Ternatin
(Synonyms: 特拉廷) 目录号 : GC45016
An anti-adipogenic cyclic peptide
Cas No.:148619-41-4
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
Ternatin is a cyclic heptapeptide first isolated from the mushroom C. versicolor that has been shown to have cytotoxic and anti-adipogenic effects in vitro. It inhibits adipogenesis with an IC50 value of 27 nM and becomes cytotoxic to 3T3-L1 mouse adipocytes at 10-fold higher concentrations. Ternatin is reported to inhibit HCT116 cell proliferation with an IC50 value of 71 nM. Note that this metabolite should not be confused with the plant flavonoid of the same name.
| Cas No. | 148619-41-4 | SDF | |
| 别名 | 特拉廷 | ||
| Canonical SMILES | O=C(N[C@@H](CC(C)C)C(N(C)[C@H]1C)=O)[C@H](CC(C)C)N(C)C([C@H](C)N(C([C@]([C@H](CC)C)([H])NC([C@@](NC([C@@H](C)N(C)C1=O)=O)([H])[C@@H](C(C)C)O)=O)=O)C)=O | ||
| 分子式 | C37H67N7O8 | 分子量 | 738 |
| 溶解度 | DMF: soluble,DMSO: soluble,Ethanol: soluble,Methanol: soluble | 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 | 1.355 mL | 6.7751 mL | 13.5501 mL |
| 5 mM | 0.271 mL | 1.355 mL | 2.71 mL |
| 10 mM | 0.1355 mL | 0.6775 mL | 1.355 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。
(-)-Ternatin inhibits adipogenesis and lipid metabolism in 3T3-L1 cells
Peptides 2009 Jun;30(6):1074-81.PMID:19463739DOI:10.1016/j.peptides.2009.02.008.
(-)-Ternatin, a highly N-methylated cyclic peptide, inhibits fat accumulation in 3T3-L1 cells and reduces fat mass in mice. However, the mechanism for its anti-adipogenic effect has remained unknown. To examine the mechanism used by (-)-ternatin to inhibit adipocyte differentiation, we examined the effects of (-)-ternatin and [l-Ala(4)]Ternatin, an inactive analog of (-)-ternatin, on the expression of adipocyte markers and lipogenic enzymes. We found that (-)-ternatin potently reduced mRNA expression of several adipocyte markers in a dose-dependent manner, whereas [l-Ala(4)]Ternatin showed no effects. At the immediate early phase, (-)-ternatin, but not [l-Ala(4)]Ternatin, reduced the expression of Srebp1c, Fas, Acc2 and C/EBP-alpha while showing no effects on C/EBP-beta and C/EBP-delta. These results suggest that (-)-ternatin affects the mid-to late differentiation stages of adipocytes. Consistent with the decreased expression of lipogenic enzymes, (-)-ternatin potently inhibited triglyceride synthesis. Intriguingly, (-)-ternatin also inhibited triglyceride synthesis in rat primary hepatocytes, suggesting that the potential action sites for (-)-ternatin are shared by adipocytes and liver. Although the target molecule of (-)-ternatin remains unknown, our data suggest that (-)-ternatin and its potential target might provide a new therapeutic approach to metabolic disorders.
Molecular docking of anthocyanins and Ternatin in Clitoria ternatea as coronavirus disease oral manifestation therapy
J Adv Pharm Technol Res 2021 Oct-Dec;12(4):362-367.PMID:34820310DOI:10.4103/japtr.japtr_126_21.
Herbal active compound with immunoregulator ability is considered a potential therapy for COVID-19 oral manifestation by downregulating pro-inflammatory cytokine storm. Meanwhile, anthocyanin and Ternatin are the active compounds in Clitoria ternatea, which may act as a potential immunoregulator for COVID-19 therapy. The intention of this investigation was to investigate anthocyanin and Ternatin as active compounds in C. ternatea that may be able to increase anti-inflammatory cytokine and inhibit pro-inflammatory cytokine and key proteins of severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2). This study implemented bioinformatic approach to analyze anthocyanin and Ternatin as active compounds in C. ternatea with anti- and pro-inflammatory cytokines and antiviral examination history through blind molecular docking study (in silico). Moreover, anthocyanins and Ternatin were obtained from PubChem database by minimizing ligand structure in PyRx software to increase the flexibility. RCSB database was employed for preparing the protein samples consisting of interleukin (IL)-6, SARS-CoV-2-ACE2 glycoprotein complex, tumor necrosis factor-α receptor (TNF-αR), matrix metalloproteinase-9 (MMP-9), IL-6, IL-10, and human beta defensin-2 (HBD-2). In addition, The PyMol sofware was used to sterilize the protein samples to obtain the molecular docking optimization. This investigation found that, in the molecular docking simulation, the anthocyanin and Ternatin showed producing the negative binding affinity to the ACE2 domain which interacted with RBD glycoprotein SARS-CoV-2. Anthocyanin and Ternatin were then predicted to be able to influence any inhibitory activity of TNF-αR, MMP-9, and IL-6; increase IL-10; and increase HBD2 binding affinity values negatively. It can be predicted through molecular docking that anthocyanin and Ternatin as the active compounds in C. ternatea contribute as a potential agent for COVID-19 oral manifestation therapy.
