Name | Physcione |
Synonyms | Physcione MethyleModin Physcic acid Przewalskinone B 3-methoxy-6-methyl- Emodin-3-methyl ether Rheochrysidin (Physcione) EMODIN-3-METHYLETHER(RG)(CALL) 1,8-Dihydroxy-3-Methoxy-6-Methyl- 1,8-Dihydroxy-3-methoxy-6-methyl-9,10-anthraquinone 1,8-dihydroxy-3-methoxy-6-methylanthracene-9,10-dione 1,8-dihydroxy-3-methoxy-6-methylanthraquinone emodin 3-methyl ether |
CAS | 521-61-9 |
EINECS | 208-315-7 |
InChI | InChI=1/C16H12O5/c1-7-3-9-13(11(17)4-7)16(20)14-10(15(9)19)5-8(21-2)6-12(14)18/h3-6,17-18H,1-2H3 |
InChIKey | FFWOKTFYGVYKIR-UHFFFAOYSA-N |
Molecular Formula | C16H12O5 |
Molar Mass | 284.26 |
Density | 1.448±0.06 g/cm3(Predicted) |
Melting Point | 196-206°C |
Boling Point | 560.5±50.0 °C(Predicted) |
Flash Point | 215.4°C |
Solubility | Almost insoluble in water, slightly soluble in cold ethanol, easily soluble in boiling ethanol, soluble in benzene, chloroform, ether, acetone, glacial acetic acid, sodium hydroxide and hot sodium carbonate solution, very slightly soluble in petroleum ether. |
Vapor Presure | 3.6E-13mmHg at 25°C |
Appearance | Yellow crystal |
Color | Yellow to Dark Yellow to Dark Orange |
BRN | 6770499 |
pKa | 6.23±0.20(Predicted) |
Storage Condition | -20°C Freezer, Under Inert Atmosphere |
Refractive Index | 1.677 |
MDL | MFCD00017374 |
Physical and Chemical Properties | Roots derived from Rheum palmatum L., a plant of the Polygonaceae family |
Hazard Symbols | Xi - Irritant |
Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
WGK Germany | 3 |
RTECS | CB6720000 |
FLUKA BRAND F CODES | 10 |
HS Code | 29146990 |
Reference Show more | 1. Liu Meiting, Li Qian, Qu Minhong et al. Study on HPLC fingerprint of Polygonum multiflorum and radix polygoni multiflori [J]. West China Pharmaceutical Journal 2018v.33(02):89-92. 2. GE, Zhao, Liang, Cheng, gang, Yu, Jianping, Xu, Dujuan. Effects of traditional processing on the main chemical components of Polygonum multiflorum Thunb. [J]. Modern Chinese medicine research and practice 2017 31(03):43-47. 3. Wang Liping, Zhang Huailiang. Simultaneous determination of six components in Tianma Xifeng granules by HPLC [J]. Journal of Medicine Forum 2018 v.39(06):20-23. 4. Lin Yan, Liu Yuexin, Li Chun, etc. Study on quality control of raw/processed Polygonum multiflorum Thunb. HPLC fingerprint combined with pattern recognition and content determination [J]. Chinese Journal of Information on traditional Chinese medicine, 2018, 25(12):67-71. 5. Yang Guojing, Zhang Yuqi, Chen Jiaqing, etc. Quality Analysis of cassia seed with different commercial specifications [J]. Modern Chinese medicine, 2018 v.20(08):963-967. 6. Zhou Yangjing, Tang Junfeng, Gao Feng, Wei Peifeng. Experimental study on the content changes of main chemical components of Polygonum multiflorum Thunb. Processed by "nine steam nine Sun" and its effect on rat liver [J]. Central South pharmacy, 2020,18(04):543-548. 7. Li Hongying made longlan to the pole, etc. Determination of five free anthraquinones in rhubarb by HPLC [J]. Anhui Agricultural Sciences 2013(12):5278-5279. 8. Wei Yanting Zhang Jingyi Zhang huatan et al. Simultaneous determination of five anthraquinones in Sanhuang dropping pills by HPLC [J]. China pharmacy 2015. 9. Li Xiaohua Guo Yun Li Jia Yuan Qi Pu Xiaohui Wang peak. Simultaneous determination of seven index components in Sanhuang tablets by RP-HPLC [J]. Journal of Shenyang Pharmaceutical University 2016 33(08):637-642. 10. Yang qiangpu Xiaohui Li Xiaohua. Determination of seven index components in Yiqing capsule [J]. West China Journal of Pharmacy 2017(3). 11. Guo Yun, Chen Yongchao, Li Xiaohua, etc. Determination of six index components in Niuhuang Jiedu tablets [J]. Journal of Shenyang Pharmaceutical University, 2016, 29 (6):454-458. 12. Zhang Mingming. Study on the construction of core collection and selection of superior germplasm of rhubarb [D]. Beijing University of Chinese Medicine, 2020. 