WordNet

street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

PrepTutorEJDIC

酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/11/28 13:20:48」(JST)

wiki en

Glycyrrhetinic acid is a pentacyclic triterpenoid derivative of the beta-amyrin type obtained from the hydrolysis of glycyrrhizic acid, which was obtained from the herb liquorice. It is used in flavoring and it masks the bitter taste of drugs like aloe and quinine. It is effective in the treatment of peptic ulcer and also has expectorant (antitussive) properties.^[1] It has some additional pharmacological properties including antiviral, antifungal, antiprotozoal, and antibacterial activities.^[2]^[3]^[4]^[5]

Mechanism of action[edit]

Glycyrrhetinic acid inhibits the enzymes (15-hydroxyprostaglandin dehydrogenase and delta-13-prostaglandin) that metabolize the prostaglandins PGE-2 and PGF-2α to their respective 15-keto-13,14-dihydro metabolites which are inactive. This causes an increased level of prostaglandins in the digestive system. Prostaglandins inhibit gastric secretion but stimulate pancreatic secretion and mucous secretion in the intestines and markedly increase intestinal motility. They also cause cell proliferation in the stomach. The effect on gastric acid secretion, promotion of mucous secretion and cell proliferation shows why licorice has potential in treating peptic ulcer.

PGF-2α stimulates activity of the uterus during pregnancy and can cause abortion, therefore, licorice should not be taken during pregnancy.

The structure of glycyrrhetinic acid is similar to that of cortisone. Both molecules are flat and similar at position 3 and 11. This might be the basis for licorice's anti-inflammatory action.

3-β-D-(monoglucuronyl)-18-β-glycyrrhetinic acid, a metabolite of glycyrrhetinic acid, inhibits the conversion of active cortisol to inactive cortisone in the kidneys. This occurs via inhibition of the enzyme by inhibiting the enzyme 11-β-hydroxysteroid dehydrogenase. As a result, cortisol levels are high within the collecting duct of the kidney. Cortisol has intrinsic mineralocorticoid properties (that is, it acts like aldosterone and increases sodium reabsorption) that work on ENaC channels in the collecting duct. Hypertension develops due to this mechanism of sodium retention. People often have high blood pressure with a low renin and low aldosterone blood level. The increased amounts of cortisol binds to the unprotected, unspecific mineralocorticoid receptors and induce sodium and fluid retention, hypokalaemia, high blood pressure and inhibition of the renin-angiotensin-aldosterone system. Therefore licorice should not be given to patients with a known history of hypertension in doses sufficient to inhibit 11-β-hydroxysteroid dehydrogenase.

Derivatives[edit]

Glycyrrhetinic acid derivatives, where R is a variable functional group

In glycyrrhetinic acid, the functional group (R) is a hydroxyl group. Research in 2005 demonstrated that with a proper functional group a very effective glycyrrhetinic artificial sweetener can be obtained.^[6] When R is an anionic NHCO(CH₂)CO₂K side chain, the sweetening effect is found to 1200 times that of sugar (human sensory panel data). A shorter or longer spacer reduces the sweetening effect. One explanation is that the taste bud cell receptor has 1.3 nanometers (13 angstroms) available for docking with the sweetener molecule. In addition the sweetener molecule requires three proton donor positions of which two reside at the extremities to be able to interact efficiently with the receptor cavity.

A synthetic analog, carbenoxolone, was developed in Britain.^{[citation needed]} Both glycyrrhetinic acid and carbenoxolone have a modulatory effect on neural signaling through gap junction channels.

Acetoxolone, the acetyl derivative of glycyrrhetinic acid, is a drug used in the treatment of peptic ulcer and gastroesophageal reflux disease.

