Isonotholaenic acid

Last updated
Isonotholaenic acid
Isonotholaenic acid.svg
Names
Preferred IUPAC name
4-Hydroxy-2-methoxy-6-[2-(4-methoxyphenyl)ethyl]benzoic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C17H18O5/c1-21-14-7-4-11(5-8-14)3-6-12-9-13(18)10-15(22-2)16(12)17(19)20/h4-5,7-10,18H,3,6H2,1-2H3,(H,19,20)
    Key: GAWSNXBLUNVZCK-UHFFFAOYSA-N
  • InChI=1/C17H18O5/c1-21-14-7-4-11(5-8-14)3-6-12-9-13(18)10-15(22-2)16(12)17(19)20/h4-5,7-10,18H,3,6H2,1-2H3,(H,19,20)
    Key: GAWSNXBLUNVZCK-UHFFFAOYAW
  • c2cc(OC)ccc2CCc1cc(O)cc(OC)c1C(O)=O
Properties
C17H18O5
Molar mass 302.326 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Isonotholaenic acid is a dihydrostilbenoid first isolated from the Andean fern Argyrochosma nivea (formerly Notholaena nivea), and is also found in other species of that genus. Before its discovery and structure determination, it had been misidentified as notholaenic acid. [2] Its derivatives have been suggested as possible antiplasmodial compounds. [3] This compound shows an anti-chagasic activity. [4]

References

  1. ↑ "KNApSAcK Metabolite Information - C00015795". www.knapsackfamily.com.
  2. ↑ Wollenweber, Eckhard; Doerr, Marion; Waton, Hugues; Favre-Bonvin, Jean (1993). "Flavonoid aglycones and a dihydrostilbene from the frond exudate of Notholaena nivea". Phytochemistry . 33 (3): 611–612. doi:10.1016/0031-9422(93)85457-3.
  3. ↑ del Olmo, Esther; Armas, Marlon Garcia; Ybarra, Ma Inèss; Lopez, José Luis; Oporto, Patricia; Giménez, Alberto; Deharo, Eric; San Feliciano, Arturo (2003). "The Imidazo[2,1-a]isoindole System. A New Skeletal Basis for Antiplasmodial Compounds". Bioorganic & Medicinal Chemistry Letters. 13 (16): 2769–2772. doi:10.1016/S0960-894X(03)00509-2. PMID   12873511.
  4. ↑ del Olmo, Esther; Armas, Marlon Garcia; López-Pérez, JL; Ruiz, G; Vargas, F; Giménez, Alberto; Deharo, Eric; San Feliciano, Arturo (2001). "Anti-Trypanosoma activity of some natural stilbenoids and synthetic related heterocyclic compounds". Bioorganic & Medicinal Chemistry Letters. 11 (20): 2755–2757. doi:10.1016/s0960-894x(01)00562-5. PMID   11591517.
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