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Details

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
Structure of BRAZILIN

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

HIDE SMILES / InChI

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

Description

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

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown
Preventing
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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.
Substance Class Chemical
Record UNII
FZ39SW1K10
Record Status Validated (UNII)
Record Version