Ternatin, a cyclic peptide isolated from mushroom, and its derivative suppress hyperglycemia and hepatic fatty acid synthesis in spontaneously diabetic KK-A(y) mice
Biochem Biophys Res Commun 2012 Oct 19;427(2):299-304.PMID:23000156DOI:10.1016/j.bbrc.2012.09.045.
(-)-Ternatin is a highly methylated cyclic heptapeptide isolated from mushroom Coriolus versicolor. Ternatin has an inhibitory effect on fat accumulation in 3T3-L1 adipocytes. [D-Leu(7)]Ternatin, a Ternatin derivative, also inhibited fat accumulation in 3T3-L1 cells, although the effectiveness of [D-Leu(7)]Ternatin was lower than that of Ternatin. In this study, we investigated the effects of Ternatin and [D-Leu(7)]Ternatin on obesity and type 2 diabetes in KK-A(y) mice, an animal model for spontaneously developed type 2 diabetes. We continuously administered Ternatin (8.5 or 17 nmol/day) or [D-Leu(7)]Ternatin (68 nmol/day) to mice via a subcutaneous osmotic pump. Unexpectedly, neither Ternatin nor [D-Leu(7)]Ternatin affected body weight or adipose tissue weight in KK-A(y) mice. In contrast, it was demonstrated that both Ternatin and [D-Leu(7)]Ternatin suppress the development of hyperglycemia. In liver, the SREBP-1c mRNA level tended to be lower or significantly decreased in mice treated with Ternatin or [D-Leu(7)]Ternatin, respectively. Moreover, we found that Ternatin directly lowered the SREBP-1c mRNA level in Hepa1-6 hepatocyte cells. This study showed that Ternatin and [D-Leu(7)]Ternatin each had a preventive effect on hyperglycemia and a suppressive effect on fatty acid synthesis in KK-A(y) mice.
Ternatin and improved synthetic variants kill cancer cells by targeting the elongation factor-1A ternary complex
Elife 2015 Dec 10;4:e10222.PMID:26651998DOI:10.7554/eLife.10222.
Cyclic peptide natural products have evolved to exploit diverse protein targets, many of which control essential cellular processes. Inspired by a series of cyclic peptides with partially elucidated structures, we designed synthetic variants of Ternatin, a cytotoxic and anti-adipogenic natural product whose molecular mode of action was unknown. The new Ternatin variants are cytotoxic toward cancer cells, with up to 500-fold greater potency than Ternatin itself. Using a Ternatin photo-affinity probe, we identify the translation elongation factor-1A ternary complex (eEF1A·GTP·aminoacyl-tRNA) as a specific target and demonstrate competitive binding by the unrelated natural products, didemnin and cytotrienin. Mutations in domain III of eEF1A prevent Ternatin binding and confer resistance to its cytotoxic effects, implicating the adjacent hydrophobic surface as a functional hot spot for eEF1A modulation. We conclude that the eukaryotic elongation factor-1A and its ternary complex with GTP and aminoacyl-tRNA are common targets for the evolution of cytotoxic natural products.
Ternatin, a flavonoid, prevents cyclophosphamide and ifosfamide-induced hemorrhagic cystitis in rats
Phytother Res 2004 Feb;18(2):135-41.PMID:15022166DOI:10.1002/ptr.1379.
To compare the classical uroprotective efficacy of mesna (2-mercaptoethanesulfonic acid) with Ternatin (flavonoid isolated from Egletes viscosa Less.) in cyclophosphamide (CYP) and ifosfamide (IFS) induced hemorrhagic cystitis (HC). Male Wistar rats received an intraperitoneal injection of saline, CYP or IFS and were treated with saline or mesna, 5 min before, 4 and 8 h after CYP or IFS administration. In other animals, 1, 2 or 3 doses of mesna were replaced with Ternatin or 3 doses of mesna were replaced with dimethylsulphoxide (DMSO), Ternatin diluent. In an additional group, the last 2 doses of mesna were replaced with saline. HC was evaluated 24 h after CYP or IFS administration. CYP or IFS treatment induced marked changes in macroscopic and microscopic evaluation and in bladder wet weight (BWW), and these alterations were significantly inhibited by treatment with 3 doses of mesna, as well as by the replacement of 1 or 2 doses of mesna with Ternatin. The replacement of 2 doses of mesna with saline or all doses of mesna with Ternatin or DMSO did not prevent HC. In conclusion, the replacement of 1 or 2 doses of mesna with Ternatin efficiently blocked CYP- or IFS-induced HC, however mesna is necessary for initial uroprotection.