Orientin
Orientin
CAS: 28608-75-5
Molecular Formula: C21H20O11
Orientin - Names and Identifiers
| Name | Orientin |
| Synonyms | Orientin ORIENTIN ORIENTINE Aids026706 Aids-026706 ORIDONIN (RG) 8-Glucosylluteolin 2-(3,4-Dihydroxyphenyl)-8-beta-D-glucopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-one 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-8-.beta.-D-glucopyranosyl-5,7-dihydroxy- (1S)-1,5-anhydro-1-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-8-yl]-D-glucitol |
| CAS | 28608-75-5 |
| InChI | InChI=1/C21H20O11/c22-6-14-17(28)18(29)19(30)21(32-14)16-11(26)4-10(25)15-12(27)5-13(31-20(15)16)7-1-2-8(23)9(24)3-7/h1-5,14,17-19,21-26,28-30H,6H2/t14-,17-,18+,19-,21+/m1/s1 |
Orientin - Physico-chemical Properties
| Molecular Formula | C21H20O11 |
| Molar Mass | 448.38 |
| Density | 1.759±0.06 g/cm3(Predicted) |
| Melting Point | 260-285°C |
| Boling Point | 816.1±65.0 °C(Predicted) |
| Specific Rotation(α) | (c, 1.4 in Py)+18.4 |
| Flash Point | 289.1°C |
| Solubility | Soluble in DMSO |
| Vapor Presure | 3.63E-28mmHg at 25°C |
| Appearance | Yellow powder |
| Color | yellow |
| pKa | 6.24±0.40(Predicted) |
| Storage Condition | 2-8°C(protect from light) |
| Stability | Hygroscopic |
| Refractive Index | 1.767 |
| MDL | MFCD00017432 |
| Physical and Chemical Properties | From a plant called Trollius chinensis, Ranunculaceae |
Orientin - Risk and Safety
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| RTECS | DJ3009300 |
| HS Code | 29389090 |
Orientin - Reference
| Reference Show more | 1. Zhang Yong, Feng Yuting, Ma Ninghui, etc. Comprehensive Evaluation of extraction technology of bamboo leaves [J]. Chinese Journal of Experimental prescriptions, 2018, 3 (17). 2. Guo Jing, Wang Haoran, Shen Zhouyuan, Zhang Tong, Yuan Xiurong, Ding Yue. Analysis of antioxidant components in three kinds of bamboo leaves [J]. Chinese patent medicine 2019 41(11):2688-2694. 3. Dianpejuan, Duan Xuchang, Wang Min, et al. Antioxidant activity of each polar component of methanol extract from Sonchus Albus [J]. Science and Technology of Food Industry, 2016, 37(16):146-150. 4. Wang Wei, He Ping, Jiang Xiaoming. Anti-inflammatory and antioxidant effects of luteolin and its flavonoid glycosides [J]. Food Science, 2020,41(17):208-215. 5. Wang, Chu-Yang, et al. "Isolation of wheat mutants with higher grain phenolics to enhance anti-oxidant potential." Food chemistry 303 (2020): 125363.https://doi.org/10.1016/j.foodchem.2019.125363 6. [IF = 5.279] Yong Sun et al."Qualitative and Quantitative Analysis of Phenolics in Tetrastigma hemsleyanum and Their Antioxidant and Antiproliferative Activities."J Agr Food Chem. 2013;61(44):10507-10515 7. [IF=7.514] Chu-Yang Wang et al."Isolation of wheat mutants with higher grain phenolics to enhance anti-oxidant potential."Food Chem. 2020 Jan;303:125363 8. [IF=5.396] Mingfang Tao et al."Flavonoids from the mung bean coat promote longevity and fitness in Caenorhabditis elegans."Food Funct. 2021 Aug;12(17):8196-8207 9. [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 10. [IF=4.35] Liangqin Xie et al."Comparison of Flavonoid O-Glycoside C- Glycoside and Their Aglycones on Antioxidant Capacity and Metabolism during In Vitro Digestion and In Vivo."Foods. 2022 Jan;11(6):882 11. [IF=3.373] Yiyuan Luo et al."Quality evaluation of Tetrastigma hemsleyanum different parts based on quantitative analysis of 42 bioactive constituents combined with multivariate statistical analysis."PHYTOCHEMICAL ANALYSIS. 2022 Apr 05 12. [IF=7.514] Jie Meng et al."Conduction of a chemical structure-guided metabolic phenotype analysis method targeting phenylpropane pathway via LC-MS: Ginkgo biloba and soybean as examples."FOOD CHEMISTRY. 2022 Oct;390:133155 13. [IF=6.576] Junkun Pan et al."Inhibition of Dipeptidyl Peptidase-4 by Flavonoids: Structure-Activity Relationship, Kinetics and Interaction Mechanism."Frontiers in Nutrition. 2022; 9: 892426 |
Orientin - Reference Information