13. Lu Jie, Wang Tingting, Liang Yi, an Yi, Wang Xinhong, Chen Ying. Analysis of chemical constituents of dachengqi decoction by UPLC-LTQ-Orbitrap-MS [J]. Chinese traditional medicines, 2020,42(12):3275-3280. 14. Wang Yingshu, Zhu Guangyan, Wang Bing, Li Jierong, Li Qianfei, He Xiaoyan, Zhao Jiayi, xiaoyanfeng. Effects of conventionally steaming and pharmacopoeia continuous steaming of black bean juice on contents of 12 components in Polygonum multiflorum [J]. Chinese herbal medicine, 2020,51(19):4972-4982. 15. Lanjile, Ruan Yeping, Qiu Luqi. Multi-index optimization of extraction process of wind-induced decoction based on BAS-GA-BP neural network combined with entropy weight method [J]. Chinese Journal of Traditional Chinese Medicine, 2020,45(23):5686-5693. 16. Wu Yuyan, Ren huixu, Feng Youlong, Zhang Li, Zhang Changlin. Study on HPLC fingerprint and content determination of three components of Anshen Bunao capsules [J]. Journal of Guangdong Pharmaceutical University, 2020,36(06):778-783. 17. Xie, Li, et al. "Development of an UHPLC-MS/MS method for comparative pharmacokinetics of nine anthraquinones in rats and application to dosage conversion between different Semen Cassiae forms." Journal of pharmaceutical and biomedical analysis 174 (2019): 18. [IF=3.366] Wu Xingqiang et al."A Novel Selective Accelerated Solvent Extraction for Effective Separation and Rapid Simultaneous Determination of Six Anthraquinones in Tartary Buckwheat and Its Products by UPLC-DAD."Food Anal Method. 2015 May;8(5):1124-1132 19. [IF=5.81] Zhihui Yin et al."Rhein Relieves Oxidative Stress in an Aβ1-42 Oligomer-Burdened Neuron Model by Activating the SIRT1/PGC-1α-Regulated Mitochondrial Biogenesis."Front Pharmacol. 2021; 12: 746711 20. [IF=5.645] Li-Xia Dai et al."Ultrasound-assisted extraction of five anthraquinones from Rheum palmatum water extract residues and the antimicrobial activities."Ind Crop Prod. 2021 Apr;162:113288 21. [IF=4.759] Yueping Jiang et al."Application of multifold characteristic ion filtering combined with statistical analysis for comprehensive profiling of chemical constituents in anti-renal interstitial fibrosis I decoction by ultra-high performance liquid chromatogra 22. [IF=4.36] Li Lin et al."Study on the protection of water extracts of Polygoni Multiflori Radix and Polygoni Multiflori Radix Praeparata against NAFLD and its mechanism."J Ethnopharmacol. 2020 Apr;252:112577 23. [IF=4.142] Wang Chenxi et al."Systematic quality evaluation of Peiyuan Tongnao capsule by offline two-dimensional liquid chromatography/quadrupole-Orbitrap mass spectrometry and adjusted parallel reaction monitoring of quality markers."Anal Bioanal Chem. 2019 Nov;4 24. [IF=3.935] Yanchao Xing et al."An effective strategy for distinguishing the processing degree of Polygonum multiflorum based on the analysis of substance and taste by LC-MS ICP-OES and electronic tongue."J Pharmaceut Biomed. 2021 Oct;205:114328 25. [IF=3.935] Li Xie et al."Development of an UHPLC-MS/MS method for comparative pharmacokinetics of nine anthraquinones in rats and application to dosage conversion between different Semen Cassiae forms."J Pharmaceut Biomed. 2019 Sep;174:696 26. [IF=3.882] Kunpeng Yin et al."Lanthanide Metal-Organic Framework-Based Fluorescent Sensor Arrays to Discriminate and Quantify Ingredients of Natural Medicine."Langmuir. 2021;37(17):5321-5328 27. [IF=3.503] Luping Zhang et al."The anti-breast cancer property of physcion via oxidative stress-mediated mitochondrial apoptosis and immune response."Pharm Biol. 2021;59(1):303-310 28. [IF=3.361] Rong Wang et al."Resonant waveguide grating based assays for colloidal aggregate detection and promiscuity characterization in natural products."Rsc Adv. 2019 Nov;9(65):38055-38064 29. [IF=0.986] Ji-le Lan et al."Q-marker Prediction Analysis of Rhubarb in Fengyin Decoction Based on Fingerprint and Network Pharmacology:."Nat Prod Commun. 