Dipsacoside B

CAS# 33289-85-9

Dipsacoside B

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Quality Control of Dipsacoside B

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Chemical structure

Dipsacoside B

3D structure

Chemical Properties of Dipsacoside B

Cas No. 33289-85-9 SDF Download SDF
PubChem ID 3084573 Appearance White powder
Formula C53H86O22 M.Wt 1075.2
Type of Compound Triterpenoids Storage Desiccate at -20°C
Synonyms Glycoside L-G3; Tauroside G3; Tauroside St-G3
Solubility Soluble in methanol and pyridine; insoluble in water
Chemical Name [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl] (4aS,6aS,6bR,9R,10S,12aR)-10-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
SMILES CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C(C3(C)CO)CCC5(C4CC=C6C5(CCC7(C6CC(CC7)(C)C)C(=O)OC8C(C(C(C(O8)COC9C(C(C(C(O9)CO)O)O)O)O)O)O)C)C)C)O)O)O)O)O
Standard InChIKey GFPLPBCJRRNZHM-AYFSCGOGSA-N
Standard InChI InChI=1S/C53H86O22/c1-23-32(57)36(61)40(65)44(70-23)74-42-33(58)26(56)20-68-46(42)73-31-11-12-49(4)29(50(31,5)22-55)10-13-52(7)30(49)9-8-24-25-18-48(2,3)14-16-53(25,17-15-51(24,52)6)47(67)75-45-41(66)38(63)35(60)28(72-45)21-69-43-39(64)37(62)34(59)27(19-54)71-43/h8,23,25-46,54-66H,9-22H2,1-7H3/t23-,25?,26-,27+,28+,29?,30?,31-,32-,33-,34+,35+,36+,37-,38-,39+,40+,41+,42+,43+,44-,45-,46-,49-,50-,51+,52+,53-/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 Dipsacoside B

The flowerbuds of Lonicera confusa DC.

Biological Activity of Dipsacoside B

DescriptionDipsacoside B shows strong antimicrobial activity (MIC values 1.80-2.50 μg/mL).
TargetsAntifection
In vitro

Biologically active triterpenoids from Cephalaria ambrosioides.[Pubmed: 19152225 ]

Planta Med. 2009 Feb;75(2):163-7.


METHODS AND RESULTS:
The roots of Cephalaria ambrosioides yielded a new triterpene, 6alpha-hydroxyhederagenic acid ( 1), in addition to the known triterpene hederagenic acid ( 2) and four corresponding saponins, leontoside A (or akeboside Stb) ( 3), kalopanax saponin A (or alpha-hederin) ( 4), saponin PG (or sapindoside B) ( 5), and Dipsacoside B ( 6). Their structures have been elucidated on the basis of their spectral data (MS, 1 D and 2 D NMR) and by some chemical transformations. The extract and all isolated compounds were evaluated for their antimicrobial, molluscicidal and IN VITRO cytotoxic activities.
CONCLUSIONS:
All compounds showed strong antimicrobial activity (MIC values 1.80 - 2.50 microg/mL), with 5 and 6 exhibiting activities comparable to those of standard antibiotics. Moreover, compounds 3 - 5 were active against all assayed cancer cell lines, whereas compounds 3 and 4 exhibited higher activities against Biomphalaria Glabrata snails, with minimum inhibitory concentrations of 5.4 and 6.2 microg/mL, respectively.

Protocol of Dipsacoside B

Structure Identification
Zhongguo Zhong Yao Za Zhi. 2013 Mar;38(5):762-7.

