Sterculic Acid
(Synonyms: 苹婆酸) 目录号 : GC44952
A cyclopropane fatty acid
Cas No.:738-87-4
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
Sterculic acid is a cyclopropene fatty acid that has been found in S. foetida. It is an inhibitor of δ9-desaturase that decreases 9(Z)-myristoleic acid and increases oleic acid and 9(Z),11(E)-conjugated linoleic acid levels in the milk of lactating ewes when administered at a dose of 0.5 g per day. It also inhibits endoplasmic reticulum stress induced by 7-keto cholesterol in ARPE-19 cells when used at a concentration of 1 µM and prevents the formation of choroidal neovascularization when applied to eyes at concentrations of 0.1 to 10 mM in a rat model of macular degeneration induced by laser injury. Sterculic acid binds to a variety of kinases, including calcium/calmodulin-dependent protein kinase kinase 2 (CAMKK2), mammalian sterile20-related kinase 3 (MST3), and p90 ribosomal S5 kinase 4 (RSK4).
| Cas No. | 738-87-4 | SDF | |
| 别名 | 苹婆酸 | ||
| 化学名 | 2-octyl-1-cyclopropene-1-octanoic acid | ||
| Canonical SMILES | CCCCCCCCC1=C(CCCCCCCC(O)=O)C1 | ||
| 分子式 | C19H34O2 | 分子量 | 294.5 |
| 溶解度 | Soluble in chloroform, hexane, ethyl ether, methanol | 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 | 3.3956 mL | 16.9779 mL | 33.9559 mL |
| 5 mM | 0.6791 mL | 3.3956 mL | 6.7912 mL |
| 10 mM | 0.3396 mL | 1.6978 mL | 3.3956 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。
Sterculic Acid: The Mechanisms of Action beyond Stearoyl-CoA Desaturase Inhibition and Therapeutic Opportunities in Human Diseases
Cells 2020 Jan 7;9(1):140.PMID:31936134DOI:10.3390/cells9010140.
In many tissues, stearoyl-CoA desaturase 1 (SCD1) catalyzes the biosynthesis of monounsaturated fatty acids (MUFAS),(i.e., palmitoleate and oleate) from their saturated fatty acid (SFA) precursors (i.e., palmitate and stearate), influencing cellular membrane physiology and signaling, leading to broad effects on human physiology. In addition to its predominant role in lipid metabolism and body weight control, SCD1 has emerged recently as a potential new target for the treatment for various diseases, such as nonalcoholic steatohepatitis, Alzheimer's disease, cancer, and skin disorders. Sterculic Acid (SA) is a cyclopropene fatty acid originally found in the seeds of the plant Sterculia foetida with numerous biological activities. On the one hand, its ability to inhibit stearoyl-CoA desaturase (SCD) allows its use as a coadjuvant of several pathologies where this enzyme has been associated. On the other hand, additional effects independently of its SCD inhibitory properties, involve anti-inflammatory and protective roles in retinal diseases such as age-related macular degeneration (AMD). This review aims to summarize the mechanisms by which SA exerts its actions and to highlight the emerging areas where this natural compound may be of help for the development of new therapies for human diseases.
Sterculic Acid and Its Analogues Are Potent Inhibitors of Toxoplasma gondii
Korean J Parasitol 2016 Apr;54(2):139-45.PMID:27180571DOI:10.3347/kjp.2016.54.2.139.
Toxoplasmosis is a serious disease caused by Toxoplasma gondii, one of the most widespread parasites in the world. Lipid metabolism is important in the intracellular stage of T. gondii. Stearoyl-CoA desaturase (SCD), a key enzyme for the synthesis of unsaturated fatty acid is predicted to exist in T. gondii. Sterculic Acid has been shown to specifically inhibit SCD activity. Here, we examined whether Sterculic Acid and its methyl ester analogues exhibit anti-T. gondii effects in vitro. T. gondii-infected Vero cells were disintegrated at 36 hr because of the propagation and egress of intracellular tachyzoites. All test compounds inhibited tachyzoite propagation and egress, reducing the number of ruptured Vero cells by the parasites. Sterculic Acid and the methyl esters also inhibited replication of intracellular tachyzoites in HFF cells. Among the test compounds, Sterculic Acid showed the most potent activity against T. gondii, with an EC50 value of 36.2 μM, compared with EC50 values of 248-428 μM for the methyl esters. Our study demonstrated that Sterculic Acid and its analogues are effective in inhibition of T. gondii growth in vitro, suggesting that these compounds or analogues targeting SCD could be effective agents for the treatment of toxoplasmosis.
