Marmin

CAS# 14957-38-1

Marmin

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Quality Control of Marmin

Number of papers citing our products

Chemical structure

Marmin

3D structure

Chemical Properties of Marmin

Cas No. 14957-38-1 SDF Download SDF
PubChem ID 6450230 Appearance Powder
Formula C19H24O5 M.Wt 332.4
Type of Compound Coumarins Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 7-[(E,6R)-6,7-dihydroxy-3,7-dimethyloct-2-enoxy]chromen-2-one
SMILES CC(=CCOC1=CC2=C(C=C1)C=CC(=O)O2)CCC(C(C)(C)O)O
Standard InChIKey QYYKWTUUCOTGNS-JIIJFUIFSA-N
Standard InChI InChI=1S/C19H24O5/c1-13(4-8-17(20)19(2,3)22)10-11-23-15-7-5-14-6-9-18(21)24-16(14)12-15/h5-7,9-10,12,17,20,22H,4,8,11H2,1-3H3/b13-10+/t17-/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.
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.
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.

Source of Marmin

The herbs of Citrus maxima

Biological Activity of Marmin

Description1. Marmin can inhibit contraction of the guinea-pig tracheal smooth muscle, especially by interfering histamine receptor, inhibiting the histamine release from mast, inhibiting intracellular Ca2+ release from the intracellular store and the Ca2+ influx through voltage-dependent Ca2+ channels. 2. Marmin, skimmianine, aegeline, aurapten, zeorin, and dustanin are potential to develop as antihistamine agents, especially as histamine H1 receptor antagonists by interacting with amino acid residues, Asp107, Lys179, Lys191, Asn198, and Trp428 of histamine H1 receptor. 3. S-trans-Marmin shows potent antibacterial, fungicidal, and algicidal properties. 4. Marmin shows a cell-growth inhibitory effect against L1210 and K562 in vitro. 5. Marmin and nobiletin have anti-ulcer effects, which are ascribed primarily to the maintenance of the mucosal barrier integrity and inhibition of gastric motor activity and secondarily due to the prevention of the effects of endogenous acetylcholine and histamine.
TargetsCalcium Channel | Histamine Receptor | Antifection

Marmin Dilution Calculator

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Marmin Molarity Calculator

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Preparing Stock Solutions of Marmin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.0084 mL 15.0421 mL 30.0842 mL 60.1685 mL 75.2106 mL
5 mM 0.6017 mL 3.0084 mL 6.0168 mL 12.0337 mL 15.0421 mL
10 mM 0.3008 mL 1.5042 mL 3.0084 mL 6.0168 mL 7.5211 mL
50 mM 0.0602 mL 0.3008 mL 0.6017 mL 1.2034 mL 1.5042 mL
100 mM 0.0301 mL 0.1504 mL 0.3008 mL 0.6017 mL 0.7521 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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References on Marmin

Interaction of active compounds from Aegle marmelos CORREA with histamine-1 receptor.[Pubmed:23750086]

Bioinformation. 2013 Apr 30;9(8):383-7.

UNLABELLED: The aim of this study is to determine the affinity of six active compounds of Aegle Marmelos Correa, they are (E, R)-Marmin, skimmianine, (S)-aegeline, aurapten, zeorin, and dustanin as antihistamines in histamine H1 receptor in comparison to cetirizin, diphenhydramine and chlorpheniramine as ligands comparison. Previously, in the in vitro study Marmin obviously antagonized the histamine H1 receptor in a competitive manner. METHODS: molecular docking to determine the interaction of ligand binding to its receptor. Lower docking score indicates more stable binding to that protein. RESULTS: Marmin, skimmianine, aegeline, aurapten, zeorin, and dustanin were potential to develop as antihistamine agents, especially as histamine H1 receptor antagonists by interacting with amino acid residues, Asp107, Lys179, Lys191, Asn198, and Trp428 of histamine H1 receptor. CONCLUSIONS: Based on molecular docking, Amino acid residues involved in ligand protein interactions were Asp107, Lys179, Lys191, Asn198, and Trp428.

Pharmacological profile of gastric mucosal protection by marmin and nobiletin from a traditional herbal medicine, Aurantii fructus immaturus.[Pubmed:7861659]

Jpn J Pharmacol. 1994 Sep;66(1):139-47.

