Stereochemistry | ABSOLUTE |
Molecular Formula | C16H14O5 |
Molecular Weight | 286.2794 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12C3=CC(O)=C(O)C=C3C[C@@]1(O)COC4=C2C=CC(O)=C4
InChI
InChIKey=UWHUTZOCTZJUKC-JKSUJKDBSA-N
InChI=1S/C16H14O5/c17-9-1-2-10-14(4-9)21-7-16(20)6-8-3-12(18)13(19)5-11(8)15(10)16/h1-5,15,17-20H,6-7H2/t15-,16+/m0/s1
Molecular Formula | C16H14O5 |
Molecular Weight | 286.2794 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Brazilin isolated from Caesalpinia sappan has long been known as a natural red pigment. Brazilin is the safe natural compound having the potential to develop as a medicinal compound with application in food, beverage, cosmetics and pharmaceutical industries. It was shown, that brazilin exerts protective effects against renal ischemia-reperfusion injury by inhibiting the NF-κB signaling pathway. In addition, was revealed, that this compound prevented hyperglycemia, renal fibrosis, and inflammation, thus ameliorating renal functional decline in diabetic mice and may be a useful treatment for diabetic nephropathy. Brazilin isolated from H. brasiletto exhibited a moderate antiproliferative activity on the human non-cancer cell line, at the same time demonstrated to have antiproliferative activity against human cancer cell lines, and thus can be a potential source of anticancer agents.
Approval Year
PubMed
Patents
Sample Use Guides
Treatment with brazilin (30 mg/kg, administered intravenously at 30 min prior to ischemia) led to the reversal of renal ischemia-reperfusion (I/R)-induced changes in serum creatinine (Scr) and blood urea nitrogen (BUN) levels, and also attenuated the histopathological damage induced by I/R.
db/db mice: brazilin (40 mg/kg/day i.p.)
Route of Administration:
Other
Brazilin was used to inhibit Zn2+-mediated Aβ aggregation and alleviate its cytotoxicity. The binding properties of brazilin and Zn2+ were first probed using Fourier transform infrared (FTIR) spectroscopy and isothermal titration calorimetry (ITC) assays. Both the FTIR and ITC results have shown that brazilin is able to bind Zn2+ in a physiologically suitable range of concentrations. The dissociation constant (Kd) between brazilin and Zn2+ was about 46.0±6.8μM, which makes brazilin a potential drug model for the chelation of free Zn2+. Moreover, the higher affinity of brazilin for Aβ42 (Kd=2.5±1.6μM) than that of Zn2+ (Kd=6.2±0. 9μM), enables brazilin to sequester Zn2+ from the Aβ42-Zn2+ complex.