Citrusin B

CAS# 105279-10-5

Citrusin B

2D Structure

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Citrusin B

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Chemical Properties of Citrusin B

Cas No. 105279-10-5 SDF Download SDF
PubChem ID 11972318 Appearance Powder
Formula C27H36O13 M.Wt 568.6
Type of Compound Lignans Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (2S,3R,4S,5S,6R)-2-[4-[1,3-dihydroxy-2-[4-[(E)-3-hydroxyprop-1-enyl]-2,6-dimethoxyphenoxy]propyl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES COC1=CC(=CC(=C1OC(CO)C(C2=CC(=C(C=C2)OC3C(C(C(C(O3)CO)O)O)O)OC)O)OC)C=CCO
Standard InChIKey XMGKCJUCYBLMBY-ONCYFVLKSA-N
Standard InChI InChI=1S/C27H36O13/c1-35-17-11-15(6-7-16(17)39-27-25(34)24(33)23(32)21(13-30)40-27)22(31)20(12-29)38-26-18(36-2)9-14(5-4-8-28)10-19(26)37-3/h4-7,9-11,20-25,27-34H,8,12-13H2,1-3H3/b5-4+/t20?,21-,22?,23-,24+,25-,27-/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 Citrusin B

The stems of Sambucus williamsii

Biological Activity of Citrusin B

DescriptionCitrusin B exhibits moderate in vitro inhibitory effect on tobacco mosaic virus replication with IC₅₀ values 0.26 mmol L⁻1.
In vitro

A new seco-neolignan glycoside from the root bark of Ailanthus altissima.[Pubmed: 21916771 ]

Nat Prod Res. 2012;26(15):1375-80.


METHODS AND RESULTS:
A new seco-neolignan glycoside, seco-dehydrodiconiferyl alcohol-4-O-β-D-glucopyranoside, together with eight known compounds, were obtained from the EtOH extract of the root bark of Ailanthus altissima. Their structures were elucidated based on the spectroscopic data.
CONCLUSIONS:
Three neolignan glycosides including 7,9,9'-trihydroxy-3,3',5'-trimethoxy-8-O-4'-neolignan-4-O-β-D-glucopyranoside, sonchifolignan B and Citrusin B exhibited moderate in vitro inhibitory effect on tobacco mosaic virus replication with IC₅₀ values 0.30, 0.35 and 0.26 mmol L⁻¹, respectively.

Protocol of Citrusin B

Structure Identification
Zhongguo Zhong Yao Za Zhi. 2013 Jul;38(13):2118-24.

A new lignan from stems of Sargentodoxa cuneata.[Pubmed: 24079238]

Sargentodoxae Caulis was prepared from the stems of Sargentodoxa cuneata.
METHODS AND RESULTS:
Twenty compounds from the the stems of S. cuneata collected in Huangshan Mountain, Anhui province, were isolated and purified by column chromatography on macroporous resin (HPD100), silica gel, Sephadex LH-20 and semi-preparative HPLC. Their structures were elucidated on the basis of physico-chemical properties and spectral data analyses as (7R,8S)-3,3 '-5-trimethoxy-4,9-dihydroxy-4',7-expoxy-5',8-lignan-7'-en-9'-oic acid 4-O-beta-D-glucopyranoside(1), 1-O-(vanillic acid) -6-O-vanilloyl-beta-D-glucopyranoside(2), 4-hydroxyphenylethyl-6-O-coumaroyl-beta-D-glucopyranoside(3), Citrusin B(4), cinnamoside(5), (-) -isolariciresinol 4'-O-beta-D-glucopyranoside (6), (-) -isolariciresinol 4-O-beta-D-glucopyranoside (7), 1-O-(vanillic acid) -6-(3", 5"-dimethoxy-galloyl) -beta-D-glucopyranoside (8), 4-hydroxyphenyl-ethyl-6-O-(E) -caffeoyl-beta-D-glucopyranoside (9), (-)-syringaresinol 4'-O-beta-D-glucopyranoside (10), (-)-syringaresinol di-O-beta-D-glucopyranoside (11), aegineoside (12), calceolarioside B (13), 4-hydroxy-3-methoxy-acetophenone-4-O-alpha-L-rhamnopyranosyl-(1 --> 6)-beta-D-glucopyranoside (14), 4-hydroxy-3-methoxy-acetophenone-4-O-beta-D-apiofuranosyl-(1 --> 6) -beta-D-glucopyranoside (15), (-) -epicatechin (16), salidroside (17), 3,4-dihydroxy-phenyl ethyl-beta-D-glucopyranoside (18), chlorogenic acid (19) and protocatechuic acid (20).
CONCLUSIONS:
Compound 1 was a new compound and compounds 2-7 were isolated from this plant for the first time.

