482-36-0 Usage
Abstract
Hyperoside is an active ingredient of traditional Chinese medicine extracted from Hypericum perforatum. Modern pharmacological studies have shown that it has a strong analgesic effect, and it could protect the heart, brain, liver, anti-myocardial hypoxia damage and protect cerebral ischemic injury. In recent years, the development of hypericin for the treatment of depression, hepatitis B and other diseases has become a hotspot both in domestic and foreign research.
Extraction
1.? According to Zhongcheng Ke and others, the volume fraction of ethanol, the ratio of material to liquid and the extraction time were independent variables, the extraction rate of hyperoside was the dependent variable, Through the regression of the independent variables and the dependent variables, extraction technology is screened by response surface method predict the best extraction conditions. The results showed that the extraction process was 11.0 times the amount of 77.6% ethanol, and twice with each for 2.7 h.
2.? According to Zhuoheng Li and others, taking ethanol concentration, ethanol addition factor, extraction temperature and extraction times as the influencing factors, using the extraction rate of hyperoside as an index, the orthogonal experiment was used to optimize the optimum conditions of hyperoside ethanol extraction. The optimum extraction process is 20 times the amount of 60% ethanol, and 4 times at 90 ℃ with each for 2 h. The method is simple, accurate and reproducible.
Natural occurance
Hyperoside is an important natural substance extracted from the dried flowers of the mallow leaves. It is a pale yellow needle-like crystal, and soluble in ethanol, methanol, acetone and pyridine, and stable usually. It could react with hydrochloric acid-magnesium powder to generate cherry red material.
Hyperoside is a flavonol glycoside compound. Hyperoside also has a strong role in inhibiting oogidity reductase, and may be beneficial to the prevention of diabetic cataracts.
Synthetic method
Hyperoside is a natural extract and can also be synthesized now. For the synthesis process, re-read the relevant literature to add. Rutin was used as raw material to obtain hyperoside by benzylation, acid hydrolysis, glycoside condensation through phase transfer catalyzing, deacetylation and debenzylation.
Pharmacological effects
Pharmacological effects
Hyperoside has a significant local analgesic effect with no dependence. Its analgesic effect is weaker than morphine, stronger than aspirin, and it is a new type of local analgesic drug.
The drug has shown a good protective effect on myocardial ischemia and reperfusion, cerebral ischemia and reperfusion, cerebral infarction.
Hypericin has a significant anti-inflammatory effect: rats implanted wool ball, intraperitoneal injection for 7 days with 20mg/Kg daily, significantly inhibiting the inflammatory process.
The drug has a strong cough effect.
Hyperoside also has a strong role in inhibiting oogidity reductase, and may be beneficial to the prevention of diabetic cataracts.
Description
Hypericin, which is widely found in various plants, such as Hypericum, Rosaceae,
Campanulaceae, Labiatae, Rhododendron, Asteraceae Kwai, Garciniaceae,
Leguminosae, Euonymus, and other fruits and whole grass, is a flavonoid compound.
Chemical Properties
Yellow Solid
Physical properties
Appearance: yellowish needlelike crystals. Melting point: 227–229 °C. Specific
optical rotation: ?83° (c = 0.2, pyridine). Solubility: soluble in ethanol, methanol,
acetone, and pyridine. Hydrochloric acid–magnesium powder reaction yielded formation
of cherry red; ferric chloride reaction was green; α-naphthol reaction was
positive.
History
In 1960, Nair et al. isolated hyperin from redosier dogwood, in which its content
is 0.075%. Flavonoids in the treatment of cardiovascular and cerebrovascular diseases
play a pivotal role, among which rutin is a typical representative. Isoquetin mainly presents in the leaves of kumquat flowers and the oleander plant kenaf, and it can also be obtained by chemical synthesis. It shows an anti-inflammatory effect through the capillary permeability test and other animal experiments. It also has a toxic effect on the larvae of Chilohabala larvae. It is one of the active ingredients of Hypericum japonicum, which is used in the treatment of hepatitis because of its inhibition of the activities of hepatic enzyme.
Uses
Different sources of media describe the Uses of 482-36-0 differently. You can refer to the following data:
1. It may be used as calibration standard solutions in method validation of polyphenols from leaf extracts using HPLC method.
2. Hyperoside is used as a primary reference standard in the analysis of herbal medicinal products. It may be used as a calibration standard in method validation of polyphenols from leaf extracts using HPLC method.
3. A major flavonoid in apple peels; a bioactive constituent of apple peels
Indications
This product is available in the British Pharmacopoeia (2017) and the European
Pharmacopoeia (9.0th ed.).
Monomeric compounds are currently used clinically. In clinical practice, hypericin
is the main active ingredient of proprietary Chinese medicines, such as
Acanthopanax capsules, of which Acanthopanax stem and leaf extract are the raw
materials for the preparation. Xin’an capsules, prepared with hawthorn leaf extract,
are rich in flavonoids, in which hyperoside, a kind of flavonoid, is one of the main
components. Qi yue lipid-lowering tablets are prepared from the effective parts of
Chinese medicinal herbs such as hawthorn (Nucleation) and Astragalus membranaceus.
Flavonoid is one of the main active ingredients in hawthorn, in which hyperoside
content is higher. Xinxuening tablets, containing ursolic acid, vitexin
rhamnoside, hyperoside, citric acid, and others, is a preparation made from hawthorn
and pueraria and other traditional Chinese medicines, in which hawthorn
enhances the actions of the medicine. Clinical indications of Xinxuening tablets are
coronary heart disease, angina pectoris, chest tightness, palpitations, high blood
pressure, arrhythmia, hyperlipidemia, and mental depression.
