HaplopineCAS# 5876-17-5 |
Quality Control & MSDS
3D structure
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Number of papers citing our products
| Cas No. | 5876-17-5 | SDF | Download SDF |
| PubChem ID | 165368 | Appearance | Powder |
| Formula | C13H11NO4 | M.Wt | 245.2 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | 4,8-dimethoxy-9H-furo[2,3-b]quinolin-7-one | ||
| SMILES | COC1=C2C=CC(=O)C(=C2NC3=C1C=CO3)OC | ||
| Standard InChIKey | WXPKAFIGBNLGNT-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C13H11NO4/c1-16-11-7-3-4-9(15)12(17-2)10(7)14-13-8(11)5-6-18-13/h3-6,14H,1-2H3 | ||
| 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. | ||
| Description | 1. Haplopine shows photo-activated antimicrobial activity against S. aureus. 2. Haplopine exhibits potent melanogenesis-inhibitory activities with almost no toxicity to the cells. |
| Targets | Tyrosinase | Antifection |
Haplopine Dilution Calculator
Haplopine Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 4.0783 mL | 20.3915 mL | 40.783 mL | 81.5661 mL | 101.9576 mL |
| 5 mM | 0.8157 mL | 4.0783 mL | 8.1566 mL | 16.3132 mL | 20.3915 mL |
| 10 mM | 0.4078 mL | 2.0392 mL | 4.0783 mL | 8.1566 mL | 10.1958 mL |
| 50 mM | 0.0816 mL | 0.4078 mL | 0.8157 mL | 1.6313 mL | 2.0392 mL |
| 100 mM | 0.0408 mL | 0.2039 mL | 0.4078 mL | 0.8157 mL | 1.0196 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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Photo-activated DNA binding and antimicrobial activities of furoquinoline and pyranoquinolone alkaloids from rutaceae.[Pubmed:15229804]
Planta Med. 2004 Jun;70(6):531-5.
To find novel photo-active compounds of potential use in photochemotherapy from higher plants, photo-activated antimicrobial and DNA binding activities of the furoquinolines, skimmianine, kokusaginine, and Haplopine, and a pyranoquinolone, flindersine, from two species of Rutaceae plants were investigated. TLC overlay assays against a methichillin-resistant strain of Staphylococcus aureus and Candida albicans were employed to test antimicrobial properties. All of the tested compounds showed photo-activated antimicrobial activity against S. aureus in the order of kokusaginine > Haplopine, flindersine > skimmianine. Weaker activity was found for C. albicans. Photo-activated DNA binding activity of these compounds was investigated by a method using restriction enzymes and a specially designed 1.5 kb DNA fragment. Kokusaginine showed inhibition against all of the 16 restriction enzymes. Haplopine showed a similar inhibition pattern but the binding activity against Asc I and Sma I with restriction sequences consisting only of G and C was very weak. Skimmianine showed binding activity against Xba I, BciV I, Sal I, Pst I, Sph I and Hind III, but very weak or no activity was found for the other restriction enzymes. A pyranoquinolone, flindersine, showed no activity against any of the restriction enzymes. Photo-activated DNA binding activity of furoquinolines was therefore in the order of kokusaginine > Haplopine > skimmianine, which was the same order as their photo-activated antimicrobial activity against S. aureus. Therefore, it was concluded that DNA is one of the cellular targets for the furoquinolines to exert their biological activities, similar to psoralens. However, because flindersine showed photo-activated antimicrobial activity against S. aureus but did not show photo-activated DNA binding activity, it is clear that there are other cellular target components for this compound to exert photo-toxic activity.
In vivo and in vitro production of alkaloids by Haplophyllum patavinum.[Pubmed:11990434]
Nat Prod Lett. 2002 Apr;16(2):95-100.
A protocol for shoot induction from callus of Haplophyllum patavinum was established. Two known furoquinoline (skimmianine and Haplopine), and three quinolone (edulinine, ribalinine and isoplatydesmine) alkaloids were isolated for the first time from plant material, callus and shoot cultures of this species. The structures of these compounds have been characterised on the basis of spectroscopic evidence.
Melanogenesis-Inhibitory and Cytotoxic Activities of Limonoids, Alkaloids, and Phenolic Compounds from Phellodendron amurense Bark.[Pubmed:28425165]
Chem Biodivers. 2017 Jul;14(7).
Four limonoids, 1 - 4, five alkaloids, 5 - 9, and four phenolic compounds, 10 - 13, were isolated from a MeOH extract of the bark of Phellodendron amurense (Rutaceae). Among these, compound 13 was new, and its structure was established as rel-(1R,2R,3R)-5-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-6-methoxy-1-(methoxycarbon ylmethyl)indane-2-carboxylic acid methyl ester (gamma-di(methyl ferulate)) based on the spectrometric analysis. Upon evaluation of compounds 1 - 13 against the melanogenesis in the B16 melanoma cells induced with alpha-melanocyte-stimulating hormone (alpha-MSH), four compounds, limonin (1), noroxyhydrastinine (6), Haplopine (7), and 4-methoxy-1-methylquinolin-2(1H)-one (8), exhibited potent melanogenesis-inhibitory activities with almost no toxicity to the cells. Western blot analysis revealed that compound 6 inhibited melanogenesis, at least in part, by inhibiting the expression of protein levels of tyrosinase, TRP-1, and TRP-2 in alpha-MSH-stimulated B16 melanoma cells. In addition, when compounds 1 - 13 were evaluated for their cytotoxic activities against leukemia (HL60), lung (A549), duodenum (AZ521), and breast (SK-BR-3) cancer cell lines, five compounds, berberine (5), 8, canthin-6-one (9), alpha-di-(methyl ferulate) (12), and 13, exhibited cytotoxicities against one or more cancer cell lines with IC50 values in the range of 2.6 - 90.0 mum. In particular, compound 5 exhibited strong cytotoxicity against AZ521 (IC50 2.6 mum) which was superior to that of the reference cisplatin (IC50 9.5 mum).