Citrusin B Dilution Calculator

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Preparing Stock Solutions of Citrusin B

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.7587 mL 8.7935 mL 17.5871 mL 35.1741 mL 43.9676 mL
5 mM 0.3517 mL 1.7587 mL 3.5174 mL 7.0348 mL 8.7935 mL
10 mM 0.1759 mL 0.8794 mL 1.7587 mL 3.5174 mL 4.3968 mL
50 mM 0.0352 mL 0.1759 mL 0.3517 mL 0.7035 mL 0.8794 mL
100 mM 0.0176 mL 0.0879 mL 0.1759 mL 0.3517 mL 0.4397 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 Citrusin B

[Chemical constituents from whole plants of Aconitum tanguticum].[Pubmed:24380304]

Zhongguo Zhong Yao Za Zhi. 2013 Sep;38(17):2818-25.

Nineteen compounds were isolated from the whole plants of Aconitum tanguticum by means of various of chromatographic techniques such as silica gel, ODS, sephadex LH-20 and preparative HPLC, and their structures were elucidated as syringin (1), vanillic acid-4-O-beta-D-allopyranoside (2), (E) -ferulic acid 4-O-beta-D-allopyranoside (3), (E) -ferulic acid-4-O-beta-glucopysoside (4), (E) -sinapic acid-4-O-beta-glucopyranoside (5), (E) 4-hydroxycinnamyl alcohol 4-O-beta-D-glucopyranoside (6), quercetin 3-O-alpha-L-rhamnopyranosyl-(1 --> 2) -[alpha-L-rhamnopyranosyl-(1 --> 6)] -beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (7), kaempferol 3-O-alpha-L-rhamnopyranosyl-(1 --> 2) - [alpha-L-rhamnopyranosyl-(1 --> 6)] -beta-D-galactopyranside-7-O-alpha-L-rhamnopyranoside (8), quercetin 3-O-alpha-L-rhamnopyranosyl-(1 --> 6) -beta-D-glucopyranoside-7-O-alpha-L-rhamnopyranoside (9), kaempferol 3-O-[beta-D-glucopyranosyl-(1 --> 3)-(4-O-trans-p-coumaroyl) ] -alpha-L-rhamnopyranosyl-(1 --> 6) -beta-D-galactopyranside-7-O-alpha-L-rhamnopyranoside (10), quercetin 3-O- [beta-D-glucopyranosyl-(1 --> 3 ) -(4-O-trans-p-coumaroyl)] -alpha-L-rhamnopyranosyl-(1--> 6) -beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (11), salidroside (12), 2-(3,4-dihydroxyphenyl) ethanol 1-O-beta-D-glucopyranoside (13), (7S, 8R) -dehydrodiconiferyl alcohol-9'-O-beta-D-glucopyranoside (14), Citrusin B (15), heteratisine (16), tanaconitine (17), shanzhiside methyl ester (18) and icariside B1 (19). Except compounds 4, 13, 16 and 17, the other compounds were separated from the species for the first time.

[A new lignan from stems of Sargentodoxa cuneata].[Pubmed:24079238]

Zhongguo Zhong Yao Za Zhi. 2013 Jul;38(13):2118-24.

