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Betaenone A

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Betaenone A
Names
IUPAC name (3Z)-4,6,9-trihydroxy-3-(hydroxymethylidene)-1,6,8,9-tetramethyl-10-(1-methylpropyl)octahydro-1,4-ethanonaphthalen-2(1H)-one
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C21H34O5/c1-7-11(2)16-19(5)15-12(3)8-18(4,24)9-13(15)21(26,20(16,6)25)14(10-22)17(19)23/h10-13,15-16,22,24-26H,7-9H2,1-6H3/b14-10+Key: FHJXKTOXQHRDTL-GXDHUFHOSA-N
SMILES
  • OC12C(O)(C)C(C(C)CC)C(C)(C(=O)\C2=C\O)C3C1CC(O)(C)CC3C
Properties
Chemical formula C21H34O5
Molar mass 366.498 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Betaenone A, like other betaenones (B and C), is a secondary metabolite isolated from the fungus Pleospora betae, a plant pathogen. Of the seven phytotoxins isolated in fungal leaf spots from sugar beet (Beta vulgaris), it showed 73% growth inhibition.

Molecular structures of betaenone A, B and C.

References

  1. Ichihara A.; Oikawa, Hideaki; Hayashi, Kazuko; Sakamura, Sadao; Furusaki, Akio; Matsumoto, Takeshi (1983). "Structures of Betaenones A and B, Novel Phytotoxins from Phoma betae Fr". J. Am. Chem. Soc. 105 (9): 2907–2908. doi:10.1021/ja00347a070.
  2. Haraguchi, T.; Oguro, Mieko; Nagano, Hiroshi; Ichihara, Akitami; Sakamura, Sadao (1983). "Specific inhibitors of eukaryotic DNA synthesis and DNA polymerase α, 3-deoxyaphidicolin and aphidicolin-17-monoacetate". Nucleic Acids Res. 11 (4): 1197–2000. doi:10.1093/nar/11.4.1197. PMC 325786. PMID 6402759.


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