Thevetiaflavone
(Synonyms: 黄花夹竹桃黄酮,Apigenin-5-methyl ether) 目录号 : GC37780Thevetiaflavone 可以上调 Bcl?2 的表达,下调 Bax 和 caspase-3 的表达。
Cas No.:29376-68-9
Sample solution is provided at 25 µL, 10mM.
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Thevetiaflavone could upregulate the expression of Bcl?2 and downregulate that of Bax and caspase?3. Bcl-2 Bax Caspase-3
Thevetiaflavone, a natural flavonoid obtained from Wikstroemia indica, could improve cell viability and suppresses the leakage of lactate dehydrogenase from the cytoplasm. Further investigation of the mechanisms demonstrated that Thevetiaflavone decreases overproduction of ROS and ameliorates ROS?mediated mitochondrial dysfunction, including collapse of mitochondrial membrane potential and mitochondrial permeability transition pore opening. Thevetiaflavone reduces the intracellular Ca2+ level, which is closely associated with mitochondrial function and interplays with ROS. Furthermore, Thevetiaflavone inhibits apoptosis in PC12 cells through upregulating the expression of Bcl?2 and downregulating that of Bax and caspase?3 in addition to increasing the activity of caspase?3. These results further indicate the protective effects of thevetiaflavone in vivo and its application in the clinic[1].
[1]. Yao H, et al. Thevetiaflavone from Wikstroemia indica ameliorates PC12 cells injury induced by OGD/R via improving ROS?mediated mitochondrial dysfunction. Mol Med Rep. 2017 Dec;16(6):9197-9202.
Cas No. | 29376-68-9 | SDF | |
别名 | 黄花夹竹桃黄酮,Apigenin-5-methyl ether | ||
Canonical SMILES | O=C1C=C(C2=CC=C(O)C=C2)OC3=CC(O)=CC(OC)=C13 | ||
分子式 | C16H12O5 | 分子量 | 284.26 |
溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg | |
1 mM | 3.5179 mL | 17.5895 mL | 35.1791 mL |
5 mM | 0.7036 mL | 3.5179 mL | 7.0358 mL |
10 mM | 0.3518 mL | 1.759 mL | 3.5179 mL |
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2.
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Thevetiaflavone from Wikstroemia indica ameliorates PC12 cells injury induced by OGD/R via improving ROS‑mediated mitochondrial dysfunction
Mol Med Rep 2017 Dec;16(6):9197-9202.PMID:28990067DOI:10.3892/mmr.2017.7712.
Cerebral ischemia and following reperfusion affects many people worldwide. To discover efficient therapeutic approaches, numerous natural products have been investigated. The current study investigated the protective effects of Thevetiaflavone, a natural flavonoid obtained from Wikstroemia indica, and the associated mechanisms using PC12 cells induced by oxygen and glucose deprivation. As a result, Thevetiaflavone improves cell viability and suppresses the leakage of lactate dehydrogenase from the cytoplasm. Further investigation of the mechanisms demonstrated that Thevetiaflavone decreases overproduction of ROS and ameliorates ROS‑mediated mitochondrial dysfunction, including collapse of mitochondrial membrane potential and mitochondrial permeability transition pore opening. Thevetiaflavone reduces the intracellular Ca2+ level, which is closely associated with mitochondrial function and interplays with ROS. Furthermore, Thevetiaflavone inhibits apoptosis in PC12 cells through upregulating the expression of Bcl‑2 and downregulating that of Bax and caspase‑3 in addition to increasing the activity of caspase‑3. These results further indicate the protective effects of Thevetiaflavone in vivo and its application in the clinic.
Anticancer potential of Thevetia peruviana fruit methanolic extract
BMC Complement Altern Med 2017 May 2;17(1):241.PMID:28464893DOI:10.1186/s12906-017-1727-y.