2021;16(8): 30. [IF=3.205] Jiayun Chen et al."HRPIF data mining based on data-dependent/independent acquisition for Rhei Radix et Rhizoma metabolite screening in rats."J Chromatogr B. 2022 Feb;1190:123095 31. [IF=5.811] Kong Wei-Song et al."Beware of the Potential Risks for Polygoni Multiflori Caulis-Induced Liver Injury."Front Pharmacol. 2022 Apr;0:928 32. [IF=3.645] Xi Zhou et al."Preparation of magnetic metal-organic framework MIL-101(Fe) and its application in the extraction of anthraquinones in rhubarb."JOURNAL OF SEPARATION SCIENCE |
Plant source: | Rhubarb |
rhubarb | rhubarb is a commonly used Chinese medicine. It was first published in "Shen Nong's Materia Medica" and listed as inferior. Materia Medica has been recorded in the past dynasties. Rhubarb is the dry rhizome of the Polygonaceae plant, Rheum palmatum L., Rheum tanguticum Maxim. ex Balf., or Rheum officinale Baill. The palm leaf rhubarb is mainly produced in Shaanxi, Gansu, Akan and Ganzi prefectures in western Sichuan, northwestern Yunnan and the two stems of Qamdo and Nagqu regions. This product has a large output and is sold all over the country and exported. Tanggu extra-large yellow is mainly produced in Qinghai and the northern foot of the Qilian Mountains in Gansu, northeastern Tibet and northwestern Sichuan. The output is in the middle and it is self-produced and sold. Medicinal rhubarb is mainly produced in western Henan, western Hubei, southern Shaanxi, northern, eastern and southern basin edges of Sichuan, northern, western Guizhou and northwestern Yunnan. The output is very small, and it is mostly sold locally. It is commonly known as "Horseshoe Rhubarb". [main ingredient] anthraquinone derivatives, the total amount is about 2% ~ 5%, exist in two forms, most of which are combined with glucose to form anthracene glycosides, and a small part is free aglycone. The aglycones are rhein, chrysophanol (Chrysophanol), emodin (Emodin), aloe-emodin (Aloe-emodin) and emodin (Physcion). The combined anthracene glycosides are the active ingredients of diarrhea, mainly anthraquinone glycosides and dianthrone glycosides. There are sennoside A, B, C, D, E, F (Sennoside A, B, C, D, E, F) in dianthrone glycosides. Its purgative effect is stronger than anthraquinone glycosides, but its content is less. Anthrone is gradually oxidized to anthraquinone during storage. It is difficult to detect anthrone components in rhubarb stored for more than 3 years. Rhubarb also contains tannins and similar substances, such as d-catechin and gallic acid. It also contains many trace elements. [Functions and Indications] Purging heat and defecation, cooling blood and detoxification, removing blood stasis and dredging meridians. It is used for constipation with real heat, abdominal pain, diarrhea and dysentery, damp-heat jaundice, blood heat vomiting, red eyes, pharyngeal swelling, intestinal carbuncle abdominal pain, carbuncle swelling and boils, blood stasis and meridian closure, bruise injury, external treatment Water and fire scald; upper gastrointestinal bleeding. fig. 2 is a process flow chart for extracting and separating physcion methyl ether from free anthraquinone ether solution. |
