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(+)-Nortrachelogenin

CAS# 61521-74-2

(+)-Nortrachelogenin

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Chemical structure

(+)-Nortrachelogenin

3D structure

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Chemical Properties of (+)-Nortrachelogenin

Cas No. 61521-74-2 SDF Download SDF
PubChem ID 479756 Appearance Powder
Formula C20H22O7 M.Wt 374.38
Type of Compound Lignans Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (3R,4R)-3-hydroxy-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
SMILES COC1=C(C=CC(=C1)CC2COC(=O)C2(CC3=CC(=C(C=C3)O)OC)O)O
Standard InChIKey ZITBJWXLODLDRH-JLTOFOAXSA-N
Standard InChI InChI=1S/C20H22O7/c1-25-17-8-12(3-5-15(17)21)7-14-11-27-19(23)20(14,24)10-13-4-6-16(22)18(9-13)26-2/h3-6,8-9,14,21-22,24H,7,10-11H2,1-2H3/t14-,20-/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 (+)-Nortrachelogenin

The roots of Wikstroemia indica.

Biological Activity of (+)-Nortrachelogenin

Description1. (+)-Nortrachelogenin shows effects on the central nervous system producing depression in rabbits. 2. (+)-Nortrachelogenin can induce morphological deformation of P. oryzae mycelia with the MMDC value of 31.3 +/- 1.8 microM. 3. (+)-Nortrachelogenin is moderately active against HIV-1 in vitro.
TargetsHIV | Antifection

(+)-Nortrachelogenin Dilution Calculator

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(+)-Nortrachelogenin Molarity Calculator

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Preparing Stock Solutions of (+)-Nortrachelogenin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.6711 mL 13.3554 mL 26.7108 mL 53.4217 mL 66.7771 mL
5 mM 0.5342 mL 2.6711 mL 5.3422 mL 10.6843 mL 13.3554 mL
10 mM 0.2671 mL 1.3355 mL 2.6711 mL 5.3422 mL 6.6777 mL
50 mM 0.0534 mL 0.2671 mL 0.5342 mL 1.0684 mL 1.3355 mL
100 mM 0.0267 mL 0.1336 mL 0.2671 mL 0.5342 mL 0.6678 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 (+)-Nortrachelogenin

Antiausterity activity of arctigenin enantiomers: importance of (2R,3R)-absolute configuration.[Pubmed:24660468]

Nat Prod Commun. 2014 Jan;9(1):79-82.

From a MeOH extract of powdered roots of Wikstroemia indica, six dibenzyl-gamma-butyrolactone-type lignans with (2S,3S)-absolute configuration [(+)-arctigenin (1), (+)-matairesinol (2), (+)-trachelogenin (3), (+)-Nortrachelogenin (4), (+)-hinokinin (5), and (+)-kusunokinin (6)] were isolated, whereas three dibenzyl-gamma-butyrolactone-type lignans with (2R,3R)-absolute configuration [(-)-arctigenin (1*), (-)-matairesinol (2*), (-)-trachelogenin (3*)] were isolated from Trachelospermum asiaticum. The in vitro preferential cytotoxic activity of the nine compounds was evaluated against human pancreatic PANC-1 cancer cells in nutrient-deprived medium (NDM), but none of the six lignans (1-6) with (2S,3S)-absolute configuration showed preferential cytotoxicity. On the other hand, three lignans (1*-3*) with (2R,3R)-absolute configuration exhibited preferential cytotoxicity in a concentration-dependent manner with PC50 values of 0.54, 6.82, and 5.85 microM, respectively. Furthermore, the effect of (-)- and (+)-arctigenin was evaluated against the activation of Akt, which is a key process in the tolerance to nutrition starvation. Interestingly, only (-)-arctigenin (1*) strongly suppressed the activation of Akt. These results indicate that the (2R,3R)-absolute configuration of (-)-enantiomers should be required for the preferential cytotoxicity through the inhibition of Akt activation.

New guaian-type sesquiterpene from Wikstroemia indica.[Pubmed:24660446]

Nat Prod Commun. 2014 Jan;9(1):1-2.

From a MeOH extract of powdered roots of Wikstroemia indica, we isolated a new guaian-type sesquiterpene (1) and two known guaian-type sesquiterpenes [oleodaphnal (2), 1alpha,7alpha,10alphaH-guaia-4,11-dien-3-one (3)], together with twelve known compounds: (+)-arctigenin, (+)-matairesinol, (+)-trachelogenin, (+)-Nortrachelogenin, (+)-hinokinin, (+)-kusunokinin, 7-methoxycoumarin, 7-hydroxycoumarin (umbelliferone), daphnogitin, daphnoretin, salicifoliol, and (-)-pinoresinol. The structure of compound 1 was determined to be 4,10,11-guaiatrien-3-one-14-oic acid, by the analyses of spectral data.

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