Effect of 18β-glycyrrhetinic acid and hydroxypropyl γcyclodextrin complex on indomethacin-induced small intestinal injury in mice

European Journal of Pharmacology

Volumn 714, Issue 1-3, 2013, Pages 125-131

  Ishida, Tsukasa ^a,b   Miki, Ikuya ^a,b   Tanahashi, Toshihito ^a,b   Yagi, Saori ^b   Kondo, Yasuyuki ^a,b   Inoue, Jun ^a,b   Kawauchi, Shoji ^b   Nishiumi, Sin ^a   Yoshida, Masaru ^a   Maeda, Hideko ^b   Tode, Chisato ^b   Takeuchi, Atsuko ^b   Nakayama, Hirokazu ^b   Azuma, Takeshi ^a   Mizuno, Shigeto ^b  

^a KOBE UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

^b KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

18 Glycyrrhetinic acid; Glycyrrhizin; Hydroxypropyl cyclodextrin; Indomethacin; Small intestinal injury

Indexed keywords

2 HYDROXYPROPYL BETA CYCLODEXTRIN; GLYCYRRHETINIC ACID; INDOMETACIN; INTERLEUKIN 1BETA; INTERLEUKIN 6; MESSENGER RNA; TUMOR NECROSIS FACTOR ALPHA;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG EFFECT; DRUG STRUCTURE; GENE EXPRESSION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HISTOPATHOLOGY; INTESTINE INJURY; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; TANDEM MASS SPECTROMETRY;

18Β-GLYCYRRHETINIC ACID; GLYCYRRHIZIN; HYDROXYPROPYL ΓCYCLODEXTRIN; INDOMETHACIN; SMALL INTESTINAL INJURY;

ANIMALS; BIOLOGICAL AVAILABILITY; GAMMA-CYCLODEXTRINS; GENE EXPRESSION REGULATION; GLYCYRRHETINIC ACID; INDOMETHACIN; INTERLEUKIN-1BETA; INTERLEUKIN-6; INTESTINE, SMALL; MALE; MICE; MICE, INBRED C57BL; RNA, MESSENGER; SOLUBILITY; TUMOR NECROSIS FACTOR-ALPHA;

EID: 84880181946     PISSN: 00142999     EISSN: 18790712     Source Type: Journal    
DOI: 10.1016/j.ejphar.2013.06.007     Document Type: Article

References (35)

