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Episyringaresinol

CAS# 51152-20-6

Episyringaresinol

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Chemical structure

Episyringaresinol

3D structure

Chemical Properties of Episyringaresinol

Cas No. 51152-20-6 SDF Download SDF
PubChem ID 12309694 Appearance Powder
Formula C22H26O8 M.Wt 418.44
Type of Compound Lignans Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 4-[(3R,3aR,6S,6aR)-6-(4-hydroxy-3,5-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxyphenol
SMILES COC1=CC(=CC(=C1O)OC)C2C3COC(C3CO2)C4=CC(=C(C(=C4)OC)O)OC
Standard InChIKey KOWMJRJXZMEZLD-GKHNXXNSSA-N
Standard InChI InChI=1S/C22H26O8/c1-25-15-5-11(6-16(26-2)19(15)23)21-13-9-30-22(14(13)10-29-21)12-7-17(27-3)20(24)18(8-12)28-4/h5-8,13-14,21-24H,9-10H2,1-4H3/t13-,14-,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 Episyringaresinol

The herbs of Kalimeris indica.

Biological Activity of Episyringaresinol

DescriptionEpisyringaresinol is a natural product from Kalimeris indica.
In vitro

Lignans and triterpenes from the root of Pseuderanthemum carruthersii var. atropurpureum.[Pubmed: 22976320]

Chem Pharm Bull (Tokyo). 2012;60(9):1125-33.


METHODS AND RESULTS:
Two new lignans, pseuderesinol (1), pseuderanoside (2) and a new triterpene, pseuderanic acid (3) were isolated from the dried root of Pseuderanthemum carruthersii (SEEM.) GUILL. var. atropurpureum (BULL.) FOSB. (Acanthaceae), together with ten known compounds, including five lignans, (+)-eudesmin (4), (+)-magnolin (5), (+)-syringaresinol (6), (+)-Episyringaresinol (7), (+)-1-hydroxysyringaresinol (8) and five triterpenes, squalene (9), oleanolic acid (10), lupeol (11), betulin (12), betulinic acid (13). Their chemical structures were elucidated by 1D- and 2D-NMR, computational quantum chemistry, as well as high resolution-electrospray ionization (HR-ESI)-MS spectroscopic analysis. The acetylcholinesterase inhibition and cytotoxic activities against HeLa and MCF-7 cancer cell lines were evaluated on some purified compounds at the concentration of 100 µg/mL.
CONCLUSIONS:
Pseuderesinol (1) and magnolin (5) exhibited moderate cytotoxic activities against the MCF-7 cancer cell line.

Protocol of Episyringaresinol

Structure Identification
Nat Prod Res. 2017 Oct;31(20):2348-2353.

Two new terpenoids from Kalimeris indica.[Pubmed: 28326842 ]


METHODS AND RESULTS:
A new nor-sesquiterpene kalimeristone A (1), a new nor-triterpenoid kalimerislactone B (2) and eight known compounds 7-hydroxy-4'methoxyisoflavone (3), Episyringaresinol (4), epipinoresinol (5), rhamnetin (6), vanillin (7), p-hydroxybenzaldehyde (8), syringic acid (9) and 3, 4-dihydroxybenzaldehyde (10) were isolated from the herbs of Kalimeris indica. The structures of these compounds were elucidated using spectroscopic techniques, such as NMR and MS.
CONCLUSIONS:
All of the compounds were isolated from this genus for the first time. The cytotoxicities against four cancer cell lines were evaluated in vitro, but were inactive.

Episyringaresinol Dilution Calculator

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Episyringaresinol Molarity Calculator

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Preparing Stock Solutions of Episyringaresinol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.3898 mL 11.9491 mL 23.8983 mL 47.7966 mL 59.7457 mL
5 mM 0.478 mL 2.3898 mL 4.7797 mL 9.5593 mL 11.9491 mL
10 mM 0.239 mL 1.1949 mL 2.3898 mL 4.7797 mL 5.9746 mL
50 mM 0.0478 mL 0.239 mL 0.478 mL 0.9559 mL 1.1949 mL
100 mM 0.0239 mL 0.1195 mL 0.239 mL 0.478 mL 0.5975 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 Episyringaresinol

[Studies on non-alkaloid constituents from Ochrosia elliptica].[Pubmed:26281589]

Zhongguo Zhong Yao Za Zhi. 2015 Apr;40(8):1508-13.

