関: diammonium glycyrrhizinate、glycyrrhizin、glycyrrhizinate、glycyrrhizinate dipotassium、glycyrrhizinic acid、monoammonium glycyrrhizinate

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

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/03/07 08:33:54」(JST)

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Glycyrrhizin (or glycyrrhizic acid or glycyrrhizinic acid) is the chief sweet-tasting constituent of Glycyrrhiza glabra (liquorice) root. Structurally it is a saponin and has been used as an emulsifier and gel-forming agent in foodstuff and cosmetics. Its aglycone is enoxolone and it has therefore been used as a prodrug for that compound, for example it is used in Japan to prevent liver carcinogenesis in patients with chronic hepatitis C.^[3]

Medical uses

Glycyrrhizin inhibits liver cell injury and is given intravenously for the treatment of chronic viral hepatitis and cirrhosis in Japan.^[4]^[5] It has also proven itself effective in the treatment of autoimmune hepatitis in one clinical trial.^[6]

Adverse effects

The most widely reported side effects of glycyrrhizin use are fluid retention. These effects are related to the inhibition of cortisol metabolism within the kidney, and the subsequent stimulation of the mineralocorticoid receptors.^[7] Other side effects include:^[8]

Headache
Paralysis
Transient visual loss
Torsades de pointes
Tachycardia
Cardiac arrest
Hypokalaemia
Reduced testosterone
Premature birth
Acute kidney failure
Muscle weakness
Myopathy
Myoglobinuria
Rhabdomyolysis
Increased body weight

Mechanism of action

It inhibits the enzyme 11beta-hydroxysteroid dehydrogenase, which likely contributes to its anti-inflammatory and mineralocorticoid activity.^[8] It has a broad-spectrum of antiviral activity in vitro against:^[8]^[9]

Herpes simplex virus,^[10] which has also been confirmed in vivo.^[11]
Influenzavirus (including H5N1)^[12]
Varicella zoster virus^[13]
SARS coronavirus
HIV
Hepatitis A virus
Hepatitis B virus
Hepatitis C virus
Hepatitis E virus
Epstein-barr virus
Human cytomegalovirus
Flavivirus
Japanese encephalitis virus

Pharmacokinetics

After oral ingestion, glycyrrhizin is first hydrolysed to 18β-glycyrrhetinic acid by intestinal bacteria. After complete absorption from the gut, β-glycyrrhetinic acid is metabolised to 3β-monoglucuronyl-18β-glycyrrhetinic acid in the liver. This metabolite then circulates in the bloodstream. Consequently its oral bioavailability is poor. The main part is eliminated by bile and only a minor part (0.31–0.67%) by urine.^[14] After oral ingestion of 600 mg of glycyrrhizin the metabolite appeared in urine after 1.5 to 14 hours. Maximal concentrations (0.49 to 2.69 mg/l) were achieved after 1.5 to 39 hours and metabolite can be detected in the urine after 2 to 4 days.^[14]

Organoleptic properties

It is 30-50 times as sweet as sucrose (table sugar).^[8]^[15]

