Yangambin

CAS# 13060-14-5

Yangambin

Catalog No. BCN6706----Order now to get a substantial discount!

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Chemical structure

Yangambin

3D structure

Chemical Properties of Yangambin

Cas No. 13060-14-5 SDF Download SDF
PubChem ID 443028 Appearance Powder
Formula C24H30O8 M.Wt 446.49
Type of Compound Lignans Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (3S,3aR,6S,6aR)-3,6-bis(3,4,5-trimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan
SMILES COC1=CC(=CC(=C1OC)OC)C2C3COC(C3CO2)C4=CC(=C(C(=C4)OC)OC)OC
Standard InChIKey HRLFUIXSXUASEX-RZTYQLBFSA-N
Standard InChI InChI=1S/C24H30O8/c1-25-17-7-13(8-18(26-2)23(17)29-5)21-15-11-32-22(16(15)12-31-21)14-9-19(27-3)24(30-6)20(10-14)28-4/h7-10,15-16,21-22H,11-12H2,1-6H3/t15-,16-,21+,22+/m0/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 Yangambin

The leaves of Ocotea duckei Vattimo.

Biological Activity of Yangambin

Description1. Yangambin is a selective antagonist of the cardiovascular effects of platelet activating factor (PAF) and therefore constitutes a potential therapeutic agent in different shock states where abnormal PAF release is supposed to play an important role. 2. Yangambin has central nervous system activity, it presents a depressant activity in the open field, forced swimming and pentobarbital sleeping time tests. 3. Yangambin has hypotensive effect, which is probably due to a peripheral vasodilatation that involves, at least, the inhibition the Ca2+ influx through voltage-gated Ca2+ channels.
TargetsPAFR | Calcium Channel

Yangambin Dilution Calculator

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Preparing Stock Solutions of Yangambin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.2397 mL 11.1985 mL 22.3969 mL 44.7938 mL 55.9923 mL
5 mM 0.4479 mL 2.2397 mL 4.4794 mL 8.9588 mL 11.1985 mL
10 mM 0.224 mL 1.1198 mL 2.2397 mL 4.4794 mL 5.5992 mL
50 mM 0.0448 mL 0.224 mL 0.4479 mL 0.8959 mL 1.1198 mL
100 mM 0.0224 mL 0.112 mL 0.224 mL 0.4479 mL 0.5599 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 Yangambin

Calcium influx inhibition is involved in the hypotensive and vasorelaxant effects induced by yangambin.[Pubmed:24858272]

Molecules. 2014 May 23;19(5):6863-76.

The pharmacological effects on the cardiovascular system of Yangambin, a lignan isolated from Ocotea duckei Vattimo (Lauraceae), were studied in rats using combined functional and biochemical approaches. In non-anaesthetized rats, Yangambin (1, 5, 10, 20, 30 mg/kg, i.v.) induced hypotension (-3.5 +/- 0.2; -7.1 +/- 0.8; -8.9 +/- 1.3; -14 +/- 2.3, -25.5% +/- 2.6%, respectively) accompanied by tachycardia (5.9 +/- 0.5; 5.9 +/- 1.6; 8.8 +/- 1.4; 11.6, 18.8% +/- 3.4%, respectively). In isolated rat atria, Yangambin (0.1 microM-1 mM) had very slight negative inotropic (Emax = 35.6% +/- 6.4%) and chronotropic effects (Emax = 10.2% +/- 2.9%). In endothelium-intact rat mesenteric artery, Yangambin (0.1 microM-1 mM) induced concentration-dependent relaxation (pD2 = 4.5 +/- 0.06) of contractions induced by phenylephrine and this effect was not affected by removal of the endothelium. Interestingly, like nifedipine, the relaxant effect induced by Yangambin was more potent on the contractile response induced by KCl 80 mM (pD2 = 4.8 +/- 0.05) when compared to that induced by phenylephrine. Furthermore, Yangambin inhibited CaCl2-induced contractions in a concentration-dependent manner. This lignan also induced relaxation (pD2 = 4.0 +/- 0.04) of isolated arteries pre-contracted with S(-)-Bay K 8644. In fura-2/AM-loaded myocytes of rat mesenteric arteries, Yangambin inhibited the Ca2+ signal evoked by KCl 60 mM. In conclusion, these results suggest that the hypotensive effect of Yangambin is probably due to a peripheral vasodilatation that involves, at least, the inhibition the Ca2+ influx through voltage-gated Ca2+ channels.

Central nervous system activity of yangambin from Ocotea duckei Vattimo (Lauraceae) in mice.[Pubmed:16041767]

Phytother Res. 2005 Apr;19(4):282-6.

This work presents behavioral effects of Yangambin isolated from the leaves of Ocotea duckei on open field, rota rod, barbiturate sleeping time, forced swimming and elevated plus maze test in mice. Yangambin was intraperitoneally administered to male mice at single doses of 12.5, 25 and 50 mg/kg. The results showed that Yangambin in the doses of 25 and 50 mg/kg decreased the locomotor activity and the number of rearing. However, no change was observed in the rota rod test between the Yangambin groups as compared to the control group. Reduction on the sleep latency and a prolongation of the sleeping time induced by pentobarbital was observed only with the Yangambin dose of 50 mg/kg. In the forced swimming test, Yangambin (25 and 50 mg/kg) increased the immobility time. Yangambin, in the doses of 25 and 50 mg/kg, decreased the number of entries and the time of permanence in the open arms of the elevated plus maze test. However, this effect can not be related to anxiogenic effects, but to a decrease in locomotor activity. The results showed that Yangambin presents a depressant activity in the open field, forced swimming and pentobarbital sleeping time tests. These effects probably were not due to peripheral neuromuscular blockade, since there was no alteration on the rota rod test. Also, no anxiolytic effect was observed after the treatment with Yangambin.

Antagonistic effect of yangambin on platelet-activating factor (PAF)-induced cardiovascular collapse.[Pubmed:23194622]

Phytomedicine. 1996 Jan;2(3):235-42.

The cardiovascular protective effects of Yangambin, a novel and specific naturally-occurring platelet activating factor (PAF) receptor antagonist, were investigated in the pentobarbital anesthetized and artificially ventilated rat. Yangambin (3-30 mg kg(-1)) as well as the reference PAF antagonist WEB 2086 (0.1-1.0 mg kg(-1)) prevented the circulatory collapse elicited by the intravenous administration of PAF (0.5 mug kg(-1)), in a dose-dependent manner. Yangambin did not interfere with the hypotensive effect of several endogenous vasoactive mediators such as acetylcholine, bradykinin, histamine and serotonin. Moreover, when adminstered as a post-treatment the antagonist showed the ability to reverse the cardiovascular effects induced by PAF (1.0 mug kg(-1)). The protective effect of Yangambin showed to have a duration of action of more than 2 hours. It is concluded that Yangambin is a selective antagonist of the cardiovascular effects of PAF and therefore constitutes a potential therapeutic agent in different shock states where abnormal PAF release is supposed to play an important role.

Description

Yangambin, a furofuran lignan, is already isolated from plants such as member of the Annonaceae family, including species of the genus Rollinia: R. pickeli, R. exalbidaand R. mucosa, as well from the Magnolia biondii. Yangambin, a selective PAF receptor antagonist, inhibits Ca2+ influx through voltage-gated Ca2+ channels, leading to the reduction in [Ca2+]i in vascular smooth muscle cells and consequent peripheral vasodilation. Yangambin exhibits the antiallergic activity against β-hexosaminidase release with an IC50 of 33.8 μM and for anti-inflammatory activity with an IC50 of 37.4 μM.

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