Background: Thevetia peruviana (Pers.) K. Schum or Cascabela peruviana (L.) Lippold (commonly known as ayoyote, codo de fraile, lucky nut, or yellow oleander), native to Mexico and Central America, is a medicinal plant used traditionally to cure diseases like ulcers, scabies, hemorrhoids and dissolve tumors. The purpose of this study was to evaluate the cytotoxic, antiproliferative and apoptotic activity of methanolic extract of T. peruviana fruits on human cancer cell lines. Methods: The cytotoxic activity of T. peruviana methanolic extract was carried out on human breast, colorectal, prostate and lung cancer cell lines and non-tumorigenic control cells (fibroblast and Vero), using the MTT assay. For proliferation and motility, clonogenic and wound-healing assays were performed. Morphological alterations were monitored by trypan blue exclusion, as well as DNA fragmentation and AO/EB double staining was performed to evaluate apoptosis. The extract was separated using flash chromatography, and the resulting fractions were evaluated on colorectal cancer cells for their cytotoxic activity. The active fractions were further analyzed through mass spectrometry. Results: The T. peruviana methanolic extract exhibited cytotoxic activity on four human cancer cell lines: prostate, breast, colorectal and lung, with values of IC50 1.91 ± 0.76, 5.78 ± 2.12, 6.30 ± 4.45 and 12.04 ± 3.43 μg/mL, respectively. The extract caused a significant reduction of cell motility and colony formation on all evaluated cancer cell lines. In addition, morphological examination displayed cell size reduction, membrane blebbing and detachment of cells, compared to non-treated cancer cell lines. The T. peruviana extract induced apoptotic cell death, which was confirmed by DNA fragmentation and AO/EB double staining. Fractions 4 and 5 showed the most effective cytotoxic activity and their MS analysis revealed the presence of the secondary metabolites: Thevetiaflavone and cardiac glycosides. Conclusion: T. peruviana extract has potential as natural anti-cancer product with critical effects in the proliferation, motility, and adhesion of human breast and colorectal cancer cells, and apoptosis induction in human prostate and lung cancer cell lines, with minimal effects on non-tumorigenic cell lines.
[Absorption mechanism of dragon's blood phenolic extracts in Caco-2 cells]
Zhongguo Zhong Yao Za Zhi 2020 Oct;45(20):4889-4895.PMID:33350261DOI:10.19540/j.cnki.cjcmm.20200914.301.
The purpose of this study was to study the absorption characteristics of eight main components from dragon's blood phenolic extracts in Caco-2 cells based on the humancolon cancer cell Caco-2 model, and to clarify the oral absorption mechanism of such phenolic extracts. UPLC-MS/MS was used in this study to determine the content of 8 active ingredients including Thevetiaflavone, 7,4'-dihydroxyflavone, 7,4'-dihydroxy-5-methoxyhomoisoflavanone, 7,4'-dihydroxyhomoisoflavanone, loureirin C, loureirin A, loureirin B and pterostilbene from dragon's blood phenolic extracts, and Caco-2 cells were used to investigate the effects of incubation time, concentration, temperature, P-gp inhibitor, MRP inhibitor, OCTN1 inhibitor and OCTN2 inhibitor on the absorption of each component. In addition, the transport experiment was conducted to measure the apparent permeability coefficient P_(app) and transport rate of the eight main components to predict the oral absorption mechanism of dragon's blood phenolic extracts. The experimental results showed that the cell uptake of the eight main components in dragon's blood phenolic extracts was time-dependent and concentration dependent, and the uptake of each component did not need to consume energy, which was consistent with the passive diffusion process. P-gp inhibitor, MRP inhibitor and OCTN1 inhibitor had no effect on the cell uptake of each component, only the addition of OCTN2 inhibitor significantly reduced the uptake of pterostilbene(P<0.05). In the transport results, the ER values of the outflow rates of the eight components were all less than 1.5. The above results show that the absorption mechanism of the eight components in Draconis resina phenolic extract may be passive diffusion, and pterostilbene may be the substrate of OCTN2.
Metabolism of Kaempferia parviflora polymethoxyflavones by human intestinal bacterium Bautia sp. MRG-PMF1
J Agric Food Chem 2014 Dec 24;62(51):12377-83.PMID:25437273DOI:10.1021/jf504074n.