| background and overview | nasturtium is the dried flower and bud of nasturtium Trollius chinensis Bunge of Ranunculaceae, which is widely distributed in southwest, northwest, north and northeast regions. "Supplements to Compendium of Materia Medica" says that it is "bitter, cold in nature, non-toxic", and can "treat aphthous sores, swollen throats, floating hot teeth, ear pain, eye pain", and has the effect of "improving eyesight and relieving blue barrier. Previous studies have found that total flavonoids of Trollius chinensis have antioxidant and anti-tumor effects. orientin (orientin) is a kind of flavonoid monomer with biological activity. It is widely distributed and is higher in the total flavonoids of Trollius chinensis. It is also widely distributed in plants of the genus Pteridaceae (Lindsaeacea), bamboo leaves of the genus Phyllostachys, cajan (Cajanus cajan( L.) Millsp.) leaves, hawthorn light leaf mulberry (Crataegus laevigata) and other medicinal plants. Orientin has significant antioxidant, anti-apoptosis, anti-lipid formation, anti-radiation, analgesic, anti-thrombosis and other effects. Now it is the main ingredient of Hongye Xintong Soft Capsules and orientin compound freeze-dried powder preparations It has been put into clinical application, mainly treating cardiovascular diseases such as coronary heart disease, angina pectoris, and heart and blood stasis. At present, Hongyexintong soft capsule and Hongxintong compound freeze-dried powder preparations with orientin as the main active ingredient have been used in clinical practice and play an important role in the treatment of coronary heart disease, angina pectoris, and heart and blood stasis. According to the current research on orientin, orientin has a protective effect on ischemic myocardium, can stimulate vascular cells to produce NO, and increase the level of cGMP, which can reduce myocardial ischemia through NO-cGMP signaling pathways-Reperfusion-induced myocardial cell damage; in addition, it can relax vascular smooth muscle, its relaxation effect is due to the direct effect on vascular endothelium and the inhibition of receptor-dependent Ca2 channels and voltage-dependent Ca2 channels on vascular smooth muscle, and orientin can inhibit the rapid contraction and dependent contraction of phenylephrine. At the same time, it also shows anti-thrombosis effect, which is of great significance for the prevention and treatment of cardiovascular and cerebrovascular diseases such as myocardial ischemia and cerebral ischemia. In addition, orientin also has significant effects on anti-apoptosis and analgesia, indicating that orientin has broad application prospects. |
| pharmacological action and application | protective effect of orientin on myocardial ischemia and myocardial infarction orientin has both preventive and therapeutic effects on acute myocardial ischemia in rats. Insufficient coronary blood supply or increased oxygen consumption of myocardial cells are the main causes of myocardial ischemia. Experiments show that orientin has a certain preventive effect on acute myocardial ischemia caused by pituitrin; it has a certain therapeutic effect on acute myocardial ischemia caused by isoproterenol; prophylactic administration of orientin It can enhance the myocardial contractile function of rats with myocardial infarction, reduce the degree of myocardial ischemia, and protect the ischemic myocardium, which is mainly reflected in the following aspects: 1) The activities of ischemic myocardial enzymes LDH, ALT and AST in the serum of rats with acute myocardial infarction intervened by orientin were significantly lower than those in the model group, indicating that orientin can reduce the degeneration of myocardial cells and protect myocardial ischemia damage; 2) orientin intervention increases the activity of antioxidant enzymes in the serum of rats with acute myocardial infarction, reduces the damage of free radicals produced by myocardial metabolism to myocardial cells, and reduces the degree of myocardial infarction. In addition, orientin can also inhibit atherosclerosis by inhibiting lipid absorption, promoting lipid decomposition and excretion; orientin also has anti-hypoxia and anti-platelet aggregation effects; at the same time, studies have found that orientin can significantly inhibit arachidonic acid-induced platelet aggregation, thereby inhibiting myocardial ischemia; in addition, orientin can also significantly increase the coronary flow of isolated guinea pig hearts, thereby improving the degree of myocardial ischemia, however, its specific mechanism has not yet been clarified. The protective effect of orientin on myocardium during ischemia-reperfusion Myocardial ischemia can lead to cardiovascular diseases such as angina pectoris and myocardial infarction, and can be restored by thrombolysis, coronary artery bypass surgery and other methods Blood supply to the myocardium can achieve the