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）』「2015/10/08 02:44:09」(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 emuslifier 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.
^ 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. 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

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. 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
3. 成人における急性咽頭炎の対症療法 symptomatic treatment of acute pharyngitis in adults
4. 代謝性アルカローシスの臨床症状および評価 clinical manifestations and evaluation of metabolic alkalosis
5. 小児における低カリウム血症 hypokalemia in children

English Journal

Simultaneous measurement of contents of liquirtin and glycyrrhizic acid in liquorice based on near infrared spectroscopy.

Zhu Y1, Chen X1, Wang S1, Liang S1, Chen C2.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2018 May 5;196:209-214. doi: 10.1016/j.saa.2018.02.021. Epub 2018 Feb 7.
PMID 29453095

Simultaneous quantification of multiple components in rat plasma by UPLC-MS/MS and pharmacokinetic study after oral administration of Huangqi decoction.

Zeng JK1, Li YY1, Wang TM1, Zhong J1, Wu JS1, Liu P2, Zhang H2, Ma YM1,3.
Biomedical chromatography : BMC.Biomed Chromatogr.2018 May;32(5):e4178. doi: 10.1002/bmc.4178. Epub 2018 Jan 18.
PMID 29243282

Application of High-Performance Liquid Chromatography Coupled with Linear Ion Trap Quadrupole Orbitrap Mass Spectrometry for Qualitative and Quantitative Assessment of Shejin-Liyan Granule Supplements.

Gu J1,2, Wu W3, Huang M4, Long F5, Liu X6, Zhu Y7,8.
Molecules (Basel, Switzerland).Molecules.2018 Apr 11;23(4). pii: E884. doi: 10.3390/molecules23040884.
PMID 29641474

Japanese Journal

マーケットバスケット方式によるグリチルリチン酸摂取量調査 : 2015年度

沖縄県衛生環境研究所報 (50), 82-87, 2016
NAID 40021077509

甘草およびその成分(グリチルリチン酸等)について

Foods & food ingredients journal of Japan : FFIジャーナル 217(1), 38-46, 2012
NAID 40019221640

強力ネオミノファーゲンC投与肝疾患患児の尿中グリチルリチン酸とグリチルレチン酸の同定

日本小児栄養消化器肝臓学会雑誌 = Japanese journal of pediatric gastroenterology, hepatology and nutrition 24(1), 7-13, 2010-12-27
NAID 10027694936

Related Pictures

★リンクテーブル★

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

「glycyrrhizinate」

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
Legal status	Generally regarded as safe;
Routes of; administration	Oral, intravenous
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 Registry 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
Molecular 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)