1. Albermann, M.E., Musshoff, F., Hagemeier, L., Madea, B., 2010. Determination of glycyrrhetic acid after consumption of liquorice and application to a fatality. Forensic Sci. Int. 197, 35-39.
2. Allison, M.C., Howatson, A.G., Torrance, C.J., Lee, F.D., Russell, R.I., 1992. Gastrointestinal damage associated with the use of nonsteroidal antiinflammatory drugs. N. Engl. J. Med. 327, 749-754.
3. Alsarra, I.A., Ahmed, M.O., Alanazi, F.K., Eltahir, K.E., Alsheikh, A.M., Neau, S.H., 2010. Influence of cyclodextrin complexation with NSAIDs on NSAID/cold stress-induced gastric ulceration in rats. Int. J. Med. Sci. 7, 232-239.
4. Arima, H., Nishimoto, Y., Motoyama, K., Hirayama, F., Uekama, K., 2001. Inhibitory effects of novel hydrophilic cyclodextrin derivatives on nitric oxide production in macrophages stimulated with lipopolysaccharide. Pharm. Res. 18, 1167-1173. (Pubitemid 32900403)
5. Barillaro, V., Evrard, B., Delattre, L., Piell, G., 2005. Oral bioavailability in pigs of a miconazole/hydroxypropyl-gamma-cyclodextrin/L- tartaric acid inclusion complex produced by supercritical carbon dioxide processing. AAPS J. 7, E149-E155. (Pubitemid 41554291)
6. Barillaro, V., Dive, G., Bertholet, P., Evrard, B., Delattre, L., Eric, Z., Piel, G., 2007. Theoretical and experimental investigations on miconazole/cyclodextrin/acid complexes: molecular modeling studies. Int. J. Pharm. 342, 152-160. (Pubitemid 47259335)
7. Bai, Y., Yu, B., Xu, X., Jin, Z., Tian, Y., Lu, L., 2010. Comparison of encapsulation properties of major garlic oil components by hydroxypropyl b-cyclodextrin. Eur. Food Res. Technol. 231, 519-524.
8. Cantelli-Forti, G., Maffei, F., Hrelia, P., Bugamelli, F., Bernardi, M., D'Intino, P., Maranesi, M., Raggi, M.A., 1994. Interaction of licorice on glycyrrhizin pharma-cokinetics. Environ. Health Perspect. 102 (Suppl. 9), 65-68.
9. Doll, R., Hill, I.D., 1962. Triterpenoid liquorice compound in gastric and duodenal ulcer. Lancet 2, 1166-1167.
10. Graham, D.Y., Opekun, A.R., Willingham, F.F., Qureshi, W.A., 2005. Visible small-intestinal mucosal injury in chronic NSAID users. Clin. Gastroenterol. Hepatol. 3, 55-59. (Pubitemid 40092944)
11. Higuchi, K., Umegaki, E., Watanabe, T., Yoda, Y., Morita, E., Murano, M., Tokioka, S., Arakawa, T., 2009. Present status and strategy of NSAIDs-induced small bowel injury. J. Gastroenterol. 44, 879-888.
12. Higuchi, T., Connors, K., 1965. Phase solubility diagram. Adv. Anal. Chem. Instrum. 4, 117-212.
13. Horigome, H., Hirano, T., Oka, K., 2001. Therapeutic effect of glycyrrhetinic acid in MRL lpr/lpr mice: implications of alteration of corticosteroid metabolism. Life. Sci. 69, 2429-2438. (Pubitemid 32971971)
14. Ikawa, Y., Fujino, H., Otake, S., Murayama, T., 2012. Indomethacin antagonizes EP (2) prostanoid receptor activation in LS174T human colon cancer cells. Eur. J. Pharmacol. 680, 16-21.
15. Imaoka, H., Ishihara, S., Kazumori, H., Kadowaki, Y., Aziz, M.M., Rahman, F.B., Ose, T., Fukuhara, H., Takasawa, S., Kinoshita, Y., 2010. Exacerbation of indomethacin-induced small intestinal injuries in Reg I-knockout mice. Am. J. Physiol.-Gastrointest. Liver Physiol. 299, G311-G319.
16. Ishida, T., Mizushina, Y., Yagi, S., Irino, Y., Nishiumi, S., Miki, I., Kondo, Y., Mizuno, S., Yoshida, H., Azuma, T., Yoshida, M., 2012. Inhibitory effects of glycyrrhetinic acid on DNA polymerase and inflammatory activities. Evid Based Complement Alternat Med. 2012, 650514.
17. Kawahara, R., Yasuda, M., Hashimura, H., Amagase, K., Kato, S., Takeuchi, K., 2011. Activation of alpha7 nicotinic acetylcholine receptors ameliorates indomethacin-induced small intestinal ulceration in mice. Eur. J. Pharmacol. 650, 411-417.
18. Krahenbuhl, S., Hasler, F., Krapf, R., 1994. Analysis and pharmacokinetics of glycyrrhizic acid and glycyrrhetinic acid in humans and experimental animals. Steroids 59, 121-126. (Pubitemid 24080370)
