# Stigmatellin
> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Stigmatellin
> Markdown URL: https://mediated.wiki/source/Stigmatellin.md
> Source: https://en.wikipedia.org/wiki/Stigmatellin
> Source revision: 1230336507
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)
{{cs1 config|name-list-style=vanc}}
{{chembox
| Verifiedfields = changed
| verifiedrevid = 477859381
| ImageFile=Stigmatellin.svg
| ImageSize=250px
| PIN=2-[(3''S'',4''S'',5''S'',6''S'',7''E'',9''E'',11''E'')-4,6-Dimethoxy-3,5,11-trimethyltrideca-7,9,11-trien-1-yl]-8-hydroxy-5,7-dimethoxy-3-methyl-4''H''-1-benzopyran-4-one
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|changed|??}}
| CASNo=91682-96-1
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 32155
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 486556
| PubChem=447884
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 394850
| 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
| 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
| InChIKey = UZHDGDDPOPDJGM-CVOZLMQJBZ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UZHDGDDPOPDJGM-CVOZLMQJSA-N
| MeSHName=Stigmatellin
}}
|Section2={{Chembox Properties
| Formula=C30H42O7
| MolarMass=514.65 g/mol
}}
}}
'''Stigmatellin''' is a potent [inhibitor](/source/Enzyme_inhibitor) of the quinol oxidation (Qo) site of the [cytochrome bc1](/source/cytochrome_bc1) complex in [mitochondria](/source/mitochondria)[{{cite journal | vauthors = von Jagow G, Ohnishi T | title = The chromone inhibitor stigmatellin--binding to the ubiquinol oxidation center at the C-side of the mitochondrial membrane | journal = FEBS Letters | volume = 185 | issue = 2 | pages = 311–5 | date = June 1985 | pmid = 2987042 | doi = 10.1016/0014-5793(85)80929-7 | doi-access = | bibcode = 1985FEBSL.185..311V | s2cid = 37956153 }}] and the [cytochrome b6f](/source/cytochrome_b6f) complex of [thylakoid](/source/thylakoid) [membrane](/source/Cell_membrane)s. At higher concentrations, stigmatellin also inhibits [Complex I](/source/Complex_I), as a "Class B" inhibitor of that enzyme.[{{cite journal | vauthors = Fato R, Bergamini C, Bortolus M, Maniero AL, Leoni S, Ohnishi T, Lenaz G | title = Differential effects of mitochondrial Complex I inhibitors on production of reactive oxygen species | journal = Biochimica et Biophysica Acta (BBA) - Bioenergetics | volume = 1787 | issue = 5 | pages = 384–92 | date = May 2009 | pmid = 19059197 | pmc = 2724837 | doi = 10.1016/j.bbabio.2008.11.003 }}]
Stigmatellin is isolated from the myxobacterium ''[Stigmatella aurantica](/source/Stigmatella_aurantica)'', and contains a 5,7-dimethoxy-8-hydroxychromone aromatic headgroup with a [hydrophobic](/source/hydrophobic) alkenyl chain in position 2. Crystal structures for stigmatellin-inhibited [bc1 complex](/source/bc1_complex) from bovine, avian, yeast (''[Saccharomyces cerevisiae](/source/Saccharomyces_cerevisiae)'') and bacterial (''[Rhodobacter capsulatus](/source/Rhodobacter_capsulatus)'', ''[Cereibacter sphaeroides](/source/Rhodobacter_sphaeroides)'', and ''[Paracoccus denitrificans](/source/Paracoccus_denitrificans)'') sources are available. Stigmatellin binds at the [cytochrome b](/source/cytochrome_b) Qo site in the '(heme) bl distal' position, and associates with the Rieske [iron-sulfur protein](/source/iron-sulfur_protein) via a [hydrogen bond](/source/hydrogen_bond) to [histidine](/source/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](/source/Rieske_protein).
== References ==
{{reflist}}
== Further reading ==
{{refbegin}}
* {{cite book | vauthors = von Jagow G, Link TA | chapter = Use of specific inhibitors on the mitochondrial bc1 complex | title = Biomembranes Part N: Transport in Bacteria, Mitochondria, and Chloroplasts: Protonmotive Force | series = Methods in Enzymology | volume = 126 | pages = 253–71 | date = 1986 | pmid = 2856132 | doi = 10.1016/s0076-6879(86)26026-7 | isbn = 978-0-12-182026-8 }}
{{refend}}
Category:O-methylated natural phenols
Category:Chromones
---
Adapted from the Wikipedia article [Stigmatellin](https://en.wikipedia.org/wiki/Stigmatellin) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Stigmatellin?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.