We Offer Worldwide Shipping
Login Wishlist

Ardisiacrispin B

$896

  • Brand : BIOFRON

  • Catalogue Number : BD-P0766

  • Specification : 98.5%(HPLC&TLC)

  • CAS number : 112766-96-8

  • Formula : C53H86O22

  • Molecular Weight : 1075.24

  • PUBCHEM ID : 194981

  • Volume : 25mg

Available on backorder

Quantity
Checkout Bulk Order?

Catalogue Number

BD-P0766

Analysis Method

HPLC,NMR,MS

Specification

98.5%(HPLC&TLC)

Storage

2-8°C

Molecular Weight

1075.24

Appearance

Powder

Botanical Source

Structure Type

Triterpenoids

Category

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

Synonyms

IUPAC 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

Applications

Density

1.468g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

Boiling Point

Melting Point

InChl

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

InChl Key

ZDIHSHLFPFGAGP-GRWMUYEGSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:112766-96-8) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

29747757

Abstract

Introduction: 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.

Methods: Resazurin reduction assay was used to evaluate cytotoxicity and ferroptotic cell death of samples; caspase-Glo assay was used to detect the activation of caspases in CCRF-CEM leukemia cells. Flow cytometry was used for cell cycle analysis and detection of apoptotic cells by annexin V/PI staining, analysis of mitochondrial membrane potential (MMP) and measurement of reactive oxygen species (ROS).

Results: Ardisiacrispin B displayed significant cytotoxic effects in the 9 tested cancer cell lines with IC50 values below 10 µM. The IC50 values ranges were 1.20 µM (towards leukemia CCRF-CEM cells) to 6.76 µM [against heptocarcinoma HepG2 cells] for ardisiacrispin B and 0.02 µM (against CCRF-CEM cells) to 122.96 µM (against resistant CEM/ADR5000 leukemia cells) for doxorubicin. Collateral sensitivity of resistant HCT116p53-/- colon adenocarcinoma cells to ardisiacripsin B was observed. Ardisiacrispin B induced apoptosis in CCRF-CEM cells via activation of inititator caspases 8 and 9 and effector caspase 3/7, alteration of MMP and increase in ROS production. Ferroptosis also contributed to the cytotoxicity of ardisiacrispin B.

Conclusions: The studied oleanane-type triterpene saponin is a good cytotoxic molecule that deserve more detailed exploration in the future, to develop novel cytotoxic drugs to combat both sensitive and drug-resistant cancers.

KEYWORDS

Ardisiacrispin B; Cell cycle distribution; Cytotoxicity; Ferroptosis; Mitochondrial membrane potential; Saponin.

Title

A naturally occuring triterpene saponin ardisiacrispin B displayed cytotoxic effects in multi-factorial drug resistant cancer cells via ferroptotic and apoptotic cell death

Author

Armelle T Mbaveng 1, Blanche L Ndontsa 2, Victor Kuete 1, Yves M M Nguekeu 2, İlhami celik 3, Roukayatou Mbouangouere 2, Pierre Tane 2, Thomas Efferth 4

Publish date

2018 Apr 1;

PMID

28173950

Abstract

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 μM. Simultaneously, the cytotoxic activities of foegraecumosides A and B, lysichriside A, ardisiacrispins A and B, cyclaminorin, and 3-O-α-L-rhamnopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-α-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 μM and a resistant factor (RF) of 0.9.

KEYWORDS

Cytotoxic activities; Lysimachia foenum-graecum; Myrsinaceae; Triterpenoid saponins.

Title

Cytotoxic triterpenoid saponins from Lysimachia foenum-graecum

Author

Lu-Mei Dai 1, Ri-Zhen Huang 2, Bin Zhang 1, Jing Hua 1, Heng-Shan Wang 3, Dong Liang 4

Publish date

2017 Apr;

PMID

18696326

Abstract

Ardisiacrispin (A+B) is a mixture of ardisiacrispins A and B, derived from Ardisia crenata with a fixed proportion (2:1). The present study was conducted to investigate its anticancer activity on human cancer cells and its underlying mechanism of action. The (IC50)s of ardisiacrispin (A+B) on proliferation of several human cancer cell lines were in the range of 0.9-6.5 microg/ml by sulphorhodamine B-based colorimetric assay, in which Bel-7402 was the most sensitive cell line. Moreover, ardisiacrispin (A+B) induced dose-dependent apoptosis in Bel-7402 cells at doses of 1-10 microg/ml by flow cytometry, and resulted in the changes of the mitochondrial membrane depolarization, membrane permeability enhancement, and nuclear condensation in a dose-dependent manner through high-content screening analysis. Furthermore, ardisiacrispin (A+B) could disassemble microtubule in Bel-7402 cells; the fluorescence intensity of microtubules decreased at the concentration of 5-20 microg/ml. These findings suggest that ardisiacrispin (A+B) could inhibit the proliferation of Bel-7402 cells by inducing apoptosis and disassembling microtubule.

Title

Pro-apoptotic and microtubule-disassembly effects of ardisiacrispin (A+B), triterpenoid saponins from Ardisia crenata on human hepatoma Bel-7402 cells

Author

Min Li 1, Shao-Yin Wei, Bo Xu, Wei Guo, Dai-Lin Liu, Jing-Rong Cui, Xin-Sheng Yao

Publish date

Jul-Aug 2008;