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Ardisicrenoside A

CAS# 160824-52-2

Ardisicrenoside A

Catalog No. BCN8824----Order now to get a substantial discount!

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Quality Control of Ardisicrenoside A

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Chemical structure

Ardisicrenoside A

3D structure

Chemical Properties of Ardisicrenoside A

Cas No. 160824-52-2 SDF Download SDF
PubChem ID 10260582 Appearance Powder
Formula C53H88O22 M.Wt 1077.3
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (2S,3R,4R,5R,6S)-2-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[(3S,4S,5R,6S)-4-hydroxy-6-[[(1S,2R,4S,5R,8R,10S,13R,14R,17S,18R,20S)-2-hydroxy-20-(hydroxymethyl)-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosan-10-yl]oxy]-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
SMILES CC1C(C(C(C(O1)OC2C(C(C(OC2OC3COC(C(C3O)OC4C(C(C(C(O4)CO)O)O)O)OC5CCC6(C(C5(C)C)CCC7(C6CCC89C7(CC(C1(C8CC(CC1)(C)CO)CO9)O)C)C)C)CO)O)O)O)O)O
Standard InChIKey LTTSWSWZQNISIB-LLEYBADXSA-N
Standard InChI InChI=1S/C53H88O22/c1-23-32(58)36(62)39(65)43(69-23)75-42-38(64)34(60)25(19-55)71-46(42)72-26-20-67-45(41(35(26)61)74-44-40(66)37(63)33(59)24(18-54)70-44)73-31-10-11-49(5)27(47(31,2)3)8-12-50(6)28(49)9-13-53-29-16-48(4,21-56)14-15-52(29,22-68-53)30(57)17-51(50,53)7/h23-46,54-66H,8-22H2,1-7H3/t23-,24+,25+,26-,27-,28+,29+,30+,31-,32-,33+,34+,35-,36+,37-,38-,39+,40+,41+,42+,43-,44-,45-,46-,48-,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 Ardisicrenoside A

The herbs of Ardisia crenata.

Biological Activity of Ardisicrenoside A

In vitro

Two new resorcinol derivatives with strong cytotoxicity from the roots of Ardisia brevicaulis Diels.[Pubmed: 21162003 ]

Chem Biodivers. 2010 Dec;7(12):2901-7.


METHODS AND RESULTS:
Two new resorcinol derivatives, 4-hydroxy-2-methoxy-6-[(8Z)-pentadec-8-en-1-yl]phenyl acetate (1) and 4-hydroxy-2-methoxy-6-pentadecylphenyl acetate (2), together with known compounds ardisiphenol D (3), 5-tridecylresorcinol (4), 5-pentadecylresorcinol (5), 5-[(8Z)-pentadec-8-en-1-yl]resorcinol (6), belamcandaquinones C and D (7 and 8, resp.), Ardisicrenoside A, ardisiacrispin B, (22E)-24-ethyl-5α-cholesta-7,22-dien-3-one, and (22E)-24-ethyl-5α-cholesta-7,22-dien-3β-ol were isolated from the MeOH extract of the roots of Ardisia brevicaulis Diels. Their structures were determined by spectroscopic analysis including ESI- and EI-MS, and NMR data. Cytotoxicities of 1-4 against cell lines A549, MCF-7, and PANC-1 were tested in vitro by the MTT (=3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide) method.
CONCLUSIONS:
Compounds 1-4 showed cytotoxic activity against all cell lines stronger than that of cisplatin against A549.

Protocol of Ardisicrenoside A

Structure Identification
Zhongguo Zhong Yao Za Zhi. 2012 Nov;37(22):3422-5.

Chemical constituents of Ardisia punctata.[Pubmed: 23373214]

To study chemical constituents of Ardisia punctata,in order to find pioneering compounds.
METHODS AND RESULTS:
95% ethanol extracts of A. punctata was separated and purified by using normal phase silica gel column chromatographies, Sephadex LH-20 gel column chromatography and high-pressure preparative HPLC,and their structures were identified by such spectroscopic techniques as NMR and MS. Eight compounds were separated from 95% ethanol extract of A. punctata and identified as 6-methoxy-8-hydroxy-benzoic acid butylester-5-O-beta-D-glucoside (1), aridisiacrispin B (2), Ardisicrenoside A (3), dibutyl phthalate (4), bergenin (5), quercetin-3-O-alpha-L-rhamnoside (6),3-methoxy-4-acetoxy-6-tridecyl-phenol(7) and belamcandaquinone C(8).
CONCLUSIONS:
Compound 1 was a new compound, and compounds 4 and 6 were separated from this plant for the first time.

