:Withanolide

{{Short description|Group of steroid compounds}}

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File:Withaferin A.svg]]

Image:Salpichrolide A.svg

Image:Nicandrenone-1.svg

Image:Ixocarpalactone A.svg

Withanolides are a group of at least 300 naturally occurring steroids built on an ergostane skeleton.{{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}}{{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}} 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,{{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 |volume=155 |pages=136–146 |date=November 2018 |pmid=30121428 |doi=10.1016/j.phytochem.2018.08.005 |bibcode=2018PChem.155..136G |s2cid=52068105 }} Iochroma,{{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=}} Lycium,{{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}} Nicandra,{{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}} Physalis,{{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 |volume=70 |issue=7 |pages=1146–52 |date=July 2007 |pmid=17580910 |doi=10.1021/np0701374 }} Salpichroa,{{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 |volume=76 |issue=12 |pages=2219–25 |date=December 2013 |pmid=24303781 |doi=10.1021/np400559p |url= |issn=|hdl=11336/18683 |hdl-access=free }} Solanum,{{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}} Mandragora,{{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 |volume=81 |issue=7 |pages=864–8 |date=October 2010 |pmid=20580923 |doi=10.1016/j.fitote.2010.05.013 }} Withania,{{cite journal |vauthors=Tong X, Zhang H, Timmermann BN |title=Chlorinated Withanolides from Withania somnifera |journal=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 }} and Jaborosa.{{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 }} No withanolide has been discovered in Nicotiana to date.