Notholaenic acid

Notholaenic acid
Names
IUPAC name
2-hydroxy-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]benzoic acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.069.726
UNII
  • InChI=1S/C17H18O5/c1-21-13-7-4-11(5-8-13)3-6-12-9-14(22-2)10-15(18)16(12)17(19)20/h4-5,7-10,18H,3,6H2,1-2H3,(H,19,20)
    Key: QTSHPXKETKYZMV-UHFFFAOYSA-N
  • InChI=1S/C17H18O5/c1-21-13-7-4-11(5-8-13)3-6-12-9-14(22-2)10-15(18)16 (12)17(19)20/h4-5,7-10,18H,3,6H2,1-2H3,(H,19,20)
    Key: QTSHPXKETKYZMV-UHFFFAOYSA-N
  • COC1=CC=C(C=C1)CCC2=CC(=CC(=C2C(=O)O)O)OC
Properties
C17H18O5
Molar mass 302.326 g·mol−1
Melting point 149 to 150 °C (300 to 302 °F; 422 to 423 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Notholaenic acid is a dihydrostilbenoid found in the farina of some ferns of the genus Argyrochosma (formerly part of Notholaena).

The compound was originally purified from the waxy frond exudate of Notholaena limitanea and Notholaena dealbata.[1] Subsequent analysis showed that only N. limitanea var. mexicana secretes notholaenic acid, while other taxa reported to produce it in fact secreted isonotholaenic acid.[2]

Notholaenic acid has been shown to have anti-HSV-1 (Herpes simplex virus 1) activity at high concentrations in vitro.[3] It was artificially synthesized, starting from 3-benzyloxy-5-methoxybenzyl alcohol, in 1985.[4]

References

  1. ^ Wollenweber, Eckhard; Favre-Bonvin, Jean (1979). "Novel dihydrostilbene from fronds of Notholaena dealbata and Notholaena limitanea". Phytochemistry. 18 (7): 1243–1244. doi:10.1016/0031-9422(79)80153-3.
  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. ^ Rinehart, Kenneth L.; Tom G. Holt; Nancy L. Fregeau; Paul A. Keifer; George Robert Wilson; Thomas J. Perun Jr; Ryuichi Sakai; Anthony G. Thompson; Justin G. Stroh; Lois S. Shield; David S. Seigler; Li H. Li; David G. Martin; Cornelis J. P. Grimmelikhuijzen; Gerd Gäde (July–August 1990). "Bioactive Compounds from Aquatic and Terrestrial Sources". Journal of Natural Products. 53 (4): 771–792. doi:10.1021/np50070a001. PMID 2095373.
  4. ^ El-Feraly, Farouk S.; Cheatham, Steve F.; McChesney, James D. (1985). "Total Synthesis of Notholaenic Acid". Journal of Natural Products. 48 (2): 293–298. doi:10.1021/np50038a015.
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