Guaianolide

{{Short description|Class of chemical compounds}} [[File:Guaianolide core structures.svg|thumb|right|Chemical structures of the two forms of guaianolide nucleus, 6,12-guaianolides (left) and 8,12-guaianolides (right)]] In [[organic chemistry]], a '''guaianolide''' is a type of [[sesquiterpene lactone]] consisting of a gamma-[[lactone]] and either a [[cyclopentane]] or [[cyclopentene]], both [[ring fusion|fused]] to a central [[cycloheptane]] or [[cycloheptene]] structure. There are two subclasses, [[structural isomer]]s differing in the location that part of the lactone is bonded to the central ring, known as 6,12-guaianolides and 8,12-guaianolides.<ref name=Simonsen>{{cite book | editor = K. G. Ramawat, J. M. Merillon | doi = 10.1007/978-3-642-22144-6_134 | author = Henrik Toft Simonsen, Corinna Weitzel and Søren Brøgger Christensen | title = Natural Products | chapter = Guaianolide Sesquiterpenoids: Pharmacology and Biosynthesis | year = 2013 | pages = 3069–3098 | isbn = 978-3-642-22143-9 }}</ref>

Because some of the [[natural product]]s in this class of [[tricyclic]] [[phytochemical]] have been found to be potentially [[biologically active]], there has been interest in their chemical syntheses.<ref>{{cite journal |title= Allylative Approaches to the Synthesis of Complex Guaianolide Sesquiterpenes from Apiaceae and Asteraceae |first1= Xirui |last1= Hu |first2= Andrew J. |last2= Musacchio |first3= Xingyu |last3= Shen |first4= Yujia |last4= Tao |first5= Thomas J. |last5= Maimone |journal= J. Am. Chem. Soc. |year= 2019 |volume= 141 |issue= 37 |pages= 14904–14915 |doi= 10.1021/jacs.9b08001 |pmid= 31448610 |pmc= 6818654 }}</ref> The full [[biosynthesis|biosynthetic]] origin of most of the known guaianolides has not been established, but the pathway is generally presumed to begin with the formation of a [[germacrene]] lactone derived from [[farnesyl pyrophosphate]].<ref name=Simonsen/>

==References== {{reflist}}

[[Category:Sesquiterpene lactones]] [[Category:Heterocyclic compounds with 3 rings]]