Yatein
(Synonyms: 亚太因) 目录号 : GC46238
A lignan with diverse biological activities
Cas No.:40456-50-6
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
Yatein is a lignan that has been found in C. formosana and has diverse biological activities.1,2,3,4 It inhibits the cytochrome P450 (CYP) isoform CYP3A4 (IC50 = 1 μM).1 Yatein inhibits herpes simplex virus 1 (HSV-1) replication in a plaque reduction assay (IC50 = 30.6 μM).2 It induces apoptosis and production of reactive oxygen species (ROS) in, and is cytotoxic to, A549 and CL1-5 non-small cell lung cancer (NSCLC) cells (IC50s = 3.5 and 1.9 μM, respectively).3 Yatein inhibits aggregation of rabbit platelets induced by platelet-activating factor (PAF), collagen, or arachidonic acid in a concentration-dependent manner.4
|1. Usia, T., Watabe, T., Kadota, S., et al. Potent CYP3A4 inhibitory constituents of Piper cubeba. J. Nat. Prod. 68(1), 64-68 (2005).|2. Kuo, Y.-C., Kuo, Y.-H., Lin, Y.-L., et al. Yatein from Chamaecyparis obtusa suppresses herpes simplex virus type 1 replication in HeLa cells by interruption the immediate-early gene expression. Antiviral Res. 70(3), 112-120 (2006).|3. Ho, S.-T., Lin, C.-C., Wu, T.-L., et al. Antitumor agent yatein from Calocedrus formosana Florin leaf induces apoptosis in non-small-cell lung cancer cells. J. Wood Sci. 65:59 , (2019).|4. Chen, J.-J., Chang, Y.-L., Teng, C.-M., et al. Anti-platelet aggregation alkaloids and lignans from Hernandia nymphaeifolia. Planta Med. 66(3), 251-256 (1999).
| Cas No. | 40456-50-6 | SDF | |
| 别名 | 亚太因 | ||
| Canonical SMILES | O=C(OC1)[C@H](CC2=CC(OC)=C(OC)C(OC)=C2)[C@H]1CC3=CC=C4C(OCO4)=C3 | ||
| 分子式 | C22H24O7 | 分子量 | 400.4 |
| 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 | 2.4975 mL | 12.4875 mL | 24.975 mL |
| 5 mM | 0.4995 mL | 2.4975 mL | 4.995 mL |
| 10 mM | 0.2498 mL | 1.2488 mL | 2.4975 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。
Molecular Mechanisms Underlying Yatein-Induced Cell-Cycle Arrest and Microtubule Destabilization in Human Lung Adenocarcinoma Cells
Cancers (Basel) 2019 Sep 17;11(9):1384.PMID:31533296DOI:10.3390/cancers11091384.
Yatein is an antitumor agent isolated from Calocedrus formosana Florin leaves extract. In our previous study, we found that Yatein inhibited the growth of human lung adenocarcinoma A549 and CL1-5 cells by inducing intrinsic and extrinsic apoptotic pathways. To further uncover the effects and mechanisms of yatein-induced inhibition on A549 and CL1-5 cell growth, we evaluated yatein-mediated antitumor activity in vivo and the regulatory effects of Yatein on cell-cycle progression and microtubule dynamics. Flow cytometry and western blotting revealed that Yatein induces G2/M arrest in A549 and CL1-5 cells. Yatein also destabilized microtubules and interfered with microtubule dynamics in the two cell lines. Furthermore, we evaluated the antitumor activity of Yatein in vivo using a xenograft mouse model and found that Yatein treatment altered cyclin B/Cdc2 complex expression and significantly inhibited tumor growth. Taken together, our results suggested that Yatein effectively inhibited the growth of A549 and CL1-5 cells possibly by disrupting cell-cycle progression and microtubule dynamics.
Yatein from Chamaecyparis obtusa suppresses herpes simplex virus type 1 replication in HeLa cells by interruption the immediate-early gene expression
Antiviral Res 2006 Jul;70(3):112-20.PMID:16540181DOI:10.1016/j.antiviral.2006.01.011.
