2-d)pyran-3,6a,9,10(6h)-tetrol,7,11b-dihydro-benz(b)indeno(
Brazilin
CAS: 474-07-7
Molecular Formula: C16H14O5
2-d)pyran-3,6a,9,10(6h)-tetrol,7,11b-dihydro-benz(b)indeno( - Names and Identifiers
2-d)pyran-3,6a,9,10(6h)-tetrol,7,11b-dihydro-benz(b)indeno( - Physico-chemical Properties
| Molecular Formula | C16H14O5 |
| Molar Mass | 286.28 |
| Density | 1.1924 (rough estimate) |
| Melting Point | 156-157°C |
| Boling Point | 555.8°C at 760 mmHg |
| Solubility | Soluble in ethanol and ether, soluble in water. |
| Appearance | Pale crystal |
| Storage Condition | 2-8℃ |
| Refractive Index | 1.6200 (estimate) |
| MDL | MFCD00210817 |
| Physical and Chemical Properties | The chemical properties are derived from the genus hematoxylin. |
| Use | Uses for content determination/identification/pharmacological experiments. Pharmacological Efficacy: Antioxidant Activity |
2-d)pyran-3,6a,9,10(6h)-tetrol,7,11b-dihydro-benz(b)indeno( - Risk and Safety
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| HS Code | 29329990 |
2-d)pyran-3,6a,9,10(6h)-tetrol,7,11b-dihydro-benz(b)indeno( - Reference
| Reference Show more | 1. Liu, Fufeng, et al. "Brazilin inhibits α-synuclein fibrillogenesis, disrupts mature fibrils, and protects against amyloid-induced cytotoxicity." Journal of agricultural and food chemistry 67.42 (2019): 11769-11777.https://doi.org/10.1021/acs.jafc.9b04558 2. [IF=3.361] Jingjing Guo et al."Brazilin inhibits fibrillogenesis of human islet amyloid polypeptide, disassembles mature fibrils, and alleviates cytotoxicity."Rsc Adv. 2017 Sep;7(69):43491-43501 3. [IF=2.939] Zhan-yuan Li et al."Brazilin Ameliorates Diabetic Nephropathy and Inflammation in db/db Mice."Inflammation. 2017 Aug;40(4):1365-1374 4. [IF=2.408] Amit Jaisi et al."Investigation of HIV-1 Viral Protein R Inhibitory Activities of Twelve Thai Medicinal Plants and Their Commercially Available Major Constituents."Chemistry & Biodiversity. 2021 Oct 27 |
2-d)pyran-3,6a,9,10(6h)-tetrol,7,11b-dihydro-benz(b)indeno( - Uses and methods of synthesis
Overview
hematoxylin is a leguminous cloud plant, hematoxylin (fp was applied with s dipstick p nL. Dry heartwood, with blood stasis, swelling and pain, commonly used in the treatment of traumatic injury, fracture of tendons, blood stasis, swelling and pain, amenorrhea, postpartum blood stasis, chest and abdominal pain, swelling and pain of anthrax. Brazil hematoxylin (Brazi.1in), also known as the threonine, Brazil red lignin, Su Mu cryptochrome, is the main active ingredient of hematoxylin, at the same time as a natural pigment commonly used in pathological tissue staining. Brazilian hematoxylin belongs to the high isoflavone derivatives (structure see figure 1), molecular formula C,. H,. O, with antibacterial, anti-inflammatory, hypoglycemic, immune regulation and other pharmacological activities. In addition, Brazil hematoxylin is an important basis for the evaluation of the quality of hematoxylin medicinal materials, 2010 edition of the "Chinese Pharmacopoeia" provides that the content of the compound in hematoxylin medicinal materials shall not be less than 0.5%[1].
physical data
character: Amber yellow crystal. Turn orange in air and light. Above 130 degrees C decomposition.
solubility: soluble in ethanol and ether, soluble in water, aqueous solution is colorless, in the air to red. Dissolved in alkaline solution in red, and oxidized to colored Brazilian annatto.