Ardisicrenoside A Dilution Calculator

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Ardisicrenoside A Molarity Calculator

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Preparing Stock Solutions of Ardisicrenoside A

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 0.9282 mL 4.6412 mL 9.2825 mL 18.5649 mL 23.2062 mL
5 mM 0.1856 mL 0.9282 mL 1.8565 mL 3.713 mL 4.6412 mL
10 mM 0.0928 mL 0.4641 mL 0.9282 mL 1.8565 mL 2.3206 mL
50 mM 0.0186 mL 0.0928 mL 0.1856 mL 0.3713 mL 0.4641 mL
100 mM 0.0093 mL 0.0464 mL 0.0928 mL 0.1856 mL 0.2321 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 Ardisicrenoside A

[Chemical constituents of Ardisia punctata].[Pubmed:23373214]

Zhongguo Zhong Yao Za Zhi. 2012 Nov;37(22):3422-5.

OBJECTIVE: To study chemical constituents of Ardisia punctata,in order to find pioneering compounds. METHOD: 95% ethanol extracts of A. punctata was separated and purified by using normal phase silica gel column chromatographies, Sephadex LH-20 gel column chromatography and high-pressure preparative HPLC,and their structures were identified by such spectroscopic techniques as NMR and MS. RESULT: Eight compounds were separated from 95% ethanol extract of A. punctata and identified as 6-methoxy-8-hydroxy-benzoic acid butylester-5-O-beta-D-glucoside (1), aridisiacrispin B (2), Ardisicrenoside A (3), dibutyl phthalate (4), bergenin (5), quercetin-3-O-alpha-L-rhamnoside (6),3-methoxy-4-acetoxy-6-tridecyl-phenol(7) and belamcandaquinone C(8). CONCLUSION: Compound 1 was a new compound, and compounds 4 and 6 were separated from this plant for the first time.

Two new resorcinol derivatives with strong cytotoxicity from the roots of Ardisia brevicaulis Diels.[Pubmed:21162003]

Chem Biodivers. 2010 Dec;7(12):2901-7.

Two new resorcinol derivatives, 4-hydroxy-2-methoxy-6-[(8Z)-pentadec-8-en-1-yl]phenyl acetate (1) and 4-hydroxy-2-methoxy-6-pentadecylphenyl acetate (2), together with known compounds ardisiphenol D (3), 5-tridecylresorcinol (4), 5-pentadecylresorcinol (5), 5-[(8Z)-pentadec-8-en-1-yl]resorcinol (6), belamcandaquinones C and D (7 and 8, resp.), Ardisicrenoside A, ardisiacrispin B, (22E)-24-ethyl-5alpha-cholesta-7,22-dien-3-one, and (22E)-24-ethyl-5alpha-cholesta-7,22-dien-3beta-ol were isolated from the MeOH extract of the roots of Ardisia brevicaulis Diels. Their structures were determined by spectroscopic analysis including ESI- and EI-MS, and NMR data. Cytotoxicities of 1-4 against cell lines A549, MCF-7, and PANC-1 were tested in vitro by the MTT (=3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide) method. Compounds 1-4 showed cytotoxic activity against all cell lines stronger than that of cisplatin against A549.

[Chemical constituents from roots of Ardisia punctata].[Pubmed:16780159]

Zhongguo Zhong Yao Za Zhi. 2006 Apr;31(7):562-5.

OBJECTIVE: To study the chemical constituents from the roots of Ardisia punctata. METHOD: Compounds were isolated by chromatographic techniques on silica gel and Rp-HPLC column. Their structures were elucidated by chemical and spectroscopic methods. RESULT: Twelve compounds were identified as 3-hydroxy-5-tridecyl-methyl phenyl ether (1), 5-pentadecyl-1, 3-benzenediol (2), 2-methoxy-6-tridecyl-1, 4-benzoquinone (3), 2-methoxy-6-pentadecyl-1, 4-benzoquinone (4), glutinol (5), Ardisicrenoside A (6), ardisiacrispin B (7), 24-ethyl-5a-cholesta-7, 22(E)-dien-3-one (8), 24-ethyl-5alpha-cholesta-7, 22(E)-dien-3beta-ol (9), daucosterol (10), vanillin acid (11), tetratriacontanoic acid (12). CONCLUSION: All the compounds were obtained from this plant for the first time.

Triterpenoid saponins from Ardisia crenata.[Pubmed:7765756]

Phytochemistry. 1994 Nov;37(5):1389-96.

Two novel triterpenoid saponins, Ardisicrenoside A [3 beta-O-(alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-glucopyranosyl- (1-->4)-[beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)- 13 beta,28-epoxy-16 alpha,30-oleananediol] and ardisicrenoside B [3 beta-O-(beta-D-xylopyranosyl-(1-->2)-[beta-D- glucopyranosyl-(1-->4)-[beta-D-glucopyranosyl-(1-->2)]- alpha-L-arabinopyranosyl)-13 beta,28-epoxy-16 alpha,30-oleananediol] were isolated from the roots of Ardisia crenata. Two known triterpenoid saponins, ardisiacrispins A and B were also isolated from this source. Their structures were determined mainly by 2D NMR (COSY, HOHAHA, HETCOR, HMBC and ROESY) experiments. The aglycones are the new 13 beta,28-epoxy-3 beta,16 alpha,30-oleananetriol for ardisicrenosides A and B.

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