Cristacarpin - CAS 74515-47-2
Catalog number: 74515-47-2
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C21H22O5
Molecular Weight:
354.4
COA:
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Chemical Family:
Phenols
Description:
Cristacarpin is a phenolic compound found in the herbs of Erythrina burana. Cristacarpin shows moderate but selective activity towards DNA repair-deficient yeast mutants.
Purity:
>97%
Appearance:
Powder
Synonyms:
Erythrabyssin I
MSDS:
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Quality Standard:
Enterprise Standard
Quantity:
Milligrams-Grams
1.Isoflavonoids from Erythrina poeppigiana: evaluation of their binding affinity for the estrogen receptor.
Djiogue S;Halabalaki M;Alexi X;Njamen D;Fomum ZT;Alexis MN;Skaltsounis AL J Nat Prod. 2009 Sep;72(9):1603-7. doi: 10.1021/np900271m.
Five new isoflavones, named 5,4'-dihydroxy-7-methoxy-3'-(3-methylbuten-2-yl)isoflavone (1), 5,2',4'-trihydroxy-7-methoxy-5'-(3-methylbuten-2-yl)isoflavone (2), 5,4'-dihydroxy-7-methoxy-3'-(3-methyl-2-hydroxybuten-3-yl)isoflavone (3), 3'-formyl-5,4'-dihydroxy-7-methoxyisoflavone (4), and 5-hydroxy-3''-hydroxy-2'',2''-dimethyldihydropyrano[5'',6'':3',4']isoflavone (5), as well as six known compounds, wighteone (6), 3'-isoprenylgenistein (7), isolupabigenin (8), alpinumisoflavone (9), erypoegin D (10), and crystacarpin (11), were isolated from Erythrina poeppigiana. The structures of the isolated compounds were elucidated on the basis of chemical and spectroscopic analysis. The affinity of these compounds for the estrogen receptors ERalpha and ERbeta was evaluated using a receptor binding assay. While isoprenyl and dimethylpyrano substituents in ring A reduced the affinity of binding to ERbeta ca. 100-fold compared to genistein, the isoprenyl substituent in ring B was better accommodated, allowing 7 to bind with ca. 10-fold lower affinity than genistein.
2.Three new isoflavanones from Erythrina costaricensis.
Tanaka H;Hattori H;Oh-Uchi T;Sato M;Sako M;Tateishi Y;Rizwani GH Nat Prod Res. 2009;23(12):1089-94. doi: 10.1080/14786410802292286.
Three new isoflavanones, 5,7,3'-trihydroxy-4'-methoxy-6,5'-di(gamma, gamma-dimethylallyl)-isoflavanone (1), 5,3'-dihydroxy-4'-methoxy-5'-gamma,gamma-dimethylallyl-2'',2''-dimethylpyrano[5,6 : 6,7]isoflavanone (2) and 5,3'-dihydroxy-2'',2''-dimethylpyrano[5,6 : 6,7]-2''',2'''-dimethylpyrano[5,6 : 5,4]isoflavanone (3), along with two known isoflavonoids, cristacarpin and euchrenone b(10), were isolated from the stems of Erythrina costaricensis. Their structures were established on the basis of spectroscopic evidence. Compound 3 is a rare isoflavanone possessing two 2,2-dimethylpyran moieties. Among the new isoflavanones, compound 1 showed potent antibacterial activity against methicillin-resistant Staphylococcus aureus.
3.Cristacarpin promotes ER stress-mediated ROS generation leading to premature senescence by activation of p21(waf-1).
Chakraborty S;Rasool RU;Kumar S;Nayak D;Rah B;Katoch A;Amin H;Ali A;Goswami A Age (Dordr). 2016 Jun;38(3):62. doi: 10.1007/s11357-016-9922-1. Epub 2016 May 31.
Stress-induced premature senescence (SIPS) is quite similar to replicative senescence that is committed by cells exposed to various stress conditions viz. ultraviolet radiation (DNA damage), hydrogen peroxide (oxidative stress), chemotherapeutic agents (cytotoxic threat), etc. Here, we report that cristacarpin, a natural product obtained from the stem bark of Erythrina suberosa, promotes endoplasmic reticulum (ER) stress, leading to sub-lethal reactive oxygen species (ROS) generation and which eventually terminates by triggering senescence in pancreatic and breast cancer cells through blocking the cell cycle in the G1 phase. The majority of cristacarpin-treated cells responded to conventional SA-β-gal stains; showed characteristic p21(waf1) upregulation along with enlarged and flattened morphology; and increased volume, granularity, and formation of heterochromatin foci-all of these features are the hallmarks of senescence. Inhibition of ROS generation by N-acetyl-L-cysteine (NAC) significantly reduced the expression of p21(waf1), confirming that the modulation in p21(waf1) by anti-proliferative cristacarpin was ROS dependent. Further, the elevation in p21(waf1) expression in PANC-1 and MCF-7 cells was consistent with the decrease in the expression of Cdk-2 and cyclinD1.
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