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Phomoxanthone A information


Phomoxanthone A
Names
Preferred IUPAC name
rel-(5R,5′R,6R,6′R,10aR,10′aR)-10a,10′a-Bis[(acetyloxy)methyl]-1,1′,8,8′-tetrahydroxy-6,6′-dimethyl-9,9′-dioxo-5,5′,7,7′,9,9′,10a,10′a-octahydro-6H,6′H-[4,4′-bixanthene]-5,5′-diyl diacetate
Other names
PXA
Identifiers
CAS Number
  • 359844-69-2
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:66749
ChEMBL
  • ChEMBL504079
ChemSpider
  • 10213922
PubChem CID
  • 10033008
CompTox Dashboard (EPA)
  • DTXSID401098707 Edit this at Wikidata
InChI
  • InChI=ZCLZNQUALWMDDN-ACMZUNAXSA-N
SMILES
  • CC1CC(=O)C2=C(C3=C(C=CC(=C3OC2(C1OC(=O)C)COC(=O)C)C4=C5C(=C(C=C4)O)C(=C6C(=O)CC(C(C6(O5)COC(=O)C)OC(=O)C)C)O)O)O
Properties
Chemical formula
C38H38O16
Molar mass 750.70 g/mol
Appearance yellow solid
Density ~1.53 g/cm3
Solubility in water
not soluble
Solubility in DMSO good, but unstable[1]
Solubility in EtOH moderate[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

The mycotoxin phomoxanthone A, or PXA for short, is a toxic natural product that affects the mitochondria. It is the most toxic and the best studied of the naturally occurring phomoxanthones. PXA has recently been shown to induce rapid, non-canonical mitochondrial fission by causing the mitochondrial matrix to fragment while the outer mitochondrial membrane can remain intact. This process was shown to be independent from the mitochondrial fission and fusion regulators DRP1 and OPA1.[1]

  1. ^ a b c Böhler, Philip; Stuhldreier, Fabian; Anand, Ruchika; Kondadi, Arun Kumar; Schlütermann, David; Berleth, Niklas; Deitersen, Jana; Wallot-Hieke, Nora; Wu, Wenxian; Frank, Marian; Niemann, Hendrik; Wesbuer, Elisabeth; Barbian, Andreas; Luyten, Tomas; Parys, Jan B; Weidtkamp-Peters, Stefanie; Borchardt, Andrea; Reichert, Andreas S; Peña-Blanco, Aida; García-Sáez, Ana J; Itskanov, Samuel; Van Der Bliek, Alexander M; Proksch, Peter; Wesselborg, Sebastian; Stork, Björn (2018). "The mycotoxin phomoxanthone a disturbs the form and function of the inner mitochondrial membrane". Cell Death & Disease. 9 (3): 286. doi:10.1038/s41419-018-0312-8. PMC 5833434. PMID 29459714.

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