Editing Gossypol (section)

==Biosynthesis==
Gossypol is a [[terpenoid]] [[aldehyde]] which is formed metabolically through [[Acetic acid|acetate]] via the [[isoprenoid pathway]].<ref>{{cite journal|last1=Burgos |first1=M. |last2=Ito |first2=S. |last3=Segal |first3=J. S. |last4=Tran |first4=T. P. |title=Effect of Gossypol on Ultrastructure of Spisula Sperm|journal=The Biological Bulletin |year=1997|volume=193|issue=2|pages=228–229|doi=10.1086/BBLv193n2p228|pmid=28575607 }}</ref> The [[sesquiterpene]] dimer undergoes a radical coupling reaction to form gossypol.<ref>{{cite journal|last1=Heinstein |first1=P. F. |last2=Herman |first2=L. D. |last3=Tove |first3=B. S. |last4=Smith |first4=H. F. |title=Biosynthesis of Gossypol|journal= Journal of Biological Chemistry |year=1970|volume=245|pages=4658–4665|pmid=4318479|issue=18|doi=10.1016/S0021-9258(18)62845-5 |doi-access=free }}</ref> The biosynthesis begins when [[geranyl pyrophosphate]] (GPP) and [[isopentenyl pyrophosphate]] (IPP) are combined to make the [[sesquiterpene]] precursor [[farnesyl diphosphate]] (FPP). The cadinyl cation ('''1''') is oxidized to '''2''' by [[Delta-cadinene synthase|(+)-δ-cadinene synthase]]. The [[cadinene|(+)-δ-cadinene]] ('''2''') is involved in making the basic aromatic sesquiterpene unit, homigossypol, by oxidation, which generates the '''3''' (8-hydroxy-δ-cadinene) with the help of (+)-δ-cadinene 8-hyroxylase. Compound '''3''' goes through various oxidative processes to make '''4''' (deoxyhemigossypol), which is oxidized by one electron into hemigossypol ('''5''', '''6''', '''7''') and then undergoes a phenolic [[oxidative coupling]], [[Arene substitution pattern#Ortho, meta, and para substitution|''ortho'']] to the phenol groups, to form gossypol ('''8''').<ref name="autogenerated1">{{cite book | author = Dewick, P. M. | url = https://www.dmt-nexus.com/doc/Medicinal%20Natural%20Products%20-%20A%20Biosynthetic%20Approach.pdf | title = Medicinal Natural Product: A Biosynthetic Approach | edition = 3rd | date = 2008 | isbn = 978-0-470-74167-2 }}{{Dead link|date=January 2020 |bot=InternetArchiveBot |fix-attempted=yes }}</ref> The coupling is catalyzed by a [[hydrogen peroxide]]-dependent [[peroxidase]] enzyme, which results in the final product.<ref name="autogenerated1"/>

:[[File:Gossypol biosyn.jpg|500 px]]