References

^ van Rossum, TG; Vulto, AG; Hop, WC; Schalm, SW (December 1999). "Pharmacokinetics of intravenous glycyrrhizin after single and multiple doses in patients with chronic hepatitis C infection.". Clinical Therapeutics 21 (12): 2080–90. doi:10.1016/S0149-2918(00)87239-2. PMID 10645755.
^ Ploeger, B; Mensinga, T; Sips, A; Seinen, W; Meulenbelt, J; DeJongh, J (May 2001). "The pharmacokinetics of glycyrrhizic acid evaluated by physiologically based pharmacokinetic modeling.". Drug Metabolism Reviews 33 (2): 125–47. doi:10.1081/DMR-100104400. PMID 11495500.
^ Arase, Yasuji; Ikeda, Kenji; Murashima, Naoya; Chayama, Kazuaki; Tsubota, Akihito; Koida, Isao; Suzuki, Yoshiyuki; Saitoh, Satoshi; Kobayashi, Masahiro; Kumada, Hiromitsu (15 April 1997). "The long term efficacy of glycyrrhizin in chronic hepatitis C patients". Cancer 79 (8): 1494–1500. doi:10.1002/(SICI)1097-0142(19970415)79:8%3C1494::AID-CNCR8%3E3.0.CO;2-B.
^ Sato, H; Goto, W; Yamamura, J; Kurokawa, M; Kageyama, S; Takahara, T; Watanabe, A; Shiraki, K (May 1996). "Therapeutic basis of glycyrrhizin on chronic hepatitis B.". Antiviral Research 30 (2-3): 171–7. doi:10.1016/0166-3542(96)00942-4. PMID 8783808.
^ van Rossum, TG; Vulto, AG; de Man, RA; Brouwer, JT; Schalm, SW (March 1998). "Review article: glycyrrhizin as a potential treatment for chronic hepatitis C." (PDF). Alimentary Pharmacology & Therapeutics 12 (3): 199–205. doi:10.1046/j.1365-2036.1998.00309.x. PMID 9570253. Cite uses deprecated parameter |coauthors= (help)
^ Yasui, S; Fujiwara, K; Tawada, A; Fukuda, Y; Nakano, M; Yokosuka, O (December 2011). "Efficacy of intravenous glycyrrhizin in the early stage of acute onset autoimmune hepatitis.". Digestive Diseases and Sciences 56 (12): 3638–47. doi:10.1007/s10620-011-1789-5. PMID 21681505.
^ Ferrari, P.; Sansonnens, A.; Dick, B.; Frey, F. J. (2001). "In Vivo 11 -HSD-2 Activity: Variability, Salt-Sensitivity, and Effect of Licorice". Hypertension 38 (6): 1330–6. doi:10.1161/hy1101.096112. PMID 11751713.
^ ^a ^b ^c ^d Asl, MN; Hosseinzadeh, H (June 2008). "Review of pharmacological effects of Glycyrrhiza sp. and its bioactive compounds." (PDF). Phytotherapy Research 22 (6): 709–24. doi:10.1002/ptr.2362. PMID 18446848.
^ Shamsa, F; Ohtsuki, K; Hasanzadeh, E; Rezazadeh, S (2010). "The Anti-inflammatory and Anti-viral Effects of an Ethnic Medicine: Glycyrrhizin" (PDF). Journal of Medicinal Plants 9 (Suppl. 2): 1389.
^ Pompei, Raffaello; Flore, Ornella; Marccialis, Maria Antonietta; Pani, Alessandra; Loddo, Bernardo (1979). "Glycyrrhizic acid inhibits virus growth and inactivates virus particles". Nature 281 (5733): 689–90. doi:10.1038/281689a0. PMID 233133.
^ Sekizawa, T; Yanagi, K; Itoyama, Y (February 2001). "Glycyrrhizin increases survival of mice with herpes simplex encephalitis.". Acta Virologica 45 (1): 51–4. PMID 11394578.
^ Michaelis, Martin; Geiler, Janina; Naczk, Patrizia; Sithisarn, Patchima; Leutz, Anke; Doerr, Hans Wilhelm; Cinatl, Jindrich (2011). Pekosz, Andrew, ed. "Glycyrrhizin Exerts Antioxidative Effects in H5N1 Influenza a Virus-Infected Cells and Inhibits Virus Replication and Pro-Inflammatory Gene Expression". PLoS ONE 6 (5): e19705. doi:10.1371/journal.pone.0019705. PMC 3096629. PMID 21611183.
^ Baba, M; Shigeta, S (February 1987). "Antiviral activity of glycyrrhizin against varicella-zoster virus in vitro.". Antiviral Research 7 (2): 99–107. doi:10.1016/0166-3542(87)90025-8. PMID 3034150.
^ ^a ^b Kočevar Glavač, Nina; Kreft, Samo (2012). "Excretion profile of glycyrrhizin metabolite in human urine". Food Chemistry 131: 305–308. doi:10.1016/j.foodchem.2011.08.081.
^ "Glycyrrhizic Acid". PubChem. National Institutes of Health. Retrieved 24 February 2014.

External links

CHEMICAL MODIFICATION OF GLYCYRRHIZIC ACID AS A ROUTE TO NEW BIOACTIVE COMPOUNDS FOR MEDICINE by L.A.Baltina; doi:10.2174/0929867033368538

UpToDate Contents

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Water soluble biocompatible vesicles based on polysaccharides and oligosaccharides inclusion complexes for carotenoid delivery.

Polyakov NE1, Kispert LD2.
Carbohydrate polymers.Carbohydr Polym.2015 Sep 5;128:207-219. doi: 10.1016/j.carbpol.2015.04.016. Epub 2015 Apr 22.
Since carotenoids are highly hydrophobic, air- and light-sensitive hydrocarbon compounds, developing methods for increasing their bioavailability and stability towards irradiation and reactive oxygen species is an important goal. Application of inclusion complexes of "host-guest" type with polysacch
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Glycyrrhizic acid (GA) inhibits reactive oxygen Species mediated photodamage by blocking ER stress and MAPK pathway in UV-B irradiated human skin fibroblasts.