19. Krausse, R., Bielenberg, J., Blaschek, W., Ullmann, U., 2004. In vitro anti-Helicobacter pylori activity of Extractum liquiritiae, glycyrrhizin and its metabolites. J. Antimicrob. Chemother. 54, 243-246. (Pubitemid 39029000)
20. Kumagai, A., Yano, S., Otomo, M., 1957. Study on the corticoid-like action of glycyrrhizine and the mechanism of its action. Endocrinol. Jpn. 4, 17-27.
21. Li, Z., Wang, M., Wang, F., Gu, Z., Du, G., Wu, J., Chen, J., 2007. Gamma-cyclodextrin: a review on enzymatic production and applications. Appl. Microbiol. Biotechnol. 77, 245-255. (Pubitemid 350029446)
22. Loftsson, T., Vogensen, S.B., Brewster, M.E., Konradsdottir, F., 2007. Effects of cyclodextrins on drug delivery through biological membranes. J. Pharm. Sci. 96, 2532-2546. (Pubitemid 47597809)
23. Maiden, L., Thjodleifsson, B., Theodors, A., Gonzalez, J., Bjarnason, I., 2005. A quantitative analysis of NSAID-induced small bowel pathology by capsule enteroscopy. Gastroenterology 128, 1172-1178.
24. Monnaert, V., Betbeder, D., Fenart, L., Bricout, H., Lenfant, A.M., Landry, C., Cecchelli, R., Monflier, E., Tilloy, S., 2004a. Effects of gamma- and hydroxypropyl-gamma-cyclodextrins on the transport of doxorubicin across an in vitro model of blood-brain barrier. J. Pharmacol. Exp. Ther. 311, 1115-1120. (Pubitemid 39612718)
25. Monnaert, V., Tilloy, S., Bricout, H., Fenart, L., Cecchelli, R., Monflier, E., 2004b. Behavior of alpha-, beta-, and gamma-cyclodextrins and their derivatives on an in vitro model of blood-brain barrier. J. Pharmacol. Exp. Ther. 310, 745-751. (Pubitemid 38988921)
26. Nose, M., Ito, M., Kamimura, K., Shimizu, M., Ogihara, Y., 1994. A comparison of the antihepatotoxic activity between glycyrrhizin and glycyrrhetinic acid. Planta Med. 60, 136-139. (Pubitemid 24120897)
27. Ohuchi, K., Kamada, Y., Levine, L., Tsurufuji, S., 1981. Glycyrrhizin inhibits prosta-glandin E2 production by activated peritoneal macrophages from rats. Prostaglandins Med. 7, 457-463. (Pubitemid 12249608)
28. Pfaffl, M.W., 2001. A new mathematical model for relative quantification in realtime RT-PCR. Nucleic Acids Res. 29, e45.
29. Piel, G., Piette, M., Barillaro, V., Castagne, D., Evrard, B., Delattre, L., 2007. Study of the relationship between lipid binding properties of cyclodextrins and their effect on the integrity of liposomes. Int. J. Pharm. 338, 35-42. (Pubitemid 46777214)
30. Takeda, S., Ishthara, K., Wakui, Y., Amagaya, S., Maruno, M., Akao, T., Kobashi, K., 1996. Bioavailability study of glycyrrhetic acid after oral administration of glycyrrhizin in rats; relevance to the intestinal bacterial hydrolysis. J. Pharm. Pharmacol. 48, 902-905. (Pubitemid 26364890)
31. Trotta, M., Peira, E., Debernardi, F., Gallarate, M., 2002. Elastic liposomes for skin delivery of dipotassium glycyrrhizinate. Int. J. Pharm. 241, 319-327. (Pubitemid 34718033)
32. Wang, Z., Kurosaki, Y., Nakayama, T., Kimura, T., 1994. Mechanism of gastrointestinal absorption of glycyrrhizin in rats. Biol. Pharm. Bull. 17, 1399-1403. (Pubitemid 24340181)
33. Wu, X., Zhang, L., Gurley, E., Studer, E., Shang, J., Wang, T., Wang, C., Yan, M., Jiang, Z., Hylemon, P.B., Sanyal, A.J., Pandak Jr., W.M., Zhou, H., 2008. Prevention of free fatty acid-induced hepatic lipotoxicity by 18beta-glycyrrhetinic acid through lysosomal and mitochondrial pathways. Hepatology 47, 1905-1915. (Pubitemid 351945558)
34. Yasuda, M., Kawahara, R., Hashimura, H., Yamanaka, N., Iimori, M., Amagase, K., Kato, S., Takeuchi, K., 2011. Dopamine D(2)-receptor antagonists ameliorate indomethacin-induced small intestinal ulceration in mice by activating alpha7 nicotinic acetylcholine receptors. J. Pharmacol. Sci. 116, 274-282.
35. You, R., Long, W., Lai, Z., Sha, L., Wu, K., Yu, X., Lai, Y., Ji, H., Huang, Z., Zhang, Y., 2013. Discovery of a potential anti-inflammatory agent: 3-Oxo-29-noroleana-1,9(11),12-trien-2,20-dicarbonitrile. J. Med. Chem. 56, 1984-1995.