Lupeol acetate
(Synonyms: 乙酸羽扇醇酯) 目录号 : GC60231
Lupeolacetate是Lupeol的衍生物，通过下调TNF-α、IL-1β、MCP-1、COX-2、VEGF和granzymeB来抑制类风湿关节炎的进展。
Cas No.:1617-68-1
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
Lupeol acetate, a derivative of Lupeol, suppresses the progression of rheumatoid arthritis (RA) by inhibiting the activation of macrophages and osteoclastogenesis through downregulations of TNF-α, IL-1β, MCP-1, COX-2, VEGF and granzyme B[1].
[1]. Wang WH, et al. Lupeol acetate ameliorates collagen-induced arthritis and osteoclastogenesis of mice through improvement of microenvironment. Biomed Pharmacother. 2016;79:231-240.
| Cas No. | 1617-68-1 | SDF | |
| 别名 | 乙酸羽扇醇酯 | ||
| Canonical SMILES | C[C@@]([C@@]1(CC[C@@]2([H])C3(C)C)C)(CC4)[C@@](CC[C@]1([H])[C@]2(CC[C@@H]3OC(C)=O)C)([H])[C@]([C@@H]5C(C)=C)([H])[C@@]4(CC5)C | ||
| 分子式 | C32H52O2 | 分子量 | 468.75 |
| 溶解度 | Ethanol : ≥ 2 mg/mL (4.27 mM) | 储存条件 | |
| 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 | 2.1333 mL | 10.6667 mL | 21.3333 mL |
| 5 mM | 0.4267 mL | 2.1333 mL | 4.2667 mL |
| 10 mM | 0.2133 mL | 1.0667 mL | 2.1333 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。
Lupeol acetate isolated from Chrysophyllum cainito L. fruit as a template for the synthesis of N-alkyl-arylsulfonamide derivatives and their synergistic effects with metronidazole against Trichomonas vaginalis
Nat Prod Res 2022 Nov;36(21):5508-5516.PMID:34930096DOI:10.1080/14786419.2021.2018429.
Pentacyclic triterpenes are found in a great variety of natural products and constitute an organic template for the development of new derivative compounds with therapeutic applications. In the present work, Lupeol acetate isolated from Chrysophyllum cainito L. fruit was used as a template for the synthesis of novel N-alkyl-arylsulfonamide derivatives, and their synergistic effects with metronidazole against strains of Trichomonas vaginalis were tested. A library of 18 derivatives was synthesized. Ten compounds exhibited an IC50 < 100 μM against a metronidazole-sensitive strain of T. vaginalis. Only seven of these compounds (12, 15, 18-22) also showed activity against metronidazole-resistant strains. The compounds 20 (N-cyclohexyl-p-chlorobenzenesulfonamidolupeol acetate) and 22 (N-cyclohexyl-p-nitrobenzenesulfonamidolupeol acetate) exhibited a similar IC50 against both susceptible and resistant T. vaginalis strains and enhanced the efficacy of metronidazole in a partial and total synergistic way, respectively. These data provided evidence of the trichomonicidal effect of N-alkyl-arylsulfonamide derivatives of Lupeol acetate, representing highly promising novel antiparasitic agents.
Isolation of Lupeol acetate from fruit peels of Artocarpus camansi
J Adv Pharm Technol Res 2020 Jul-Sep;11(3):148-156.PMID:33102199DOI:10.4103/japtr.JAPTR_6_20.
The purpose of this research is to find a Lupeol acetate from Artocarpus camansi fruit peel. Ethyl acetate extract of A. camansi fruit peel was obtained by maceration process. After the process of fractionation, it results 3 subfractions (A, B, and C). The subfraction B was rechromatographed and yielded B22 pure isolate. Based on data from proton nuclear magnetic resonance, Fourier transform-infrared, and mass spectrometry (MS from gas chromatography-MS), the B22 isolate was suspected as Lupeol acetate compound (in this study, the presence of Lupeol acetate in the A. camansi fruit peel has been reported for the first time).
Lupeol acetate as a potent antifungal compound against opportunistic human and phytopathogenic mold Macrophomina phaseolina
Sci Rep 2021 Apr 19;11(1):8417.PMID:33875698DOI:10.1038/s41598-021-87725-7.
