Alisol F
(Synonyms: 泽泻醇 F) 目录号 : GC30371
A triterpene with anti-inflammatory and hepatoprotective activities
Cas No.:155521-45-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Alisol F is a triterpene that has been found in A. orientale and has anti-inflammatory and hepatoprotective activities.1,2 It reduces levels of inducible nitric oxide synthase (iNOS) and COX-2 and the production of TNF-α, IL-6,and IL-1β in LPS-stimulated RAW 264.7 cells.1 Alisol F (20 mg/kg) reduces plasma alanine transaminase (ALT) and aspartate aminotransferase (AST) levels, hepatic fibrosis, and hepatic levels of phosphorylated ERK in a mouse model of LPS/D-galactosamine-induced acute liver injury.1,2
1.Bi, X., Wang, P., Ma, Q., et al.Anti-inflammatory activities and liver protection of alisol F and 25-anhydroalisol F through the inhibition of MAPK, STAT3, and NF-κB activation in vitro and in vivoMolecules22(6)951(2017) 2.Choi, E., Jang, E., and Lee, J.-H.Pharmacological activities of Alisma orientale against nonalcoholic fatty liver disease and metabolic syndrome: Literature reviewEvid. Based Complement. Alternat. Med.2943162(2019)
| Cas No. | 155521-45-2 | SDF | |
| 别名 | 泽泻醇 F | ||
| Canonical SMILES | C[C@]1(C(C[C@@H]2O)=C([C@@H]3C)[C@](O[C@@]([C@@H](O)C(C)(O)C)([H])C3)([H])C1)[C@]([C@]2([H])[C@]4(CCC5=O)C)(CC[C@@]4([H])C5(C)C)C | ||
| 分子式 | C30H48O5 | 分子量 | 488.7 |
| 溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.0462 mL | 10.2312 mL | 20.4625 mL |
| 5 mM | 0.4092 mL | 2.0462 mL | 4.0925 mL |
| 10 mM | 0.2046 mL | 1.0231 mL | 2.0462 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Anti-Inflammatory Activities and Liver Protection of Alisol F and 25-Anhydroalisol F through the Inhibition of MAPK, STAT3, and NF-κB Activation In Vitro and In Vivo
Alisol F and 25-anhydroalisol F isolated from Alisma orientale, were proved to exhibit anti-inflammatory potential in our previous work. In the current study, the anti-inflammatory effects and action mechanisms of alisol F and 25-anhydroalisol F were investigated in vitro. Moreover, the pharmacological effects of alisol F in lipopolysaccharide (LPS)/d-galactosamine (d-gal)-induced acute liver-injured mice were evaluated. The results demonstrated that alisol F and 25-anhydroalisol F could suppress LPS-induced production of nitric oxide (NO), interleukin-6 (IL-6), tumor necrosis factor alpha (TNF-α), and interleukin-1β (IL-1β), as well as inhibit the mRNA and protein levels of inducible nitric oxide (iNOS) and cyclooxygenase-2 (COX-2). In addition, we investigated the role of alisol F and 25-anhydroalisol F in mediating mitogen-activated protein kinases (MAPKs), signal transducers, and activators of transcription 3 (STAT3) and nuclear factor κB (NF-κB) pathways involved in the inflammation process of LPS-stimulated RAW 264.7 cells. The phosphorylation of ERK, JNK, p38, and STAT3, and the NF-κB signaling pathway, were obviously suppressed in alisol F and 25-anhydroalisol F treated cells. Results obtained from in vitro experiments suggested alisol F obviously improved liver pathological injury by inhibiting the production of TNF-α, IL-1β, and IL-6, and significantly decreasing the serum alanine aminotransferase (ALT) and aspartate aminotransferase (AST) levels in LPS/d-gal-induced mice. Furthermore, the reduction of phosphorylation of ERK and JNK, as well as suppression of the NF-κB signaling pathway, were also observed in liver tissues of the alisol F-treated mice model. Alisol F and 25-anhydroalisol F may serve as potential leads for development of anti-inflammatory agents for acute liver failure treatment.
Alisol F 24 Acetate Enhances Chemosensitivity and Apoptosis of MCF-7/DOX Cells by Inhibiting P-Glycoprotein-Mediated Drug Efflux
Multidrug resistance (MDR) is a prime reason for numerous failed oncotherapy approaches. In the present study, we investigated whether Alisol F 24 acetate (ALI) could reverse the MDR of MCF-7/DOX cells, a multidrug-resistant human breast cancer cell line. We found that ALI was a potent P-glycoprotein (P-gp) inhibitor, in the Caco-2-monolayer cell model. ALI showed a significant and concentration-dependent cytotoxic effect on MCF-7/DOX cells in combination with doxorubicin by increasing intracellular accumulation and inducing nuclear migration of doxorubicin. However, ALI had no such effect on MCF-7 cells. In addition, ALI also promoted doxorubicin-induced early apoptosis of MCF-7/DOX cells in a time-dependent manner. These results suggest that ALI can enhance chemosensitivity of doxorubicin and reinforce its anti-cancer effect by increasing its uptake, especially inducing its nuclear accumulation in MCF-7/DOX cells. Therefore, ALI could be developed as a potential MDR-reversing agent in cancer chemotherapy in further study.
