Demethylwedelolactone
(Synonyms: 去甲蟛蜞菊内酯) 目录号 : GC38576A coumestan with diverse biological activities
Cas No.:6468-55-9
Sample solution is provided at 25 µL, 10mM.
Quality Control & SDS
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- Purity: >98.00%
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Demethylwedelolactone (DWL) is a coumestan, originally isolated from E. alba, with diverse biological activities.1,2,3,4 It reduces cytotoxicity induced by CCL4 and galactosamine in rat hepatocytes in a dose-dependent manner.1 DWL inhibits trypsin with an IC50 value of 3.0 μg/ml in vitro.2 It is the major constituent in purified butanolic extracts of E. prostrata which inhibit lethal and hemorrhagic activities of C. rhodostoma venom.3 DWL also inhibits anchorage-independent cell growth of MDA-MB-231 breast cancer cells and decreases the number of lung metastases in an MDA-MB-231 xenograft model in nude mice.4
1.Wagner, H., Geyer, B., Kiso, Y., et al.Coumestans as the main active principles of the liver drugs Eclipta alba and Wedelia calendulaceaPlanta Med.5370-374(1986) 2.Syed, S.D., Deepak, M., Yogisha, S., et al.Trypsin inhibitory effect of wedelolactone and demethylwedelolactonePhytother. Res.17(4)420-421(2003) 3.Pithayanukul, P., Laovachirasuwan, S., Bavovada, R., et al.Anti-venom potential of butanolic extract of Eclipta prostrata against Malayan pit viper venomJ. Ethnaopharmacol.90(2-3)347-352(2004) 4.Lee, Y.-J., Lin, W.-L., Chen, N.-F., et al.Demethylwedelolactone derivatives inhibit invasive growth in vitro and lung metastasis of MDA-MB-231 breast cancer cells in nude miceEur. J. Med. Chem.56(1)631-637(2012)
Cas No. | 6468-55-9 | SDF | |
别名 | 去甲蟛蜞菊内酯 | ||
Canonical SMILES | O=C1C2=C(OC3=CC(O)=C(O)C=C32)C4=C(O)C=C(O)C=C4O1 | ||
分子式 | C15H8O7 | 分子量 | 300.22 |
溶解度 | DMF: 30 mg/ml,DMSO: 30 mg/ml,DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml,Ethanol: 20 mg/ml | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg | |
1 mM | 3.3309 mL | 16.6545 mL | 33.3089 mL |
5 mM | 0.6662 mL | 3.3309 mL | 6.6618 mL |
10 mM | 0.3331 mL | 1.6654 mL | 3.3309 mL |
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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。
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UPLC-MS/MS Assay for Quantification of Wedelolactone and Demethylwedelolactone in Rat Plasma and the Application to a Preclinical Pharmacokinetic Study
Comb Chem High Throughput Screen 2022 Jun 1;25(8):1271-1277.PMID:35708104DOI:10.2174/1386207324666210520093517.
Aims and objective: Wedelolactone and Demethylwedelolactone are the two major coumarin constituents of Herba Ecliptae. The objective of this work was to develop and validate a sensitive, rapid, and robust UPLC-MS/MS method for the simultaneous quantification of wedelolactone and Demethylwedelolactone in rat plasma. Materials and methods: Wedelolactone and Demethylwedelolactone were extracted from rat plasma by protein precipitation with acetonitrile. Electrospray ionization in negative mode and selected reaction monitoring (SRM) were used for wedelolactone and Demethylwedelolactone at the transitions m/z 312.8→298.0 and m/z 299.1→270.6, respectively. Chromatographic separation was conducted on a Venusil C18 column (50 mm × 2.1 mm, 5 μm) with isocratic elution of acetonitrile-0.1% formic acid in water (55:45, v/v) at a flow rate of 0.3 mL/min. A linear range was observed over the concentration range of 0.25-100 ng/mL for wedelolactone and Demethylwedelolactone. Results: They reached their maximum plasma concentrations (Cmax, 74.9±13.4 ng/mL for wedelolactone and 41.3±9.57 ng/mL for Demethylwedelolactone) at the peak time (Tmax) of 0.633 h and 0.800 h, respectively. The AUC0-t value of wedelolactone (260.8±141.8 ng h/mL) was higher than that of Demethylwedelolactone (127.4±52.7 ng h/mL) by approximately 2-fold, whereas the terminal elimination half-life (t1/2) of wedelolactone (2.20±0.59 h) showed the approximately same as that of Demethylwedelolactone (2.08±0.69 h). Conclusion: Based on full validation according to US FDA guidelines, this UPLC-MS/MS method was successfully applied to a pharmacokinetic study in rats.
