1,3,6,7-Tetrahydroxyxanthone C2-beta-D-glucoside
mangiferin from mangifera indica leaves
CAS: 4773-96-0
Molecular Formula: C19H18O11
1,3,6,7-Tetrahydroxyxanthone C2-beta-D-glucoside - Names and Identifiers
| Name | mangiferin from mangifera indica leaves |
| Synonyms | mangiferin Xanthone-c-glucoside mangiferin from mangifera indica leaves 1,3,6,7-TETRAHYDROXYXANTHONE-2-C-GLUCOSIDE 1,3,6,7-Tetrahydroxyxanthone C2-beta-D-glucoside 2-β-D-Glucopyranosyl-1,3,6,7-tetrahydroxy-9H-xanthen-9-one 2-beta-d-glucopyranosyl-1,3,6,7-tetrahydroxy-9h-xanthen-9-one 1,5-anhydro-1-(1,3,6,7-tetrahydroxy-9-oxo-9H-xanthen-2-yl)hexitol (1S)-1,5-anhydro-1-(1,3,6,7-tetrahydroxy-9-oxo-9H-xanthen-2-yl)-D-glucitol (1xi)-1,5-anhydro-1-(1,3,6,7-tetrahydroxy-9-oxo-9H-xanthen-2-yl)-D-glucitol 1,3,6,7-tetrahydroxy-2-[(3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]xanthen-9-one |
| CAS | 4773-96-0 |
| EINECS | 624-757-7 |
| InChI | InChI=1/C19H18O11/c20-4-11-15(25)17(27)18(28)19(30-11)12-8(23)3-10-13(16(12)26)14(24)5-1-6(21)7(22)2-9(5)29-10/h1-3,11,15,17-23,25-28H,4H2/t11-,15-,17+,18-,19?/m1/s1 |
1,3,6,7-Tetrahydroxyxanthone C2-beta-D-glucoside - Physico-chemical Properties
| Molecular Formula | C19H18O11 |
| Molar Mass | 422.34 |
| Density | 1.843±0.06 g/cm3(Predicted) |
| Melting Point | 269-270°C |
| Boling Point | 842.7±65.0 °C(Predicted) |
| Specific Rotation(α) | +43.3°（c=0.9，pyridine） |
| Flash Point | 303.6°C |
| Solubility | Slightly soluble in methanol, ethanol, water, soluble in hot dilute methanol, hot dilute ethanol, insoluble in non-polar solvents. |
| Vapor Presure | 3.67E-30mmHg at 25°C |
| Appearance | Light gray yellow needle crystal |
| Color | Pale Yellow |
| pKa | 6.09±0.20(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.788 |
| MDL | MFCD00075656 |
| Physical and Chemical Properties | Fruit derived from the plant Mangifera indica L. |
1,3,6,7-Tetrahydroxyxanthone C2-beta-D-glucoside - Risk and Safety
| Risk Codes | R28 - Very Toxic if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. R22 - Harmful if swallowed |
| Safety Description | S22 - Do not breathe dust. S28 - After contact with skin, wash immediately with plenty of soap-suds. S36/37 - Wear suitable protective clothing and gloves. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S24/25 - Avoid contact with skin and eyes. |
| UN IDs | UN 3462 6.1/PG 1 |
| WGK Germany | 3 |
| RTECS | OP1927800 |
| HS Code | 29389090 |
1,3,6,7-Tetrahydroxyxanthone C2-beta-D-glucoside - Reference
| Reference Show more | 1. Li Jianchen, Ran Yun, Zhi Haifeng, Ha Min, Duan zhiqing. Study on the quality control method of small golden grass [J]. Journal of Hebei University of Science and Technology, 2016,37(06):581-586. 2. Wang Wenjing, Yu Beibei, Sun Dandan, etc. Optimization of preparation process for substance reference of Baihu decoction by Central composite design-response surface method [J]. Chinese Journal of Traditional Chinese Medicine, 2020, v.35(03):505-509. 3. Li Fuxin, Yu Beibei, Sun Dandan, et al. Study on quality standard of white tiger decoction mixture [J]. Journal of Liaoning University of Traditional Chinese Medicine, 2018, 020(003):39-42. 4. Zhang Xiping, Tang Huaying, Zhao Lijuan, et al. Effects of mangiferin and galangin on the morphology and secretion of BCBL-1 in IL-4 cells [J]. Journal of Youjiang Medical College for Nationalities, 2016, 38(6):563-563. 5. Deng Hongmei, Chen Yijun, Lin Zhuanghui, Zheng Liwen, Sun Zefeng, Guo Weifeng. Isolation, purification and identification of mangiferin [J]. Agricultural products processing, 2018(06):1-4 9. 6. Xu Jian, Liu Xiaojuan, Lu Qingzhi, et al. Protective effect of mangiferin pretreatment on acute liver failure in mice [J]. Journal of Xinxiang Medical University, 2020, 037(004):327-331. 7. Cui, Ling, Zhang, Li, Chen, Meng, et al. Simultaneous determination of puerarin, loganin, mangiferin and rutin in Zhige capsules by HPLC [J]. Journal of Shenyang Pharmaceutical University 2018(7). 8. Concubines Zhanyan, Li Yuanyuan, an Xinxin, et al. Antiviral flavonoid fraction and effective chemical constituents of Shiwei [J]. Journal of Jinan University: natural science and medicine edition, 2018, 039(006):470-480. 