Aspergillusol A

Last updated
Aspergillusol A
Aspergillusol A Structure.svg
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
3D model (JSmol)
ChemSpider
PubChem CID
  • 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
  • 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
C22H24N2O10
Molar mass 476.438 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Aspergillusol A is an alpha-glucosidase inhibitor isolated from marine Aspergillus . [2] 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. [3]

References

  1. ↑ "KNApSAcK Metabolite Information - C00047738". www.knapsackfamily.com.
  2. ↑ 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. Bibcode:2009JNAtP..72.2049I. doi:10.1021/np9003883. PMID   19824618.
  3. ↑ Ullah, N.; Haladu, S. A. (2010). "The first total synthesis of aspergillusol A, an alpha-glucosidase inhibitor". Natural Product Communications. 5 (7): 1077–1080. doi: 10.1177/1934578X1000500719 . PMID   20734944. S2CID   29175958.


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