Definition
ChEBI: A quercetin O-glycoside that is quercetin with a beta-D-galactosyl residue attached at position 3. Isolated from Artemisia capillaris, it exhibits hepatoprotective activity.
General Description
Produced and qualified by HWI pharma services GmbH.Exact content by quantitative NMR can be found on the certificate.
Biochem/physiol Actions
Protects against peroxide-induced oxidative damage to cells by scavenging reactive oxygen species and enhancing activity of anti-oxidant enzymes, in particular, catalase and glutathione peroxidase.
Pharmacology
Hyperoside has a protective effect against myocardial ischemia. It achieves its protective effect on the myocardium by reducing the apoptosis rate of myocardial cells,
inhibiting myocardial cell lactate dehydrogenase release, enhancing anti-freeradical
effect , and inhibiting calcium influx so as to .
Hyperoside has a protective effect against cerebral ischemia. Hyperoside can
significantly lower oxygen-free radicals, reduce the content of malondialdehyde
and NO in brain tissue, inhibit the decrease of the activity of LDH, SOD and glutathione
peroxidase, and hence result in reduced brain energy, and improve the antianoxic
ability . At the same time, hyperoside can reduce the degree of cerebral edema in ischemia-reperfusion rats .
Hypericin has a significant local analgesic effect that is weaker than that of morphine
and stronger than that of aspirin and does not create dependency; it is a new
type of local analgesic. Studies have shown that the analgesic effect of hyperoside
occurs by reducing the Ca2 + of the pain nerve, thereby inhibiting high potassium-induced
Ca2 + influx, which distinguishes it from morphine and aspirin .
Hyperoside has a significant anti-inflammatory effect and a strong cough effect and inhibits the role of eye aldose reductase, which may be beneficial for the prevention
of diabetic cataracts. Hypericin has an obvious protective effect on liver tissue and gastric mucosa , and its mechanism is related to antioxidant activity and the promotion of a normal return of NO level and improvement of SOD activity.
Hyperoside significantly enhances immune function. In vivo, hyperoside has a significant inhibitory effect on spleen B, T lymphocyte proliferation and peritoneal macrophage phagocytosis, and mouse thymus index; in vitro hyperoside, at a concentration
of 6.25–100 μg/mL, significantly enhanced B, T lymphocyte proliferation and promoted the production of interleukin 2 in T lymphocytes .
In addition, hypericin still has hypolipidemic and antidepressant pharmacological
effects. Its derivative rutin has anti-inflammatory and antiviral effects. Another
derivative, quercetin, is effective at inhibiting expectorant, cough, and asthma for
use in the treatment of chronic bronchitis, coronary heart disease, and hypertension.
Check Digit Verification of cas no
The CAS Registry Mumber 482-36-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,8 and 2 respectively; the second part has 2 digits, 3 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 482-36:
(5*4)+(4*8)+(3*2)+(2*3)+(1*6)=70
70 % 10 = 0
So 482-36-0 is a valid CAS Registry Number.
InChI:InChI=1/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17+,18-,21?/m1/s1
482-36-0Relevant articles and documents
Highly Promiscuous Flavonoid 3- O-Glycosyltransferase from Scutellaria baicalensis
Wang, Zilong,Wang, Shuang,Xu, Zheng,Li, Mingwei,Chen, Kuan,Zhang, Yaqun,Hu, Zhimin,Zhang, Meng,Zhang, Zhiyong,Qiao, Xue,Ye, Min
supporting information, p. 2241 - 2245 (2019/03/19)
A highly regio-specific and donor-promiscuous 3-O-glycosyltransferase, Sb3GT1 (UGT78B4), was discovered from Scutellaria baicalensis. Sb3GT1 could accept five sugar donors (UDP-Glc/-Gal/-GlcNAc/-Xyl/-Ara) to catalyze 3-O-glycosylation of 17 flavonols, and the conversion rates could be >98%. Five new glycosides were obtained by scaled-up enzymatic catalysis. Molecular modeling and site-directed mutagenesis revealed that G15 and P187 were critical catalytic residues for the donor promiscuity. Sb3GT1 could be a promising catalyst to increase structural diversity of flavonoid 3-O-glycosides.
Effects of Functional Groups and Sugar Composition of Quercetin Derivatives on Their Radical Scavenging Properties
Kato, Komei,Ninomiya, Masayuki,Tanaka, Kaori,Koketsu, Mamoru
supporting information, p. 1808 - 1814 (2016/08/02)
Quercetin derivatives are widespread in the plant kingdom and exhibit various biological actions. The aim of this study was to investigate the structure-activity relationships of quercetin derivatives, with a focus on the influence of functional groups and sugar composition on their antioxidant capacity. A series of quercetin derivatives were therefore prepared and assessed for their DPPH radical scavenging properties. Isoquercetin O-gallates were more potent radical scavengers than quercetin. The systematic analysis highlights the importance of the distribution of hydroxy substituents in isoquercetin O-gallates to their potency.
Quercetin diacylglycoside analogues showing dual inhibition of DNA gyrase and topoisomerase IV as novel antibacterial agents
Hossion, Abugafar M. L.,Zamami, Yoshito,Kandahary, Rafiya K.,Tsuchiya, Tomofusa,Ogawa, Wakano,Iwado, Akimasa,Sasaki, Kenji
experimental part, p. 3686 - 3703 (2011/08/03)
A structure-guided molecular design approach was used to optimize quercetin diacylglycoside analogues that inhibit bacterial DNA gyrase and topoisomerase IV and show potent antibacterial activity against a wide spectrum of relevant pathogens responsible f
