Trans-MelilotosideCAS# 618-67-7 |
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| Cas No. | 618-67-7 | SDF | Download SDF |
| PubChem ID | 5280759 | Appearance | Powder |
| Formula | C15H18O8 | M.Wt | 326.3 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (E)-3-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoic acid | ||
| SMILES | C1=CC=C(C(=C1)C=CC(=O)O)OC2C(C(C(C(O2)CO)O)O)O | ||
| Standard InChIKey | GVRIYIMNJGULCZ-ZMKUSUEASA-N | ||
| Standard InChI | InChI=1S/C15H18O8/c16-7-10-12(19)13(20)14(21)15(23-10)22-9-4-2-1-3-8(9)5-6-11(17)18/h1-6,10,12-16,19-21H,7H2,(H,17,18)/b6-5+/t10-,12-,13+,14-,15-/m1/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
Trans-Melilotoside Dilution Calculator
Trans-Melilotoside Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.0647 mL | 15.3233 mL | 30.6466 mL | 61.2933 mL | 76.6166 mL |
| 5 mM | 0.6129 mL | 3.0647 mL | 6.1293 mL | 12.2587 mL | 15.3233 mL |
| 10 mM | 0.3065 mL | 1.5323 mL | 3.0647 mL | 6.1293 mL | 7.6617 mL |
| 50 mM | 0.0613 mL | 0.3065 mL | 0.6129 mL | 1.2259 mL | 1.5323 mL |
| 100 mM | 0.0306 mL | 0.1532 mL | 0.3065 mL | 0.6129 mL | 0.7662 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Evaluation of in vitro antiprotozoal activity of Ajuga laxmannii and its secondary metabolites.[Pubmed:26734766]
Pharm Biol. 2016 Sep;54(9):1808-14.
Context Some Ajuga L. (Lamiaceae) species are traditionally used for the treatment of malaria, as well as fever, which is a common symptom of many parasitic diseases. Objective In the continuation of our studies on the identification of antiprotozoal secondary metabolites of Turkish Lamiaceae species, we have investigated the aerial parts of Ajuga laxmannii. Materials and methods The aerial parts of A. laxmannii were extracted with MeOH. The H2O subextract was subjected to polyamide, C18-MPLC and SiO2 CCs to yield eight metabolites. The structures of the isolates were elucidated by NMR spectroscopy and MS analyses. The extract, subextracts as well as the isolates were tested for their in vitro antiprotozoal activities against Plasmodium falciparum, Trypanasoma brucei rhodesiense, T. cruzi and Leishmania donovani at concentrations of 90-0.123 mug/mL. Results Two iridoid glycosides harpagide (1) and 8-O-acetylharpagide (2), three o-coumaric acid derivatives cis-melilotoside (3), Trans-Melilotoside (4) and dihydromelilotoside (5), two phenylethanoid glycosides verbascoside (6) and galactosylmartynoside (7) and a flavone-C-glycoside, isoorientin (8) were isolated. Many compounds showed moderate to good antiparasitic activity, with isoorientin (8) displaying the most significant antimalarial potential (an IC50 value of 9.7 mug/mL). Discussion and conclusion This is the first report on the antiprotozoal evaluation of A. laxmannii extracts and isolates. Furthermore, isoorientin and dihydromelilotoside are being reported for the first time from the genus Ajuga.
Major constituents and cytotoxic effects of Ajuga chamaecistus ssp. tomentella.[Pubmed:22888532]
Z Naturforsch C. 2012 May-Jun;67(5-6):275-81.
The n-butanolic fraction of a methanolic extract (80%) from aerial parts of Ajuga chamaecistus ssp. tomentella was analysed using different chromatographic methods. Column (CC) and high-performance liquid chromatography (HPLC) were used for isolation and purification. 13C, H NMR, H-H COSY, HSQC, HMBC, and ESI-MS were employed for identification of the compounds isolated from this fraction. The structures of the compounds were determined to be cis-melilotoside (1), Trans-Melilotoside (2), lavandulifolioside (3), 20-hydroxyecdysone (4), leonoside B (5), martynoside (6), ajugalactone (7), makisterone A (8), and 24-dehydroprecyasterone (9). This is the first report on the presence of cis- and Trans-Melilotoside in Ajuga species. Cytotoxic evaluation of the n-butanolic fraction, cis- and Trans-Melilotoside against cancer (T47D, HT-29, and Caco-2) and normal (NIH 3T3) cell lines by the mitochondrial tetrazolium test (MTT) showed no cytotoxic effects up to 400 microg/mL. The results of this study suggest that melilotoside, phenylethyl glycosides, and phytoecdysteroids are the main constituents of the n-butanolic fraction of Ajuga chamaecistus ssp. tomentella.
