[1,1'-Biphenyl]-2,4'-diol,3',5-di-2-propenyl- (9CI) 3,3'-DIALLYL-4,6'-DIHYDROXYBIPHENYL 3',5-Diallyl-2,4'-biphenyldiol
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Melting Point | 86℃ |
Boling Point | 400.1±40.0 °C(Predicted) |
Flash Point | 184°C |
Solubility | Soluble in general organic solvents, soluble in benzene, ether, chloroform, ethanol, etc., insoluble in water. |
Vapor Presure | 5.65E-07mmHg at 25°C |
Appearance | Brown to white fine powder, the monomer is colorless scaly crystals |
Color | White to Off-White |
Merck | 14,4742 |
pKa | 9.89±0.48(Predicted) |
Storage Condition | 2-8°C |
Refractive Index | 1.601 |
MDL | MFCD00016674 |
Physical and Chemical Properties | Soluble in general organic solvents, soluble in benzene, ether, chloroform, ethanol, difficult to dissolve in water. Dry bark, root bark and branch bark from Magnolia magnolias official Rehd. et Wils, a deciduous tree plant of Magnoliaceae. |
Plant source: | Magnolia officinalis |
Magnolol isomer | Honokiol is an isomer of magnolol, which is a dimer formed by polymerizing the side chain of one phenylpropanoid and the benzene nucleus of another phenylpropanoid. It is called neo-lignans. It is found more in Lauraceae plants and is an effective ingredient for the antibacterial and anti-inflammatory of the traditional Chinese medicine Magnolia officinalis. Magnolol and Honokiol are colorless needle-like crystals, hardly soluble in water, and easily soluble in chloroform, benzene, ethanol, and caustic. Its physical and chemical constants are magnolol, mp:102 ℃,UV λ maxEtOHnm(ε): 294(8200); Honokiol, mp:87.5 ℃,UV λ maxEtOHnm(ε): 294nm (8200). fig. 1 is the chemical structural formula of magnolol and honokiol. |
Magnolia officinalis extract | Magnolia officinalis is also known as Xiangpu, Chipu, Purple Oil Magnolia officinalis, etc. It is a commonly used Chinese medicine. First published in "Shen Nong's Materia Medica", listed as a middle grade. Magnolia officinalis extract is a product extracted from dried root bark, stem bark or branch bark of Magnolia officinalis Magnolia officinalis, etc. Commercial extract usually coordinates the content of magnolol and honokiol. [distribution] there are about 90 species of Magnolia in the world and 30 species in China, of which about 20 species have medicinal value. Magnolia officinalis was born on sunny hillsides and forest edges with fertile soil and deep soil at an altitude of 300~1700m. [Origin] Magnolia officinalis is mainly distributed in western Hubei, southern Sichuan, southern Shaanxi and southern Gansu; Magnolia officinalis is mainly distributed in Jiangxi, Anhui, Zhejiang, Fujian, Hunan, Guangxi and northern Guangdong. Magnolia officinalis and Magnolia officinalis are mostly cross-distributed, and both have large-scale artificial cultivation. [main ingredients] Magnolia officinalis bark contains magnolol, honokiol, iso-magnolol and other ingredients. And from Magnolia officinalis ethyl acetate extract separation of three hydroxy magnolol, deoxy three hydroxy magnolol, three hydroxy magnolaldehyde, poly magnolol methyl, propyl. Bark contains about 1% volatile oil, and the oil mainly contains β-oleyl alcohol. It also contains α-pinene, β-pinene, limonene and borneol acetate. The bark also contains magnolia curarine. Leaves also contain magnolol and honokiol. [harvesting and processing] peel the dry skin of trees that have grown for more than 15 years from April to June, place it in boiling water for slight cooking, pile it up in a soil pit, cover it with grass to make it "sweat", and when the inner surface turns purple or brown after water seeps out from the inside, steam it soft, take it out, roll it into a tube, dry it in the sun or dry it on the kang. The root bark and branch bark can be dried directly in the shade after peeling off. Figure 2 shows Magnolia officinalis. |
extraction method | 1. production process of magnolia officinalis extract (fluid extract) the magnolia officinalis extract is pulverized, soaked with ethanol for 12 hours, placed in a percolation cylinder, percolated with about 12 times the amount of ethanol, collected the percolation solution, recovered the ethanol under reduced pressure to the end, and obtained the fluid extract. The yield is about 9%, the content of solid is 85.0%, the content of magnolol is more than 11.0%, and the content of honokiol is more than 5.0%. 2. extraction and separation of magnolol and honokiol take magnolia officinalis dry skin coarse powder, add 1/5 amount (W/W) of raw lime powder, mix well, percolate with 15-20 times of distilled water, percolate with hydrochloric acid to adjust the pH value to 2-3, and let stand. Collect the precipitated precipitate, wash with distilled water until the pH value of the precipitate is 6~7, add alumina (1:10) after drying, mix evenly, place in an extractor, and extract with ethylene. Concentrate the ethylene extract and cool it, precipitate white crystals, and filter to obtain crystals and mother liquor. The crystallization is recrystallized with cyclohexane, which is honokiol. After the mother liquor is concentrated, crystals are precipitated, and cyclohexane is recrystallized to obtain colorless flake crystals, which are magnolol crystals. The yield of magnolol was 85% and that of honokiol was 74%. |