Poylmethoxyflavones (PMFs) are major bioactive flavonoids, which exhibit various biological activities, such as anticancer effects. The biotransformation of PMFs and characterization of a PMF-metabolizing human intestinal bacterium were studied herein for the first time. Hydrolysis of aryl methyl ether functional groups by human fecal samples was observed from the bioconversion of various PMFs. Activity-guided screening for PMF-metabolizing intestinal bacteria under anaerobic conditions resulted in the isolation of a strict anaerobic bacterium, which was identified as Blautia sp. MRG-PMF1. The isolated MRG-PMF1 was able to metabolize various PMFs to the corresponding demethylated flavones. The microbial conversion of bioactive 5,7-dimethoxyflavone (5,7-DMF) and 5,7,4'-trimethoxyflavone (5,7,4'-TMF) was studied in detail. 5,7-DMF and 5,7,4'-TMF were completely metabolized to 5,7-dihydroxyflavone (chrysin) and 5,7,4'-trihydroxyflavone (apigenin), respectively. From a kinetics study, the methoxy group on the flavone C-7 position was found to be preferentially hydrolyzed. 5-Methoxychrysin, the intermediate of 5,7-DMF metabolism by Blautia sp. MRG-PMF1, was isolated and characterized by nuclear magnetic resonance spectroscopy. Apigenin was produced from the sequential demethylation of 5,7,4'-TMF, via 5,4'-dimethoxy-7-hydroxyflavone and 7,4'-dihydroxy-5-methoxyflavone (Thevetiaflavone). Not only demethylation activity but also deglycosylation activity was exhibited by Blautia sp. MRG-PMF1, and various flavonoids, including isoflavones, flavones, and flavanones, were found to be metabolized to the corresponding aglycones. The unprecedented PMF demethylation activity of Blautia sp. MRG-PMF1 will expand our understanding of flavonoid metabolism in the human intestine and lead to novel bioactive compounds.
Method development and application for multi-component quantification in rats after oral administration of Longxuetongluo Capsule by UHPLC-MS/MS
J Pharm Biomed Anal 2018 Jul 15;156:252-262.PMID:29729639DOI:10.1016/j.jpba.2018.04.030.
Although wide applications towards ischemic stroke in clinic, the therapeutic materials of Longxuetongluo Capsule (LTC) that is composed of total phenolic extract of Chinese dragon's blood, are still largely unclear. Exposure pattern characterization of those drug-derived components in vivo, notably in circulation system has been recommended as a viable approach to disclose the effective components of a given herbal medicine. Herein, we aimed to develop a robust method being capable of multi-component quantification in either rat plasma or tissues following oral administration of LTC, and to clarify the kinetic profiles of 11 primary drug-derived phenolic derivatives. Proteins precipitation was carried out for the plasma as well as homogenized tissue samples with acetonitrile. Chromatographic separations were achieved using UHPLC equipped with a shim-pack XR-ODS II column, and confidence-enhanced detection was accomplished through the joint employment of selected-reaction monitoring and tandem mass spectrometry (SRM-MS/MS) on a hybrid triple quadrupole-linear ion trap mass spectrometer. Diverse validation assays proved the method to be sensitive, precise, and rapid for simultaneous determination of those 11 components. Pharmacokinetic and tissue distribution investigations were subsequently conducted in rat after a single 500 mg/kg oral dose. Rapid absorption (Tmax, 11.53-68.27 min) and elimination (T1/2, 6.893-57.90 min) occurred for all analytes-of-interest. Extensive occurrences were observed for 7,4'-dihydroxy-5-methoxyhomoisoflavanone (Cmax, 340.0 ng/mL), Thevetiaflavone (Cmax, 42.86 ng/mL), 5,7,4'-trihydroxyhomoisoflavanone (Cmax, 41.55 ng/mL), and pterostilbene (Cmax, 25.49 ng/mL) in plasma. Significant distributions occurred for all analytes in the liver as well as kidney, and several compounds could be found in brain. The findings described are envisioned to provide promising information for the in-depth clarification of the therapeutic entities, and also to offer a practical approach for therapeutic drug monitoring of LTC in clinic.