The chemical consituents from Ochrosia elliptica were separated and purified by column chromatographies on silica gel, Sephadex LH-20, ODS and RP-HPLC. The structures of the isolated compounds were identified on the basis of physicochemical properties and spectroscopic analysis, as well as comparisons with the data in the literature. 18 compounds were isolated and elucidated as (+) -pinoresinol(1), (+) -medioresinol (2), (+) -lariciresinol (3), (+) -5'-methoxy lariciresinol(4), (+) -isolariciresinol (5), syringaresinol(6), Episyringaresinol (7), ciwujiatone (8), zhebeiresinol (9), 7-hydroxycoumarin (10), 7-methoxycoumarin (11), scopoletin(12), isofraxidin(13), caffeic acid ethyl ester (14), ferulic acid (15), p-hydroxybenzaldehyde (16), vanillin (17), and vanillic acid(18). All compounds were isolated from the genus Ochrosia for the first time.

Lignans and triterpenes from the root of Pseuderanthemum carruthersii var. atropurpureum.[Pubmed:22976320]

Chem Pharm Bull (Tokyo). 2012;60(9):1125-33.

Two new lignans, pseuderesinol (1), pseuderanoside (2) and a new triterpene, pseuderanic acid (3) were isolated from the dried root of Pseuderanthemum carruthersii (SEEM.) GUILL. var. atropurpureum (BULL.) FOSB. (Acanthaceae), together with ten known compounds, including five lignans, (+)-eudesmin (4), (+)-magnolin (5), (+)-syringaresinol (6), (+)-Episyringaresinol (7), (+)-1-hydroxysyringaresinol (8) and five triterpenes, squalene (9), oleanolic acid (10), lupeol (11), betulin (12), betulinic acid (13). Their chemical structures were elucidated by 1D- and 2D-NMR, computational quantum chemistry, as well as high resolution-electrospray ionization (HR-ESI)-MS spectroscopic analysis. The acetylcholinesterase inhibition and cytotoxic activities against HeLa and MCF-7 cancer cell lines were evaluated on some purified compounds at the concentration of 100 microg/mL. Pseuderesinol (1) and magnolin (5) exhibited moderate cytotoxic activities against the MCF-7 cancer cell line.

A new lignan glycoside from Eleutherococcus senticosus.[Pubmed:11731930]

Planta Med. 2001 Nov;67(8):776-8.

A new lignan glycoside, named eleutheroside E(2) (1), has been isolated from the roots of Eleutherococcus senticosus (known as "Siberian ginseng"), along with isomaltol 3-O-alpha-D-glucopyranoside (2), eleutherosides B, E and E(1), and thymidine. The structure of 1 was established by spectral interpretations as Episyringaresinol 4"-O-beta-D-glucopyranoside. Compound 2 is described here for the first time as a naturally occurring compound.

Two new terpenoids from Kalimeris indica.[Pubmed:28326842]

Nat Prod Res. 2017 Oct;31(20):2348-2353.

A new nor-sesquiterpene kalimeristone A (1), a new nor-triterpenoid kalimerislactone B (2) and eight known compounds 7-hydroxy-4'methoxyisoflavone (3), Episyringaresinol (4), epipinoresinol (5), rhamnetin (6), vanillin (7), p-hydroxybenzaldehyde (8), syringic acid (9) and 3, 4-dihydroxybenzaldehyde (10) were isolated from the herbs of Kalimeris indica. The structures of these compounds were elucidated using spectroscopic techniques, such as NMR and MS. All of the compounds were isolated from this genus for the first time. The cytotoxicities against four cancer cell lines were evaluated in vitro, but were inactive.

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