](/source/Solanaceae), for example in the [tomatillo](/source/tomatillo).

Structurally, withanolides consist of a [steroid backbone](/source/Steroid) bound to a [lactone](/source/lactone) or one of its [derivatives](/source/Derivative_(chemistry)); they are produced via [oxidation](/source/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](/source/Datura)'',<ref name="pmid30121428">{{cite journal |vauthors=Guo R, Liu Y, Xu ZP, Xia YG, Yang BY, Kuang HX |title=Withanolides from the leaves of ''Datura metel'' L |journal=[Phytochemistry](/source/Phytochemistry_(journal)) |volume=155 |pages=136–146 |date=November 2018 |pmid=30121428 |doi=10.1016/j.phytochem.2018.08.005 |bibcode=2018PChem.155..136G |s2cid=52068105 }}</ref> ''[Iochroma](/source/Iochroma)'',<ref>{{cite journal |last1=Alfonso |first1=D. |last2=Bernardinelli |first2=G. |last3=Kapetanidis |first3=I. |title=Withanolides from ''Iochroma coccineum'' |journal=Phytochemistry |volume=34 |issue=2 |pages=517–521 |date=1993 |doi=10.1016/0031-9422(93)80038-T |bibcode=1993PChem..34..517A |url=}}</ref> ''[Lycium](/source/Lycium)'',<ref name="HanselHuang1975">{{cite journal|last1=Hansel|first1=R.|last2=Huang|first2=J. T.|last3=Rosenberg|first3=D.|title=Zwei Withanolide aus Lycium chinense|journal=Archiv der Pharmazie|volume=308|issue=8|year=1975|pages=653–4|issn=0365-6233|doi=10.1002/ardp.19753080814|pmid=1190992|s2cid=83568459}}</ref> ''[Nicandra](/source/Nicandra)'',<ref name="CarreroBatista2017">{{cite journal|last1=Carrero|first1=Diego|last2=Batista|first2=Pedro|last3=Souza|first3=Luciana|last4=Pinto|first4=Francisco|last5=de Vasconcelos|first5=Mayron|last6=Teixeira|first6=Edson|last7=Canuto|first7=Kirley|last8=Santiago|first8=Gilvandete|last9=Silveira|first9=Edilberto|last10=Pessoa|first10=Otília|title=Withanolides from Leaves of ''Nicandra physalodes''|journal=Journal of the Brazilian Chemical Society|year=2017|issn=0103-5053|doi=10.21577/0103-5053.20170105|doi-access=free}}</ref> ''[Physalis](/source/Physalis)'',<ref name="pmid17580910">{{cite journal |vauthors=Damu AG, Kuo PC, Su CR, Kuo TH, Chen TH, Bastow KF, Lee KH, Wu TS |title=Isolation, structures, and structure — cytotoxic activity relationships of withanolides and physalins from ''Physalis angulata'' |journal=[Journal of Natural Products](/source/Journal_of_Natural_Products) |volume=70 |issue=7 |pages=1146–52 |date=July 2007 |pmid=17580910 |doi=10.1021/np0701374 }}</ref> ''[Salpichroa](/source/Salpichroa)'',<ref name="pmid24303781">{{cite journal |vauthors=Nicotra VE, Basso AV, Ramacciotti NS, Misico RI |title=Withanolides with phytotoxic activity from two species of the genus Salpichroa: ''S. origanifolia'' and ''S. tristis'' var. lehmannii |journal=[Journal of Natural Products](/source/Journal_of_Natural_Products) |volume=76 |issue=12 |pages=2219–25 |date=December 2013 |pmid=24303781 |doi=10.1021/np400559p |url= |issn=|hdl=11336/18683 |hdl-access=free }}</ref> ''[Solanum](/source/Solanum)'',<ref name="PreetGupta2019">{{cite journal|last1=Preet|first1=Raman|last2=Gupta|first2=Raghbir Chand|last3=Kaur|first3=Manjot|title=Simultaneous High-Performance Thin-Layer Chromatographic Quantification of Withaferin A and Withanolide A in ''Solanum nigrum'' L. "Black Nightshade"|journal=Journal of Planar Chromatography: Modern TLC|volume=32|issue=4|year=2019|pages=339–342|issn=0933-4173|doi=10.1556/1006.2019.32.4.10|s2cid=199075587}}</ref> ''[Mandragora](/source/Mandragora_(genus))'',<ref name="pmid20580923">{{cite journal |vauthors=Suleiman RK, Zarga MA, Sabri SS |title=New withanolides from ''Mandragora officinarum'': first report of withanolides from the Genus Mandragora |journal=[Fitoterapia](/source/Fitoterapia) |volume=81 |issue=7 |pages=864–8 |date=October 2010 |pmid=20580923 |doi=10.1016/j.fitote.2010.05.013 }}</ref> ''[Withania](/source/Withania)'',<ref name="pmid22125584">{{cite journal |vauthors=Tong X, Zhang H, Timmermann BN |title=Chlorinated Withanolides from ''Withania somnifera'' |journal=[Phytochemistry Letters](/source/Phytochemistry_Letters) |volume=4 |issue=4 |pages=411–4 |date=December 2011 |pmid=22125584 |pmc=3223914 |doi=10.1016/j.phytol.2011.04.016 |bibcode=2011PChL....4..411T }}</ref> and ''[Jaborosa](/source/Jaborosa)''.<ref name=nico>{{cite journal |vauthors=Nicotra VE, Ramacciotti NS, Gil RR, Oberti JC, Feresin GE, Guerrero CA, Baggio RF, Garland MT, Burton G |year=2006 |title=Phytotoxic withanolides from ''Jaborosa rotacea'' |journal=Journal of Natural Products |volume=69 |issue=5 |pages=783–9 |doi=10.1021/np0600090 |pmid=16724841|hdl=11336/32933 |hdl-access=free }}</ref> No withanolide has been discovered in ''[Nicotiana](/source/Nicotiana)'' to date.