[Chemical constituents of Phymatopteris hastate and their antioxidant activity].[Pubmed:22860450]
Zhongguo Zhong Yao Za Zhi. 2012 May;37(10):1402-7.
OBJECTIVE: To study chemical constituents contained in Phymatopteris hastate and their antioxidant activity. METHOD: Chemical constituents were separated and purified from P. hastate by using such methods as silica gel, Toyopearl HW-40C and HPLC preparative chromatography. Their structures were identified by spectroscopic methods such as NMR. Furthermore, 1, 1-diphenyl-2-picryl-hydrazyl(DPPH) method was used to assess the antioxidant activity of each compound. RESULT: Fourteen compounds were separated and identified as 4-O-beta-D-glucopyranosyl-ethyl-trans-caffeicate (1), kaempferlo-7-O-alpha-L-rhamnopyranside (2), kaempferol-3, 7-di-O-alpha-L-rhamnopyranoside (3), kaempferol-3-O-alpha-L-arabinofuranosyl-7-O-alpha-L-rhamnopyranoside (4), juglanin (5), naringin (6), naringenin-7-O-beta-D-glucopyranoside (7), trans-caffeic acid (8), trans-caffeic acid-3-O-beta-D-glucopyranoside (9), trans-cinnamic acid-4-O-beta-D- glucopyranoside (10), Trans-Melilotoside (11), cis-melilotoside (12), ethyl chlorogenate (13), protocatechuic acid (14). The antioxidation experiment showed an obvious antioxidant activity in compounds 1-9, 13-14. CONCLUSION: All of the compounds were separated from this genus for the first time. Among them, compound 1 was not seen in literature reports and assumed to be a new artifact derived from compound 9 and ethanol. Compounds 1-9, 13-14 showed a remarkable antioxidant activity.
High-performance liquid chromatography-diode array detection/electrospray ionization mass spectrometry for the simultaneous analysis of cis-, trans- and dihydro-2-glucosyloxycinnamic acid derivatives from Dendrobium medicinal plants.[Pubmed:17497625]
Rapid Commun Mass Spectrom. 2007;21(12):1833-40.
Sensitive, selective and reliable high-performance liquid chromatography (HPLC)-diode array detection (DAD)/electrospray ionization multi-stage mass spectrometry (ESI-MSn) methods have been developed for the characterization of nine 2-glucosyloxycinnamic acid derivatives and quantitative analysis of three of the major 2-glucosyloxycinnamic acids, cis-melilotoside, Trans-Melilotoside and dihydromelilotoside, present in Dendrobium medicinal plants. The identities of the latter three major 2-glucosyloxycinnamic acids were confirmed by comparing their retention times, UV and mass spectra with those of the reference standards. The characteristic ESI-MSn fragmentation patterns of the remaining six 2-glucosyloxycinnamic acid derivatives, which are similar to the three major compounds, have allowed the putative elucidation of their structures. The concentrations of the cis-, trans- and dihydromelilotosides were simultaneously determined by HPLC/ESI-MS2 using the multiple reaction monitoring (MRM) mode in extracts of Dendrobium species. The method was validated with respect to the overall intra- and inter-day variation (RSD less than 8%) and the limits of quantification for the cis-, trans- and dihydromelilotosides were 0.09, 0.09 and 0.01 microg/mL, respectively.
Bio-guided isolation of antioxidants from the stems of Dendrobium aurantiacum var. denneanum.[Pubmed:17421059]
Phytother Res. 2007 Jul;21(7):696-8.
Bio-guided fractionation of the stems of Dendrobium aurantiacum var. denneanum using a 1,1-diphenyl-2-picryl-hydrazyl (DPPH) radical scavenging assay, led to the isolation of three 2-glucosyloxycinnamic acid derivates, namely, cis-melilotoside, Trans-Melilotoside and dihydromelilotoside, respectively. Their structures were elucidated through the analysis of uni- and bi-dimensional NMR, UV, IR and MS data. All these three compounds were first reported from the genus Dendrobium and exhibited potent antioxidant activities.
