γ-Linolenic Acid
(Synonyms: γ-亚麻酸 ;Gamma-Linolenic acid) 目录号 : GC10283
γ-Linolenic Acid是一种来源于琉璃苣油的口服ω-6多不饱和脂肪酸，可作为β-分泌酶（BACE1）的特异性抑制剂，IC50值为7.6×10−5mol/L，Ki值为3.5×10−5mol/L。
Cas No.:506-26-3
Sample solution is provided at 25 µL, 10mM.
γ-Linolenic Acid functions as an orally omega-6 polyunsaturated fatty acid from borage oil, is a specific inhibitor of β-secretase (BACE1) with IC50 value of 7.6 × 10−5mol/L and Ki value of 3.5 × 10−5mol/L[1]. γ-Linolenic Acid is crucial for the normal development of animals and has potential anti-tumor effects[2]. γ-Linolenic Acid is typically consumed as a part of a dietary supplement[3].
In vitro, γ-Linolenic Acid showed an IC50 value of 101.59μmol/L after 24h in K562 cells for cell proliferation inhibition[4]. γ-Linolenic Acid (50-150μmol/L, 24h) induced the death of K562 cells in a dose-dependent manner, enhanced lipid peroxidation in K562 cells, and promoted the release of cytochrome c, the activation of caspase-3 and the lysis of PARP in K562 cells[4]. After incubation for 24 hours, γ-Linolenic Acid induced apoptosis with IC50 value of HT-29 colorectal cancer cells at 255μmol/L[5]. Pretreatment with γ-Linolenic Acid (100μmol/L) for 1 hour can protect PC12 cells from cell death and reduce intracellular Reactive oxygen species (ROS) accumulation induced by β-amyloid peptide (Aβ25-35), and inhibit the expression of NF-κB, IκB-α and MAPK mediated by Aβ25-35[6]. γ-Linolenic Acid (50-100μmol/L, 1h) reduced the phosphorylation of ERK1/2 and JNK induced by Aβ25-35 in a dose-dependent manner[6]. The treatment with γ-Linolenic Acid at 10μg/mL for 48 hours decreased Her-2/neu protein levels in the Her-2/neu–overexpressing cell lines BT-474, SK-Br3, and MDA-MB-453 (breast cancer), SK-OV3 (ovarian cancer), and NCI-N87 (gastrointestinal cancer), resulting in elevated levels of PEA3 transcriptional repressor of Her-2/neu in all cell lines[7].
In vivo, γ-Linolenic Acid treatment (150mg/kg, p.o.) for 14 days showed a protective effect on gastric injury in rats with gastric ulcers induced by indomethacin (20mg/kg)[8]. γ-Linolenic Acid normalized antioxidant function by regulating the protein levels of MDA, SOD, GSH and CAT in rat model of gastric ulcers[8]. In the Sprague-Dawley rat model of accelerated aging, intraperitoneal injection of γ-Linolenic Acid (1mg/kg, 40 days) could improve memory impairment caused by D-fructose (1000mg/kg plus 10% drinking water for 40 days, i.p.) and reduce the formation of advanced glycation end products (AGE)[9].
References:
[1] Youn K, Lee J, Yun E Y, et al. Biological evaluation and in silico docking study of γ-linolenic acid as a potential BACE1 inhibitor[J]. journal of functional foods, 2014, 10: 187-191.
[2]Mizock B A. Immunonutrition and critical illness: an update[J]. Nutrition, 2010, 26(7-8): 701-707.
[3] Fan Y Y, Chapkin R S. Importance of dietary γ-linolenic acid in human health and nutrition[J]. The Journal of nutrition, 1998, 128(9): 1411-1414.
[4] Ge H, Kong X, Shi L, et al. Gamma-linolenic acid induces apoptosis and lipid peroxidation in human chronic myelogenous leukemia K562 cells[J]. Cell biology international, 2009, 33(3): 402-410.
[5] González-Fernández M J, Ortea I, Guil-Guerrero J L. α-Linolenic and γ-linolenic acids exercise differential antitumor effects on HT-29 human colorectal cancer cells[J]. Toxicology research, 2020, 9(4): 474-483.
[6] Youn K, Lee S, Jun M. Gamma-linolenic acid ameliorates Aβ-induced neuroinflammation through NF-κB and MAPK signalling pathways[J]. Journal of Functional Foods, 2018, 42: 30-37.
[7] Menendez J A, Vellon L, Colomer R, et al. Effect of γ-linolenic acid on the transcriptional activity of the Her-2/neu (erbB-2) oncogene[J]. Journal of the National Cancer Institute, 2005, 97(21): 1611-1615.
[8] Rahimi K, Givi M E, Rezaie A, et al. The protective effects of Gamma-linolenic acid against indomethacin-induced gastric ulcer in rats[J]. British Journal of Nutrition, 2024, 131(11): 1844-1851.
[9] Khan S A, Haider A, Mahmood W, et al. Gamma-linolenic acid ameliorated glycation-induced memory impairment in rats[J]. Pharmaceutical biology, 2017, 55(1): 1817-1823.
