Lupiwighteone
(Synonyms: 黄羽扇豆魏特酮; 8-prenylgenistein) 目录号 : GC67936Lupiwighteone 是一种广泛存在于野生植物中的异黄酮，具有抗氧化、抗菌和抗癌作用。Lupiwighteone 通过抑制 PI3K/Akt/mTOR 通路，诱导人乳腺癌细胞 caspase 依赖性和非依赖性凋亡 (Apoptosis)。
Cas No.:104691-86-3
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
Lupiwighteone is an isoflavone present widely in wild-growing plants, with antioxidant, antimicrobial and anticancer effects. Lupiwighteone induces caspase-dependent and -independent Apoptosis on human breast cancer cells via inhibiting PI3K/Akt/mTOR pathway[1][2].
Lupiwighteone (2-100 μM; 72 hours) shows cytotoxicity towards various cell lines, especially on DU-145 cells and SGC-7901 cells with IC50s of 23.7 μM and 21 μM, respectively[2].
Lupiwighteone (20-60 μM; 48 hours) induces (cell cycle arrest in DU-145 cells[2].
Lupiwighteone (20-60 μM; 48 hours) induces cells apoptosis[2].
Lupiwighteone (20-60 μM; 48 hours) decreases the cell cycle-related protein expressions in a dose-dependent manner in DU-145 cells[2].
Lupiwighteone (20-60 μM; 48 hours) induces a dose-dependent increase in ROS production[2].
Lupiwighteone up-regulates of cytochrome c and caspase-3, and subsequent cleavage of PARP-1 and down-regulates of the p-Akt/Akt ratio and VEGF expression, suggests the activation of mitochondria-based intrinsic apoptosis in DU-145 cells[2].
Cell Viability Assay[2]
| Cell Line: | DU-145 cells, C4-2 cells, SGC-7901 cells, Hela cells, HUVEC, MCF-7 cells, CNE cells, Vero |
| Concentration: | 2 μM, 5 μM, 25 μM, 50 μM, 100 μM |
| Incubation Time: | 72 hours |
| Result: | Had inhibition on the survival of many cancer cell lines and HUVEC. |
Cell Cycle Analysis[2]
| Cell Line: | DU-145 cells |
| Concentration: | 20 μM, 40 μM, 60 μM |
| Incubation Time: | 48 hours |
| Result: | Induced cell cycle arrest. |
Apoptosis Analysis[2]
| Cell Line: | DU-145 cells |
| Concentration: | 20 μM, 40 μM, 60 μM |
| Incubation Time: | 48 hours |
| Result: | Induced apoptosis. |
Western Blot Analysis[2]
| Cell Line: | DU-145 cells |
| Concentration: | 20 μM, 40 μM, 60 μM |
| Incubation Time: | 48 hours |
| Result: | Decreased CDK1, 2, 4, 6, cyclinD1, and cyclinB1 protein expression in a dose-dependent manner. |
[1]. Won YS, et al. Lupiwighteone induces caspase-dependent and -independent apoptosis on human breast cancer cells via inhibiting PI3K/Akt/mTOR pathway. Food Chem Toxicol. 2020 Jan;135:110863.
[2]. Ren J, et al. Isoflavone lupiwighteone induces cytotoxic, apoptotic, and antiangiogenic activities in DU-145 prostate cancer cells. Anticancer Drugs. 2015 Jul;26(6):599-611.
[3]. Li XL, Sui L, Lin FH, Lian Y, Ai LZ, Zhang Y. Differential effects of genistein and 8-prenylgenistein on reproductive tissues in immature female mice. Pharm Biol. 2019;57(1):226-230.
| Cas No. | 104691-86-3 | SDF | Download SDF |
| 别名 | 黄羽扇豆魏特酮; 8-prenylgenistein | ||
| 分子式 | C20H18O5 | 分子量 | 338.35 |
| 溶解度 | DMSO : 100 mg/mL (295.55 mM; Need ultrasonic) | 储存条件 | 4°C, protect from light |
| 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 | 2.9555 mL | 14.7776 mL | 29.5552 mL |
| 5 mM | 0.5911 mL | 2.9555 mL | 5.911 mL |
| 10 mM | 0.2956 mL | 1.4778 mL | 2.9555 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。
Lupiwighteone induces caspase-dependent and -independent apoptosis on human breast cancer cells via inhibiting PI3K/Akt/mTOR pathway
Food Chem Toxicol 2020 Jan;135:110863.PMID:31604113DOI:10.1016/j.fct.2019.110863.
Breast cancer is one of the most common causes of mortality in women. Lupiwighteone has anticancer effects in prostate cancer cells and neuroblastoma cells. However, the molecular and cellular mechanisms of Lupiwighteone effects on human breast cancer cells are not as well known. In the present study, we investigated the effects of Lupiwighteone on the proliferation and apoptosis of two different human cancer cells; MCF-7, an estrogen receptor (ER)-positive human breast cancer cell, and MDA-MB-231, a triple negative human breast cancer cell. Lupiwighteone treatment decreased the viability of MCF-7 and MDA-MB-231 cells. Lupiwighteone treatment resulted in apoptotic cell death in breast cancer cells, which was characterized by DNA fragmentation, accumulation of apoptotic cells, and nuclear condensation. We also showed that treatment with Lupiwighteone induced caspase-dependent apoptosis (up-regulation of caspase-3, -7, -8, -9, PARP, and Bax or down-regulation of Bid, Bcl-2), induction of caspase-independent apoptosis (up-regulation of AIF and Endo G on cytosol), and inhibition of the PI3K/Akt/mTOR signaling pathway (down-regulation of PI3K, p-Akt, and p-mTOR) in both MCF-7 and MDA-MB-231 cells. These results suggest that Lupiwighteone induces caspase-dependent and -independent apoptosis in both breast cancer cell lines via inhibiting PI3K/Akt/mTOR pathway.
