Isolithocholic Acid
(Synonyms: 异石胆酸,isoLCA) 目录号 : GC47466Isolithocholic acid是石胆酸的异构体。异石胆酸是一种胆汁酸，由石胆酸或石胆酸3α-硫酸盐的微生物代谢形成 。
Cas No.:1534-35-6
Sample solution is provided at 25 µL, 10mM.
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Isolithocholic acid is an isomer of lithocholic acid. Isolithocholic acid is a bile acid formed through microbial metabolism of lithocholic acid or its 3α-sulfate [1]. Isolithocholic acid can be used to regulate lipid metabolism and cholesterol homeostasis [2-3].
In vitro, Isolithocholic acid (0.625, 1.25, 2.5, 5, 10, 20 and 40μM; 18h) can dose-dependently inhibit the differentiation of initial CD4+ T cells into TH17 cells, and has no significant effect on cell viability or total cell number [4]. The treatment with isolithocholic acid (0.03mM, 0.15mM; 24h) significantly reduced the viability of Clostridium difficile, and at lower inhibitory concentrations, it also decreased the expression of the toxin (tcdA) [5].
In vivo, Isolithocholic acid (50mg/kg/day; 8 weeks) orally administered to a mouse model induced by high-fat diet for Nonalcoholic Steatohepatitis (NASH) reduces the levels of ALT, AST, TC and TG in mouse serum, alleviates the increase of inflammatory cells, lipid droplets and fibrosis. At the same time, the expression levels of IL-17 A, Act 1, TRAF 6, ERK, JUN, FOSB, IL-6, TNF-α, S100 A9, IL-23 R, RORγt, MMP-1, PPARγ and FABP 1 are decreased, while the expression levels of IL-2 R and Foxp 3 are increased [6]. B6Tac mice with a filamentous bacterial (SFB) host fed a powdered diet containing Isolithocholic acid (0.3% w/w; 4 days) have a reduced level of existing TH17 cells in the intestinal lamina propria of mice [7].
References:
[1] Batta, A.K., Salen, G., and Shefer, S.Transformation of bile acids into iso-bile acids by Clostridium perfringes: Possible transport of 3β-hydrogen via the coenzymeHepatology5(6)1126-1131(1985)
[2] Lu Y, Du J, Peng S, et al. Therapeutic potential of isoallolithocholic acid in methicillin-resistant Staphylococcus Aureus peritoneal infection[J]. The Journal of Antibiotics, 2025, 78(3): 166-180.
[3] Jiang J, Zhang H, Hussain M, et al. Novel Approaches in Glucose and Lipid Metabolism Disorder Therapy: Targeting the Gut Microbiota–Bile Acid Axis[J]. Biology, 2025, 14(7): 802.
[4] Hindson J. Bile acid metabolites produced by gut bacteria suppress TH17 cells[J]. Nature Reviews Gastroenterology & Hepatology, 2022, 19(5): 280-280.
[5] Kisthardt S C, Thanissery R, Pike C M, et al. The microbial-derived bile acid lithocholate and its epimers inhibit Clostridioides difficile growth and pathogenicity while sparing members of the gut microbiota[J]. Journal of Bacteriology, 2023, 205(9): e00180-23.
[6] Wang Y, Chen X, Huws S A, et al. Ileal microbial microbiome and its secondary bile acids modulate susceptibility to nonalcoholic steatohepatitis in dairy goats[J]. Microbiome, 2024, 12(1): 247. [7] Paik D, Yao L, Zhang Y, et al. Human gut bacteria produce ΤΗ17-modulating bile acid metabolites[J]. Nature, 2022, 603(7903): 907-912.