We studied the effects of Marmin and nobiletin on the experimental acute gastric lesions, gastric transmucosal potential difference (PD) and gastric motor activity in rats and the contractions of isolated guinea pig ileum. Oral administration of Marmin and nobiletin inhibited both the appearance of ethanol-induced gastric hemorrhagic lesions dose-dependently in a dose range of 10-50 mg/kg, with ED50 values for Marmin and nobiletin being 17.2 and 8.0 mg/kg, respectively. However, Marmin and nobiletin had minimal effects on aspirin-induced gastric lesions at a dose of 50 mg/kg, respectively. Marmin and nobiletin had no significant influence on the basal PD. Intragastrical administration of Marmin and nobiletin at a dose of 25 mg/kg significantly prevented the PD reduction induced by ethanol. Both Marmin and nobiletin given intragastrically at 25 mg/kg significantly inhibited gastric motor activity measured as intraluminal pressure recordings. Marmin and nobiletin exhibited concentration-dependent relaxations of contractions induced by acetylcholine, transmural electrical stimulation and histamine in isolated guinea pig ileum, respectively. These findings suggest that the anti-ulcer effects of Marmin and nobiletin are ascribed primarily to the maintenance of the mucosal barrier integrity and inhibition of gastric motor activity and secondarily due to the prevention of the effects of endogenous acetylcholine and histamine.

Antimicrobial coumarins from the stem bark of Afraegle paniculata.[Pubmed:20433072]

Nat Prod Commun. 2010 Apr;5(4):559-61.

Eight compounds were isolated from the stem bark of the plant Afraegle paniculata. One of them, a dimethyl ether of S-trans-Marmin (1), is reported as a new natural product. The structures were determined by comprehensive analyses of their 1D and 2D NMR spectroscopic and HREIMS data. The remaining seven known compounds, identified by comparing their spectroscopic data with those reported in the literature, were S-trans-Marmin (2), psoralene (3), bergaptene (4), imperatorin (5), 2-(4-hydroxy-3,5-dimethoxyphenyl)-3-hydroxymethyl-2,3-dihydro- 1,4,5-trioxaphenanthren-6-one (6), xanthoxyletin (7), and beta-sitosterol glucopyranoside. Preliminary studies indicated that compounds 2, 3, 5, and 7 showed potent antibacterial, fungicidal, and algicidal properties, while 6 showed only moderate algicidal property.

[Studies on the bioactive constituents of Aurantii Fructus Immaturus].[Pubmed:8721353]

Yakugaku Zasshi. 1996 Mar;116(3):244-50.

An ethanol extract of "Kijitsu" (Aurantii Fructus Immaturus, Citrus aurantium L.) collected in China was assessed for the antitumor activity using murine leukemia P388 in vivo, and the extract was found to be active by the antitumor bioassay in vivo and in vitro. The extract was separated into a petroleum ether-soluble fraction and an ethyl acetate-soluble fraction. Fractionation was carried out using an index of cell-growth inhibitory activity against mouse leukemia L1210 cells to isolate antitumor active substances or compounds. The active compounds were purified employing silica gel column chromatography and HPLC. The antitumor effect of the isolated active compounds was studied. Five compounds, auraptene, Marmin, tangeretin, nobiretin and 5-[(6',7'-dihydroxy-3',7'-dimethyl-2-octenyl)oxy]psoralen were isolated from Citrus aurantium L. Though they are all known compounds, 5-(6',7'-dihydroxy-3',7-dimethyl-2-octenyl)oxy-psoralen from this plants was first isolated. These compounds showed a cell-growth inhibitory effect against L1210 and K562 in vitro.

Effects of marmin, a compound isolated from Aegle marmelos Correa, on contraction of the guinea pig-isolated trachea.[Pubmed:21959801]

Pak J Pharm Sci. 2011 Oct;24(4):427-33.

Marmin or 7-(6',7'-dihydroxygeranyl-oxy)coumarin is a compound isolated from Aegle marmelos Correa. In the study, we examined the effects of Marmin on the contraction of guinea pig-isolated trachea stimulated by several inducers, namely histamine, metacholine, compound 48/80. We also evaluated its action against contraction induced by extracellular or intracellular calcium ion. The possibility of Marmin to potentiate the relaxation effect of isoprenaline was also studied. Marmin added in the organ bath at 10 min prior to the agonist inhibited the contraction elicited by histamine and metacholine in a concentration-dependent manner. Moreover, Marmin antagonized the histamine-induced contraction in competitive manner. Marmin mildly potentiated the relaxation effect of isoprenaline. In the study, Marmin abrogated the contraction of tracheal smooth muscle induced by compound 48/80, an inducer of histamine release. Besides, Marmin successfully inhibited CaCl(2)-induced contraction in Ca(2+)-free Krebs solution. Marmin also inhibited two phases of contraction which were consecutively induced by metacholine and CaCl(2) in Ca(2+)-free Krebs solution. Based on the results we concluded that Marmin could inhibit contraction of the guinea-pig tracheal smooth muscle, especially by interfering histamine receptor, inhibiting the histamine release from mast, inhibiting intracellular Ca(2+) release from the intracellular store and the Ca(2+) influx through voltage-dependent Ca(2+) channels.

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