Limonin
(Synonyms: 柠檬苦素; Limonoic acid 3,19) 目录号 : GC16589
柠檬苦素是一种天然的四环三萜类化合物，广泛存在于桉树、黄柏和黄连中。
Cas No.:1180-71-8
Sample solution is provided at 25 µL, 10mM.
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Limonin is a natural tetracyclic triterpenoid compound, which widely exists in Euodia rutaecarpa (Juss.) Benth., Phellodendron chinense Schneid., and Coptis chinensis Franch [1]. Limonin has pharmacological effects in anti-tumor, anti-inflammatory and analgesic, anti-bacterial and anti-virus, anti-oxidation, nerve protection, liver protection, and blood lipid regulation. Modern pharmacological effects indicate that limonin has value in the prevention and treatment of certain diseases, including cancer, enteritis, hepatitis, hemorrhoids, osteoporosis, obesity, anaphylactic reaction, and brain aging [2].
Limonin has an anti-hepatocarcinoma effect. In vitro, limonin inhibited the growth of hepatocellular carcinoma cell line (SMMC-7721) cells (IC50 = 24.42 μg/mL) in a concentration and time-dependent manner [3]. Limonin has certain cytotoxicity to human colon cancer (Caco-2) cells [4]. Limonin has a good antiproliferative effect on lung cancer cells A549 (IC50 = 82.5 uM) [5].
In vivo, limonin (200 mg/kg) diets inhibited cell proliferation and promoted apoptosis through suppressing the levels of both inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in azoxymethane (AOM)-injected rats, therefore, it was considered that limonin has the effect of inhibiting colon cancer [6]. Limonin (50 mg/kg) has excellent antioxidant and therapeutic effects on N-nitroethylenediamine (DEN)-induced hepatocarcinoma rats by suppressing lipid peroxidation (LPO) and oxidative stress-mediated free radicals generation, and through modulating antioxidants` defense mechanism [7]. Limonin significantly decreased the levels of tumor necrosis factor-α (TNF-α), interleukin (IL-1β and IL-6), and inhibited the expression of inflammatory factors in lipopolysaccharide (LPS)-induced acute lung injury mice [8].
References:
[1].Fan S, Zhang C, Luo T, et al. Limonin: A review of its pharmacology, toxicity, and pharmacokinetics[J]. Molecules, 2019, 24(20): 3679.
[2].Gualdani R, Cavalluzzi M M, Lentini G, et al. The chemistry and pharmacology of citrus limonoids[J]. Molecules, 2016, 21(11): 1530.
[3].Zhang J J, Luo G, He R L, et al. Inhibiting effects of limonin on human hepatocarcinoma cells SMMC-7721 in vitro[J]. Sichuan J. Physiolog. Sci, 2007, 29: 157-160.
[4].Qian P, Jin H W, Yang X W. New limonoids from Coptidis Rhizoma–Euodiae Fructus couple[J]. Journal of Asian natural products research, 2014, 16(4): 333-344.
[5].Bai Y, Jin X, Jia X, et al. Two new apotirucallane-type isomeric triterpenoids from the root bark of Dictamnus dasycarpus with their anti-proliferative activity[J]. Phytochemistry Letters, 2014, 10: 118-122.
[6].Vanamala J, Leonardi T, Patil B S, et al. Suppression of colon carcinogenesis by bioactive compounds in grapefruit[J]. Carcinogenesis, 2006, 27(6): 1257-1265.
[7].Langeswaran K, Kumar S G, Perumal S, et al. Limonin–A citrus limonoid, establish anticancer potential by stabilizing lipid peroxidation and antioxidant status against N-nitrosodiethylamine induced experimental hepatocellular carcinoma[J]. Biomedicine & Preventive Nutrition, 2013, 3(2): 165-171.
[8].WANG D, ZHANG H, FANG J, et al. Effects of limoninon on LPS-induced acute lung injury in mice[J]. Chinese Journal of Clinical Pharmacology and Therapeutics, 2018, 23(1): 8.
