lithocholic acid

リトコール酸

WordNet

1. 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
2. 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
3. having the characteristics of an acid; "an acid reaction"

PrepTutorEJDIC

1. 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）』「2013/04/09 20:59:49」(JST)

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Lithocholic acid
IUPAC name (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-Hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
Other names Lithocholate; Lithocolic acid; 3α-Hydroxy-5β-cholan-24-oic acid; 3α-Hydroxy-5β-cholanic acid; 5β-Cholan-24-oic acid-3α-ol
Identifiers
CAS number	434-13-9 Y
PubChem	9903
ChemSpider	9519 Y
EC number	207-099-1
ChEBI	CHEBI:16325 N
ChEMBL	CHEMBL1478 Y
IUPHAR ligand	611
RTECS number	FZ2275000
Jmol-3D images	Image 1
SMILES O=C(O)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]4[C@H]2CC[C@@H]3C[C@H](O)CC[C@@]34C)C
InChI InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1 Y Key: SMEROWZSTRWXGI-HVATVPOCSA-N Y InChI=1/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1 Key: SMEROWZSTRWXGI-HVATVPOCBI
Properties
Molecular formula	C24H40O3
Molar mass	376.57 g/mol
Melting point	183-188 °C
Hazards
S-phrases	S22 S24/25
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Lithocholic acid (LCA) is a bile acid that acts as a detergent to solubilize fats for absorption. Bacterial action in the colon produces LCA from chenodeoxycholic acid by reduction of the hydroxyl functional group at carbon-7 in the "B" ring of the steroid framework.

It has been implicated in human and experimental animal carcinogenesis. Preliminary in vitro research suggests that LCA selectively kills neuroblastoma cells, while sparing normal neuronal cells and is cytotoxic to numerous other malignant cell types at physiologically relevant concentrations.

Dietary fiber can bind to lithocholic acid and aid in its excretion in stool; as such, fiber can protect against colon cancer.

LCA (and LCA acetate and LCA propionate) can activate the vitamin D receptor without raising calcium levels as much as vitamin D itself.

References

Further reading

• Goldberg, AA; Richard, VR; Kyryakov, P; Bourque, SD; Beach, A; Burstein, MT; Glebov, A; Koupaki, O et al. (2010). "Chemical genetic screen identifies lithocholic acid as an anti-aging compound that extends yeast chronological life span in a TOR-independent manner, by modulating housekeeping longevity assurance processes". Aging 2 (7): 393–414. PMC 2933888. PMID 20622262. Citation uses old-style implicit et al. for authors

UpToDate Contents

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• 1. 胎児の酸塩基の生理学 fetal acid base physiology
• 2. Folic acid supplementation in pregnancy
• 3. ポルフィリン症：概要 porphyrias an overview
• 4. 疾患予防におけるビタミン補給 vitamin supplementation in disease prevention
• 5. 胃酸分泌の生理学 physiology of gastric acid secretion

English Journal

• Biochemical characterization of EphA2 antagonists with improved physico-chemical properties by cell-based assays and surface plasmon resonance analysis.

• Giorgio C1, Russo S1, Incerti M1, Bugatti A2, Vacondio F1, Barocelli E1, Mor M1, Pala D1, Hassan-Mohamed I1, Gioiello A3, Rusnati M2, Lodola A4, Tognolini M5.
• Biochemical pharmacology.Biochem Pharmacol.2015 Oct 10. pii: S0006-2952(15)00660-7. doi: 10.1016/j.bcp.2015.10.006. [Epub ahead of print]
• Amino acid conjugates of lithocholic acid (LCA) have been recently described as effective disruptors of the EphA2-ephrin-A1 interaction able to inhibit EphA2 phosphorylation in intact cells and thus able to block prometastatic responses such as cellular retraction and angiogenesis. However, these LC
• PMID 26462575

• Cellular Accumulation and Toxic Effects of Bile Acids in Cyclosporine A-Treated HepaRG Hepatocytes.

