Asterric acid

Last updated
Asterric acid
Asterric acid.svg
Names
Preferred IUPAC name
2-Hydroxy-6-[4-hydroxy-2-methoxy-6-(methoxycarbonyl)phenoxy]-4-methylbenzoic acid
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 804-200-6
PubChem CID
  • InChI=1S/C17H16O8/c1-8-4-11(19)14(16(20)21)12(5-8)25-15-10(17(22)24-3)6-9(18)7-13(15)23-2/h4-7,18-19H,1-3H3,(H,20,21)
    Key: XOKVHFNTYHPEHN-UHFFFAOYSA-N
  • InChI=1/C17H16O8/c1-8-4-11(19)14(16(20)21)12(5-8)25-15-10(17(22)24-3)6-9(18)7-13(15)23-2/h4-7,18-19H,1-3H3,(H,20,21)
    Key: XOKVHFNTYHPEHN-UHFFFAOYAF
  • CC1=CC(=C(C(=C1)OC2=C(C=C(C=C2C(=O)OC)O)OC)C(=O)O)O
Properties
C17H16O8
Molar mass 348.307 g·mol−1
Hazards
GHS labelling: [1]
GHS-pictogram-pollu.svg
Warning
H410
P273, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Asterric acid is a fungal metabolite that can inhibit endothelin binding, [2] [3] first isolated from Aspergillus terreus . [4] Its derivatives and similar phenolic fungal isolates are a subject of research on anti-angiogenic compounds. [5]

Notes

  1. ↑ Sigma-Aldrich Co., Asterric acid.
  2. ↑ Ohashi, H; Akiyama, H; Nishikori, K; Mochizuki, J (1992). "Asterric acid, a new endothelin binding inhibitor". The Journal of Antibiotics. 45 (10): 1684–5. doi: 10.7164/antibiotics.45.1684 . PMID   1473998.
  3. ↑ Yang, Xiao-Long; Zhang, Jing-Ze; Luo, Du-Qiang (2012-06-01). "The taxonomy, biology and chemistry of the fungal Pestalotiopsis genus" . Natural Product Reports. 29 (6): 622–641. doi:10.1039/C2NP00073C. ISSN   1460-4752. PMID   22249927.
  4. ↑ Curtis, R. F.; Hassall, C. H.; Jones, D. W.; Williams, T. W. (1960-01-01). "940. The biosynthesis of phenols. Part II. Asterric acid, a metabolic product of aspergillus terreus thom" . Journal of the Chemical Society (Resumed): 4838–4842. doi:10.1039/JR9600004838. ISSN   0368-1769.
  5. ↑ Lee, Hee Jung; Lee, Jeong Hyeong; Hwang, Bang Yeon; Kim, Hang Sub; Lee, Jung Joon (2002). "Fungal Metabolites, Asterric Acid Derivatives Inhibit Vascular Endothelial Growth Factor (VEGF)-induced Tube Formation of HUVECs". The Journal of Antibiotics. 55 (6): 552–556. doi: 10.7164/antibiotics.55.552 . ISSN   0021-8820. PMID   12195960.
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