Farrukh MR1, Nissar UA2, Kaiser PJ1, Afnan Q1, Sharma PR3, Bhushan S4, Tasduq SA5.
Journal of photochemistry and photobiology. B, Biology.J Photochem Photobiol B.2015 May 15;148:351-357. doi: 10.1016/j.jphotobiol.2015.05.003. [Epub ahead of print]
BACKGROUND: Previously we have reported that generation of reactive oxygen species is the prime event responsible for calcium mediated activation of PERK-eIF2α-CHOP pathway and apoptosis in UV-B irradiated human skin fibroblasts (Hs68). We have also reported that glycyrrhizic acid (GA) mediates pot
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Determination of high-intensity sweeteners in river water and wastewater by solid-phase extraction and liquid chromatography-tandem mass spectrometry.

Arbeláez P1, Borrull F1, Pocurull E2, Marcé RM1.
Journal of chromatography. A.J Chromatogr A.2015 May 8;1393:106-14. doi: 10.1016/j.chroma.2015.03.035. Epub 2015 Mar 21.
High-intensity sweeteners have been suggested as potential organic contaminants due to their widespread use in food, drugs and sanitary products. As a consequence, they are introduced into the environment by different pathways, affecting aquatic life. In this study, a method based on solid-phase ext
PMID 25840659

Japanese Journal

薬用植物甘草の栽培とグリチルリチン酸の分析

和歌山大学教育学部紀要. 自然科学 = Bulletin of the Faculty of Education, Wakayama University. 和歌山大学教育学部紀要委員会編 66, 9-11, 2016-02
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葛根湯エキス製剤および湯剤の同等性に関する研究(II)

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グリチルリチン酸に含まれるグルクロン酸の立体化学の確認

日本食品化学学会誌 22(1), 32-37, 2015-04-24
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★リンクテーブル★

リンク元	「グリチルリチン酸」「glycyrrhizinate」「diammonium glycyrrhizinate」「グリシルリジン酸」「グリチルリジン酸」

「グリチルリチン酸」

Glycyrrhizic acid
Systematic (IUPAC) name
	(3β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-β-D-glucopyranuronosyl-α-D-glucopyranosiduronic acid
Clinical data
Trade names	Epigen, Glycyron
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral, intravenous
Legal status	Generally regarded as safe;
Pharmacokinetic data
Metabolism	Hepatic and by intestinal bacteria
Biological half-life	6.2-10.2 hours
Excretion	Faeces, urine (0.31-0.67%)
Identifiers
CAS Number	1405-86-3 (α-D-Glucopyranosiduronic acid), 103000-77-7 (β-D-Glucopyranosiduronic acid)
ATC code	A05BA08
PubChem	CID 128229
ChemSpider	14263
UNII	6FO62043WK
ChEBI	CHEBI:15939
ChEMBL	CHEMBL441687
Chemical data
Formula	C42H62O16
Molar mass	822.93 g/mol
	SMILES O=C(O)[C@H]7O[C@@H](O[C@@H]6[C@@H](O)[C@H](O)[C@H](O[C@@H]6O[C@@H]2C(C)(C)[C@@H]3CC[C@@]1(C)[C@]5(C(=C/C(=O)[C@@H]1[C@@]3(C)CC2)\[C@@H]4C[C@](C(=O)O)(C)CC[C@]4(C)CC5)C)C(=O)O)[C@H](O)[C@@H](O)[C@@H]7O ;
	InChI InChI=1S/C42H62O16/c1-37(2)21-8-11-42(7)31(20(43)16-18-19-17-39(4,36(53)54)13-12-38(19,3)14-15-41(18,42)6)40(21,5)10-9-22(37)55-35-30(26(47)25(46)29(57-35)33(51)52)58-34-27(48)23(44)24(45)28(56-34)32(49)50/h16,19,21-31,34-35,44-48H,8-15,17H2,1-7H3,(H,49,50)(H,51,52)(H,53,54)/t19-,21-,22-,23-,24-,25-,26-,27+,28-,29-,30+,31+,34-,35-,38+,39-,40-,41+,42+/m0/s1 ; Key:LPLVUJXQOOQHMX-QWBHMCJMSA-N ;
Physical data
Solubility in water	1-10 mg/mL (20 °C)