γ-Linolenic Acid是一种来源于琉璃苣油的口服ω-6多不饱和脂肪酸，可作为β-分泌酶（BACE1）的特异性抑制剂，IC50值为7.6×10−5mol/L，Ki值为3.5×10−5mol/L[1]。γ-Linolenic Acid对动物的正常发育至关重要，具有潜在的抗肿瘤效应[2]。γ-Linolenic Acid通常作为膳食补充剂成分被摄入[3]。
在体外，γ-Linolenic Acid处理K562细胞24小时后，对细胞增殖抑制的IC50值为101.59μmol/L[4]。γ-Linolenic Acid以浓度为50-150μmol/L处理24小时后，能剂量依赖性地诱导K562细胞死亡，增强细胞脂质过氧化水平，促进细胞色素c释放，并激活caspase-3及引发PARP蛋白水解[4]。γ-Linolenic Acid处理HT-29结肠癌细胞24小时后可诱导凋亡，IC50值为255μmol/L[5]。使用γ-Linolenic Acid（100μmol/L）预处理1小时，可保护PC12细胞免受β-淀粉样肽（Aβ25-35）诱导的细胞死亡和减少细胞内活性氧（ROS）积累，并抑制Aβ25-35介导的NF-κB、IκB-α和MAPK表达[6]。γ-Linolenic Acid（50-100μmol/L，1小时处理）能以剂量依赖性方式降低Aβ25-35诱导的ERK1/2和JNK磷酸化[6]。当以10μg/mL浓度处理48小时后，γ-Linolenic Acid能降低Her-2/neu过表达细胞系（包括乳腺癌细胞BT-474、SK-Br3和MDA-MB-453，卵巢癌细胞SK-OV3，以及胃肠道癌细胞NCI-N87）中Her-2/neu蛋白水平，并使所有细胞系中Her-2/neu转录抑制因子PEA3的表达水平升高[7]。
在体内，γ-Linolenic Acid处理（150mg/kg，口服给药，持续14天）对吲哚美辛（20mg/kg）诱导的胃溃疡大鼠模型显示出胃黏膜保护作用[8]。γ-Linolenic Acid通过调节胃溃疡大鼠模型中MDA、SOD、GSH和CAT的蛋白水平，使抗氧化功能恢复正常[8]。在加速衰老的Sprague-Dawley大鼠模型中，腹腔注射γ-Linolenic Acid（1mg/kg，持续40天）能够改善由D-果糖（1000mg/kg联合10%饮用水，腹腔注射40天）引起的记忆功能障碍，并减少晚期糖基化终末产物（AGEs）的形成[9]。
| Cell experiment [1]: | |
Cell lines | C6 cells (rat glioma) |
Preparation Method | C6 cells underwent cultivation in Dulbecco’s modified Eagle’s medium (DMEM) which contained 10% fetal calf serum (FCS), 50U/mL penicillin, and 50μg/mL streptomycin. The cell cultures used had reached their exponential growth phase while being maintained in 75cm2 flasks under humidified conditions with 5% CO2 and 95% air at 37°C. C6 cells reached the targeted density were first washed using PBS prior to trypsinization with 0.025% trypsin and 0.02% EDTA for later plating. The cell migration assay was executed with a 24-well Boyden chamber plate equipped with polycarbonate membrane filters that had 8μm pores. The upper part of the Boyden chamber contained C6 cells suspended in DMEM with 10% FCS while the lower chamber held DMEM with 10% FCS. Following a 12-hour cell adhesion period the medium was replaced with a solution containing γ-Linolenic Acid at a concentration of 100μmol/L. The laboratory established all treatment concentrations before this study. The culture media containing γ-Linolenic Acid received daily replacement for 48 hours. The membrane filter cells received methanol fixation followed by a 30-minute stain with 0.05% crystal violet after incubation. A cotton swab removed the cells present on the filter's upper surface. The membranes received PBS rinses to eliminate the surplus stain. The membranes received 20 minutes of air drying. The number of migratory cells was recorded by counting the cells that moved to the filter's lower side under bright field microscopy at 200× magnification. Filters received counts from five random fields and each treatment underwent triplicate assays. |
Reaction Conditions | 100μmol/L; 48h |
Applications | γ-Linolenic Acid (100μmol/L) significantly inhibits the proliferation and migration of C6 cells. |
| Animal experiment [2]: | |
Animal models | Male Wistar rats |
Preparation Method | A total of thirty Male Wistar rats were randomly divided into five groups which included six rats in each group. The control group and indomethacin (IND) group received sunflower oil by oral gavage over 14 successive days. The γ-Linolenic Acid 100 and 150mg/kg groups received oral doses of γ-Linolenic Acid at 100 or 150mg/kg concentrations mixed in sunflower oil containing 15% saturated and 85% unsaturated fatty acids with 14-43% oleic and 44-75% linoleic acids for 14 consecutive days. During the study, rats in the omeprazole 20mg/kg group received oral doses of 20mg/kg omeprazole for 14 continuous days. All the rats except the control group received one oral dose of IND (50mg/kg) on day 14 of the study. For 24 hours before receiving the IND rats were allowed only water access but prohibited from eating. Thiopental Na served as an anesthetic agent for rats at a dosage of 50mg/kg through intraperitoneal injection. The rats received euthanasia through decapitation 4 hours following the administration of IND. |
Dosage form | 100mg/kg and 150mg/kg for 14 days; p.o. |
Applications | γ-Linolenic Acid treatment (100 and 150mg/kg) demonstrated protection from gastric damage caused by IND. γ-Linolenic Acid treatment lowered COX1, TNF-1, IL-6 and ICAM levels while elevating PGE2 levels. |
References: | |
| Cas No. | 506-26-3 | SDF | |
| 别名 | γ-亚麻酸 ;Gamma-Linolenic acid | ||
| 化学名 | 6Z,9Z,12Z-octadecatrienoic acid | ||
| Canonical SMILES | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O | ||
| 分子式 | C18H30O2 | 分子量 | 278.4 |
| 溶解度 | ≤100mg/ml in DMSO;100mg/ml in dimethyl formamide | 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 | 3.592 mL | 17.9598 mL | 35.9195 mL |
| 5 mM | 0.7184 mL | 3.592 mL | 7.1839 mL |
| 10 mM | 0.3592 mL | 1.796 mL | 3.592 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 |
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| % DMSO % % Tween 80 % saline | ||||||||||
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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，
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2.
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