high-activity plant-derived fungicide | early phytosine methyl ether was mainly used in the pharmaceutical industry. at present, with the in-depth research on the application of phytosine in agriculture, it is gradually opened up. with the natural plant rhubarb as raw material, after careful extraction of its active ingredients, processed and developed phytosine methyl ether is a high-activity plant-derived fungicide. practice has proved that, 0.5% Physcion AS has a good control effect on powdery mildew, downy mildew, gray mold, anthracnose, etc. Low toxicity to humans and animals, environmentally friendly, and not easy to produce drug resistance. Because it contains a large amount of humic acid and amino acids, it can also effectively promote the growth of new crop shoots and buds. It can be used as an alternative to conventional high-toxic and high-residue pesticides. The use of products is especially suitable for the production of green and organic vegetables. Physcion is a protective fungicide, which induces the protection response of crops, inhibits the germination of pathogenic bacteria spores, the growth of hyphae, and the formation of suction devices, so that crops are protected from pathogenic bacteria and achieve the effect of disease prevention. |
pharmacological effects | physcion has inhibitory effects on 26 kinds of bacteria such as Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Streptococcus and Shigella; It has mutation effect in Salmonella TA1535 test. It has strong inhibitory effect on the longevity of human cervical cancer Hela cells. Antibacterial, used as laxatives, etc. |
content determination | [test article] Polygonum multilorum Thunb of Polygonaceae Polygonum multiflorum. Dry roots and vines. (1) chromatographic conditions: silica gel column (5-10 μm, Qingdao ocean chemical plant, 6mm × 15cm); Cyclohexane-ethyl acetate (80:20) is the mobile phase; The flow rate is 1ml/min; The detection wavelength is 254nm. (2) preparation of reference substance solution: precisely weigh physcion methyl ether reference substance, add chloroform to dissolve and make 0.1 mg/ml solution as reference substance solution. (3) preparation of sample solution ① free type: accurately weigh a certain amount of sample powder, place it in a Soxhlet extractor, add 130ml of chloroform, reflux in a boiling water bath until the extraction solution is colorless, evaporate to remove chloroform and adapt it, quantitatively transfer it to a 10ml volumetric flask, add chloroform to dilute to scale, shake well, filter, collect the filtrate as the sample solution. ② binding type: accurately weigh a certain amount of sample powder, place it in a 10ml beaker, add 4ml of 1mol/L sulfuric acid, and place it for 12 hours. when hydrolysis is complete, filter, discard the filtrate, squeeze out the acid in the filter residue, then place the filter residue and filter paper in a Soxhlet extractor together, and operate according to the above method from "chloroform 130ml" to the sample solution. (4) determination: accurately absorb 10 μl of reference substance solution and 10 μl of sample solution, inject it into liquid chromatograph, and measure it. (5) chromatogram fig. 3 is a high performance liquid chromatogram of physcion. 1. physcion (6) determination results the content of physcion in polygonum multiflorum from different origins was determined by HPLC. the results are shown in the figure: fig. 4 shows the content determination results of physcion in polygonum multiflorum from different origins (%) |
use | used for content determination/identification/pharmacological experiments, etc. Pharmacological effects: physcion has inhibitory effects on 26 kinds of bacteria such as Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Streptococcus and Shigella; it has mutation effect in Salmonella TA1535 test; it has strong inhibitory effect on human cervical cancer Hela cells longevity; antibacterial, used for laxatives, etc. It has antibacterial effect. Mainly used as a laxative. The physcion can be used to study antibiotics, antifungal agents, small molecules of biological activity and cell biology. In a study, physcion has been used to test the cytotoxicity of human cancer cell juglanthraquinone C. physcion was also used in a study to investigate the metabolic regulation of rhubarb (Rheum undulatum) on high-fat diet patterns |