石胆酸
石胆酸[1] | |
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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 | |
别名 | 3α-羟基-5β-胆烷-24-羧酸 LCA |
识别 | |
CAS号 | 434-13-9 ![]() |
PubChem | 9903 |
ChemSpider | 9519 |
SMILES |
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InChI |
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InChIKey | SMEROWZSTRWXGI-HVATVPOCBI |
EINECS | 207-099-1 |
ChEBI | 16325 |
RTECS | FZ2275000 |
IUPHAR配体 | 611 |
性质 | |
化学式 | C24H40O3 |
摩尔质量 | 376.57 g·mol⁻¹ |
熔点 | 183—188 °C(361—370 °F;456—461 K) |
危险性 | |
安全术语 | S:S22 S24/25 |
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。 |
石胆酸(英语:Lithocholic acid,也被称为3α-羟基-5β-胆烷-24-羧酸,3α-hydroxy-5β-cholan-24-oic acid,缩写LCA)是一种胆汁酸,可作为溶解剂促进脂肪的吸收。结肠中的石胆酸主要来自鹅去氧胆酸,由肠道细菌的酶将其甾体骨架B环上的7α-羟基还原而来。
石胆酸已证明对实验动物和人类具有致癌性[2]。初步的 in vitro 实验发现石胆酸可以选择性的杀死成神经细胞瘤细胞,同时保留正常的神经元细胞,并且在生理相关浓度下对许多其他恶性细胞类型具有细胞毒性[3]。
参考文献
- ^ Lithocholic acid (页面存档备份,存于互联网档案馆) 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.
延伸阅读
- 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.