柠檬苦素是一种天然的四环三萜类化合物,广泛存在于桉树、黄柏和黄连[1]中。柠檬苦素具有抗肿瘤、抗炎镇痛、抗菌抗病毒、抗氧化、保护神经、保肝、调节血脂等药理作用。现代药理作用表明柠檬苦素对某些疾病具有防治价值,包括癌症、肠炎、肝炎、痔疮、骨质疏松、肥胖、过敏反应、脑老化等[2]。\n
柠檬苦素具有抗肝癌作用。在体外,柠檬苦素以浓度和时间依赖性方式抑制肝细胞癌细胞系 (SMMC-7721) 细胞的生长 (IC50 = 24.42 μg/mL) [3]。柠檬苦素对人结肠癌（Caco-2）细胞具有一定的细胞毒性[4]。柠檬苦素对肺癌细胞A549具有良好的抗增殖作用(IC50 = 82.5 uM)[5]。
在体内,柠檬苦素 (200 mg/kg) 饮食通过抑制偶氮甲烷 (AOM) 注射大鼠中诱导型一氧化氮合酶 (iNOS) 和环氧合酶 2 (COX-2) 的水平来抑制细胞增殖并促进细胞凋亡,因此,人们认为柠檬苦素具有抑制结肠癌的作用[6]。柠檬苦素 (50 mg/kg) 通过抑制脂质过氧化 (LPO) 和氧化应激介导的自由基生成,并通过调节抗氧化剂的防御机制,对 N-硝基乙二胺 (DEN) 诱导的肝癌大鼠具有出色的抗氧化和治疗作用 [7].柠檬苦素显着降低脂多糖（LPS）诱导的急性肺损伤小鼠肿瘤坏死因子-α（TNF-α）、白细胞介素（IL-1β和IL-6）的水平,并抑制炎症因子的表达[ 8].
| Cell experiment [1]: | |
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Cell lines |
Colon cancer (SW480) and fibroblast (112CoN) cells |
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Preparation Method |
Cells were treated with different concentrations (6.25, 12.5,25,50 and 100 µM) of limonin, LG, and camptothecin after incubation for 24, 48, and 72 h; 50 µL of supernatant medium was removed without disturbing the cells, mixed with an equal volume of LDH reagent, and incubated for 30 min in the dark at ambient temperature. |
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Reaction Conditions |
6.25, 12.5,25,50 and 100 µM for 24, 48, and 72 h |
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Applications |
Maximum release of LDH into the medium was observed after 48 h of incubation with limonoids. |
| Animal experiment [2]: | |
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Animal models |
Male Wistar rats |
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Preparation Method |
Animals were randomly divided into three experimental groups (each containing eight animals): sham, ischemia/reperfusion (I/R) injury, limonin (100 mg/kg). Sham group received vehicle then anesthetized, the portal vein and bile duct exposed but not occluded. Rats of I/R group were anesthetized by i.p injection of ketamine (75 mg/kg) and subjected to partial liver ischemia (70%) followed by reperfusion. Ischemia was induced by occluding hepatic portal vein and bile duct with a traumatic vascular clamp. After 45 min of ischemia, the clamp was removed to start reperfusion for 1 h. Limonin dissolved in dimethyl sulfoxide (DMSO) then given i.p as single dose 30 min before ischemia. Blood was collected from the retro-orbital plexus and centrifuged (3000×g, 4 °C, 20 min) for separation of serum. |
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Dosage form |
15 or 30 mg/kg, Miniature osmotic infusion pump |
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Applications |
Rats subjected to I/R showed a marked increase in inflammatory cytokines (TNF-α) by 347.4%, and marked decrease in anti-inflammatory mediators (IL-10) in liver tissue by 54.5% as compared to sham group. Limonin treatment significantly reduced liver TNF-α by 43.8%, and increased liver IL-10 by 154.9% as compared to I/R group. |
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References: [1]: Chidambara Murthy K N, Jayaprakasha G K, Kumar V, et al. Citrus limonin and its glucoside inhibit colon adenocarcinoma cell proliferation through apoptosis[J]. Journal of agricultural and food chemistry, 2011, 59(6): 2314-2323. |
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| Cas No. | 1180-71-8 | SDF | |
| 别名 | 柠檬苦素; Limonoic acid 3,19 | ||
| 化学名 | 12-(furan-3-yl)-6,6,8a,12a-tetramethyldecahydrooxireno[2,3-d]pyrano[4',3':3,3a]isobenzofuro[5,4-f]isochromene-3,8,10(1H,6H,8aH)-trione | ||
| Canonical SMILES | CC1(C2CC(=O)C3(C(C24COC(=O)CC4O1)CCC5(C36C(O6)C(=O)OC5C7=COC=C7)C)C)C | ||
| 分子式 | C26H30O8 | 分子量 | 470.51 |
| 溶解度 | ≥ 23.9 mg/mL 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 | 2.1254 mL | 10.6268 mL | 21.2535 mL |
| 5 mM | 0.4251 mL | 2.1254 mL | 4.2507 mL |
| 10 mM | 0.2125 mL | 1.0627 mL | 2.1254 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。
Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet