Viriditoxin

Viriditoxin
Names
	Other names (-)-Viriditoxin; (M)-Viriditoxin
Identifiers
CAS Number	35483-50-2 ;
3D model ( JSmol)	Interactive image;
ChEBI	CHEBI:146007 ;
ChemSpider	58828231 ;
PubChem CID	53343291;
UNII	6TAK972FMC;
CompTox Dashboard (EPA)	DTXSID70956888 ;
	InChI InChI=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 Key: GMCZVCXZGZGZPX-HOTGVXAUSA-N ;
	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;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Viriditoxin (VDT^[1]^[2]) is a secondary metabolite produced by fungi.^[3] Viriditoxin is a type of mycotoxin.^[1] The biosynthesis of the compound has been investigated.^[3]

Occurrence

It is produced by several Aspergillus species including A. aureoluteus,^[4] A. brevipes,^[5] and A. viridinutans in which it was first identified in 1971.^[6] It has been isolated from Paecilomyces variotii, which was obtained from Nomura's jellyfish.^[2] It is also produced by Cladosporium cladosporioides.^[1]

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.^[6]