viriditoxin
{{mdy|date=July 2023}}
{{Chembox
| Name = Viriditoxin
| ImageFile = Viriditoxin.svg
| OtherNames = (-)-Viriditoxin
(M)-Viriditoxin
|Section1 ={{Chembox Identifiers
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 58828231
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/C34H30O14/c1-43-21-11-19(35)27-17(7-13-5-15(9-23(37)45-3)47-33(41)25(13)31(27)39)29(21)30-18-8-14-6-16(10-24(38)46-4)48-34(42)26(14)32(40)28(18)20(36)12-22(30)44-2/h7-8,11-12,15-16,35-36,39-40H,5-6,9-10H2,1-4H3/t15-,16-/m0/s1
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = GMCZVCXZGZGZPX-HOTGVXAUSA-N
|CASNo_Ref = {{cascite|correct|CAS}}
|CASNo= 35483-50-2
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI = 146007
|ChEMBL_Ref = {{ebicite|correct|EMBL}}
|ChEMBL =
|EINECS =
|PubChem = 53343291
|KEGG_Ref = {{keggcite|correct|kegg}}
|KEGG =
|DrugBank_Ref = {{drugbankcite|correct|drugbank}}
|DrugBank =
|UNII = 6TAK972FMC
|SMILES = COc1cc(c2c(c1c3c4cc5c(c(c4c(cc3OC)O)O)C(=O)O[C@@H](C5)CC(=O)OC)cc6c(c2O)C(=O)O[C@@H](C6)CC(=O)OC)O
}}
| Section2 = {{Chembox Properties
| Formula =
| Appearance =
| Density =
| MeltingPtC =
| BoilingPtC =
| Solubility =
}}
}}
Viriditoxin (VDT) is a secondary metabolite produced by fungi.{{Cite journal |last1=Urquhart |first1=Andrew S. |title=The fungal gene cluster for biosynthesis of the antibacterial agent viriditoxin |last2=Hu |first2=Jinyu |last3=Chooi |first3=Yit-Heng |last4=Idnurm |first4=Alexander |journal=Fungal Biology and Biotechnology |year=2019 |volume=6 |page=2 |doi=10.1186/s40694-019-0072-y |pmc=6600887 |pmid=31304040 |doi-access=free}} {{Free-content attribution |this=yes |license= Creative Commons Attribution 4.0}} Viriditoxin is a type of mycotoxin. {{primary source-inline|date=July 2023}} {{Cite journal |last1=Stuhldreier |first1=Fabian |title=The mycotoxin viriditoxin induces leukemia- and lymphoma-specific apoptosis by targeting mitochondrial metabolism |last2=Schmitt |first2=Laura |last3=Lenz |first3=Thomas |last4=Hinxlage |first4=Ilka |last5=Zimmermann |first5=Marcel |last6=Wollnitzke |first6=Philipp |last7=Schliehe-Diecks |first7=Julian |last8=Liu |first8=Yang |last9=Jäger |first9=Paul |date=2022-11-08 |journal=Cell Death & Disease |volume=13 |page=938 |language=en |doi=10.1038/s41419-022-05356-w |pmc=9643474 |pmid=36347842 |issue=11 |last10=Geyh |first10=Stefanie |last11=Teusch |first11=Nicole |last12=Peter |first12=Christoph |last13=Bhatia |first13=Sanil |last14=Haas |first14=Rainer |last15=Levkau |first15=Bodo |s2cid=253387328}} {{Free-content attribution |this=yes |license= Creative Commons Attribution 4.0}} The biosynthesis of the compound has been investigated.
Occurrence
It is produced by several Aspergillus species including A. aureoluteus,{{Cite journal |last1=Samson |first1=R.A. |title=Polyphasic taxonomy of Aspergillus section Fumigati and its teleomorph Neosartorya |last2=Hong |first2=S. |last3=Peterson |first3=S.W. |last4=Frisvad |first4=J.C. |last5=Varga |first5=J. |date=2007 |journal=Studies in Mycology |volume=59 |pages=147–203 |doi=10.3114/sim.2007.59.14 |pmc=2275200 |pmid=18490953}} A. brevipes,{{Cite book |last1=Frederic |first1=Lamoth |title=Advances in Aspergillus fumigatus pathobiology |last2=William J. |first2=Steinbach |date=2016 |publisher=Frontiers Media SA |isbn=978-2-889-19789-7}} and A. viridinutans in which it was first identified in 1971.{{Cite journal |last1=Smyth |first1=Jamie E. |url=https://ro.uow.edu.au/cgi/viewcontent.cgi?article=4391&context=smhpapers |title=A twist of nature – the significance of atropisomers in biological systems |last2=Butler |first2=Nicholas M. |last3=Keller |first3=Paul A. |journal=Natural Product Reports |year=2015 |volume=32 |pages=1562–1583 |doi=10.1039/c4np00121d |pmid=26282828 |issue=11 |access-date=June 12, 2023 |archive-date=January 28, 2023 |archive-url=https://web.archive.org/web/20230128235327/https://ro.uow.edu.au/cgi/viewcontent.cgi?article=4391&context=smhpapers |url-status=live }} It has been isolated from Paecilomyces variotii, which was obtained from Nomura's jellyfish.{{Cite journal |last1=Kundu |first1=Soma |title=Viriditoxin regulates apoptosis and autophagy via mitotic catastrophe and microtubule formation in human prostate cancer cells |last2=Kim |first2=Tae Hyung |last3=Yoon |first3=Jung Hyun |last4=Shin |first4=Han-Seung |last5=Lee |first5=Jaewon |last6=Jung |first6=Jee H. |last7=Kim |first7=Hyung Sik |date=2014-12-01 |journal=International Journal of Oncology |volume=45 |pages=2331–2340 |doi=10.3892/ijo.2014.2659 |pmid=25231051 |issue=6 |doi-access=free }} It is also produced by Cladosporium cladosporioides.
Structure
Natural viriditoxin exists as a single atropisomer owing to restricted rotation about the C-C bond which joins the two naphthol rings. It has been confirmed by total synthesis to be twisted into the so-called M isomer.
Biosynthesis
File:Viriditoxin biosynthesis.svg
Viriditoxin is a secondary metabolite, a polyketide produced from multiple acetyl-CoA and malonyl-CoA units which are combined by a polyketide synthase (PKS) enzyme complex. A chain of eight acetate units are cyclised to give the three-ring system which forms half of the carbon framework of the final product. After selective methylation of one of the phenol groups and reduction of the pyrone ring, the resulting intermediate (semiviriditoxin) is dimerised by a laccase enzyme, generating specifically the minus M atropisomer.{{Cite journal |last1=Hüttel |first1=Wolfgang |title=Regio- and stereoselective intermolecular phenol coupling enzymes in secondary metabolite biosynthesis |last2=Müller |first2=Michael |journal=Natural Product Reports |year=2021 |volume=38 |pages=1017–1020 |doi=10.1039/d0np00010h |pmid=33196733 |issue=5 |s2cid=226987404}}
Uses
In nature, viriditoxin likely is used against microbial competition. On mangroves, P. variotii