Zeylenone
(Synonyms: 山椒子烯酮) 目录号 : GC37964
Zeylenone，可从 Uvaria grandiflora Roxb 的叶子的乙醇萃取物分离。Zeylenone 是一种天然存在的环己烯氧化物，通过 PI3K/AKT/mTOR 和 MAPK/ERK 信号通路抑制宫颈癌细胞增殖并诱导细胞凋亡 (apoptosis)。
Cas No.:193410-84-3
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
Zeylenone, isolated from ethanol extract of the leaves of Uvaria grandiflora Roxb. Zeylenone, a naturally occurring cyclohexene oxide, inhibits proliferation and induces apoptosis in cervical carcinoma cells via PI3K/AKT/mTOR and MAPK/ERK pathways[1].
[1]. Zhang L, et al. Zeylenone, a naturally occurring cyclohexene oxide, inhibits proliferation and induces apoptosis in cervical carcinoma cells via PI3K/AKT/mTOR and MAPK/ERK pathways. Sci Rep. 2017 May 10;7(1):1669.
| Cas No. | 193410-84-3 | SDF | |
| 别名 | 山椒子烯酮 | ||
| Canonical SMILES | O=C1C=C[C@@H](OC(C2=CC=CC=C2)=O)[C@H](O)[C@]1(COC(C3=CC=CC=C3)=O)O | ||
| 分子式 | C21H18O7 | 分子量 | 382.36 |
| 溶解度 | Soluble 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 | 2.6153 mL | 13.0767 mL | 26.1534 mL |
| 5 mM | 0.5231 mL | 2.6153 mL | 5.2307 mL |
| 10 mM | 0.2615 mL | 1.3077 mL | 2.6153 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。
Discovery of Zeylenone from Uvaria grandiflora as a potential botanical fungicide
Pest Manag Sci 2021 Dec;77(12):5407-5417.PMID:34314099DOI:10.1002/ps.6580.
Background: Botanical pesticides play an important role in organic agricultural practices and are widely used in integrated pest management (IPM). Uvaria grandiflora was mainly reported as traditional medicines and possessed antibacterial, antioxidant, and antiprotozoal activities. Therefore, important biological activities of U. grandiflora may suggest that they have the potential to be used as botanical pesticides. Results: The extract of U. grandiflora exhibited broad-spectrum inhibitory activity toward phytopathogenic fungi and oomycetes, particularly against Colletotrichum musae and Phytophthora capsici, and its secondary metabolite Zeylenone also displayed strong antifungal and anti-oomycete activities against phytopathogens. Particularly, half maximal effective concentration (EC50 ) values of Zeylenone against Phytophthora capsici and C. musae were 6.98 and 3.37 μg mL-1 , showing better inhibitory effects than those of commercial fungicides (azoxystrobin and osthole). Additionally, the pot experiments showed that the extract of U. grandiflora could effectively control Pseudoperonospora cubensis, Phytophthora infestans, Phytophthora capsici and Podosphaera xanthii. In the field experiment, 5% microemulsion of U. grandiflora extract exhibited 79.72% efficacy against cucumber powdery mildew at 87.5 g ha-1 on the 14th day after two sprayings, which was better than that of 21.5% trifloxystrobin and 21.5% fluopyram SC at 200.9 g ha-1 . Surprisingly, 5% microemulsion of U. grandiflora extract could promote cucumber growth significantly. Furthermore, the action mechanism analysis indicated that Zeylenone may damage the cytoderm and affect energy metabolism of Phytophthora capsici. Conclusion: It is the first time that the extract of U. grandiflora and Zeylenone have been discovered leading to broad application prospects in the development as botanical fungicides. © 2021 Society of Chemical Industry.
Concise total synthesis of (+)-Zeylenone with antitumor activity and the structure-activity relationship of its derivatives
Bioorg Chem 2021 Nov;116:105333.PMID:34537516DOI:10.1016/j.bioorg.2021.105333.
Natural products--polyoxygenated cyclohexenes exhibited potent anti-tumor activity, such as Zeylenone, which is a natural product isolated from Uvaria grandiflora Roxb. This article will attempt to establish a gram-scale synthesis method of (+)-zeylenone and explain the structure-activity relationship of this kind of compound. Total synthesis of (+)-zeylenone was completed in 13 steps with quinic acid as the starting material in 9.8% overall yield. The highlight of the route was the control of the three carbon's chirality by single step dihydroxylation. In addition, different kinds of derivatives were designed and synthesized. Cell Counting Kit-8 (CCK8) assay was used for evaluating antitumor activity against three human cancer cell lines. The structure--activity relationship suggested that compounds with both absolute configurations exhibited tumor-suppressive effects. Moreover, hydroxyls at the C-1/C-2 position were crucial to the activity, and the esterification of large groups at C-1 hydroxyl eliminated the activity. Hydroxyl at the C-3 position was also important as proper ester substituent could increase the potency.