Research on quality standards of zhuang medicine Lonicerae dasystylae flos[Pubmed: 23724691]

To establish quality standard of Zhuang medicine Lonicera dasystyla, and provide scientific basis for the quality control of L. dasystyla.
METHODS AND RESULTS:
Characteristics of materia medica, microscopic features, TLC indentification, inspection, extractum and determination of chlorogenic acid, macranthoidin B, Dipsacoside B were carried out through the experience, microscopic, physical and chemical methods, respectively. The standard of quality control was formulated thereafter. The characteristics of materia medica, microscopic features, TLC indentification were specified, the average contents of water, total ash, acid-insoluble ash, alcohol-soluble extracts, chlorogenic acid were 11.6%, 6.6%, 0.2% , 24.4%, 1.16%, respectively, the total amount of macranthoidin B and Dipsacoside B was 3.13%. Quality standard of L. dasystyla was proposed according to experimental results.
CONCLUSIONS:
The quality of L. dasystyla can be controlled effectively with the quality standard.

Dipsacoside B Dilution Calculator

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Dipsacoside B Molarity Calculator

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Preparing Stock Solutions of Dipsacoside B

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 0.9301 mL 4.6503 mL 9.3006 mL 18.6012 mL 23.2515 mL
5 mM 0.186 mL 0.9301 mL 1.8601 mL 3.7202 mL 4.6503 mL
10 mM 0.093 mL 0.465 mL 0.9301 mL 1.8601 mL 2.3251 mL
50 mM 0.0186 mL 0.093 mL 0.186 mL 0.372 mL 0.465 mL
100 mM 0.0093 mL 0.0465 mL 0.093 mL 0.186 mL 0.2325 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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Background on Dipsacoside B

Dipsacoside B is a major bioactive saponin, which can be used as a marker.

In Vivo:A liquid chromatography-electrospray ionization-mass spectrometry method has been developed and validated for identification and quantification of four major bioactive saponins in rat plasma after oral administration of extraction of saponins from Flos Lonicerae, i.e., Macranthoidin B, Macranthoidin A, Dipsacoside B, and Macranthoside B. The retention time of Macranthoidin B, Macranthoidin A, Dipsacoside B, Macranthoside B and IS are 10.65, 12.11, 13.81, 23.31 and 5.47 min, respectively[1]. Taking Macranthoidins A, B, Dipsacoside B (saponins), sweroside (iridoids), and luteolin-7-O-d-glucoside (flavonoids) as markers, a method of ultra high performance liquid chromatography with triple quadrupole mass spectrometry is employed to determine their amounts in Lonicerae Flos, Lonicerae Japonicae Flos, and Lonicerae Japonicae Flos preparations[2].

References:
[1]. Chen CY, et al. Liquid chromatography-mass spectrometry analysis of macranthoidin B, macranthoidin A, Dipsacoside B, and macranthoside B in rat plasma for the pharmacokinetic investigation. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Jan 15;877(3):159-65. [2]. Zhang X, et al. Rapid quantitative analysis of adulterant Lonicera species in preparations of Lonicerae Japonicae Flos. J Sep Sci. 2015 Dec;38(23):4014-20.

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References on Dipsacoside B

[Research on quality standards of zhuang medicine Lonicerae dasystylae flos].[Pubmed:23724691]

Zhongguo Zhong Yao Za Zhi. 2013 Mar;38(5):762-7.

OBJECTIVE: To establish quality standard of Zhuang medicine Lonicera dasystyla, and provide scientific basis for the quality control of L. dasystyla. METHOD: Characteristics of materia medica, microscopic features, TLC indentification, inspection, extractum and determination of chlorogenic acid, macranthoidin B, Dipsacoside B were carried out through the experience, microscopic, physical and chemical methods, respectively. The standard of quality control was formulated thereafter. RESULT: The characteristics of materia medica, microscopic features, TLC indentification were specified, the average contents of water, total ash, acid-insoluble ash, alcohol-soluble extracts, chlorogenic acid were 11.6%, 6.6%, 0.2% , 24.4%, 1.16%, respectively, the total amount of macranthoidin B and Dipsacoside B was 3.13%. Quality standard of L. dasystyla was proposed according to experimental results. CONCLUSION: The quality of L. dasystyla can be controlled effectively with the quality standard.

Description

Dipsacoside B is a major bioactive saponin, which can be used as a marker.

Keywords:

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