effect of fighting myocardial ischemia. However, cardiology research and cardiac surgery have found that after cardiac ischemia, the reperfusion process can significantly induce myocardial cell apoptosis and aggravate myocardial damage, it is called ischemia-reperfusion injury (ischemia-reperfusion injury,I/R). Orientin can inhibit the expression of pro-apoptotic protein Bax Cty-c Caspase-3 in a dose-dependent manner within a certain concentration range, thus reducing myocardial I/R-induced myocardial cell apoptosis. In addition, orientin can also significantly increase the expression of anti-apoptosis gene bcl-2 in neonatal mouse cardiomyocytes and inhibit the expression of Bax Cyt-c Caspase-3, thus inhibiting hypoxia-reoxygenation-induced apoptosis of neonatal mouse cardiomyocytes. Antithrombotic activity of orientin Thrombosis is an important factor causing myocardial infarction. Thrombolysis is one of the medical methods for the treatment of myocardial infarction. Experiments show that orientin can significantly prolong the clotting time of mice, KPTT and TT of rabbits, suggesting that it inhibits the production of fibrin by interfering with the activity of endogenous coagulation system factors. Orientin can also significantly prolong the PT of rabbits, suggesting that it inhibits the transition from prothrombin to thrombin by interfering with the activity of exogenous coagulation system factors, thus inhibiting the transition from fibrinogen to fibrin. Orientin can significantly inhibit platelet aggregation caused by ADP in rabbits, thus inhibiting arterial thrombosis. Orientin cannot shorten ELT, nor can it reduce the weight of mouse whole blood clots, indicating that orientin does not have fibrinolytic activity. To sum up, orientin has the effect of promoting blood circulation and removing stasis. It can inhibit the production of fibrin and prolong the coagulation time of mice and rabbits by interfering with the activity of endogenous coagulation system factors. Anti-radiation effect of orientin Studies have found that orientin has anti-radiation effect. After the mice received 11Gy γ-ray total body irradiation, the mice were given orientin by intraperitoneal injection to prevent the mice from dying from gastrointestinal syndrome and bone marrow syndrome. The best therapeutic dose was 50mg/kg body weight, and the protective effect of increasing the dose did not increase. In addition, after the mice received 1 Gy60Coγ-ray total body irradiation, the intraperitoneal injection of orientin, compared with the control group, can significantly reduce fetal mouse chromosome variation, adult hematopoietic cell abnormalities, and the whole blood cell count returned to normal. At the same time, it can reduce the incidence of tumors and delay tumor spread. The anti-radiation mechanism of orientin may be related to its antioxidant activity, but its specific mechanism has not been clarified. Analgesic effect of orientin orientin also has analgesic effect. Studies have found that orientin can inhibit the pain induced by acetic acid, capsaicin and glutamate in a dose-dependent manner. Its analgesic effect is 20 times that of antipyretic analgesic acetylsalicylic acid and 3. 5 times that of indomethacin (indomethacin). Antioxidation The experiment showed that within a certain concentration range, orientin has a good scavenging effect on O2-and DPPH; it has an efficient scavenging effect on ONOO-, and has a certain protective effect on SIN-1-induced oxidation-induced myocardial cells. Orientin has a good application prospect for disease prevention and treatment of pathological damage caused by ONOO-. orientin may have autoxidation at high concentration, which needs further experimental confirmation. Anti-cancer antiviral activity orientin and DNA mainly combine in an embedding mode through hydrophobic force, thus changing the double helix structure of DNA and affecting its replication, which may be one of the reasons for its anti-cancer and anti-virus activity. Orientin can inhibit the growth and proliferation of EC-109 cells and induce early apoptosis of esophageal EC-109 cells. As a flavonoid carbon glycoside, it may become a new anti-esophageal cancer drug. |
