Honokiol
Honokiol
CAS: 35354-74-6
Molecular Formula: C18H18O2
Honokiol - Names and Identifiers
| Name | Honokiol |
| Synonyms | Honokiol HONOKIOL NSC 293100 Honokiol,(S) HONEYSUCKLEFLOWEREXTRACT 3',5-Diallyl-2,4'-biphenyldiol 5,3'-DIALLYL-BIPHENYL-2,4'-DIOL 3,3'-DIALLYL-4,6'-DIHYDROXYBIPHENYL 3,5'-Diallyl-4,2'-dihydroxybiphenyl 3',5-Diallyl[1,1'-biphenyl]-2,4'-diol 3',5-di(prop-2-en-1-yl)biphenyl-2,4'-diol 1'-Biphenyl]-2,4'-diol,3',5-di-2-propenyl-[1 |
| CAS | 35354-74-6 |
| EINECS | 609-119-8 |
| InChI | InChI=1/C18H18O2/c1-3-5-13-7-9-18(20)16(11-13)14-8-10-17(19)15(12-14)6-4-2/h3-4,7-12,19-20H,1-2,5-6H2 |
| InChIKey | FVYXIJYOAGAUQK-UHFFFAOYSA-N |
Honokiol - Physico-chemical Properties
| Molecular Formula | C18H18O2 |
| Molar Mass | 266.33 |
| Density | 1.107±0.06 g/cm3(Predicted) |
| 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. |
Honokiol - Risk and Safety
| Risk Codes | R41 - Risk of serious damage to eyes R51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S39 - Wear eye / face protection. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | UN 3077 9/PG 3 |
| WGK Germany | 3 |
| HS Code | 29072990 |
| Hazard Class | 9 |
Honokiol - Reference
| Reference Show more | 1. Tang lanru, Chen Yizhen, Zhang Wenjuan, Wang Qiao, Liu Hong, Chen Yong. Optimization of Pegylated honokiol long-circulating nanoliposomes by Box-Behnken Design-response surface methodology [J]. Journal of Hubei University (Natural Science Edition) 2018 40(04):418-423. 2. ZHU Linfeng, ZHU Linfeng, Zhang Yuan, et al. Study on the effect of "sweating" on the quality of Magnolia officinalis and the establishment of its process [J]. Modern Chinese medicine, 2019, 21(11):1551-1556. 3. Jingwen-guang, Zhang Quan, Du Jie, et al. Determination and cluster analysis of three lignans in Magnolia officinalis from different habitats [J]. World Science and Technology: modernization of traditional Chinese medicine 2018 020(010):1822-1827. 4. Li Yang, Luo Ju, yuan, Chen gongsen, et al. Quality Analysis of ginger Magnolia officinalis in retail pharmacies in Beijing [J]. Modern Chinese medicine research and practice 2018 032(002):58-61. 5. Yang Yan, Xiao Jia-Mei, Yi Zi Yang, et al. Optimization of supercritical CO_2 extraction of Magnolia officinalis and antioxidant activity of extracts [J]. Chinese herbal medicine 2020. 6. Zhao Na Shi Yu, Wang Zhongyan. Preparation and characterization of solid dispersion of honokiol [J]. Journal of Shenyang Pharmaceutical University 2019 036(006):469-473. 7. Yizhu Chen. Preparation and pharmacokinetics of honokiol long circulating liposomes [J]. Hubei University, 2018. 8. Zhang Quan, Jing Wen-guang, Deng Zhen, et al. Grade Evaluation of decoction pieces of ginger Magnolia officinalis based on relative mass constant [J]. Chinese Journal of Experimental prescriptions, 2019, v.25(22):122-127. 9. Huang Chen, Liu Chunming, Wu Tong, et al. In vitro metabolism of magnolol and honokiol in rat liver microsomes by ultra performance liquid chromatography-high resolution mass spectrometry [J]. Journal of Analytical Science, 2019, 035(002):145-151. 10. Huang Wei, Wu Tong, Liu Chunming, etc. Inhibitory effects of magnolol and honokiol on CYP450 in rat liver microsomes evaluated by probe drug method [J]. China Modern Applied Pharmacy, 2019, 36(04):392-396. 11. Zhang Quan, Jing Wengang, Cheng Xianlong, et al. Study on mass transfer law of Magnolia officinalis during processing based on determination of 9 components [J]. Chinese herbal medicine, 2020, v.51;No.662(03):96-101. 