Antifungal activity of Monotheca buxifolia methanolic extract and its various fractions were assessed against Macrophomina phaseolina, a soil-borne fungal pathogen of more than 500 vegetal species as well as rare and emerging opportunistic human pathogen. Different concentrations of methanolic extract (3.125 to 200 mg mL-1) inhibited fungal biomass by 39-45%. Isolated n-hexane, chloroform and ethyl acetate fractions suppressed fungal biomass by 32-52%, 29-50% and 29-35%, respectively. Triterpenes lupeol and Lupeol acetate (1, 2) were isolated from n-hexane while betulin, β-sitosterol, β-amyrin, oleanolic acid (3-6) were isolated from chloroform fraction. Vanillic acid, protocatechuic acid, kaempferol and quercetin (7-10) were isolated from the ethyl acetate fraction and identified using various spectroscopic techniques namely mass spectroscopy and NMR. Antifungal activity of different concentrations (0.0312 to 2 mg mL-1) of the isolated compounds was evaluated and compared with the activity of a broad spectrum fungicide mancozeb. Different concentrations of mencozeb reduced fungal biomass by 83-85%. Among the isolated compounds Lupeol acetate (2) was found the highest antifungal against M. phaseolina followed by betulin (3), vanillic acid (7), protocatechuic acid (8), β-amyrin (5) and oleanolic acid (6) resulting in 79-81%, 77-79%, 74-79%, 67-72%, 68-71% and 68-71%, respectively. Rest of the compounds also showed considerable antifungal activity and reduced M. phaseolina biomass by 41-64%.
Lupeol acetate ameliorates collagen-induced arthritis and osteoclastogenesis of mice through improvement of microenvironment
Biomed Pharmacother 2016 Apr;79:231-40.PMID:27044833DOI:10.1016/j.biopha.2016.02.010.
Lupeol has been shown with anti-inflammation and antitumor capability, however, the poor bioavailability limiting its applications in living subjects. Lupeol acetate (LA), a derivative of lupeol, shows similar biological activities as lupeol but with better bioavailability. Here RAW 264.7 cells and bone marrow-derived macrophages (BMDMs) stimulated by lipopolysaccharide (LPS) were treated with 0-80μM of LA, and assayed for TNF-α, IL-1β, COX-2, MCP-1 using Western blotting. Moreover, osteoclatogenesis was examined with reverse transcription PCR (RT-PCR) and tartrate-resistant acid phosphatase (TRAP) staining. For in vivo study, collagen-induced arthritis (CIA)-bearing DBA/1J mice were randomly separated into three groups: vehicle, LA-treated (50mg/kg) and curcumin-treated (100mg/kg). Therapeutic efficacies were assayed by the clinical score, expression levels of serum cytokines including TNF-α and IL-1β, (18)F-fluorodeoxyglucose ((18)F-FDG) microPET/CT and histopathology. The results showed that LA could inhibit the activation, migration, and formation of osteoclastogenesis of macrophages in a dose-dependent manner. In RA-bearing mice, the expressions of inflammation-related cytokines were suppressed, and clinical symptoms and bone erosion were ameliorated by LA. The accumulation of (18)F-FDG in the joints of RA-bearing mice was also significantly decreased by LA. The results indicate that LA significantly improves the symptoms of RA by down-regulating expressions of inflammatory cytokines and osteoclastogenesis.
Balanophora spicata and Lupeol acetate Possess Antinociceptive and Anti-Inflammatory Activities In Vivo and In Vitro
Evid Based Complement Alternat Med 2012;2012:371273.PMID:23243439DOI:10.1155/2012/371273.
Aims of the present study were to investigate effects of Balanophora spicata (BS) on antinociception and anti-inflammation both in vivo and in vitro. Crude extract of BS inhibited vascular permeability induced by histamine, serotonin, bradykinin, and PGE(2), but not by PAF. Furthermore, BS crude extract, different layers (n-hexane, ethyl acetate, n-butanol, and water layer), and Lupeol acetate had significant antinociceptive and anti-inflammatory effects on acetic acid-induced abdominal writhing response, formalin-induced licking behavior, carrageenan-, and serotonin-induced paw edema. The n-hexane layer had the most effective potency among all layers (IC50: 67.33 mg/kg on writhing response; IC50s: 34.2 mg/kg and 21.29 mg/kg on the early phase and late phase of formalin test, resp.). Additionally, Lupeol acetate which was isolated from the n-hexane layer of BS effectively inhibited the acetic acid-induced writhing response (IC50: 28.32 mg/kg), formalin-induced licking behavior (IC50: 20.95 mg/kg), NO production (IC50: 4.102 μM), iNOS expression (IC50: 5.35 μM), and COX2 expression (IC50: 5.13 μM) in LPS-stimulated RAW 264.7 cells. In conclusion, BS has antinociceptive and anti-inflammatory effects which may be partially due to the inhibition of changes in vascular permeability induced by histamine, serotonin, bradykinin, and PGE(2) and the attenuation of iNOS and COX-2 expression.