Zeylenone synergizes with cisplatin in osteosarcoma by enhancing DNA damage, apoptosis, and necrosis via the Hsp90/AKT/GSK3β and Fanconi anaemia pathway
Phytother Res 2021 Oct;35(10):5899-5918.PMID:34585447DOI:10.1002/ptr.7299.
A safer and more effective combination strategy designed to enhance the efficacy and minimize the toxicity of cisplatin in osteosarcoma (OS) is urgently needed. Zeylenone (zey), a cyclohexene oxide compound, exerted an obvious inhibitory effect on several cancer cell lines and exhibited little cytotoxicity towards normal cells, enabling zey to play a unique role in combination therapy. Thus, the study aimed to determine whether the combination of zey and cisplatin produces synergistic antitumour effects on OS and to further explore molecular mechanisms. Initially, we found that zey potentiated the anti-osteosarcoma efficacy of cisplatin and exhibited synergistic interactions with cisplatin in vitro, which also were confirmed in vivo by using xenograft model. Mechanistically, zey and cisplatin synergistically induced DNA damage, cell cycle arrest, necrosis, and apoptosis in OS cells. Importantly, zey had a high binding affinity for Hsp90 and reduced the expression of Hsp90, which further induced the suppression of AKT/GSK3β signalling axis and the degradation of Fanconi anaemia (FA) pathway proteins. Thus, the Hsp90/AKT/GSK3β and FA pathway are the key to the synergism between zey and cisplatin. Overall, zey shows promise for development as a cisplatin chemosensitizer with clinical utility in restoring cisplatin sensitivity of cancer cells.
Zeylenone Induces Mitochondrial Apoptosis and Inhibits Migration and Invasion in Gastric Cancer
Molecules 2018 Aug 27;23(9):2149.PMID:30150551DOI:10.3390/molecules23092149.
The mortality of gastric cancer (GC) is increasing due to its high rates of recurrence and metastasis. Zeylenone (Zey), a type of naturally occurring cyclohexene oxide, was demonstrated to be effective in cancer patients. The aim of this study is to explore the anti-cancer effect of Zey against gastric cancer both in vitro and in vivo, as well as the underlying mechanisms. We found that Zey inhibited gastric tumor growth, as demonstrated by in vitro gastric cancer cell lines and in a human gastric cancer xenograft mouse model. Furthermore, Zey induced substantial apoptosis through a mitochondrial apoptotic pathway, involving mitochondrial transmembrane potential loss, caspase-3 activation, anti-apoptotic protein downregulation, and pro-apoptotic protein upregulation. Notably, we revealed for the first time that Zey suppressed invasion and migration by wound healing and transwell chamber assays. Through Western blotting, we further explored the potential mechanism of Zey's anti-cancer activity. We found that Zey downregulated the expression of matrix metalloproteinase 2/9 (MMP 2/9) and inhibited the phosphorylation of AKT and ERK. In short, Zey, which induced mitochondrial apoptosis and inhibited proliferation, migration, and invasion, may be developed as a novel drug for the treatment of gastric cancer.
Zeylenone inhibits proliferation and promotes apoptosis in ovarian carcinoma cells via Janus kinase 2 / signal transducers and activators of transcription 3 pathways
J Obstet Gynaecol Res 2018 Aug;44(8):1451-1457.PMID:29974554DOI:10.1111/jog.13690.
Aim: Ovarian cancer is the fifth common cancer in females. The aim of our study was to determine function of Zeylenone on cell viability and apoptosis of ovarian carcinoma SKOV3 cells. Methods: Cell viability was measured by Cell counting kit-8 (CCK8) assay; Mitochondrial membrane potential (MMP) and apoptosis were detected by flow cytometry. The mRNA and protein levels of related factors were determined by Real-time quantitative polymerase chain reaction (RT-qPCR) and Western blot, respectively. Results: Cell viability was decreased by Zeylenone in a dose-dependent manner. Zeylenone with concentrations of 2.5, 5 and 10 μmol/L was used to treat ovarian carcinoma SKOV3 cells for 24 h in the following study. The loss of MMP and apoptosis were both significantly increased by Zeylenone. The mRNA and protein levels of cytochrome c (cyto c) and apoptosis inducing factor (AIF) in cytosol were increased by Zeylenone. The mRNA and protein levels of Caspase-3, Fas, Fasl and Bax were increased; while the expression of Bcl-2 was decreased by Zeylenone. The expression of (Janus family of tyrosine kinase) p-JAK and signal transducer and activator of transcription (p-STAT) was decreased significantly by Zeylenone. Conclusion: Zeylenone inhibited cell proliferation and promoted apoptosis in ovarian carcinoma cells. The JAK-STAT pathway was involved in this progress.