3681-99-0 Usage
Uses
Used in Traditional Chinese Medicine:
Puerarin is used as a natural isoflavone for treating various cardiovascular diseases, including its potential as a novel approach to lowering the risk of or improving function in ischemia-reperfusion brain injury-related disorders.
Used as a Beta-Adrenergic Blocker:
Puerarin is used as a beta-adrenergic blocker for its antithrombotic, antiallergic, and other salutary effects.
Used in Pharmaceutical Applications:
Puerarin is used as a bioactive compound for modulating serotonin receptors and suppressing lipopolysaccharide-mediated activation of NF-κB in RAW 264.6 macrophages.
Physical Properties:
Appearance: White to light-yellow crystalline powder.
Solubility: Soluble in methanol, freely soluble in ethanol, slightly soluble in water, insoluble in chloroform and ether.
Melting point: 187–189°C.
Chemical Properties:
Puerarin is a hydroxyisoflavone that is isoflavone substituted by hydroxy groups at positions 7 and 4' and a beta-D-glucopyranosyl residue at position 8 via a C-glycosidic linkage. It is a white powder in appearance.
History
In 1959, Japanese chemist Shibata Shoji first studied the chemical production of
pueraria root, indicating that isoflavones are the main active ingredients of pueraria
root, including puerarin, daidzin and daidzein . Then in 2003, David Lee first
total synthesized analogical puerarin . And it was in 1974 that puerarin was first
extracted by Fang Qicheng and other chemists in China . Due to its strong activity of anti-cardiovascular and anti-cerebrovascular ischemia and hypoxia, expanding the coronary artery and cerebrovascular, reducing myocardial oxygen
consumption, and improving myocardial systolic and microcirculation function,
puerarin was approved for clinical use by the Ministry of Health in 1993.
In recent years,
researchers have synthesized a series of puerarin derivatives, and active research
showed that the part of the puerarin derivatives has a good biological activity and
bioavailability. In a new dosage form
research, researchers have developed several types of dosage forms such as quickrelease solid dispersions, solid from microemulsion preparation, etc., which greatly
increase the solubility of puerarin, thus improving bioavailability. In recent years,the research on crystal drug has opened up new ways for the application of
puerarin.
Indications
At present the most widely used medicinal formulation of puerarin in clinical application is puerarin injection, with more than 90 enterprises producing it. The injection was mainly used for the treatment of coronary heart disease, angina pectoris,
myocardial infarction, retinal movement, vein occlusion, sudden deafness and other
diseases. Another dosage form of puerarin is eye drops for the treatment of primary
open-angle glaucoma, ocular hypertension, primary angle closure glaucoma and
secondary glaucoma. In addition, there are puerarin tablets and puerarin capsules,
belonging to the health-care product.
Biochem/physiol Actions
Isoflavone component of kudzu. Reduces anxiety symptoms associated with alcohol withdrawal.
Pharmacology
Contemporary pharmacological research has demonstrated that puerarin has wide
pharmacological activities on the cardiovascular system, nervous system, liver
impairments, osteoporosis and hangover .
The clinical and experimental researches have shown that puerarin has a significant role in the prevention of cerebral vascular disease, which can expand the
coronary artery and improve the metabolism of an ischemic heart muscle, improving brain circulation, increasing cerebral blood flow and reducing blood volume and
heart rate. There is good control of puerarin on myocardial ischemia and cerebral
ischemic disease.
A large number of experiments have proved that puerarin can promote the glucose and lipid metabolism and reduce blood sugar and blood lipid. The protection
of puerarin on diabetes was attributed to its functions on inhibiting apoptosis and
oxidative stress.
Puerarin have protection efficacy on liver damage induced by chemical substances, alcohol, surgery and other experimental damage. This effect is closely
related to the antioxidant effect, resisting lipid peroxidation, inhibiting platelet
aggregation and improving circulation.
Puerarin can also improve the eye microcirculation obviously and reduce the
pressure of the eyes, thus acting obvious therapeutic effect on glaucoma. In addition, it has a variety of preparations, such as liquors, which are still under
development.
Clinical Use
Currently, puerarin is used clinically for the treatment of hypertension, coronary
heart disease, angina pectoris, arrhythmia, myocardial infarction, ischemic cerebrovascular disease, retinal arteriovenous obstruction, sudden deafness, diabetes complications, dizziness and other diseases. Besides, it also is used to treat chronic
pharyngitis, cerebral infarction and Parkinson’s syndrome.
However, puerarin also has adverse reactions in clinical therapy. Fever is the
main symptom. In addition, allergic dermatitis, anaphylactic shock, laryngeal
oedema, increased transaminase, gastrointestinal bleeding, haemolysis phenomenon and kidney damage occurred occasionally, and these symptoms disappeared
after withdrawal of the medication.
Check Digit Verification of cas no
The CAS Registry Mumber 3681-99-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,6,8 and 1 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 3681-99:
(6*3)+(5*6)+(4*8)+(3*1)+(2*9)+(1*9)=110
110 % 10 = 0
So 3681-99-0 is a valid CAS Registry Number.
