石胆酸
石胆酸[1]
|
|
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 Y
|
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(英語: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.
Template:Vitamin D receptor modulators
|
|