Notes[edit]

^ Chandler, RF (1985). "Liquorice, more than just a flavour". Canadian Pharmaceutical Journal (118): 420–4.
^ Badam, L., Amagaya, S. and Pollard, B. (1997). "In vitro activity of licorice and glycyrrhetinic acid on Japanese encephalitis virus.". J. Community Dis. 29: 91–99.
^ Fuji, H.Y., Tian, J. and Luka, C. (1986). "Effect of glycyrrhetinic acid on influenza virus and pathogenic bacteria.". Bull. Chin. Mater. Med. 11: 238–241.
^ Guo, N., Takechi, M. and Uno, C. (1991). "Protective effect of glycyrrhizine in mice with systemic Candida albicans infection and its mechanism". J. Pharm. Pharmacol. 12 (5): 380–383. PMID 1839259.
^ Salari, M. H., Sohrabi, N., Kadkhoda, Z., and Khalili, M. B. (2003). "Antibacterial effects of Enoxolone on periodontopathogenic and capnophilic bacteria isolated from specimens of periodontitis patients". Iran. Biomed. J. 7: 39–42.
^ Ijichi, So; Seizo Tamagaki (2005). "Molecular Design of Sweet Tasting Compounds Based on 3β-Amino-3β-deoxy-18β-glycyrrhetinic Acid: Amido Functionality Eliciting Tremendous Sweetness". Chemistry Letters 34 (3): 356. doi:10.1246/cl.2005.356. Retrieved 2010-09-28.

References[edit]

Saponin Glycosides, by Georges-Louis Friedli, URL accessed Sept 2010.

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. 見かけの鉱質コルチコイド過剰（AME）症候群（長期甘草摂取を含む） apparent mineralocorticoid excess syndromes including chronic licorice ingestion
2. 漢方薬および栄養補助食品の概要 overview of herbal medicine and dietary supplements
3. Chapter 6C：アルドステロン chapter 6c aldosterone
4. アレルギー疾患の治療のための漢方薬 chinese herbal medicine for the treatment of allergic diseases
5. 成人における急性咽頭炎の対症療法 symptomatic treatment of acute pharyngitis in adults

English Journal

Inhibitory effects of glycyrrhetinic Acid on DNA polymerase and inflammatory activities.

Ishida T, Mizushina Y, Yagi S, Irino Y, Nishiumi S, Miki I, Kondo Y, Mizuno S, Yoshida H, Azuma T, Yoshida M.SourceDepartment of Medical Pharmaceutics, Kobe Pharmaceutical University, Higashinada-ku, Kobe 658-8558, Japan.
Evidence-based complementary and alternative medicine : eCAM.Evid Based Complement Alternat Med.2012;2012:650514. Epub 2011 Jul 14.
We investigated the inhibitory effect of three glycyrrhizin derivatives, such as Glycyrrhizin (compound 1), dipotassium glycyrrhizate (compound 2) and glycyrrhetinic acid (compound 3), on the activity of mammalian pols. Among these derivatives, compound 3 was the strongest inhibitor of mammalian pol
PMID 21785649

Japanese Journal

β-グリチルレチン酸の抗菌効果と制汗デオドラント剤への応用

後藤佳子
ファインケミカル 40(9), 34-39, 2011-09
NAID 40018956992

Related Pictures

★リンクテーブル★

リンク元	「グリチルレチン酸」「グリシルレチン酸」「enoxolone」

「グリチルレチン酸」

Glycyrrhetinic acid
	IUPAC name (2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid
	Other names Enoxolone; Glycyrrhetin; Uralenic acid; Glycyrrhetinate; Arthrodont; 3β-Hydroxy-11-oxoolean-12-en-30-olic acid
Identifiers
CAS number	471-53-4
PubChem	10114
ChemSpider	9710
ChEBI	CHEBI:30853
ChEMBL	CHEMBL230006
ATC code	D03AX10
Jmol-3D images	Image 1
	SMILES O=C(O)[C@]5(C)C[C@H]4/C3=C/C(=O)[C@H]1[C@](CC[C@@H]2[C@]1(C)CC[C@H](O)C2(C)C)(C)[C@]3(C)CC[C@@]4(C)CC5 ;
	InChI InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21-,22-,23+,26+,27-,28-,29+,30+/m0/s1 ; Key: MPDGHEJMBKOTSU-YKLVYJNSSA-N InChI=1/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21-,22-,23+,26+,27-,28-,29+,30+/m0/s1; Key: MPDGHEJMBKOTSU-YKLVYJNSBE ;
Properties
Molecular formula	C30H46O4
Molar mass	470.68 g mol−1
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references