Sterculic Acid antagonizes 7-ketocholesterol-mediated inflammation and inhibits choroidal neovascularization
Biochim Biophys Acta 2012 Apr;1821(4):637-46.PMID:22342272DOI:10.1016/j.bbalip.2012.01.013.
Sterculic Acid is a cyclopropene fatty acid with numerous biological activities. In this study we demonstrate that Sterculic Acid is a potent inhibitor of endoplasmic reticulum (ER) stress and related inflammation caused by 7-ketocholesterol (7KCh). 7KCh is a highly toxic oxysterol suspected in the pathogenesis of various age-related diseases such as atherosclerosis, Alzheimer's disease and age-related macular degeneration. Sterculic Acid demonstrated to be 5-10 times more effective than other anti-inflammatory fatty acids at inhibiting 7KCh-mediated inflammatory responses in cultured cells. In vivo, Sterculic Acid was effective at inhibiting the formation of choroidal neovascularization (CNV) in the laser-injury rat model. Our data suggests that Sterculic Acid may be useful in treating CNV in certain forms of age-related macular degeneration.
Sterculic Acid Alters Adhesion Molecules Expression and Extracellular Matrix Compounds to Regulate Migration of Lung Cancer Cells
Cancers (Basel) 2021 Aug 29;13(17):4370.PMID:34503180DOI:10.3390/cancers13174370.
Sterculic Acid (SA) is a cyclopropenoid fatty acid isolated from Sterculia foetida seeds. This molecule is a well-known inhibitor of SCD1 enzyme, also known as ∆9-desaturase, which main function is related to lipid metabolism. However, recent studies have demonstrated that it also modifies many other pathways and the underlying gene expression. SCD overexpression, or up-regulated activity, has been associated with tumor aggressiveness and poor prognosis in many cancer types. Scd1 down-regulation, with different inhibitors or molecular strategies, reduces tumor cell survival and cell proliferation, as well as the chemoresistance associated with cancer stem cell presence. However, SA effects over cancer cell migration and extracellular matrix or adhesion molecules have not been described in cancer cells up to now. We used different migration assays and qPCR gene expression analysis to evaluate the effects of SA treatment in cancer cells. The results reveal that SA induces tumoral cell death at high doses, but we also observed that lower SA-treatments induce cell adhesion-migration capacity reduction as a result of modifications in the expression of genes related to integrins and extracellular matrix compounds. Overall, the functional and transcriptomic findings suggest that SA could represent a new inhibitor activity of epithelial to mesenchymal transition.
Pretreatment of human retinal pigment epithelial cells with Sterculic Acid forestalls fenretinide-induced apoptosis
Sci Rep 2022 Dec 23;12(1):22442.PMID:36575190DOI:10.1038/s41598-022-26383-9.
The ratio of saturated to monounsaturated fatty acids, thought to play a critical role in many cellular functions, is regulated by stearoyl-CoA desaturase (SCD), a rate-limiting enzyme in the biosynthesis of monounsaturated fatty acids. Previously, we observed a decrease in both SCD protein and enzymatic activity in apoptosis induced by fenretinide, a synthetic analog of retinoic acid, in the human retinal pigment epithelial (RPE) cell line ARPE-19. Here, we investigated the effect of pretreating ARPE-19 with Sterculic Acid, a cyclopropenoic fatty acid inhibitor of SCD, on preventing fenretinide-induced apoptosis, given the role of SCD in cell proliferation and apoptosis. We show that Sterculic Acid pretreatment prevents the effects of fenretinide-induced apoptosis shown by changes in cell morphology, viability, and caspase-3 activation. Analysis of endoplasmic reticulum (ER)-associated proteins shows that Sterculic Acid pretreatment reduced the fenretinide-induced upregulation of heme oxygenase-1, ATF3 and GADD153 expression that are in response to reactive oxygen species (ROS) generation. Sterculic Acid is as effective as allopurinol in inhibition of xanthine oxidase (XDH), and this may play a role in reducing the potential role of XDH in fenretinide-induced ROS generation. Sterculic Acid pretreatment also results in a reduction in SOD2 mRNA expression. Dihydroceramide accumulation, compared to ceramide, and ROS generation indicate that a ceramide-independent pathway mediates fenretinide-induced apoptosis, and ROS mediation is borne out by activation of the NF-κBp50 and NF-κBp65 downstream signaling cascade. Its prevention by Sterculic Acid pretreatment further indicates the latter's antioxidant/anti-inflammatory effect. Taken together, our results suggest that Sterculic Acid pretreatment can mitigate ROS-mediated fenretinide-induced apoptosis. Thus, Sterculic Acid may serve as a potential antioxidant and therapeutic agent. These effects may be independent of its effects on SCD activity.