{{Short description|Class of chemical compounds}} [[File:Phomoxanthone A structure.svg|thumb|right|Phomoxanthone A]] [[File:Phomoxanthone B structure.svg|thumb|right|Phomoxanthone B]] [[File:Dicerandrol C structure.svg|thumb|right|Dicerandrol C]] The '''phomoxanthones''' are a loosely defined class of natural products. The two founding members of this class are phomoxanthone A and phomoxanthone B. Other compounds were later also classified as phomoxanthones, although a unifying nomenclature has not yet been established.<ref name=Isaka2001>{{cite journal|pmid=11520217|year=2001|last1=Isaka|first1=M|title=Phomoxanthones a and B, novel xanthone dimers from the endophytic fungus Phomopsis species|journal=Journal of Natural Products|volume=64|issue=8|pages=1015–8|last2=Jaturapat|first2=A|last3=Rukseree|first3=K|last4=Danwisetkanjana|first4=K|last5=Tanticharoen|first5=M|last6=Thebtaranonth|first6=Y|doi=10.1021/np010006h}}</ref> The structure of all phomoxanthones is derived from a dimer of two covalently linked tetrahydroxanthones, and they differ mainly in the position of this link as well as in the acetylation status of their hydroxy groups. The phomoxanthones are structurally closely related to other tetrahydroxanthone dimers such as the secalonic acids and the eumitrins. While most phomoxanthones were discovered in fungi of the genus ''Phomopsis'', most notably in the species ''Phomopsis longicolla'', some have also been found in ''Penicillium'' sp.<ref name=Cao2012>{{cite journal|doi=10.1021/np2009863|pmid=22458669|title=Inhibition of Tumor Cells Interacting with Stromal Cells by Xanthones Isolated from a Costa Rican Penicillium sp|journal=Journal of Natural Products|volume=75|issue=4|pages=793–7|year=2012|last1=Cao|first1=Shugeng|last2=McMillin|first2=Douglas W|last3=Tamayo|first3=Giselle|last4=Delmore|first4=Jake|last5=Mitsiades|first5=Constantine S|last6=Clardy|first6=Jon|pmc=3338863}}</ref>
== Known phomoxanthones ==
* Dicerandrol A<ref name=Wagenaar2001>{{cite journal|doi=10.1021/np010020u|pmid=11520215|title=Dicerandrols, New Antibiotic and Cytotoxic Dimers Produced by the Fungus ''Phomopsis longicolla'' Isolated from an Endangered Mint|journal=Journal of Natural Products|volume=64|issue=8|pages=1006–9|year=2001|last1=Wagenaar|first1=Melissa M|last2=Clardy|first2=Jon}}</ref><ref name=Cao2012/><ref name=Ding2013/> * Dicerandrol B<ref name=Wagenaar2001/><ref name=Cao2012/><ref name=Ding2013/><ref name=Rönsberg2013/> * Dicerandrol C<ref name=Wagenaar2001/><ref name=Cao2012/><ref name=Ding2013/><ref name=Rönsberg2013/> * Penexanthone A<ref name=Cao2012/><ref name=Ding2013/> * Phomolactonexanthone A<ref name=Ding2013/> * Phomolactonexanthone B<ref name=Ding2013/> * Phomoxanthone A<ref name=Isaka2001/><ref name=Elsässer>{{cite journal|doi=10.1002/ejoc.200500265|title=X-ray Structure Determination, Absolute Configuration and Biological Activity of Phomoxanthone A|journal=European Journal of Organic Chemistry|volume=2005|issue=21|pages=4563|year=2005|last1=Elsässer|first1=Brigitta|last2=Krohn|first2=Karsten|last3=Flörke|first3=Ulrich|last4=Root|first4=Natalia|last5=Aust|first5=Hans-Jürgen|last6=Draeger|first6=Siegfried|last7=Schulz|first7=Barbara|last8=Antus|first8=Sándor|last9=Kurtán|first9=Tibor|hdl=2437/92715|hdl-access=free}}</ref><ref name=Rönsberg2013/> and its derivatives: ** 1-acetylphomoxanthone A<ref name=Frank2015>{{cite journal|doi=10.2174/0929867322666150716115300|pmid=26179997|year=2015|last1=Frank|first1=M|title=Phomoxanthone A--From Mangrove Forests to Anticancer Therapy|journal=Current Medicinal Chemistry|volume=22|issue=30|pages=3523–32|last2=Niemann|first2=H|last3=Böhler|first3=P|last4=Stork|first4=B|last5=Wesselborg|first5=S|last6=Lin|first6=W|last7=Proksch|first7=P}}</ref> ** 1,1′-diacetylphomoxanthone A<ref name=Frank2015/> ** 1,1′,8-triacetylphomoxanthone A<ref name=Frank2015/> ** 1,1′,8,8′-tetraacetylphomoxanthone A<ref name=Frank2015/> ** 12-deacetylphomoxanthone A<ref name=Rönsberg2013>{{cite