Isogentisin

For research use only. Not for therapeutic Use.

  • CAT Number: I029562
  • CAS Number: 491-64-5
  • Molecular Formula: C14H10O5
  • Molecular Weight: 258.229
  • Purity: 98%
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Isogentisin (CAT: I029562) is a natural compound belonging to the class of benzofurans. It is derived from various plant sources and possesses diverse biological activities. Isogentisin has been found to exhibit antioxidant properties, helping to combat oxidative stress and protect cells from damage caused by reactive oxygen species. Additionally, it has been studied for its potential anti-inflammatory effects, which may contribute to its therapeutic applications in conditions associated with inflammation.


Catalog Number I029562
CAS Number 491-64-5
Synonyms

Isogentisin; BRN 0258402; BRN-0258402; BRN0258402.

Molecular Formula C14H10O5
Purity 98%
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name 1,3-Dihydroxy-7-methoxy-9H-xanthen-9-one
InChI InChI=1S/C14H10O5/c1-18-8-2-3-11-9(6-8)14(17)13-10(16)4-7(15)5-12(13)19-11/h2-6,15-16H,1H3
InChIKey FVIYCYAHKMJVJK-UHFFFAOYSA-N
SMILES O=C1C2=C(OC3=C1C=C(OC)C=C3)C=C(O)C=C2O
Reference

1: Yin C, Xie L, Guo Y. Phytochemical analysis and antibacterial activity of Gentiana macrophylla extract against bacteria isolated from burn wound infections. Microb Pathog. 2018 Jan;114:25-28. doi: 10.1016/j.micpath.2017.10.049. Epub 2017 Oct 27. PubMed PMID: 29111322.
2: Amakura Y, Yoshimura M, Morimoto S, Yoshida T, Tada A, Ito Y, Yamazaki T, Sugimoto N, Akiyama H. Chromatographic Evaluation and Characterization of Components of Gentian Root Extract Used as Food Additives. Chem Pharm Bull (Tokyo). 2016;64(1):78-82. doi: 10.1248/cpb.c15-00776. PubMed PMID: 26726749.
3: Mustafa AM, Caprioli G, Ricciutelli M, Maggi F, Marín R, Vittori S, Sagratini G. Comparative HPLC/ESI-MS and HPLC/DAD study of different populations of cultivated, wild and commercial Gentiana lutea L. Food Chem. 2015 May 1;174:426-33. doi: 10.1016/j.foodchem.2014.11.089. Epub 2014 Nov 22. PubMed PMID: 25529701.
4: Wani BA, Ramamoorthy D, Rather MA, Arumugam N, Qazi AK, Majeed R, Hamid A, Ganie SA, Ganai BA, Anand R, Gupta AP. Induction of apoptosis in human pancreatic MiaPaCa-2 cells through the loss of mitochondrial membrane potential (ΔΨm) by Gentiana kurroo root extract and LC-ESI-MS analysis of its principal constituents. Phytomedicine. 2013 Jun 15;20(8-9):723-33. doi: 10.1016/j.phymed.2013.01.011. Epub 2013 Mar 1. PubMed PMID: 23453831.
5: Balijagić J, Janković T, Zdunić G, Bosković J, Savikin K, Godevac D, Stanojković T, Jovancević M, Menković N. Chemical profile, radical scavenging and cytotoxic activity of yellow gentian leaves (Genitaneae luteaefolium) grown in northern regions of Montenegro. Nat Prod Commun. 2012 Nov;7(11):1487-90. PubMed PMID: 23285813.
6: Klein-Júnior LC, Meira NA, Bresolin TM, Cechinel-Filho V, Quintão NL. Antihyperalgesic activity of the methanol extract and some constituents obtained from Polygala cyparissias (Polygalaceae). Basic Clin Pharmacol Toxicol. 2012 Sep;111(3):145-53. doi: 10.1111/j.1742-7843.2012.00876.x. Epub 2012 Mar 22. PubMed PMID: 22381005.
7: Klein LC Jr, Gandolfi RB, Santin JR, Lemos M, Cechinel Filho V, de Andrade SF. Antiulcerogenic activity of extract, fractions, and some compounds obtained from Polygala cyparissias St. Hillaire & Moquin (Polygalaceae). Naunyn Schmiedebergs Arch Pharmacol. 2010 Feb;381(2):121-6. doi: 10.1007/s00210-009-0485-x. Epub 2010 Jan 8. PubMed PMID: 20054524.
8: Savikin K, Menković N, Zdunić G, Stević T, Radanović D, Janković T. Antimicrobial activity of Gentiana lutea L. extracts. Z Naturforsch C. 2009 May-Jun;64(5-6):339-42. PubMed PMID: 19678535.
9: Citová I, Ganzera M, Stuppner H, Solich P. Determination of gentisin, isogentisin, and amarogentin in Gentiana lutea L. by capillary electrophoresis. J Sep Sci. 2008 Jan;31(1):195-200. PubMed PMID: 18064621.
10: Aberham A, Schwaiger S, Stuppner H, Ganzera M. Quantitative analysis of iridoids, secoiridoids, xanthones and xanthone glycosides in Gentiana lutea L. roots by RP-HPLC and LC-MS. J Pharm Biomed Anal. 2007 Nov 5;45(3):437-42. Epub 2007 Jul 10. PubMed PMID: 17697760.
11: Schmieder A, Schwaiger S, Csordas A, Backovic A, Messner B, Wick G, Stuppner H, Bernhard D. Isogentisin–a novel compound for the prevention of smoking-caused endothelial injury. Atherosclerosis. 2007 Oct;194(2):317-25. Epub 2006 Dec 1. PubMed PMID: 17141243.
12: Matsushima T, Araki A, Yagame O, Muramatsu M, Koyama K, Ohsawa K, Natori S, Tomimori H. Mutagenicities of xanthone derivatives in Salmonella typhimurium TA100, TA98, TA97, and TA2637. Mutat Res. 1985 Jun-Jul;150(1-2):141-6. PubMed PMID: 3889613.
13: Morimoto I, Nozaka T, Watanabe F, Ishino M, Hirose Y, Okitsu T. Mutagenic activities of gentisin and isogentisin from Gentianae radix (Gentianaceae). Mutat Res. 1983 Feb;116(2):103-17. PubMed PMID: 6338357.
14: Suzuki O, Katsumata Y, Oya M, Chari VM, Klapfenberger R, Wagner H, Hostettmann K. Inhibition of type A and type B monoamine oxidase by isogentisin and its 3-O-glucoside. Planta Med. 1980 May;39(1):19-23. PubMed PMID: 7403306.
15: Suzuki O, Katsumata Y, Oya M. Inhibition of monoamine oxidase by isogentisin and its 3-O-glucoside. Biochem Pharmacol. 1978;27(16):2075-8. PubMed PMID: 718732.
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