== Examples ==
[Withaferin A](/source/Withaferin_A), the first withanolide to be isolated, was found in [winter cherry](/source/Withania_somnifera) (''Withania somnifera'')<ref>{{cite journal |doi=10.1039/JR9650007517 |title=1371. Constituents of ''Withania somnifera'' Dun. Part IV. The structure of withaferin A |year=1965 |last1=Lavie |first1=D. |last2=Glotter |first2=E. |last3=Shvo |first3=Y. |journal=Journal of the Chemical Society |pages=7517–7531 }}</ref> and ''[Acnistus arborescens](/source/Acnistus_arborescens)''.<ref>{{cite journal |doi=10.1021/jo01264a027 |title=Tumor inhibitors. XXXIX. Active principles of ''Acnistus arborescens''. Isolation and structural and spectral studies of withaferin a and withacnistin |year=1969 |last1=Kupchan |first1=S. Morris |last2=Anderson |first2=Wayne Keith |last3=Bollinger |first3=Pietro |last4=Doskotch |first4=Raymond W. |last5=Smith |first5=Roger M. |last6=Saenz-Renauld |first6=Jose A. |last7=Schnoes |first7=Heinrich K. |last8=Burlingame |first8=Alma L. |last9=Smith |first9=Dennis H. |journal=The Journal of Organic Chemistry |volume=34 |issue=12 |pages=3858–66 |pmid=5357526 }}</ref>

Salpichrolides A, B and G (isolated from ''[Salpichroa origanifolia](/source/Salpichroa_origanifolia)'') exhibit an inhibitory effect on the growth of larva of the [Mediterranean fruit fly](/source/Ceratitis_capitata) (''Ceratitis capitata''). For this reason, potential pesticide uses for the compounds are being explored.<ref>{{ cite journal | last1 = Bado | first1 = S. | last2 = Mareggiani | first2 = G. | last3 = Amiano | first3 = N. | last4 = Burton | first4 = G. | last5 = Veleiro | first5 = A. S. | title = Lethal and Sublethal Effects of Withanolides from ''Salpichroa origanifolia'' and Analogues on ''Ceratitis capitata'' | journal = Journal of Agricultural and Food Chemistry | year = 2004 | volume = 52 | issue = 10 | pages = 2875–8 | doi = 10.1021/jf035508a | pmid = 15137828 | hdl = 11336/88183 | hdl-access = free }}</ref>

== References ==
{{reflist}}

Category:Steroids
Category:Pyrones
Category:Epoxides
Category:Hydroxymethyl compounds
Category:Cyclic ketones

---
Adapted from the Wikipedia article [Withanolide](https://en.wikipedia.org/wiki/Withanolide) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Withanolide?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.