Inhibitory effects of methanolic extracts from nine Chinese herbs on herpes simplex virus type 1 (HSV-1) replication were studied. By a bioassay-guided fractionation procedure, Yatein (C(22)H(23)O(7); M.W.399) was isolated from Chamaecyparis obtusa; Yatein significantly suppressed HSV-1 multiplication in HeLa cells without apparent cytotoxicity. To further localize the point in the HSV-1 replication cycle where arrest occurred, a set of key regulatory events leading to the viral multiplication was examined, including viral immediate-early (alpha) and late (gamma) gene expression and DNA replication. Results indicated that levels of glycoprotein B (gB) and gC mRNA expression in HeLa cells were impeded by Yatein. Data from polymerase chain reaction showed that replication of HSV-1 DNA in HeLa cells was arrested by Yatein. Furthermore, Yatein decreased ICP0 and ICP4 gene expression in HeLa cells. Results of an electrophoretic mobility shift assay demonstrated that Yatein interrupted the formation of alpha-trans-induction factor/C1/Oct-1/GARAT multiprotein complex. The mechanisms of antiviral action of Yatein seem to be mediated, by inhibiting HSV-1 alpha gene expression, including expression of the ICP0 and ICP4 genes, and by arresting HSV-1 DNA synthesis and structural protein expression in HeLa cells. These results suggest that Yatein is an antiviral agent against HSV-1 replication.
Biosynthesis of Yatein in Anthriscus sylvestris
Org Biomol Chem 2003 Jul 21;1(14):2474-85.PMID:12956064DOI:10.1039/b304411d.
Little is known about the biosynthesis of Yatein, in spite of its importance as a typical heartwood lignan and a key biosynthetic intermediate of the antitumor lignan podophyllotoxin. The present study, based on individual administration of [13C]phenylalanine and deuterium labelled lignans and simultaneous administration of two distinct lignans labelled with deuterium atoms to Anthriscus sylvestris, established the two independent branch pathways from matairesinol, one to afford Yatein via thujaplicatin, 5-methylthujaplicatin, and 4,5-dimethylthujaplicatin and the other to bursehernin via pluviatolide. The latter pathway did not lead to Yatein, eliminating the presence of a metabolic grid from matairesinol to Yatein.
Antiproliferative activity of Yatein isolated from Austrocedrus chilensis against murine myeloma cells: cytological studies and chemical investigations
Pharm Biol 2015 Mar;53(3):378-85.PMID:25420758DOI:10.3109/13880209.2014.922588.
Context: Fitzroya cupressoides (Molina) I. M. Johnst. and Austrocedrus chilensis (D. Don) Pic.Serm. & Bizzarri are two Chilean Cupressaceae that are naturally resistant to biodegradation. Secondary metabolites from these species display a variety of biological activities. Objective: To evaluate the antiproliferative activity of two lignans, a diterpene and a flavonol isolated from A. chilensis and F. cupressoides, to elucidate their cytological effects on P3X murine myeloma cells. Materials and methods: The antiproliferative activity of Yatein, isotaxiresinol, ferruginol, and isorhamnetin was evaluated in vitro using the MTT assay. The effect of Yatein at the cellular level, due to its high antiproliferative activity was evaluated. P3X cells treated for 24 h with 12.5 and 25 µg/mL of Yatein were also examined at the cytological level using immunofluorescence and scanning and transmission electron microscopy. Results: Yatein, a lignan isolated from A. chilensis, potentially inhibited P3X murine myeloma cell proliferation, resulting in approximately 75% cell death in response to a 25 µg/mL treatment with the lignan. P3X cells lost membrane integrity at the nuclear and cytoplasmic levels, including organelles, in response to Yatein treatment (12.5 µg/mL), and we observed changes in the cytoplasmic organization and distribution of microtubules. The other compounds tested had low activity. Discussion and conclusions: Yatein is a lignan precursor of podophyllotoxin, a key agent in anticancer drugs. Due to its structural similarities to podophyllotoxin, Yatein could have similar cytoplasmic target(s), such as the microtubular apparatus. These findings suggest that Yatein may be of potential pharmacological interest and warrants further investigation in human cell lines.
Distribution of (-)-yatein in Cupressaceae family analysed by high performance liquid chromatography
Arch Pharm Res 2004 Jan;27(1):35-9.PMID:14969335DOI:10.1007/BF02980042.
The method for the chiral analysis of (-)-yatein was developed and the distribution of this component in the plants of three genera like Juniperus, Thuja and Chamaecyparis belonging to Cupressaceae family was examined. The chiral analysis of (-)-yatein from the plants was carried out by high performance liquid chromatography on (R,R)-Whelk-O1 column using 81 v/v% methanol as mobile phase. The Yatein content in the leaves of Juniperus was the highest in compare with that of the other two genera, providing the possibility of the chemical discrimination of the plants in Juniperus from the other plants in the Cupressaceae family. In general, the Yatein content in the leaves was much higher than that in the twigs. This method could be applied for the quality control of (-)-yatein in the plants belonging to Cupressaceae family.