Demethylwedelolactone derivatives inhibit invasive growth in vitro and lung metastasis of MDA-MB-231 breast cancer cells in nude mice
Eur J Med Chem 2012 Oct;56:361-7.PMID:22926226DOI:10.1016/j.ejmech.2012.07.041.
The anticancer properties of Demethylwedelolactone (DWEL) and wedelolactone (WEL), which are naturally occurring coumestans, have not been well characterized. In this study, we investigated the anti-invasive effects of synthetic WEL and DWEL on human MDA-MB-231 breast cancer cells. We found that WEL and DWEL inhibited the anchorage-independent growth and also suppressed cell motility and cell invasion of MDA-MB-231 cells. In addition, WEL and DWEL reduced the activity and expression of matrix metalloproteinases (MMPs) involved in blocking the IκB-α/NFκB and MEK/ERK signaling pathways in MDA-MB-231 cells. Furthermore, DWEL suppressed the metastasis and lung colonization of the tumor cells in the nude mice. Altogether, these data suggest that DWEL derivatives exert anti-invasive growth effect on breast cancer cells.
Trypsin inhibitory effect of wedelolactone and Demethylwedelolactone
Phytother Res 2003 Apr;17(4):420-1.PMID:12722155DOI:10.1002/ptr.1153.
Wedelolactone (WL) and Demethylwedelolactone (DWL) isolated from Eclipta alba were tested in the trypsin inhibition bioassay (in vitro). Both compounds showed potent activity. IC(50) values of WL and DWL were found to be 2.9 and 3.0 microg/mL respectively.
Jasmonates promote enhanced production of bioactive caffeoylquinic acid derivative in Eclipta prostrata (L.) L. hairy roots
Plant Cell Tissue Organ Cult 2022;149(1-2):363-369.PMID:34840370DOI:10.1007/s11240-021-02201-4.
Eclipta prostrata (L.) L. is widely used in traditional medicine for treatment of hepatitis, poisoning from snake bites and viral infections. Pharmacological studies confirmed its antioxidant, anti-inflammatory and anticancer activities. The efficacy of E. prostrata (L.) L. extracts has been correlated to phenylpropanoids such as flavonoids, coumestans and caffeoylquinic acid derivatives. In this work, the production of wedelolactone, Demethylwedelolactone and 3,5-di-O-caffeoylquinic acid (3,5-diCQA) in hairy root cultures of E. prostrata (L.) L. C19 clone was increased after addition of eliciting agents jasmonic acid (JA) or methyl jasmonate (MeJA) at multiple concentrations. Cultures elicited with 100 μM of JA saw a 5.2 fold increase in wedelolactone (from 0.72 to 3.72 mg/g d.w.), a 1.6 fold increase in Demethylwedelolactone (from 5.54 to 9.04 mg/g d.w.) and a 2.47 fold increase in 3,5-diCQA (from 18.08 to 44.71 mg/g d.w.). Obtained data validate the potential of E. prostrata (L.) L. hairy root cultures as a production system of wedelolactone, Demethylwedelolactone and especially 3,5-diCQA, which has recently been reported to possess activity against coronavirus disease (Covid-19) by in silico computational studies. Supplementary information: The online version contains supplementary material available at 10.1007/s11240-021-02201-4.
Biosynthetic studies through feeding experiments in Eclipta prostrata (L.) L. hairy roots
Plant Cell Tissue Organ Cult 2022;151(1):215-219.PMID:35875188DOI:10.1007/s11240-022-02342-0.
Eclipta prostrata (L.) L. is a medicinal plant of the Asteraceae family, and several extracts and isolated compounds of E. prostrata (L.) L. showed a wide range of biological activities such as antimicrobial, anticancer, hepatoprotective, neuroprotective, hair growth promoting activities, and more recently against covid-19. Eclipta prostrata (L.) L. hairy roots produce wedelolactone (WL), Demethylwedelolactone (DWL) and 3,5-di-O-caffeoylquinic acid (3,5-diCQA), and there is no data in literature regarding biosynthetic pathways are involved. To verify the biosynthetic route, feeding experiments were carried out using sodium [2-13C]acetate, [3-13C]dl-phenylalanine, and 13C-labeled compounds (WL, DWL and 3,5-diCQA) were detected by ultra-high-performance liquid chromatography-quadrupole time of flight mass spectrometry (HPLC-QTOF-MS). Analysis showed that the metabolic pathways operative of coumestans (WL and DWL) are derived from acetate and shikimate pathways, while that the phenylpropanoid (3,5-diCQA) biosynthesis is exclusively from shikimate pathway. Supplementary information: The online version contains supplementary material available at 10.1007/s11240-022-02342-0.