journal|doi=10.1021/jo402066b|pmid=24295452|title=Pro-Apoptotic and Immunostimulatory Tetrahydroxanthone Dimers from the Endophytic Fungus Phomopsis longicolla|journal=The Journal of Organic Chemistry|volume=78|issue=24|pages=12409–25|year=2013|last1=Rönsberg|first1=David|last2=Debbab|first2=Abdessamad|last3=Mándi|first3=Attila|last4=Vasylyeva|first4=Vera|last5=Böhler|first5=Philip|last6=Stork|first6=Björn|last7=Engelke|first7=Laura|last8=Hamacher|first8=Alexandra|last9=Sawadogo|first9=Richard|last10=Diederich|first10=Marc|last11=Wray|first11=Victor|last12=Lin|first12=Wenhan|last13=Kassack|first13=Matthias U|last14=Janiak|first14=Christoph|last15=Scheu|first15=Stefanie|last16=Wesselborg|first16=Sebastian|last17=Kurtán|first17=Tibor|last18=Aly|first18=Amal H|last19=Proksch|first19=Peter}}</ref><ref name=Shiono2013>{{cite journal|pmid=24555286|year=2013|last1=Shiono|first1=Y|title=Isolation of a phomoxanthone a derivative, a new metabolite of tetrahydroxanthone, from a Phomopsis sp. Isolated from the mangrove, Rhizhopora mucronata|journal=Natural Product Communications|volume=8|issue=12|pages=1735–7|last2=Sasaki|first2=T|last3=Shibuya|first3=F|last4=Yasuda|first4=Y|last5=Koseki|first5=T|last6=Supratman|first6=U|doi=10.1177/1934578X1300801220|doi-access=free}}</ref><ref name=Frank2015/> ** 12,12′-dideacetylphomoxanthone A (deacetylphomoxanthone C)<ref name=Ding2013/><ref name=Frank2015/> ** 12,12′,13,13′-tetradeacetylphomoxanthone A (deacetylphomoxanthone A)<ref name=Isaka2001/><ref name=Rönsberg2013/><ref name=Frank2015/> * Phomoxanthone B<ref name=Isaka2001/> and its derivatives: ** 12-deacetylphomoxanthone B<ref name=Choi2013>{{cite journal|doi=10.1038/ja.2012.105|pmid=23211934|title=Identification of a new phomoxanthone antibiotic from Phomopsis longicolla and its antimicrobial correlation with other metabolites during fermentation|journal=The Journal of Antibiotics|volume=66|issue=4|pages=231–3|year=2012|last1=Choi|first1=Jung Nam|last2=Kim|first2=Jiyoung|last3=Ponnusamy|first3=Kannan|last4=Lim|first4=Chaesung|last5=Kim|first5=Jeong Gu|last6=Muthaiya|first6=Maria John|last7=Lee|first7=Choong Hwan|doi-access=free}}</ref> ** 12,12′,13,13′-tetradeacetylphomoxanthone B (deacetylphomoxanthone B)<ref name=Rukachaisirikul2008>{{cite journal|doi=10.1016/j.phytochem.2007.09.006|pmid=17950385|title=Metabolites from the endophytic fungus Phomopsis sp. PSU-D15|journal=Phytochemistry|volume=69|issue=3|pages=783–7|year=2008|last1=Rukachaisirikul|first1=Vatcharin|last2=Sommart|first2=Ubonta|last3=Phongpaichit|first3=Souwalak|last4=Sakayaroj|first4=Jariya|last5=Kirtikara|first5=Kanyawim|bibcode=2008PChem..69..783R }}</ref><ref name=Ding2013>{{cite journal|doi=10.3390/md11124961|pmid=24335522|title=New Dimeric Members of the Phomoxanthone Family: Phomolactonexanthones A, B and Deacetylphomoxanthone C Isolated from the Fungus Phomopsis sp|journal=Marine Drugs|volume=11|issue=12|pages=4961–72|year=2013|last1=Ding|first1=Bo|last2=Yuan|first2=Jie|last3=Huang|first3=Xishan|last4=Wen|first4=Weitao|last5=Zhu|first5=Xu|last6=Liu|first6=Yayue|last7=Li|first7=Hanxiang|last8=Lu|first8=Yongjun|last9=He|first9=Lei|last10=Tan|first10=Hongmei|last11=She|first11=Zhigang|pmc=3877896|doi-access=free }}</ref>
== Further reading == * {{cite journal|doi=10.1021/cr100446h|pmid=22617028|title=Xanthones from Fungi, Lichens, and Bacteria: The Natural Products and Their Synthesis|journal=Chemical Reviews|volume=112|issue=7|pages=3717–76|year=2012|last1=Masters|first1=Kye-Simeon|last2=Bräse|first2=Stefan}} * {{cite journal|doi=10.1039/C4NP00050A|pmid=25226564|title=Xanthone dimers: A compound family which is both common and privileged|journal=Natural Product Reports|volume=32|issue=1|pages=6–28|year=2015|last1=Wezeman|first1=Tim|last2=Bräse|first2=Stefan|last3=Masters|first3=Kye-Simeon|doi-access=free}}
== References == {{Commons category|Phomoxanthones}} {{reflist|2}}
Category:Mycotoxins Category:Natural products Category:Xanthonoids