Stigmatellin

Stigmatellin is a potent inhibitor of the quinol oxidation (Qo) site of the cytochrome bc1 complex in mitochondria and the cytochrome b6f complex of thylakoid membranes.

Stigmatellin

Identifiers
CAS Number	91682-96-1
3D model (JSmol)	Interactive image
ChEBI	CHEBI:32155
ChEMBL	ChEMBL486556
ChemSpider	394850
ECHA InfoCard	100.149.842
MeSH	Stigmatellin
PubChem CID	447884
CompTox Dashboard (EPA)	DTXSID40903940
InChI InChI=1S/C30H42O7/c1-10-18(2)13-11-12-14-22(33-6)21(5)29(36-9)19(3)15-16-23-20(4)27(31)26-24(34-7)17-25(35-8)28(32)30(26)37-23/h10-14,17,19,21-22,29,32H,15-16H2,1-9H3/b13-11+,14-12+,18-10+/t19-,21+,22-,29-/m0/s1 Key: UZHDGDDPOPDJGM-CVOZLMQJSA-N InChI=1/C30H42O7/c1-10-18(2)13-11-12-14-22(33-6)21(5)29(36-9)19(3)15-16-23-20(4)27(31)26-24(34-7)17-25(35-8)28(32)30(26)37-23/h10-14,17,19,21-22,29,32H,15-16H2,1-9H3/b13-11+,14-12+,18-10+/t19-,21+,22-,29-/m0/s1 Key: UZHDGDDPOPDJGM-CVOZLMQJBZ
SMILES O=C\1c2c(O/C(=C/1C)CC[C@H](C)[C@H](OC)[C@H](C)[C@@H](OC)\C=C\C=C\C(=C\C)C)c(O)c(OC)cc2OC
Properties
Chemical formula	C30H42O7
Molar mass	514.65 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Stigmatellin is isolated from the myxobacterium Stigmatella aurantica, and contains a 5,7-dimethoxy-8-hydroxychromone aromatic headgroup with a hydrophobic alkenyl chain in position 2. Crystal structures for stigmatellin-inhibited bovine and yeast (Saccharomyces cerevisiae) bc1 complex are available. Stigmatellin binds at the cytochrome b Qo site in the '(heme) bl distal' position, and associates with the Rieske iron-sulfur protein via a hydrogen bond to histidine residue 181 (His-181), a ligand to the [2Fe2S] iron-sulfur cluster of this subunit. This association raises the midpoint potential of the iron-sulfur cluster from 290 to 540 mV and restricts movement of the cytoplasmic domain of the Rieske protein.

References

• von Jagow, G., and Link, T.A. Methods in Enzymology 126: 253-271 (1986)