InChI:InChI=1/C21H20O9/c22-7-14-17(26)18(27)19(28)21(30-14)15-13(24)6-5-11-16(25)12(8-29-20(11)15)9-1-3-10(23)4-2-9/h1-6,8,14,17-19,21-24,26-28H,7H2/t14-,17-,18+,19-,21?/m1/s1
3681-99-0Relevant articles and documents
A new strategy for isoflavone C-glycoside synthesis: The total synthesis of puerarin
Zou, Yunpeng,Peng, Tao,Wang, Gang,Wen, Xiaoxue,Liu, Shuchen,Sun, Yunbo,Zhang, Shouguo,Gao, Yue,Wang, Lin
, p. 461 - 470 (2018)
Given that C-glucosylisoflavones often possess promising biological activities, the development of an efficient synthetic method for this type of molecules is useful for drug discovery. Accordingly, a highly efficient five-step strategy was developed for the total synthesis of puerarin, an isoflavone C-glycoside. An alkyl substituent 4-CH3OC6H4CH2CH2 with an electron-donating group on the aromatic ring was used to enhance the reactivity of phenol and the regioselectivity of O-C rearrangement of phenol glycoside. Thus, coupling of the ethylbenzene derivative of a phenol 1c with glycosyl trifluoroacetimidate 2 resulted in C-glycoside 3c in a 46.2% yield, which was easily de-tert-butylated with trifluoroacetic acid and oxidized with 2,3-dicyano-5,6-dichlorobenzoquinone to produce deoxybenzoin 5. The ring closure reaction of 5 followed by deprotection gave puerarin. This new synthetic strategy is also suitable for the total synthesis of other C-glucosylisoflavones.
Isolation of two new C-glucofuranosyl isoflavones from Pueraria lobata (Wild.) Ohwi with HPLC-MS guiding analysis
Zhang, Hai-Jiang,Yang, Xiao-Ping,Wang, Kui-Wu
, p. 293 - 299 (2010)
A profiling analysis of the total isoflavone extract of the root of Pueraria lobata (Wild.) Ohwi was performed using HPLC coupled with ESI-ion trap mass spectrometry. A total of seven isoflavones were identified according to their retention times, UV, MS data, and comparing with the literature data. Among them, two proposed new compounds were isolated and their structures were determined to be 8-C-α-glucofuranosyl-7,4'-dihydroxyisoflavone and 8-C-β-glucofuranosyl-7,4'-dihydroxyisoflavone, named as neopuerarin A (7) and neopuerarin B (6), on the basis of chemical and spectral analyses.
Isoflavone glucosides exist as their 6''-O-malonyl esters in Pueraria lobata and its cell suspension cultures
Park,Hakamatsuka,Noguchi,Sankawa,Ebizuka
, p. 1978 - 1980 (1992)
Methanol extracts prepared by mild and careful procedure from cultured cells of P. lobata were analyzed by reverse phase high performance liquid chromatography (HPLC) to reveal that most of the isoflavone 7-O-glucosides daidzin(1) and genistin(2), and 8-C-glucoside puerarin(3), exiost as their 6''-O-malonyl esters. The presence of malonyl esters of 1, 2 and 3 was also detected in the fresh roots and stems of P. lobata.
Glucose uptake enhancing activity of puerarin and the role of C-glucoside suggested from activity of related compounds
Kato, Eisuke,Kawabata, Jun
supporting information; experimental part, p. 4333 - 4336 (2010/09/18)
Chemical treatment of diabetes mellitus is widely studied and controlling of blood glucose level is the main course of therapy. In type 2 diabetes mellitus, insulin resistance is the major problem. An isoflavone C-glucoside, puerarin (1), is known to enhance glucose uptake into the insulin sensitive cell and is thought to be a candidate for treatment of diabetes mellitus. We synthesized 1 and several derivatives to apply for the structure-activity relationship study. The result against 3T3-L1 adipocyte indicated that the C-glucoside part of 1 is unconcerned in its activity when tested in vitro and the main structure responsible for its activity was the isoflavone moiety.
Synthesis of tritium-labeled puerarin - A potential antidipsotropic agent
Lee,Ji,Zhang
, p. 702 - 705 (2008/02/11)
Puerarin 1 (8-β-D-Glucopyranosyl-4′-7-dihydroxyisoflavone, NPI-031G) is the major isoflavone C-glycoside isolated from Pueraria lobata, a traditional Chinese medicine widely used for the treatment of alcohol intoxication. In order to understand the mode of action of puerarin in the reward pathway of the central nervous system and to study its bioavailability and pharmacokinetics, we developed a synthetic route for the preparation of tritium-labeled puerarin. The key intermediate 4 was obtained by trimethylsilyl protection of all hydroxyl groups followed by selective deprotection. The corresponding aldehyde 5 was obtained through the subsequent oxidation of the primary alcohol. Standard NaB[3H]4 reduction and hydrolysis produced the tritium-labeled puerarin 6. Copyright
Total synthesis of puerarin, an isoflavone C-glycoside
Lee, David Y. W.,Zhang, Wu-Yan,Karnati, Vishnu Vardhan R.
, p. 6857 - 6859 (2007/10/03)
We completed the first total synthesis of puerarin (1), an isoflavone C-glycoside. The key intermediate, β-D-glucopyranosyl-2,6-dimethoxybenzene (9), was obtained by coupling of a lithiated aromatic reagent (3) with pyranolactone (2) in 56% yield. Condensation of (16) with p-methoxybenzaldehyde gave the chalcone (17). The protected chalcone (18) was cyclized to (19) in the presence of Tl(NO3)3. Demethylation of (19) was accomplished by refluxing with TMSI in CH3CN to give puerarin (1).