Isolithocholic acid是石胆酸的异构体。异石胆酸是一种胆汁酸，由石胆酸或石胆酸3α-硫酸盐的微生物代谢形成 [1]。Isolithocholic acid可用于调节脂质代谢 、 胆固醇稳态 [2-3]。
在体外，Isolithocholic acid（0.625, 1.25, 2.5, 5,10, 20 and 40μM; 18h）能够剂量依赖性地抑制初始CD4+ T细胞向TH17细胞的分化作用，且对细胞活力或总细胞数量没有显著影响 [4]。Isolithocholic acid（0.03mM, 0.15mM; 24h）处理显著降低了艰难梭菌的活力，并且在亚抑制浓度下，降低了毒素（tcdA）的表达 [5]。
在体内， Isolithocholic acid（50mg/kg/day; 8周）口服治疗高脂肪饮食诱导非酒精性脂肪性肝炎（NASH）的小鼠模型，降低了小鼠血清中ALT、AST、TC和TG水平，缓解了炎性细胞、脂滴和纤维化的增加。同时，检测到IL-17 A、Act 1、TRAF 6、ERK、JUN、FOSB、IL-6、TNF-α、S100 A9、IL-23 R、RORγt、MMP-1、PPARγ和FABP 1的表达水平降低，而IL-2 R和Foxp 3的表达水平升高 [6]。富含丝状细菌（SFB）宿主的B6Tac小鼠喂食含Isolithocholic acid（0.3% w/w; 4天）的粉状饲料，小鼠回肠固有层中已存在的TH17细胞水平降低 [7]。
| Cell experiment [1]: | |
Cell lines | Clostridium difficile |
Preparation Method | Overnight Clostridium difficile cultures were back diluted 1:10 into pre-reduced BHI plus 100mg/L L-cysteine broth and allowed to grow until OD600 reached mid log (0.45–0.50). The cells were challenged with or without bile acids (Isolithocholic acid) or DMSO (solvent). All tubes were incubated anaerobically at 37°C for 24h. At intervals of 0, 2, 4, and 24h, aliquots were removed and serially diluted. Unheated samples were plated on either BHI agar containing 100mg/L L-cysteine to enumerate only vegetative cells or on brain heart infusion agar with taurocholate (TBHI) agar (BHI containing 100mg/L L-cysteine and 0.1% taurocholate) to enumerate total vegetative cells and spores. After heat treatment (65°C for 20min), samples were plated on TBHI to enumerate total spores. Colonies were counted the next day to determine colony-forming units per milliliters (CFU/mL). Experiments were performed with three biological replicates. |
Reaction Conditions | 0.03mM, 0.15mM; 0, 2, 4 and 24h |
Applications | Isolithocholic acid could reduce the activity of Clostridium difficile in a time-dependent manner, and at sub-inhibitory concentrations, it also reduced the expression of the toxin (tcdA). |
| Animal experiment [2]: | |
Animal models | C57BL/6J mice |
Preparation Method | After the Nonalcoholic Steatohepatitis (NASH) model was successfully established, the mice were randomly divided into two groups: the NASH group, the Isolithocholic acid group. Isolithocholic acid group were administered orally at a dose of 200μL 50mg/kg per day for 8 weeks. After oral administration of BA on the last day of the 8th week, the mice were fasted for 24h and weighed. Blood samples were collected for ALT, AST, TC and TG assays. Liver tissues were collected for histopathological analysis (the methods for H&E staining, Oil red O staining and Sirius red staining were the same as those used for goat examination) and flow cytometry. |
Dosage form | 50mg/kg/day for 8 weeks; p.o. |
Applications | Isolithocholic acid reduced the levels of ALT, AST, TC and TG in the mouse serum, alleviated the increase in inflammatory cells, lipid droplets and fibrosis. At the same time, the expression levels of IL-17A, Act 1, TRAF 6, ERK, JUN, FOSB, IL-6, TNF-α, S100 A9, IL-23 R, RORγt, MMP-1, PPARγ and FABP 1 were decreased, while the expression levels of IL-2R and Foxp 3 were increased. |
References: | |
| Cas No. | 1534-35-6 | SDF | |
| 别名 | 异石胆酸,isoLCA | ||
| 化学名 | (3β,5β)-3-hydroxy-cholan-24-oic acid | ||
| Canonical SMILES | C[C@H](CCC(O)=O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@@]21C | ||
| 分子式 | C24H40O3 | 分子量 | 376.6 |
| 溶解度 | DMSO : 28.57 mg/mL (75.87 mM; Need ultrasonic) | 储存条件 | Store at -20°C |
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| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.6553 mL | 13.2767 mL | 26.5534 mL |
| 5 mM | 0.5311 mL | 2.6553 mL | 5.3107 mL |
| 10 mM | 0.2655 mL | 1.3277 mL | 2.6553 mL |
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动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
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| % DMSO % % Tween 80 % saline | ||||||||||
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2.
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