12. Liu Na, Yuan Jinfeng, Xie Deng Xiang, etc. Quantitative Comparison of chemical composition changes of Magnolia officinalis ginger before and after processing based on multi-component [J]. Central South pharmacy, 2020, v.18;No.173(06):118-122. 13. Jing Wen-guang, Zhang Quan, Deng Zhi, et al. Quality Evaluation of Magnolia officinalis based on fingerprint, multi-component quantitative analysis and chemometrics [J]. Chinese Journal of Traditional Chinese Medicine, 2019, 44(5). 14. Jiao Yunping, Zhang Heng, Li thinking, Song Yu. Molecular mechanism of honokiol on proliferation, migration and invasion of nasopharyngeal carcinoma cells [J]. Clinical Research and Practice, 2020,5(28):5-8. 15. Lili, Chen Yong, Zhang Mengwei, Huang Hongxia, Gao Shouhong, Chen Wansheng. Determination of 11 main components in UHPLC-MS experience prescription cold dampness lung decoction by Novel coronavirus pneumonia (COVID-19)/MS [J]. Journal of Pharmaceutical Practice, 2021,39(02):148-151 156. 16. Li, J. , et al. "A novel quality evaluation method for magnolia bark using electronic nose and colorometer data with multiple statistical algorithms-ScienceDirect." Journal of Traditional Chinese Medical Sciences 7. 2(2020):221-227.doi: 10.1016/j.jtcms. 17. Zhang X, Han L, Liu J, et al. Pharmacokinetic Study of 7 Compounds Following Oral Administration of Fructus Aurantii to Depressive Rats. Frontiers in Pharmacology. 2018 ;9:131. DOI: 10.3389/fphar.2018.00131. PMID: 29556193; PMCID: PMC5845165. 18. Qiu, Ling, et al. "Honokiol ameliorates endothelial dysfunction through suppression of PTX3 expression, a key mediator of IKK/IκB/NF-κB, in atherosclerotic cell model ." Experimental & molecular medicine 47.7 (2015): e171-e171. 19. [IF=5.81] Zhang Xianhua et al."Pharmacokinetic Study of 7 Compounds Following Oral Administration of Fructus Aurantii to Depressive Rats."Front Pharmacol. 2018 Mar;0:131 20. [IF=5.418] Qiu Ling et al."Honokiol ameliorates endothelial dysfunction through suppression of PTX3 expression, a key mediator of IKK/IκB/NF-κB in atherosclerotic cell model."Exp Mol Med. 2015 Jul;47(7):e171-e171 21. [IF=3.205] Dong-Dong Hu et al."Simultaneous determination of ten compounds in rat plasma by UPLC-MS/MS: Application in the pharmacokinetic study of Ma-Zi-Ren-Wan."J Chromatogr B. 2015 Sep;1000:136 22. [IF=2.939] Fan Shuli et al."Honokiol Inhibits Tumor Necrosis Factor-α-Stimulated Rat Aortic Smooth Muscle Cell Proliferation via Caspase- and Mitochondrial-Dependent Apoptosis."Inflammation. 2014 Feb;37(1):17-26 23. [IF=1.902] Junjun Wang et al."The pharmacokinetics and tissue distribution of curcumin and its metabolites in mice."Biomed Chromatogr. 2018 Sep;32(9):e4267 24. [IF=1.719] Xiaoying Zhu et al."Honokiol suppresses TNF-α-induced migration and matrix metalloproteinase expression by blocking NF-κB activation via the ERK signaling pathway in rat aortic smooth muscle cells."Acta Histochem. 2014 May;116:588 25. [IF=3.373] Kewei Zhang et al."Discrimination between raw and ginger juice processed Magnoliae officinalis cortex based on HPLC and Heracles NEO ultra-fast gas phase electronic nose."Phytochemical Analysis. 2022 Mar 22 |
Honokiol - Reference Information
| 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. |
Last Update：2024-04-09 21:54:55
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