9. Tang Yanan, Xu Jinkai, Han Xitao, Han Shu, Liu Kaiyang, Zhu Meiru, Liu Ziqin, Li Weifei, Li Fei, Du Hong. Tissue distribution of mangiferin in Rhizoma anemarrhenae decoction in rats [J]. Modern Chinese medicine, 2021,23(01):73-76 93. 10. Gu Liyan, Huang Qingquan, He Songhua, Huang Bo, Luo Yi. Establishment of a method for the determination of mangiferin and isosaminiferin in guangshiwei [J]. Journal of Food Safety and quality testing, 2020,11(17):6235-6240. 11. Yang Yawen, Liu Yong, Liu Yu, Du Hongzhi, Liu assembly, Huang Bicheng. Effects of different drying methods on drying characteristics, appearance and effective components of Belamcanda chinensis [J]. Chinese Journal of Traditional Chinese Medicine, 2021,46(02):366-373. 12. Feng Zifang, Fei Yiming, Yuan Xiaohang, Chen Xiaowei, Hu Minmin, Fei Qianqian. Simultaneous determination of six components in Baoshen mixture by HPLC with wavelength switching [J]. Central South pharmacy, 2021,19(01):114-117. 13. Qiu Feng, Song Chunyan, Qin Fu-chuan, tian Si-Qi, Huang Rong, Ma Xi-Li, Zeng Jianping. Effect of mangiferin on Pneumonia induced by Staphylococcus aureus [J]. Chinese Journal of General Practice, 2021,19(04):558-560. 14. Jia Xinxin, Liu Haifan, si Mingdong, Li Xinrui, Song Junna, Zheng Yuguang, Ma Donglai. Study on the establishment of fingerprint and the spectrum-effect relationship of antioxidant activity of anemarrhenae Rhizoma and its different processed products [J]. China Pharmacy, 2020,31(22):2706-2712. 15. Liu, Mengshun, et al. "Folding fan mode counter-current chromatography offers fast blind screening for drug discovery. Case study: Finding anti-enterovirus 71 agents from Anemarrhena asphodeloides." Journal of Chromatography A 1368 (2014): 116-124.https:// 16. Xia, Gen, et al. "Mangiferin protects osteoblast against oxidative damage by modulation of ERK5/Nrf2 signaling." Biochemical and biophysical research communications 491.3 (2017): 807-813.https://doi.org/10.1016/j.bbrc.2017.06.184 17. Song, Junna, et al. "Mangiferin activates Nrf2 to attenuate cardiac fibrosis via redistributing glutaminolysis-derived glutamate." Pharmacological research 157 (2020): 104845.https://doi.org/10.1016/j.phrs.2020.104845 18. [IF=7.514] Kai Hu et al."Phytochemical profiling of the ripening of Chinese mango (Mangifera indica L.) cultivars by real-time monitoring using UPLC-ESI-QTOF-MS and its potential benefits as prebiotic ingredients."Food Chem. 2018 Aug;256:171 19. [IF=4.759] Mengshun Liu et al."Folding fan mode counter-current chromatography offers fast blind screening for drug discovery. Case study: Finding anti-enterovirus 71 agents from Anemarrhena asphodeloides."J Chromatogr A. 2014 Nov;1368:116 20. [IF=2.985] Gen Xia et al."Mangiferin protects osteoblast against oxidative damage by modulation of ERK5/Nrf2 signaling."Biochem Bioph Res Co. 2017 Sep;491:807 21. [IF=6.558] Qingqing Song et al."Binary code, a flexible tool for diagnostic metabolite sequencing of medicinal plants."Anal Chim Acta. 2019 Dec;1088:89 22. [IF=5.893] Junna Song et al."Mangiferin activates Nrf2 to attenuate cardiac fibrosis via redistributing glutaminolysis-derived glutamate."Pharmacol Res. 2020 Jul;157:104845 23. [IF=4.818] Yong Zhang et al."Mangiferin Ameliorates HFD-Induced NAFLD through Regulation of the AMPK and NLRP3 Inflammasome Signal Pathways."J Immunol Res. 2021;2021:4084566 24. [IF=3.209] Pengchao Pan et al."A stop-flow comprehensive two-dimensional HK-2 and HK-2/CIKI cell membrane chromatography comparative analysis system for screening the active ingredients from Pyrrosia calvata (Bak.) Ching against crystal-induced kidney injury."J Phar 25. [IF=3] Qu Lala et al."Phenotypic assessment and ligand screening of ETA/ETB receptors with label-free dynamic mass redistribution assay."N-S Arch Pharmacol. 2020 Jun;393(6):937-950 26. [IF=4.932] Ran Wang et al.Mangiferin exert protective effects on joints of adjuvant-induced arthritis rats by regulating the MAPKs/NF-κB pathway of fibroblast-like synoviocytes.Int Immunopharmacol. 2021 Dec;101:108352 27. [IF=6.529] Fanying Meng et al."Virtual screening and in vitro experimental verification of LuxS inhibitors from natural products for Lactobacillus reuteri."Biomed Pharmacother. 2022 Mar;147:112521 |
