Cajanin - CAS 32884-36-9
Catalog number: 32884-36-9
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Molecular Formula:
C16H12O6
Molecular Weight:
300.3
COA:
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Chemical Family:
Flavonoids
Description:
Cajanin is a natural flavonoid found in the herbs of Kadsura interior. It has been shown to be promising anticancer compound with low toxicity.
Purity:
>98%
Appearance:
Yellow powder
Synonyms:
3-(2,4-Dihydroxyphenyl)-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one
MSDS:
Inquire
Application:
anticancer
Quality Standard:
Enterprise Standard
Quantity:
Milligrams-Grams
1.Correlation between the Potency of Flavonoids on Mushroom Tyrosinase Inhibitory Activity and Melanin Synthesis in Melanocytes.
Promden W;Viriyabancha W;Monthakantirat O;Umehara K;Noguchi H;De-Eknamkul W Molecules. 2018 Jun 9;23(6). pii: E1403. doi: 10.3390/molecules23061403.
Twenty-seven flavonoids isolated from ;Dalbergia parviflora; with vast structural diversity were screened for inhibitory activity against mushroom and murine tyrosinases using l-DOPA as the substrate. Among the flavonoids tested, only four—khrinone (;5;), cajanin (;9;), (3;RS;)-3′-hydroxy-8-methoxy vestitol (;21;), and (6a;R;,11a;R;)-3,8-dihydroxy-9-methoxy pterocarpan (;27;)—reacted with mushroom tyrosinase, with IC;50; values of 54.0, 67.9, 67.8, and 16.7 μM, respectively, and only compound ;27; showed inhibitory activity against murine tyrosinase. With cell-based assays, only compounds ;9; and ;27; effectively inhibited melanogenesis in B16-F10 melanoma cells (by 34% and 59%, respectively), at a concentration of 15 μM, without being significantly toxic to the cells. However, the crude extract of ;D. parviflora; and some of the flavonoid constituents appeared to increase melanin production in B16-F10 cells, suggesting that there are flavonoids with both inhibitory and stimulatory melanogenesis in the crude extract. Studies on the correlation between the enzyme-based and cell-based assays showed that only the flavonoids with IC;50; values below 50 μM against mushroom tyrosinase could inhibit the mammalian tyrosinase, and thus, reduce melanogenesis in B16-F10.
2.Activity of the antiestrogenic cajanin stilbene acid towards breast cancer.
Fu Y;Kadioglu O;Wiench B;Wei Z;Wang W;Luo M;Yang X;Gu C;Zu Y;Efferth T J Nutr Biochem. 2015 Nov;26(11):1273-82. doi: 10.1016/j.jnutbio.2015.06.004. Epub 2015 Jul 22.
Antiestrogenic therapy is a mainstay for estrogen receptor (ERα)-positive breast cancer. Due to the development of resistance to established antihormones such as tamoxifen, novel compounds are required. The low abundant cajanin stilbene acid (CSA) recently isolated by us from Pigeon Pea (Cajanus cajan) has structural similarities with estrogen. We analyzed the cytotoxic and anticancer activity of CSA in ERα-positive and -negative human breast cancer cells in vitro, in vivo and in silico. CSA exerts anticancer and antiestrogenic activities towards ERα-positive breast cancer, and it showed cytotoxicity towards tamoxifen-resistant MCF-7 cells, implying that CSA may be active against tamoxifen-resistant breast cancer cells. CSA showed low cytotoxicity in ERα-negative breast tumor cells as expected. Comparable cytotoxicity was observed towards p53 negative MCF-7 cells, implying that CSA is effective independent of the p53 status. Xenografted MCF-7 cells in nude mice were better inhibited by CSA than by cyclophosphamide. Testing of 8 primary cell cultures derived from human breast cancer biopsies showed that cell cultures from ER-positive tumors were more sensitive than from ER-negative ones.
3.Cell cycle arrest and induction of apoptosis by cajanin stilbene acid from Cajanus cajan in breast cancer cells.
Fu Y;Kadioglu O;Wiench B;Wei Z;Gao C;Luo M;Gu C;Zu Y;Efferth T Phytomedicine. 2015 Apr 15;22(4):462-8. doi: 10.1016/j.phymed.2015.02.005. Epub 2015 Mar 11.
BACKGROUND: ;The low abundant cajanin stilbene acid (CSA) from Pigeon Pea (Cajanus cajan) has been shown to kill estrogen receptor α positive cancer cells in vitro and in vivo. Downstream effects such as cell cycle and apoptosis-related mechanisms have not been analyzed yet.;MATERIAL AND METHODS: ;We analyzed the activity of CSA by means of flow cytometry (cell cycle distribution, mitochondrial membrane potential, MMP), confocal laser scanning microscopy (MMP), DNA fragmentation assay (apoptosis), Western blotting (Bax and Bcl-2 expression, caspase-3 activation) as well as mRNA microarray hybridization and Ingenuity pathway analysis.;RESULTS: ;CSA induced G2/M arrest and apoptosis in a concentration-dependent manner from 8.88 to 14.79 µM. The MMP broke down, Bax was upregulated, Bcl-2 downregulated and caspase-3 activated. Microarray profiling revealed that CSA affected BRCA-related DNA damage response and cell cycle-regulated chromosomal replication pathways.;CONCLUSION: ;CSA inhibited breast cancer cells by DNA damage and cell cycle-related signaling pathways leading to cell cycle arrest and apoptosis.;Copyright © 2015 Elsevier GmbH. All rights reserved.
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CAS 32884-36-9 Cajanin

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