pharmacological action | 1. the role of anti-pathogenic microorganisms magnolia officinalis decoction is effective against staphylococcus, hemolytic streptococcus, pneumococcus, pertussis bacillus and other gram-positive bacteria, and Bacillus anthracis, Shigella, Typhoid bacillus, Paratyphoid bacillus, Vibrio cholerae, Escherichia coli, Proteus, Bacillus subtilis, Diphtheria and other gram-negative bacteria have inhibitory effects, of which the inhibitory effect on Staphylococcus is the strongest. At the 15% concentration, it has inhibitory effect on dermatophytes such as small spores, trichophyton concentric, trichophyton rubrum, trichophyton methanus and other dermatophytes in experimental animals. Magnolia decoction has some effects on improving substantial pathological damage of experimental viral hepatitis in mice. magnolol has significant antibacterial activity against gram-positive bacteria and acid-resistant bacteria. The anti-dental caries effect of magnolol is very significant, the minimum inhibitory concentration is 6.3 μg/ml, and its antibacterial activity is stronger than that of the typical antibacterial alkaloid berberine (MIC:50 μg/ml). The saturated aqueous solution of Magnolia officinalis and Magnolia officinalis volatile oil has certain antibacterial effects on Staphylococcus aureus, Artemisia occidentalis and Bacillus subtilis. 2. Effects on the cardiovascular system Magnolol and honokiol inhibit the formation of thromboxane B2 under various conditions, and the increase of intracellular Ca2 caused by arachidonic acid or collagen is also inhibited by both. honokiol can inhibit the activity of cyclic nucleotide phosphodiesterase stimulated by CaM, and honokiol can bind to CaM in the presence of Ca2 +, thus antagonizing its activation of phosphodiesterase. In addition, honokiol has a stimulating effect on the basal activity of CaM-dependent phosphodiesterase. 3. anti-tumor effect magnolol and its hydroxymethyl derivatives have obvious inhibitory effect on secondary skin tumors in mice. The three extracted components of Magnolia officinalis, lignans, magnolol, honokiol and monoterpene magnoliol are antagonists of 12-O-decyl phorbol -13-acetate (TPA)-induced activation of Epstein-Barr virus early antigen (EBv-EA). The methanol extract of Magnolia officinalis and Honokiol have obvious inhibitory effects on mouse skin tumors caused by the second-stage carcinogenic experiment in vivo. |
Toxic and side effects | Magnolia officinalis is less toxic. The LD50 injected intraperitoneally by Magnolia officinalis decoction mice was 6.12±0.038 g/kg, while the LD50 injected intraperitoneally by magnolia curarine was 45.55 mg/kg. The MLD of Magnolia officinalis decoction for intravenous injection of cats was 4.25±1.25 g/kg. Under the general muscle relaxation dose, the electrocardiogram of experimental animals has no effect, and large doses can cause respiratory depression and death. |
pharmacokinetics | 14C isotope tracer study showed that magnolol was absorbed rapidly by oral administration to rats, and the blood concentration reached a peak at 15 minutes. After 1 hour of oral administration, except for several radioactivity observed in liver and kidney, obvious radioactivity was seen in stomach. At 8 h, approximately the same results as after 1 h were obtained, and significant radioactivity was observed in the intestine. magnolol is distributed in brain, spinal cord, liver, stomach, intestine, kidney, lung, heart, muscle and other tissues of rats after intravenous injection. Intravenous administration, 1 hour later, obvious blackening in the lung was seen, which was caused by the suspension of magnolol and the capture of its particles in the lung. Magnolol is mainly distributed in the liver, and significant melanization is also seen in the intestine. Radioactivity is basically uniformly distributed in other tissues, and the brain is also generally distributed in tissues such as muscles. After 8 hours, some radioactivity was still seen in the liver, lungs, kidneys, etc., obvious blackening was seen in the intestine, and generally seen in the stomach. the main metabolites of magnolol were analyzed by mass spectrometry. the excreta detected in rat feces mainly included M1, M2, M3, M4, M5, M6, glucuronic acid compounds and sulfate esters. |
clinical efficacy | bitter taste, pungent and warm. Return to the spleen meridian, stomach meridian, lung meridian, large intestine meridian. Dry dampness and eliminate phlegm, and the lower qi is full. It is used for wet stagnation injury, epigastric vomiting and diarrhea, stagnation of food and qi, abdominal distension and constipation, phlegm drinking and cough. Magnolia officinalis can be used to treat acute enteritis, bacterial or amoebic dysentery, chronic gastritis, etc. |
application overview | Magnolia officinalis is a traditional Chinese medicine in China, which is used in various prescriptions such as Magnolia officinalis Sanwu Decoction, Banxia Houpu Decoction, Dachengqi Decoction, Xiangsha Yangwei Capsule, Huoxiang Zhengqi Water (pill), etc. In recent years, domestic and foreign scholars have conducted in-depth research on the effective ingredients, pharmacodynamics and clinical pharmacy of Magnolia officinalis, and the antibacterial "chewing gum" prepared by Magnolia officinalis extract has appeared on the market. |
use | honokiol is a natural magnolia biphenyl new lignan extract. It is anti-angiogenesis, anti-tumor, and anti-anxiety. A natural biphenyl new lignan from magnolia extract. |
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