1,3,6,7-Tetrahydroxyxanthone C2-beta-D-glucoside - Reference Information
| Overview | Mangiferin (mangiferin), also known as Guanzhenning or Mangoin, is a tetrahydroxypyridone carbocarbon glycoside, which belongs to diphenylpyridone Flavonoids, mainly derived from the dry rhizome of the Liliaceae perennial herb Anemarrhena, the leaves, fruits, and bark of the plants almond and mango, the roots of the five-layer dragon plant of the genus Pterodactylaceae, Hainan, etc.; it has cough, asthma and expectorant, immune, anti-inflammatory and analgesic, liver and gallbladder, anti-lipid peroxidation, anti-cancer, anti-diabetes, antibacterial, anti-virus and other pharmacological activities. At present, the main clinical applications are Mango Zhike Tablets, Mango Zhike Capsules, Mangiferin Tablets, Mangiferin Dropping Pills, and these drugs are only used for respiratory diseases. Fig. 1 is the structural formula of mangiferin |
| Mango | Mango, a plant of the Lacquer family, records in "Kaibao Materia Medica" that food quenches thirst, leaves are decocted in soup to cure thirst; "Compendium of Materia Medica" records that it is the best in fruit; "Compendium of Materia Medica" records the effects of mango on stomach qi and vomiting. The present study found that mangiferin in branches, leaves and bark of mango has a wide range of pharmacological effects such as anti-inflammatory, antipyretic and analgesic, antibacterial, immune regulation, hypoglycemic, antioxidant, etc. |
| pharmacological action | 1. antioxidant effect due to the particularity of mangiferin structure, there are multiple phenolic hydroxyl groups in the molecule, and phenolic hydroxyl groups happen to be important groups for scavenging free radicals and reactive oxygen species. The mechanism of its action on free radicals can be attributed to two aspects: on the one hand, it directly acts on scavenging free radicals, and on the other hand, it acts on iron and copper ions to reduce its further reaction with free radicals. 2. The occurrence of anti-tumor leukemia is related to the disorder of cell cycle regulation, and there is a close relationship between cell cycle regulation and telomerase activity expression. Therefore, the study of abnormal regulation of telomerase and cell cycle has become a new direction to explore the occurrence and treatment of leukemia. The occurrence of leukemia is related to the disorder of cell cycle regulation, and there is a close relationship between cell cycle regulation and telomerase activity expression. Therefore, the study of abnormal regulation of telomerase and cell cycle has become a new direction to explore the occurrence and treatment of leukemia. 3. Neuroprotective effect Mangiferin with polyphenol structure can protect neurons by reducing the degree of Ca2 + influx and oxidative stress, thus reducing the cell death caused by glutamate in neurons. 4. Antiviral effect has anti-herpes simplex virus type I (HSV-I) effect in vitro, with a plaque reduction rate of 56.8%. Its antiviral effect is attributed to its ability to inhibit intracellular virus replication. 5. The antipyretic effect has a good antipyretic effect on the experimental animal model of fever caused by endotoxin, and is positively correlated with the dose, which has a good protective effect on heat injury. 6. Analgesic effect has significant analgesic effect on pain induced by acetic acid and hot plate test. Compared with naloxone hydrochloride, it is found that mangiferin-induced pain loss is not dependent on opioid receptors, its analgesic effect is significant, and its effect on peripheral nerves is slight. 7. Anti-parasitic effect Mangiferin has obvious inhibitory effect on Cryptosporidium parvum in young rats. Effect of mangiferin on mice infected with nematodes, Trichinella spiralis. 8. Anti-diabetic Effect After oral administration of mangiferin and glucoside, the blood sugar level of normal mice has no change, but it can reduce the blood sugar concentration of mice KK-Ay spontaneous diabetes animal model, and the insulin level in serum also has a decreasing trend. Fruit glycosides and their glucosides may show antidiabetic activity through insulin sensitization. 