Product name: Brazilin
Synonym name:
Catalogue No.: BP0281
Cas No.: 474-07-7
Formula: C₁₆H₁₄O₅
Mol Weight: 286.283
Botanical Source:
Physical Description: Red powder
Type of Compound: Flavonoids

Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle

Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.

The product could be supplied from milligrams to grams, up to kilograms
Inquire for bulk scale.

Descriptions:
Brazilin, isolated from Caesalpinia sappan has been known as a natural red pigment, exhibits the inhibitory effect on lipopolysaccharide (LPS)-stimulated NO production in a dose-dependent manner (IC50=24.3 microM), might be associated with the regulation of transcription factors NF-kappaB and AP-1; inducible isoform of nitric oxide synthase (NOS) plays an important role in inflammation and carcinogenesis, suggests that the suppressive effect of iNOS gene expression by brazilin might provide one possible mechanism for its anti-inflammatory and cancer chemopreventive activity. [1]
Brazilin exhibits anti-hepatotoxicity, antiplatelet activity, and anti-inflammatory activities, it also inhibits UVB-induced MMP-1/3 expressions and secretions by suppressing of NF-κB activation in human dermal fibroblasts, thus, it might be used as a potential agent for treatment of UV-induced skin photoaging.[2]
Brazilin protects the cells against t -butyl hydroperoxide ( t -BHP)-induced cell death, and the protective effect was abrogated by anti-sense oligodeoxynucleotides (ODN) against the HO-1 gene, suggests that the expression of HO-1 by brazilin is mediated via the PI3K/Akt and ERK pathways, and this expression inhibits t -BHP-induced cell death in House Ear Institute-Organ of Corti 1 (HEI-OC1) cells.[3]
Brazilin induces vasorelaxation by the increasing intracellular Ca(2+) concentration in endothelial cells of blood vessels and hence activating Ca(2+)/calmodulin-dependent NO synthesis, the NO is released and then transferred into smooth muscle cells to activate guanylyl cyclase and increase cGMP content, resulting in vasorelaxation.[4]
Brazilin, the main principle of Caesalpinia sappan, was able to improve the altered immune functions caused by halothane administration in mice.[5]
Brazilin induces apoptosis and G2/M arrest via inactivation of histone deacetylase in multiple myeloma U266 cells, suggests that it has potential as a chemotherapeutic agent alone or in combination with an anticancer agent for multiple myeloma treatment.[6]
Brazilin shows dose-dependent inhibition of cell proliferation and induction of apoptosis in glioma cells, it also increases the ratio of cleaved poly-(ADP)-ribose polymerase and decreases the expression of caspase-3 and caspase-7.[7]
Brazilin has anti-IKK activity , can selectively disrupt proximal IL-1 receptor signaling complex formation by targeting an IKK-upstream signaling components.[8]

References:
[1] Bae I K, Min H Y, Han A R, et al. Eur J Pharmacol, 2005, 513(3):237-42.
[2] Lee Y R, Noh E M, Han J H, et al. Eur J Pharmacol, 2012, 674(2–3):80-6.
[3] Choi B M, Kim B R. Eur J Pharmacol, 2008, 580(1–2):12-8.
[4] Hu C M, Kang J J, Chen C L, et al. Eur J Pharmacol, 2003, 468(1):37-45.
[5] Choi S Y, Yang K M, Jeon S D, et al. Planta Medica, 1997, 63(5):405-8.
[6] Kim B, Kim S H, Jeong S J, et al. J Agr Food Chem, 2012, 60(39):9882-9.
[7] Lee D Y, Lee M K, Kim G S, et al. Molecules, 2013, 18(2):2449-57.
[8] Jeon J, Ji H L, Park K A, et al. Biochem Pharmacol, 2014, 89(4):515-25.
[9] Zhao H X, Bai H, Wang Y S, et al. West China J Pharm Sci, 2010, 25(3):363-4.