Sargentodoxae Caulis was prepared from the stems of Sargentodoxa cuneata. Twenty compounds from the the stems of S. cuneata collected in Huangshan Mountain, Anhui province, were isolated and purified by column chromatography on macroporous resin (HPD100), silica gel, Sephadex LH-20 and semi-preparative HPLC. Their structures were elucidated on the basis of physico-chemical properties and spectral data analyses as (7R,8S)-3,3 '-5-trimethoxy-4,9-dihydroxy-4',7-expoxy-5',8-lignan-7'-en-9'-oic acid 4-O-beta-D-glucopyranoside(1), 1-O-(vanillic acid) -6-O-vanilloyl-beta-D-glucopyranoside(2), 4-hydroxyphenylethyl-6-O-coumaroyl-beta-D-glucopyranoside(3), Citrusin B(4), cinnamoside(5), (-) -isolariciresinol 4'-O-beta-D-glucopyranoside (6), (-) -isolariciresinol 4-O-beta-D-glucopyranoside (7), 1-O-(vanillic acid) -6-(3", 5"-dimethoxy-galloyl) -beta-D-glucopyranoside (8), 4-hydroxyphenyl-ethyl-6-O-(E) -caffeoyl-beta-D-glucopyranoside (9), (-)-syringaresinol 4'-O-beta-D-glucopyranoside (10), (-)-syringaresinol di-O-beta-D-glucopyranoside (11), aegineoside (12), calceolarioside B (13), 4-hydroxy-3-methoxy-acetophenone-4-O-alpha-L-rhamnopyranosyl-(1 --> 6)-beta-D-glucopyranoside (14), 4-hydroxy-3-methoxy-acetophenone-4-O-beta-D-apiofuranosyl-(1 --> 6) -beta-D-glucopyranoside (15), (-) -epicatechin (16), salidroside (17), 3,4-dihydroxy-phenyl ethyl-beta-D-glucopyranoside (18), chlorogenic acid (19) and protocatechuic acid (20). Compound 1 was a new compound and compounds 2-7 were isolated from this plant for the first time.

[One new lignan glycoside from whole plants of Senecio chrysanthemoides].[Pubmed:22032139]

Zhongguo Zhong Yao Za Zhi. 2011 Jul;36(13):1755-62.

OBJECTIVE: To investigate the chemical constituents from the whole plants of Senecio chrysanthemoides. METHOD: Constituents were isolated by using a combination of various chromatographic techniques including column chromatography over silica gel, Sephadex LH-20, and ODS C18, as well as reversed-phase HPLC. Structures of the isolates were identified by spectroscopic and chemical methods. RESULT: Eighteen glycosides were obtained from a H2O-soluble portion of an ethanolic extract of the whole plants of Senecio chrysanthemoides and their structures were elucidated as 5'-methoxyligusinenoside B (1), hyuganoside III b (2), citrusin A (3), alaschanioside A (4), Citrusin B (5), dehydrodieoniferyl alcohol 4, gamma'-di-O-beta-D-glucopyranoside (6), osmanthuside G (7), syringin (8), dehydrosyringin (9), 2-(4-hydroxy-3,5-dimethoxyphenyl) ethanol 4-O-beta-D-glucopyranoside (10), 2-phenylethyl beta-gentiobioside (11), phenethyl beta-D-glucopyranoside (12), nikoenoside (13), benzyl beta-D-glucopyranoyl (1 --> 6 ) -beta-D-glucopyranoside (14), 3,5-dimethoxy-4-hydroxybenzyl alcohol 4-O-beta-D-glucopyranoside (15), icariside B2 (16), sonchuionoside C (17), and 1-[(beta-D-glucopyranosyloxy) methyl] -5,6-dihydropyrrolizin-7-one (18). CONCLUSION: Compound 1 was a new lignan glycoside, and the remaining compounds were obtained from this plant for the first time.

A new seco-neolignan glycoside from the root bark of Ailanthus altissima.[Pubmed:21916771]

Nat Prod Res. 2012;26(15):1375-80.

A new seco-neolignan glycoside, seco-dehydrodiconiferyl alcohol-4-O-beta-D-glucopyranoside, together with eight known compounds, were obtained from the EtOH extract of the root bark of Ailanthus altissima. Their structures were elucidated based on the spectroscopic data. Three neolignan glycosides including 7,9,9'-trihydroxy-3,3',5'-trimethoxy-8-O-4'-neolignan-4-O-beta-D-glucopyranoside, sonchifolignan B and Citrusin B exhibited moderate in vitro inhibitory effect on tobacco mosaic virus replication with IC(5)(0) values 0.30, 0.35 and 0.26 mmol L(-)(1), respectively.

[Studies on phenylpropanoids from herbs of Eriophyton wallichii].[Pubmed:19216160]

Zhongguo Zhong Yao Za Zhi. 2008 Nov;33(22):2636-9.

OBJECTIVE: To study the chemical constituents of Eriophyton wallichii. METHOD: Compounds were separated and purified by column chromatographic methods, and their structures were elucidated by spectroscopic methods. RESULT: Eight phenylpropanoids were isolated and identified as martynoside (1), leucosceptoside A (2), Citrusin B (3), (+)-dehydrodiconiferyl alcohol-4, 9-beta-D-glucopyranoside (4), liriodendrin (5), velutinoside 11[ (6), jionoside B, (7), stachysoside D (8), respectively. CONCLUSION: The eight compounds were firstly isolated from E. wallichii.

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