Isoflavone Lupiwighteone induces cytotoxic, apoptotic, and antiangiogenic activities in DU-145 prostate cancer cells
Anticancer Drugs 2015 Jul;26(6):599-611.PMID:25734831DOI:10.1097/CAD.0000000000000224.
Isoflavones constitute a large series of compounds found in many plants. They make up an important part of the diet and have a broad spectrum of biological activities such as cytotoxic and antitumor effects. Lupiwighteone (Lup) is an isoflavone-type compound. It is distributed widely in wild-growing plants such as Glycyrrhiza glabra, Lupinus, and Lotus pedunculatus. On the basis of existing research, Lup shows antioxidant and antimicrobial effects, but its antitumor activity has not been reported as yet. This study aimed to examine the antitumor activity of Lup, explore its antitumor mechanism in a human prostate carcinoma cell line (DU-145), and evaluate its antiangiogenetic activity in the human umbilical vein endothelial cell line (HUVEC). The results showed that Lup could inhibit the growth of DU-145 and HUVEC cells in a concentration-dependent and time-dependent manner by a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay. Flow cytometry analysis indicated that Lup could induce cell cycle arrest, cells apoptosis, mitochondrial membrane potential loss, and an increase in intracellular reactive oxygen species of DU-145 cells. Upregulation of Bax, cytochrome c, caspase-3, and PARP-1 protein expressions and downregulation of Bcl-2, procaspase-9, and p-Akt protein expressions were observed by western blot after the treatment of Lup. Furthermore, the effects of Lup on the cellular behavior of HUVECs were also investigated. Altogether, our data proved the anticancer and antiangiogenesis potential of Lup.
Lupiwighteone induces cell cycle arrest and apoptosis and activates the Nrf2/ARE pathway in human neuroblastoma cells
Biomed Pharmacother 2015 Feb;69:153-61.PMID:25661352DOI:10.1016/j.biopha.2014.11.016.
Lupiwighteone (Lup) is a kind of natural isoflavone, but its pharmacological effect and active mechanism are rarely reported. This study aimed to investigate the anticancer and cancer preventive effects of Lup on human neuroblastoma (SH-SY5Y) cells. We found that Lup could inhibit SH-SY5Y cells growth in a concentration- and time-dependent manner. Further studies suggested that Lup could induce G2/M phase arrest associated with an evident decrease in cyclin B1/D1 and cyclin dependent kinase (CDK) 1/2/4/6 protein expressions. Moreover, Lup could regulate the changes of mitochondrial membrane potential and increase intracellular reactive oxygen species (ROS) production. After the cells were treated with Lup, topical morphological characteristics were observed; apoptosis-related protein expressions, such as Bax, cytochrome c, cleaved caspase-9, cleaved caspase-3 and cleaved PARP-1 were increased; and protein expressions, such as Bcl-2, procaspase-9, PARP-1 and P-Akt were decreased. These changes were observed simultaneously. In addition, Nrf2 transcription factor activation was detected by an ARE-GFP reporter assay. Nrf2 nuclear localization was then investigated using a fluorescence microscope. Furthermore, Nrf2 and Keap1 protein levels were determined by western blot. Our results may provide a scientific basis for the application of the anticancer and cancer preventive effects of Lup on SH-SY5Y cells.
Macluracochinones A-E, antimicrobial flavonoids from Maclura cochinchinensis (Lour.) Corner
Phytochemistry 2021 Jul;187:112773.PMID:33873019DOI:10.1016/j.phytochem.2021.112773.
The phytochemical investigation of the fruit and leaf extracts of Maclura cochinchinensis (Lour.) Corner (Moraceae) resulted in the isolation and identification of four undescribed isoflavones (macluracochinones A-D) and one undescribed flavone (macluracochinone E), together with 24 known compounds. The structures of the undescribed compounds were elucidated using nuclear magnetic resonance (NMR) and high-resolution electrospray ionization time-of-flight mass spectrometry (HRESITOFMS) experiments. Gancaonin M, Lupiwighteone, lupalbigenin, warangalone, auriculatin, and millexatin F displayed good antibacterial activities against Gram-positive bacteria with MIC values in the range of 1-8 μg/mL. Lupalbigenin showed strong activities against methicillin-resistant Staphylococcus aureus (MRSA) and S. aureus with the same MIC value of 1 μg/mL.
Dihydrostilbene derivatives from Glycyrrhiza glabra leaves
J Nat Prod 2005 Jul;68(7):1099-102.PMID:16038558DOI:10.1021/np050034q.
Four new dihydrostilbenes, alpha,alpha'-dihydro-3,5-dihydroxy-4'-acetoxy-5'-isopentenylstilbene (1), alpha,alpha'-dihydro-3,3',4'-trihydroxy-5-O-isopentenyl-6-isopentenylstilbene (2), alpha,alpha'-dihydro-3,5,3'-trihydroxy-4'-methoxystilbene (3), and alpha,alpha'-dihydro-3,3'-dihydroxy-5beta-d-O-glucopyranosyloxy-4'-methoxystilbene (4), together with seven known flavonoids, glabranin isomer, naringenin, Lupiwighteone, pinocembrin 7-O-glucoside, astragalin, isoquercitrin, vicenin II, and the inositol, pinitol, were isolated from the leaves of Glycyrrhiza glabra grown in Sicily. The structures of 1-4 were elucidated by spectroscopic methods.