• Sharanek A1, Burban A2, Humbert L3, Bachour-El Azzi P2, Felix-Gomes N3, Rainteau D3, Guillouzo A1.
• Toxicological sciences : an official journal of the Society of Toxicology.Toxicol Sci.2015 Oct;147(2):573-87. doi: 10.1093/toxsci/kfv155. Epub 2015 Jul 20.
• Alteration of bile acid (BA) profiles and secretion by cholestatic drugs represents a major clinical issue. Species differences exist in BA composition, synthesis, and regulation; however presently, there is no in vitro reproducible cell model to perform studies on BAs in humans. We have evaluated
• PMID 26198044

• Impact of confinement on proteins concentrated in lithocholic acid based organic nanotubes.

• Lu Q1, Kim Y2, Bassim N3, Collins GE4.
• Journal of colloid and interface science.J Colloid Interface Sci.2015 Sep 15;454:97-104. doi: 10.1016/j.jcis.2015.05.004. Epub 2015 May 13.
• Organic nanotubes form in aqueous solution near physiological pH by self-assembly of lithocholic acid (LCA) with inner diameters of 20-40nm. The encapsulation of enhanced green fluorescent protein (eGFP) and resultant confinement effect for eGFP within these nanotubes is studied via confocal microsc
• PMID 26004574

Japanese Journal

• Gastrectomy Increases the Expression of Hepatic Cytochrome P450 3A by Increasing Lithocholic Acid-Producing Enteric Bacteria in Mice

• Ishii Makoto,Toda Takahiro,Ikarashi Nobutomo [他],Kusunoki Yoshiki,Kon Risako,Ochiai Wataru,Machida Yoshiaki,Sugiyama Kiyoshi
• Biological and Pharmaceutical Bulletin 37(2), 298-305, 2014
• … The levels of lithocholic acid (LCA)-producing bacteria (Bacteroides fragilis) and LCA in the colon did not show a significant increase up to 4 weeks after gastrectomy compared to the sham operation group. … The intraperitoneal administration of taurolithocholic acid (TLCA), a taurine conjugate of LCA, caused no change in the expression level of CYP3A11. …
• NAID 130003382122

• Hyperchromisity and Molecular Recognition of a Novel Modified β-Cyclodextrin Tethering with Phenylaminoazobenzene

• KUWABARA Tetsuo,SUGIYAMA Kosuke
• Analytical Sciences 29(9), 905-909, 2013
• … Among various guests, 1 was found to be highly sensitive to a steroidal guest having a C12 hydroxyl group in the framework, such as ursodeoxycholic acid and lithocholic acid in an acidic aqueous solution. …
• NAID 130004442224

• Burdock Fermented by Aspergillus awamori Elevates Cecal Bifidobacterium, and Reduces Fecal Deoxycholic Acid and Adipose Tissue Weight in Rats Fed a High-Fat Diet

• OKAZAKI Yukako,SITANGGANG Novita Vivi,SATO Satoko,OHNISHI Nanae,INOUE Junji,IGUCHI Takafumi,WATANABE Toshiro,TOMOTAKE Hiroyuki,HARADA Kazuki,KATO Norihisa
• Bioscience, Biotechnology, and Biochemistry 77(1), 53-57, 2013
• … Consumption of the burdock and fermented burdock diets significantly elevated fecal IgA and mucins (indices of intestinal immune and barrier functions) and reduced fecal lithocholic acid (a risk factor for colon cancer) (p<0.05). …
• NAID 130004137986

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★リンクテーブル★

リンク元	「LCA」「リトコール酸」
拡張検索	「taurolithocholic acid」

「LCA」

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• CD45 leukocyte common antigen
• left coronary artery
• 肝細胞腺腫 liver cell adenoma
• レーバー先天黒内障 Leber congenital amaurosis
• リトコール酸 lithocholic acid

「リトコール酸」

　　[★]

英

lithocholic acid LCA

同

3α-ヒドロキシ-5β-コラン-24-酸 3α-hydroxy-5β-cholan-24-oic acid

関

胆汁酸

「taurolithocholic acid」

　　[★]

タウロリソコール酸