Ardisiacrispin BCAS# 112766-96-8 |
Quality Control & MSDS
3D structure
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| Cas No. | 112766-96-8 | SDF | Download SDF |
| PubChem ID | 194981 | Appearance | Powder |
| Formula | C53H86O22 | M.Wt | 1075.3 |
| Type of Compound | Triterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (2R,4S,5R,8R,10S,13R,14R,18R,20S)-10-[(2S,3R,4S,5S)-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-3-[(2S,3R,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-hydroxy-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracosane-20-carbaldehyde | ||
| 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)C=O)CO9)O)C)C)C)CO)O)O)O)O)O | ||
| Standard InChIKey | ZDIHSHLFPFGAGP-GRWMUYEGSA-N | ||
| Standard InChI | InChI=1S/C53H86O22/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/h21,23-46,54-55,57-66H,8-20,22H2,1-7H3/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. |
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| 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. |
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| 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. | ||
| Description | Ardisiacrispin B displays cytotoxic effects in multi-factorial drug resistant cancer cells via ferroptotic and apoptotic cell death. |
| Cell Research | A naturally occuring triterpene saponin ardisiacrispin B displayed cytotoxic effects in multi-factorial drug resistant cancer cells via ferroptotic and apoptotic cell death.[Pubmed: 29747757 ]Phytomedicine. 2018 Apr 1;43:78-85.Multidrug resistance of cancer cells constitutes a serious problem in chemotherapy and a challenging issue in the discovery of new cytotoxic drugs. Many saponins are known to display anti-cancer effects. In this study, the cytotoxicity and the modes of action of a naturally occuring oleanane-type tritepene saponin, Ardisiacrispin B isolated from the fruit of Ardisia kivuensis Taton (Myrsinaceae) was evaluated on a panel of 9 cancer cell lines including various sensitive and drug-resistant phenotypes.
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| Structure Identification | Phytochemistry. 1994 Nov;37(5):1389-96.Triterpenoid saponins from Ardisia crenata.[Pubmed: 7765756 ]
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Ardisiacrispin B Dilution Calculator
Ardisiacrispin B Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 0.93 mL | 4.6499 mL | 9.2997 mL | 18.5995 mL | 23.2493 mL |
| 5 mM | 0.186 mL | 0.93 mL | 1.8599 mL | 3.7199 mL | 4.6499 mL |
| 10 mM | 0.093 mL | 0.465 mL | 0.93 mL | 1.8599 mL | 2.3249 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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Cytotoxic triterpenoid saponins from Lysimachia foenum-graecum.[Pubmed:28173950]
Phytochemistry. 2017 Apr;136:165-174.
Eleven oleanane-type triterpenoid saponins, foegraecumosides A-K, and eight known ones, were isolated from the aerial parts of Lysimachia foenum-graecum. Their structures were elucidated by spectroscopic data analyses and chemical methods. All isolated saponins were evaluated for their cytotoxicity against four human cancer cell lines (NCI-H460, MGC-803, HepG2, and T24). Seven saponins containing the aglycone cyclamiretin A exhibited moderate cytotoxicity against all tested human cancer cell lines, with IC50 values of 9.3-24.5 muM. Simultaneously, the cytotoxic activities of foegraecumosides A and B, lysichriside A, ardisiacrispins A and B, cyclaminorin, and 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-beta-d-glucopyranosyl-(1 --> 4)-alpha-l-arabinopyranosyl-cyclamiretin A were tested on drug-resistant lung cancer cell lines (A549 and A549/CDDP, respectively). Ardisiacrispin B displayed moderate cytotoxicity against A549/CDDP, with an IC50 value of 8.7 muM and a resistant factor (RF) of 0.9.
A simple and rapid method to identify and quantitatively analyze triterpenoid saponins in Ardisia crenata using ultrafast liquid chromatography coupled with electrospray ionization quadrupole mass spectrometry.[Pubmed:25459939]
J Pharm Biomed Anal. 2015 Jan;102:400-8.
Ardisia plant species have been used in traditional medicines, and their bioactive constituents of 13,28-epoxy triterpenoid saponins have excellent biological activities for new drug development. In this study, a fast and simple method based on ultrafast liquid chromatography coupled to electrospray ionization mass spectrometry (UFLC-MS) was developed to simultaneously identify and quantitatively analyze triterpenoid saponins in Ardisia crenata extracts. In total, 22 triterpenoid saponins, including two new compounds, were identified from A. crenata. The method exhibited good linearity, precision and recovery for the quantitative analysis of eight marker saponins. A relative quantitative method was also developed using one major saponin (Ardisiacrispin B) as the standard to break through the choke-point of the lack of standards in phytochemical analysis. The method was successfully applied to quantitatively analyze saponins in commercially available plant samples. This study describes the first systematic analysis of 13,28-epoxy-oleanane-type triterpenoid saponins in the genus Ardisia using LC-ESI-MS. The results can provide the chemical support for further biological studies, phytochemotaxonomical studies and quality control of triterpenoid saponins in medicinal plants of the genus Ardisia.
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.
Two new triterpenoid saponins cytotoxic to human glioblastoma U251MG cells from Ardisia pusilla.[Pubmed:19774606]
Chem Biodivers. 2009 Sep;6(9):1443-52.
Two new triterpenoid saponins, ardipusillosides IV and V (1 and 2, resp.), together with one known saponin, Ardisiacrispin B(3), were isolated from the whole plants of Ardisia pusilla A. DC. Their structures were deduced by extensive spectral analysis and chemical evidences. Compound 1 contains a glycosylated glycerol residue which is a very rare structural feature among triterpenoid glycosides and has been so far found only in the genus Ardisia. All the saponins exhibited significant cytotoxicity against human glioblastoma U251MG cells, but did not affect the growth of primary cultured human astrocytes.
Triterpenoid saponins from Ardisia pusilla and their cytotoxic activity.[Pubmed:19039733]
Planta Med. 2009 Jan;75(1):70-5.
Three new triterpenoid saponins 3, 4 and 5, together with two known saponins, Ardisiacrispin B (1) and ardisiacrispin A (2), were isolated from the whole plants of Ardisia pusilla A. DC. Their structures were elucidated by extensive spectral analysis and chemical evidence. Compound 3 is a hexaglycoside with a 13,28-epoxyoleanane type aglycone, while both 4 and 5 are triterpenoid tetraglycosides related to the olean-12-ene skeleton. Saponins 1-4 exhibited significant cytotoxicity against human glioblastoma U251MG cells, but did not affect the growth of primary cultured human astrocytes.
[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.
Cytotoxic saponins from New Zealand Myrsine species.[Pubmed:7807121]
J Nat Prod. 1994 Oct;57(10):1354-60.
The observed biological activity in two New Zealand Myrsine species has been shown to be due to the presence of triterpene saponins. From Myrsine australis a series of eight oleanane-type saponins was obtained, with compounds 1-4 and 7 and 8 being novel. Also isolated were ardisiacrispin A [5] and Ardisiacrispin B [6]. The structures of the new compounds were determined by chemical and spectroscopic techniques. Extracts of Myrsine salicina yielded only one saponin, 5. Saponins 1-8 were shown to be combinations of four oleanane triterpenes bonded to beta-D-xylp(1-->2)-beta-D-glcp(1-->4)-[beta-D-glcp(1-->2)]-alpha-L -arap (compounds 1, 3, 5, 7) and this same tetrasaccharide with alpha-L-rhap replacing the beta-D-xylp unit (compounds 2, 4, 6, 8).