Structures and biological activities of the triterpenoids and sesquiterpenoids from Alisma orientale
Sixteen triterpenoids and nine sesquiterpenoids were isolated from the rhizome of Alisma orientale. Structures of 16-oxo-11-anhydroalisol A 24-acetate, 13β,17β-epoxy-24,25,26,27-tetranor-alisol A 23-oic acid, 1αH,5αH-guaia-6-ene-4β,10β-diol, and alisguaiaone were elucidated by comprehensive spectroscopic data analysis. The cytotoxic, antibacterial, antifungal, anti-inflammatory, and α-glucosidase inhibitory activities of isolated terpenoids were evaluated. Triterpenoids alisol A, alisol A 24-acetate, 25-O-ethylalisol A, 11-deoxyalisol A, alisol E 24-acetate, alisol G, alisol B 23-acetate and sesquiterpenoids 1αH,5αH-guaia-6-ene-4β,10β-diol, 10-hydroxy-7,10-epoxysalvialane exhibited cytotoxicities against the three tested human cancer cell lines with IC50 values ranging from 11.5 ± 1.7 μM to 76.7 ± 1.4 μM. Triterpenoids alisol A, 25-O-ethylalisol A, 11-deoxyalisol A, alisol E 24-acetate, alisol G, and 25-anhydroalisol F showed antibacterial activities against the Gram-positive strains Bacillus subtilis and Staphylococcus aureus with MIC values of 12.5-100 μg/mL. Sesquiterpenoid 4β,10β-dihydroxy-1αH,5βH-guaia-6-ene exhibited antibacterial activity against B. subtilis with an MIC value of 50 μg/mL, and 10-hydroxy-7,10-epoxysalvialane exhibited activity against S. aureus with an MIC value of 100 μg/mL. Compounds 16-oxo-11-anhydroalisol A 24-acetate, alisol F, 25-anhydroalisol F, and alisguaiaone exhibited inhibitory effects on lipopolysaccharide-induced NO production in RAW 264.7 macrophage cells. None of the compounds showed obvious inhibitory activity against α-glucosidase.
Pharmacological Activities of Alisma orientale against Nonalcoholic Fatty Liver Disease and Metabolic Syndrome: Literature Review
Nonalcoholic fatty liver disease (NAFLD) is a rapidly emerging hepatic manifestation of metabolic syndrome. However, its unrevealed mechanism and complicated comorbidities have led to no specific medication, except for weight loss and lifestyle modification. Alisma orientale (Sam.) Juzep (A. orientale, Alismataceae) has been increasingly reported on therapeutic effects of A. orientale against NAFLD and metabolic syndrome such as insulin resistance, hyperlipidemia, and obesity. Therefore, this study aimed to review the preclinical efficacy of A. orientale and its chemical constituents including Alisol A 24-acetate, Alisol B 23-acetate, Alisol F, and Alismol against NAFLD and metabolic syndrome. A. orientale prevented hepatic triglyceride accumulation through suppressing de novo lipogenesis and increasing lipid export. In addition, it controlled oxidative stress markers, lipoapoptosis, liver injury panels, and inflammatory and fibrotic mediators, eventually influencing steatohepatitis and liver fibrosis. Moreover, it exhibited pharmacological activities against hyperlipidemia, obesity, and hyperglycemia as well as appetite. These biological actions of A. orientale might contribute to adiponectin activation or a role as a farnesoid X receptor agonist. In particular, Alisol A 24-acetate and Alisol B 23-acetate could be expected as main compounds. Taken together, A. orientale might be an effective candidate agent for the treatment of NAFLD and its comorbidities, although further assessment of its standardization, safety test, and clinical trials is consistently required.
Hypolipidemic effect of Alisma orientale (Sam.) Juzep on gut microecology and liver transcriptome in diabetic rats
Alisma orientale (Sam.) Juzep (A. orientale) is a traditional herb that is often used to treat disease including edema and hyperlipidemia. However, the molecular mechanism by which Alisma orientale (Sam.) Juzep exerts its hypolipidemic effects remains unclear. In this study, a diabetic rat model was established by feeding a high-fat and high-sugar diet combined with a low-dose streptozotocin injection (HFS). Then the rats were treated with an A. orientale water extract (AOW), an A. orientale ethanolic extract (AOE) or metform (MET). The gut microflora and liver transcriptome were analyzed by high-throughput next-generation sequencing. Ultra-performance liquid chromatography-triple quadrupole-mass spectrometry was employed to analyze the major compounds in the AOE. The results showed that the serum total cholesterol (TC) and low density lipoprotein cholesterol (LDL-C) levels in rats of the AOE group (2.10 g/kg/day, 14 days) were significantly lower than those in the HFS group (p<0.01). Moreover, AOE treatment altered the gut microecology, particularly modulating the relative abundance of gut microflora involved in lipid metabolism compared with the HFS group. Furthermore, compared with the HFS group, the mRNA expression levels of Fam13a, Mapk7, Mpp7, Chac1, Insig1, Mcpt10, Noct, Greb1l, Fabp12 and Hba-a3 were upregulated after the administration of AOE. In contrast, the mRNA expression levels of Lox, Mybl1, Arrdc3, Cyp4a2, Krt20, Vxn, Ggt1, Nr1d1 and S100a9 were downregulated. Moreover, AOE treatment for two weeks markedly promoted the relative abundance of Lachnospiraceae (p = 0.0013). The triterpenoids contents in AOE were alisol A, alisol A 24-acetate, alisol B, alisol B 23-acetate, alisol C 23-acetate, alisol F, alisol F 24-acetate, and alisol G. Our findings above illustrated that the hypolipidemic effect of the triterpenoids of A. orientale is mediated mainly through alteration of the gut microecology and the regulation of genes involved in cholesterol metabolism, especially Insig1.