Aspergillusol A

Aspergillusol A

Names
IUPAC name [(2S,3R)-2,3-Dihydroxy-4-[(2Z)-2-hydroxyimino-3-(4-hydroxyphenyl)propanoyl]oxybutyl] (2Z)-2-hydroxyimino-3-(4-hydroxyphenyl)propanoate
Identifiers
ChemSpider	24667436
Jmol interactive 3D	Image
PubChem	44605528
InChI InChI=1S/C22H24N2O10/c25-15-5-1-13(2-6-15)9-17(23-31)21(29)33-11-19(27)20(28)12-34-22(30)18(24-32)10-14-3-7-16(26)8-4-14/h1-8,19-20,25-28,31-32H,9-12H2/b23-17-,24-18-/t19-,20+ Key: BXRQJOBHKCDAJW-KMMADPOHSA-N InChI=1/C22H24N2O10/c25-15-5-1-13(2-6-15)9-17(23-31)21(29)33-11-19(27)20(28)12-34-22(30)18(24-32)10-14-3-7-16(26)8-4-14/h1-8,19-20,25-28,31-32H,9-12H2/b23-17-,24-18-/t19-,20+ Key: BXRQJOBHKCDAJW-KMMADPOHBB
SMILES C1=CC(=CC=C1C/C(=N/O)/C(=O)OC[C@@H](O)[C@@H](O)COC(=O)/C(=N\O)/CC2=CC=C(C=C2)O)O
Properties
Chemical formula	C22H24N2O10
Molar mass	476.44 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Aspergillusol A is an alpha-glucosidase inhibitor isolated from marine Aspergillus.^[1] Structurally, it consists of an erythritol group in the center, with two hydroxyimino-phenylpropanoyl groups attached to it from either side. It was synthesized in 2010 by researchers from King Fahd University of Petroleum and Minerals, starting with 4-hydroxybenzaldehyde.^[2]

References

1. Ingavat, N; Dobereiner, J; Wiyakrutta, S; Mahidol, C; Ruchirawat, S; Kittakoop, P (2009). "Aspergillusol A, an alpha-glucosidase inhibitor from the marine-derived fungus Aspergillus aculeatus". Journal of Natural Products 72 (11): 2049–52. doi:10.1021/np9003883. PMID 19824618.
2. Ullah, N.; Haladu, S. A. (2010). "The first total synthesis of aspergillusol A, an alpha-glucosidase inhibitor". Natural product communications 5 (7): 1077–1080. PMID 20734944.