extraction
The extraction and separation methods of Brazilian hematoxylin reported in the literature and patent reports are similar, and the crude extract is usually extracted by heating and refluxing with aqueous ethanol or methanol, and the solvent is recovered to obtain the crude extract, then it was extracted with solvent of different polarity such as petroleum ether, ethyl acetate and n-butanol successively. For ethyl acetate extract, combined with a variety of column chromatography (such as silica gel column chromatography, dextran gel column chromatography, polyamide column chromatography and macroporous resin column chromatography, etc.), brazilian hematoxylin & uml; "J can be obtained. Because the traditional column chromatographic separation technology has the disadvantages of long time and large solvent consumption, the high isoflavone compounds in hematoxylin were prepared by high speed Countercurrent Chromatography (HSCCC) for the first time, with chloroform methanol water (4:3:2,v/v/v) as the two-phase solvent system, the upper phase as the stationary phase, the lower phase as the mobile phase, under the conditions of a flow rate of 1.0M L/quotient n, a rotation speed of 900rpm, a detection wavelength of 280nm and a temperature of 25 ℃, 18mg of Brazilian hematoxylin was isolated from 120mg of the crude extract in one step, the purity and average recovery were both 85%.
pharmacological activity
1. Antibacterial effect
as an antibacterial active ingredient, hematoxylin against some antibiotic-resistant bacteria, such as methicillin-resistant Staphylococcus aureus, vancomycin-resistant Enterococcus and multi-drug resistant Burkholderia cepacia and other bacteria have significant inhibitory effect, the minimum inhibitory concentration of 4~32g/m L[2]. Batub hoes et al in the study of 28 kinds of plant anti-acne efficacy, found that hematoxylin methanol extract and 50% ethanol extract on the growth of Propionibacterium acnes has obvious inhibitory effect, the methanol extract was further separated to obtain the Brazilian hematoxylin, the original hematoxylin A and hematoxylin B. The activity screening results showed that the Brazilian hematoxylin had stronger antibacterial activity than the original hematoxylin A and hematoxylin B, the minimum inhibitory concentration was 0.5mg/ml.
2. Hypoglycemic effect
von et al. H71 investigated the effect of Brazilian hematoxylin on the glycogen neogenesis and ketogenesis in rat hepatocytes. It was found that Brazilian hematoxylin may reduce the ability of glycogen neogenesis in rat hepatocytes, so as to achieve the purpose of reducing blood sugar. Khil et al. investigated the key molecular structure of Brazilian hematoxylin promoting glucose transport in adipocytes. The results showed that the peroxide produced by the oxidation of Catechol hydroxyl in Brazilian hematoxylin regulates sugar transport by inhibiting phosphatase. In addition, the study found that the Brazilian hematoxylin can inhibit the insulin signaling pathway related to protein kinase C and insulin receptor serine enzyme, indicating that the Brazilian hematoxylin may increase the function of insulin receptor by reducing the phosphorylation of serine, thereby reducing blood glucose concentration [3].
synthesis
In recent years, the total synthesis route of Brazilian hematoxylin has been studied, through special chemical transformation methods, such as the use of IBx to oxidize phenol to O-quinone, further isomerization, the racemate of Brazilian hematoxylin was obtained by intramolecular cyclization and other methods
.references
[1][Journal article] WANG Xin, ZHAO Huanxin, BAI Hong, WANG Xin, ZHAO Huan-xin, BAI Hong-Journal of Traditional Chinese Medicine, Issue 3, 2013
[2]Xu Hx, Lee Sf. The antibacterial principle of Caesalpina Appan [J].Phytother Res,2004 ,18 ( 8) :647-651.
[3]Kim SG, Kim YM, Khil LY, et al. Brazilin inhibitors activities of pro-tein Kinase C and insulin receptor serine kinase in rat Liver [J].ArchPharm Res,1998,21(2);140 A 146.
[4] Brazilian hematoxylin. Chemical Database. [reference date 2017.08.24]
Last Update：2024-04-09 21:54:55
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Product Name: Brazilin Visit Supplier Webpage Request for quotationCAS: 474-07-7
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
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