HPLC of Brazilin

Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃

Introduction/Overview

Brazilin (CAS No.: 474-07-7) is a natural red dye precursor mainly found in the heartwood of several tropical hardwoods, especially plants such as Caesalpinia sappan L. As a natural pigment with a long history of use, Brazilian hematoxylin not only holds an important position in the traditional dye industry but has also become a hot topic in pharmacological research of natural products in recent years due to its diverse bioactivity. Numerous studies have shown that Brazil hematoxylin possesses significant anti-inflammatory, anti-tumor, antioxidant, and cartilage-protective effects, especially exhibiting unique molecular mechanisms in regulating cell proliferation, inducing apoptosis, and autophagy. By modulating the AMPK/mTOR signaling pathway, it influences cellular metabolism and survival status, demonstrating therapeutic potential for various disease models.

In addition, the application prospects of Brazilian hematoxylin in inflammatory bowel disease (IBD) have attracted widespread attention. Related studies have revealed that it can regulate the expression and activity of inflammatory factors such as TNF, IL-1β, IL-18, and NLRP3 inflammasomes, thereby alleviating intestinal inflammatory responses and improving pathological conditions. This paper aims to systematically review the chemical structure and physicochemical properties of Brazilian hematoxin, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics, and finally to prospect its clinical application potential, providing a theoretical foundation and reference for future related research.

Chemical structure and physicochemical properties

Brazil hematoxylin is a typical natural diphenylmethane compound, with a molecular formula of C16H14O5 and a molecular weight of 286.28. Its chemical structure consists of two aromatic rings connected by methane bridges, and the molecule contains multiple hydroxyl and phenolic carboxyl groups, giving it excellent polarity and biological activity. The presence of hydroxyl groups in the molecular structure not only enhances its water solubility but also enables its binding to various biological targets.

In terms of physicochemical properties, Brazilian hematoxylin has a LogP value of about 0.7, indicating moderate lipophilic properties, which facilitate cell membrane penetration without excessive lipophilusis and thus affecting bioavailability. The topological pole surface area (TPSA) is 92.89 Ų, indicating certain polarity that facilitates interaction with polar targets. The molecule contains five hydrogen bond receptors that can form stable binding to protein targets through hydrogen bonds. The blood-brain barrier penetration ability is relatively low, suggesting its limited role in the central nervous system. Toxicity evaluations showed that Brazilian hematoxylin had no hepatotoxicity, cardiotoxicity, or hERG channel inhibitory effects, nor showed mutagenicity (Ames test was negative), indicating a relatively high safety profile.

Plant Origins and Extraction Methods

Brazil hematoxylin is mainly found in the heartwood of Brazilian sappanwood (Caesalpinia sappan L.) and its related species. This plant is distributed in tropical Asia and parts of South America. Its heartwood is bright red in color and has long been used as a natural dye and traditional Chinese medicine. In traditional Chinese medicine, Brazilian hematone is used to promote blood circulation, relieve pain, reduce inflammation, and detoxify. Modern research has confirmed that its main active ingredient is Brazil hematoxylin and its derivatives.

There are various methods for extracting Brazil hematoxylin, commonly including solvent extraction, ultrasound-assisted extraction, and microwave-assisted extraction. Ethanol or methanol is generally used as the extraction solvent, and extraction efficiency is improved through reflux or ultrasonic treatment. The extract is concentrated, separated, and purified by column chromatography to obtain high-purity Brazilian hematoxylin. In recent years, green extraction technologies such as supercritical CO2 extraction and hydrothermal extraction have also been attempted, aiming to improve extraction efficiency and environmental friendliness.

Pharmacological activity research

Anti-inflammatory activity

Brazil hematoxylin demonstrates significant anti-inflammatory effects across various inflammation models. It alleviates inflammatory responses by inhibiting the activation of inflammatory mediators such as tumor necrosis factor α (TNF-α), interleukin-1β (IL-1β), interleukin-18 (IL-18), and the inflammasome NLRP3. Especially in anti-inflammatory bowel disease models, Brazilian hematoxylin can regulate the intestinal immune microenvironment, reduce inflammatory cell infiltration, promote intestinal mucosal repair, and demonstrate excellent cartilage protection and anti-inflammatory effects.

