石膽酸

石膽酸
	IUPAC名; (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
別名	3α-羥基-5β-膽烷-24-羧酸; LCA
識別
CAS號	434-13-9
PubChem	9903
ChemSpider	9519
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	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;
InChIKey	SMEROWZSTRWXGI-HVATVPOCBI
EINECS	207-099-1
ChEBI	16325
RTECS	FZ2275000
IUPHAR配體	611
性質
化學式	C24H40O3
莫耳質量	376.57 g·mol⁻¹
熔點	183—188 °C（361—370 °F；456—461 K）
危險性
安全術語	S：S22 S24/25
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

石膽酸（英語：Lithocholic acid，也被稱為3α-羥基-5β-膽烷-24-羧酸，3α-hydroxy-5β-cholan-24-oic acid，縮寫LCA）是一種膽汁酸，可作為溶解劑促進脂肪的吸收。結腸中的石膽酸主要來自鵝去氧膽酸，由腸道細菌的酶將其甾體骨架B環上的7α-羥基還原而來。

石膽酸已證明對實驗動物和人類具有致癌性^[2]。初步的 in vitro 實驗發現石膽酸可以選擇性的殺死成神經細胞瘤（英語：neuroblastoma）細胞，同時保留正常的神經元細胞，並且在生理相關濃度下對許多其他惡性細胞類型具有細胞毒性^[3]。

參考文獻

^ Lithocholic acid （頁面存檔備份，存於網際網路檔案館） at Sigma-Aldrich
^ Kozoni, V.; Tsioulias, G; Shiff, S; Rigas, B. The effect of lithocholic acid on proliferation and apoptosis during the early stages of colon carcinogenesis: Differential effect on apoptosis in the presence of a colon carcinogen. Carcinogenesis. 2000, 21 (5): 999–1005. PMID 10783324. doi:10.1093/carcin/21.5.999.
^ Goldberg, AA; Beach, A; Davies, GF; Harkness, TA; Leblanc, A; Titorenko, VI. Lithocholic bile acid selectively kills neuroblastoma cells, while sparing normal neuronal cells. Oncotarget. 2011, 2 (10): 761–82. PMC 3248158 . PMID 21992775. doi:10.18632/oncotarget.338.

延伸閱讀

Goldberg, AA; Richard, VR; Kyryakov, P; Bourque, SD; Beach, A; Burstein, MT; Glebov, A; Koupaki, O; et al. 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. 2010, 2 (7): 393–414. PMC 2933888 . PMID 20622262.

Template:Vitamin D receptor modulators

[1] Lithocholic acid （頁面存檔備份，存於網際網路檔案館） at Sigma-Aldrich

[Kozoni1999-2] Kozoni, V.; Tsioulias, G; Shiff, S; Rigas, B. The effect of lithocholic acid on proliferation and apoptosis during the early stages of colon carcinogenesis: Differential effect on apoptosis in the presence of a colon carcinogen. Carcinogenesis. 2000, 21 (5): 999–1005. PMID 10783324. doi:10.1093/carcin/21.5.999.

[3] Goldberg, AA; Beach, A; Davies, GF; Harkness, TA; Leblanc, A; Titorenko, VI. Lithocholic bile acid selectively kills neuroblastoma cells, while sparing normal neuronal cells. Oncotarget. 2011, 2 (10): 761–82. PMC 3248158 . PMID 21992775. doi:10.18632/oncotarget.338.

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