9. The protective effect of protecting liver and choleretic effect on liver. Mangiferin has the effect of stabilizing lysosomal membrane and directly inhibiting the activity of lysosomal acid phosphatase. Mangiferin also has obvious choleretic effect. 10. Effect on Central Nervous System Mangiferin has obvious excitatory effect on Central Nervous System. Mangiferin has the effect of removing lipid peroxides in brain tissue, reducing the damage of lipid peroxides to neurons, thereby protecting the normal function of neurons. 11. It has adrenal glucocorticoid-like anti-inflammatory effect on the respiratory system, can reduce capillary permeability, and its anti-inflammatory response rate reaches 38%. Due to the anti-inflammatory effect of mangiferin, it has a certain effect on bronchial asthma, which is manifested as ①It can make the asthma induction time significantly longer than that of the asthma group; ②It reduces the degree of asthma and the incidence of convulsions is significantly lower than that of the asthma group; ③The emphysema is significantly reduced, the inflammatory cell infiltration in the lung is significantly less than that of the asthma group, and the lung/body weight ratio is significantly lower than that of the asthma group, which is close to the dexamethasone group. At the same time, mangiferin can reduce the levels of serum NO and endothelin-1 (ET-1) in alveolar lavage fluid, and play a certain preventive role in asthma attack. The combination of mangiferin and dexamethasone can improve the curative effect. |
| extraction method | 1. organic solvent extraction process uses more than 90% ethanol as extraction solvent, and high purity mangiferin can be extracted from mango leaves. 2. Water-based solvent extraction process uses weak alkaline water as the extraction solvent to extract mangiferin from mango leaves, and the extract is successively eluted by D101 column macroporous resin and D301 column impurity removal and decolorization. This high-purity mangiferin extraction process is suitable for industrial production. 3. Enzymatic extraction process uses cellulase to extract mangiferin from mango leaves. The experimental conditions are as follows: enzymolysis PH is 5.0, temperature is 55 ℃, time is 2h. 4. Ultrasonic-assisted extraction process Ultrasonic-assisted extraction process has the advantages of simplicity, short time consumption, energy saving, etc., and has good development and application prospects. (2016-02-01) |
| clinical application | 1. for the treatment of upper respiratory tract infection. |
| use | used for content determination/identification/pharmacological experiments, etc. Pharmacological effects: This product has inhibitory effects on the central nervous system, anti-inflammatory, antibacterial, anti-herpes simplex virus, choleretic and immune effects, and has a protective effect on simulated high altitude acute hypoxia liver injury. Pharmacological experiments have shown that this product has a good effect in the treatment of chronic bronchitis. It is the main active ingredient in the treatment of hepatitis with Tibetan Artemisia artemisiae and the antiviral active ingredient in the rhizome of Anemarrhena. a natural phenolic flavonoids, can be used as anti-microbial or anti-diabetic drugs for research, with anti-inflammatory and antioxidant activities. Mangiferin can be used to help identify and characterize type II 5-α-reductase. MGF can be used as a reference substance for the analysis of flavonoids. MGF may act as a promoter of gastrointestinal transport (GIT). |
Last Update：2024-04-09 15:16:50
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Multiple SpecificationsSpot supply
Product Name: Mangiferin Visit Supplier Webpage Request for quotationCAS: 4773-96-0
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
Spot supply
Product Name: Mangiferin Visit Supplier Webpage Request for quotationCAS: 4773-96-0
Tel: +86-(0)731-84213302
Email: sales@staherb.cn
Mobile: +86 13875855783
QQ: 484702402
WhatsApp: +86 18374838656
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