Antitumor activity

Brazil hematoxylin demonstrates potential anti-tumor activity by inhibiting tumor cell proliferation, inducing apoptosis, and promoting autophagy. Its mechanism of action involves activating the AMPK signaling pathway, inhibiting mTOR signaling, and regulating cellular energy metabolism and growth cycles. Multiple in vitro and in vivo studies have shown that Brazil hematoxylin inhibits various tumor cells such as breast, liver, and lung cancer, and has low toxicity to normal cells.

Cartilage protection

Brazil hematoxylin demonstrates cartilage-protective functions in degenerative diseases such as osteoarthritis. By inhibiting the expression of inflammatory factors and matrix metalloproteinases (MMPs), it slows down the degradation of cartilage matrix and promotes the survival and maintenance of chondrocytes. Additionally, Brazil hematoxylin can regulate autophagy levels, maintain cellular homeostasis, and delay cartilage degeneration.

Mechanism of action and molecular targets

The pharmacological effects of Brazilian hematoxylin are mainly realized through multiple signaling pathways, with the core mechanism involving regulation of the AMPK/mTOR pathway. AMPK acts as an energy-sensing enzyme that regulates cellular metabolic balance. Brazil hematoxylin activates AMPK, thereby inhibiting mTOR signaling, promoting autophagy and apoptosis, and suppressing abnormal cell proliferation.

In terms of anti-inflammation, Brazil hematoxylin reduces the activity of CASP1 (caspase-1) by downregulating NLRP3 inflammasome activity, lowering the maturation and secretion of IL-1β and IL-18, thereby alleviating inflammatory responses. Its inhibitory effect on TNF-α further blocks the inflammatory cascade and alleviates tissue damage. Additionally, Brazil hematoxylin may also inhibit the transcription expression of inflammatory genes by modulating the NF-κB signaling pathway.

Druggability evaluation and pharmacokinetics

The druggability parameters of Brazilian hematoxylin indicate that it has good potential for drug development. Moderate molecular weight and LogP values facilitate absorption and distribution in the body. A higher number of TPSA and hydrogen bond receptors helps form stable binding to target proteins. A low blood-brain barrier penetration rate suggests it mainly acts on peripheral tissues, reducing the risk of central nervous system side effects.

Safety evaluation showed that Brazil hematoxylin showed no significant hepatotoxicity, cardiotoxicity, or hERG channel suppression, and the Ames test was negative, indicating a low risk of toxicity. Preliminary pharmacokinetic studies show that Brazil hematoxylin is well absorbed orally and widely distributed in the body, but its bioavailability is limited by first-pass effects and metabolic transformation. In the future, it is necessary to optimize its in vivo stability and duration of action through drug formulation optimization.

Prospects and outlooks for clinical applications

Given the multiple activities of Brazilian hematoxylin in anti-inflammation, anti-tumor, and cartilage protection, it has broad application prospects in clinical treatment. Especially in the treatment of anti-inflammatory bowel disease, Brazil hematoxylin demonstrates its potential as a natural anti-inflammatory drug by modulating key inflammatory factors and signaling pathways, and is expected to become a new option for adjunct or alternative treatment for IBD.

Moreover, the antitumor activity of Brazilian hematoxylin offers potential in adjuvant oncology therapy, especially suitable for combination chemotherapy or targeted therapy to enhance efficacy and reduce side effects. Cartilage-protective effects provide new approaches for treating degenerative diseases such as osteoarthritis.

Future research should focus on pharmacokinetic optimization, formulation development, and clinical safety and efficacy evaluation of Brazilian hematoxylin. At the same time, it deeply analyzes its molecular mechanisms and targets, combined with modern drug design technologies, to promote the clinical translation of Brazil hematoxylin.

Conclusion

Brazilian hematoxylin, as a natural product with a wide range of sources and unique structures, demonstrates significant potential for drug development thanks to its diverse pharmacological activities and excellent safety profile. Its research in anti-inflammation, anti-tumor, and cartilage protection has deepened, providing valuable examples for the pharmacology of natural products. In the future, through systematic pharmacological mechanism research, druggability optimization, and clinical validation, Brazil hematoxylin is expected to become a novel natural drug for treating inflammatory diseases and tumors, making significant contributions to human health.