Betaenone C

Betaenone C

Names
IUPAC name (2S,3R,4R,4aS,5R,7R,8aS)-3-[(2R)-butan-2-yl]-2,7-dihydroxy-4-[(2Z)-3-hydroxyprop-2-enoyl]-2,4,5,7-tetramethyloctahydronaphthalen-1(2H)-one
Identifiers
3D model (Jmol)	Interactive image
ChemSpider	10349243
InChI InChI=1S/C21H34O5/c1-7-12(2)17-20(5,15(23)8-9-22)16-13(3)10-19(4,25)11-14(16)18(24)21(17,6)26/h8-9,12-14,16-17,22,25-26H,7,10-11H2,1-6H3/b9-8-/t12-,13-,14+,16+,17-,19-,20-,21+/m1/s1 Key: YRYPVWAJOMXOHH-ITBWMFDCSA-N InChI=1S/C21H34O5/c1-7-12(2)17-20(5,15(23)8-9-22)16-13(3)10-19(4,25)11-14(16)18(24)21(17,6)26/h8-9,12-14,16-17,22,25-26H,7,10-11H2,1-6H3/b9-8-/t12-,13-,14+,16+,17-,19-,20-,21+/m1/s1 Key: YRYPVWAJOMXOHH-ITBWMFDCSA-N
SMILES CC2CC(C)(O)CC(C(=O)C1(C)O)C2C(C)(C(=O)\C=C/O)C1C(C)CC
Properties
Chemical formula	C21H34O5
Molar mass	366.50 g·mol^−1
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

Betaenone C, like other betaenones (A and B), is a secondary metabolite isolated from the fungus Pleospora betae, a plant pathogen.^[1] Of the seven phytotoxins isolated in fungal leaf spots from sugar beet (Beta vulgaris), it showed 89% growth inhibition. Betaenone C has been shown to act by inhibiting RNA and protein synthesis.^[2]

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: 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 Acid Res. 11: 1197–2000. doi:10.1093/nar/11.4.1197.