| preparation and separation | chromatographic conditions analytical conditions: C18 reversed-phase chromatographic column (150mm × 4.6mm,5 μm,Sigma), column temperature 30 ℃, mobile phase acetonitrile-0.3% acetic acid aqueous solution, gradient elution conditions: 0~16 min,11% acetonitrile 16~18 min,11% ~ 13% acetonitrile; 18~40 min,13% ~ 16% acetonitrile; 40~42 min,16% ~ 18% acetonitrile; 42~60 min,18% ~ 100% acetonitrile; 60~65 min,100% ~ 11% acetonitrile; The injection volume is 20 μL, the volume flow rate is 0.7 mL/min, the detection wavelength is 330 nm, and the operation time is 70 min. PHPLC conditions: C18 reversed-phase semi-prepared chromatographic column (250mm × 10mm,5 μm,SunFire TM), column temperature 20 ℃, methanol-0.3% acetic acid aqueous solution (33 ∶ 67), injection volume 400 μL, volume flow rate 5 mL/min, detection wavelength 330 nm, operation time 40 min. Adsorption and elution of the sample weigh 50 g of bamboo leaf flavonoids, dissolve them with 500 mL of absolute ethanol, remove polysaccharides with large polarity by vacuum suction filtration, then spin the clear liquid, dissolve them with 1 L of pure water, and remove flavonoids with small polarity by vacuum suction filtration. Dilute the treated sample with ultrapure water to 4 L (mass concentration is about 8g/L), adjust the pH value to 5, load the sample in an atmospheric glass column (10cm × 60cm) filled with AB-8 resin, elute with 1.5 BV of 0, 10%, 20%, 30%, 40%, 50%, 60% and 65% ethanol solutions in turn, and 1 bottle per 500 ml during collection, among them, elution solutions of isoorientin (mass fraction 18.0%) and orientin (mass fraction 10.1%) were obtained under 40% ethanol elution conditions. PHPLC separation of orientin and isoorientin monomer the obtained eluent (mass concentration is 4.2 mg/mL) was separated according to the PHPLC conditions. The components 1 and 2 are collected respectively, and the high-quality fraction of orientin and isoorientin monomers can be obtained by one-step separation, and the product powder is obtained by vacuum distillation and vacuum drying. |
| pharmacokinetics | the distribution of orientin in different animal tissues is not different, with the highest concentration in kidney, followed by liver and the lowest content in brain. |
| main reference materials | [1] Guo hong et al. research progress on pharmacological effects of orientin. Chinese folk medicine. Chinese folk medicine. Chinese folk medicine. No.10, 2014. [2] Huang xiulan et al. protective effect and mechanism of orientin on acute myocardial infarction in rats. Drug evaluation studies. 2012,35(6):412-415. [3] fu Xiaochun et al. relaxation effect of orientin on isolated rabbit aortic smooth muscle and its mechanism. journal of China pharmaceutical university. 2006 , 37(6):539 -543. [4] Zhu Dengxiang et al. Effect of orientin in Trollius chinensis on Growth and Apoptosis of Tumor Cells in Human Esophageal Cancer EC-109. Chinese patent medicine. 2012,34(11):2055-2059. [5] fu Xiaochun et al. antithrombotic effect of orientin. Chinese pharmacy. 2006 ,17 (17):1292-1294. [6] Li Jianping et al. Study on Antioxidant Effect of Hong Wei in Vitro. Chinese Journal of Hypertension. 2015,23(3): 394-395. [7] Liu Wei et al. Study on the mechanism of the interaction between orientin and DNA. Journal of Huazhong Normal University (Natural Science Edition). 2014,48(4):528-531. [8] Xu jiang et al. preparative chromatographic separation of isoorientin and orientin from bamboo leaf flavonoids. Chinese herbal medicine. 2014,45(15):2184-2187. [9] yuan danhua et al. antioxidant effects of orientin and vitexin in trollius chinensis on liver and kidney brain tissues of aging mice induced by D-galactose. Chinese journal of gerontology. 2012,32(9):1875-1877. |
| use | used for content determination/identification/pharmacological experiments, etc. Pharmacological effects: orientin has a certain protective effect on hypoxia-reoxygenation myocardial cell injury. |
Last Update：2024-04-09 21:01:54
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Tel: +86-400-900-4166
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Tel: +86-18821248368
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QQ: 495145328
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View History
Orientin
2386-53-0
(S)-3-Boc-Amino-gamma-butyrolactone
3-Bromo-2-methoxypyridine
57102-42-8
4-Methoxy-7H-furo(3,2-g)(1)benzopyran-7-one
Suprofen
2230911-59-6
4-Methyl-2-nitrobenzaldehyde
26342-66-5
2386-53-0
(S)-3-Boc-Amino-gamma-butyrolactone
3-Bromo-2-methoxypyridine
57102-42-8
4-Methoxy-7H-furo(3,2-g)(1)benzopyran-7-one
Suprofen
2230911-59-6
4-Methyl-2-nitrobenzaldehyde
26342-66-5