beta-D-Glucopyranoside, 5b-((benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta(cd)pentalen-1a(2H)-yl, 6-benzoate, (1aR-(1aalpha,2beta,3aalpha,5alpha,5aalpha,5balpha))-
Benzoylpaeoniflorin
CAS: 38642-49-8
Molecular Formula: C30H32O12
beta-D-Glucopyranoside, 5b-((benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta(cd)pentalen-1a(2H)-yl, 6-benzoate, (1aR-(1aalpha,2beta,3aalpha,5alpha,5aalpha,5balpha))- - Names and Identifiers
beta-D-Glucopyranoside, 5b-((benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta(cd)pentalen-1a(2H)-yl, 6-benzoate, (1aR-(1aalpha,2beta,3aalpha,5alpha,5aalpha,5balpha))- - Physico-chemical Properties
| Molecular Formula | C30H32O12 |
| Molar Mass | 584.57 |
| Density | 1.56±0.1 g/cm3(Predicted) |
| Melting Point | >90°C (dec.) |
| Boling Point | 742.9±60.0 °C(Predicted) |
| Flash Point | 243.058°C |
| Solubility | DMSO : ≥ 34 mg/mL (58.16 mM) |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | White crystalline powder |
| Color | White to Pale Yellow |
| pKa | 11.52±0.70(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.682 |
| MDL | MFCD00869479 |
| Physical and Chemical Properties | It is derived from the root of Paeonia albiflora Pall, a plant of the family Ranunculaceae. |
beta-D-Glucopyranoside, 5b-((benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta(cd)pentalen-1a(2H)-yl, 6-benzoate, (1aR-(1aalpha,2beta,3aalpha,5alpha,5aalpha,5balpha))- - Reference
| Reference Show more | 1. Xu Yuan, Liu Pei, Yan Hui, et al. Analysis of monoterpene glycosides and polyhydroxy compounds during the initial processing of Paeonia lactiflora pall. [J]. Chinese Herbal Medicine, 2014, 25 (5):775-780. 2. Zheng, ru, Cheng, Chen, Lei, et al. Optimization of alcohol extraction process of glycosides from fengdan peel by Box-Behnken response surface methodology [J]. Journal of Shaanxi University of Traditional Chinese Medicine, 2019 042(004):21-27. 3. Yu Xian Hua Gao Haiyan Jin Chuan Shan, etc. Fingerprint of standard decoction of Paeonia lactiflora pall from different habitats and determination of four monoterpene glycosides [J]. Chinese Journal of Modern Applied Pharmacy 2020(11):1290-1295. 4. The guard of the Army, Zheng, such as the process of calculation, etc. Comparison of Three monoterpene glycosides extracted from Cortex Moutan by different methods [J]. Journal of Yichun University, 2019(9):32-36. 5. Guard of the Army, Zheng Rucheng, Luo Qin, etc. Optimization of decocting process of monoterpene glycosides in fengdan peel by orthogonal test [J]. Journal of Hubei University of Medicine, 2019, 38(02):140-142. 6. Mo Yujia, Wang Yan, Qi Qi, et al. Establishment of HPLC fingerprint of the classic decoction and study on the value transfer of chuanxiong [J]. Chinese Journal of Traditional Chinese Medicine, 2020, v.45(03):122-128. 7. Wang Hua, He Danye, Zhu Liangyu, et al. Simultaneous determination of nine active components in Radix Paeoniae rubra by HPLC [J]. Chinese herbal medicine, 2018, 049(003):708-711. 8. Liang de Qin, Zhao Yuan Yuan, Luo Yun, etc. HPLC fingerprints and multi-component content comparison of Paeonia lactiflora pall with different processing methods [J]. Journal of Anhui University of Traditional Chinese Medicine, 2018. 9. Fu shimong, Shen Hongwei, Wang Qianbo, etc. Evaluation of quality of Radix Paeoniae rubra from different areas by fingerprint combined with gray correlation analysis [J]. Chinese herbal medicine, 50 Vol. 23,, pages 5865-5871, ISTIC PKU CSCD CA, 2019. 10. Fu shimong, Shen Hongwei, Wang Qianbo, etc. Optimization of processing technology for Radix Paeoniae rubra slices [J]. Chinese patent medicine, 2019(8). 11. Zhao Yuanyuan, Liang Deqin, Jin Chuanshan, Wei Qinghong, Zhang Wei, Xu Fengqing, Wang Lin. Determination of seven components in standard decoction of different processed products of Radix Paeoniae Alba based on HPLC fingerprint [J]. Natural product research and development, 2018,30(03):404-411 500. 12. Cheng Jiang-Xue, Tang Zhi-shu, Guo Dong-yan, et al. Effect of different compatibility ratio on dissolution of 10 components in Radix Paeoniae rubra-radix angelicae Sinensis [J]. Journal of Pharmaceutical Analysis, 2019, v.39(09):73-80. 13. Li-Mei Feng, Yan-Yan Chen, Ding-Qiao Xu, Rui-Jia Fu, Shi-Jun Yue, Qi Zhao, Yu-Xi Huang, Xue Bai, Mei Wang, Li-Ming Xing, Yu-Ping Tang, Jin-Ao Duan,An integrated strategy for discovering effective components of Shaoyao Gancao decoction for treating neuropa 14. Li-Mei Feng, Yan-Yan Chen, Ding-Qiao Xu Rui-Jia Fu, Shi-Jun Yue, Qi Zhao, Yu-Xi Huang, Xue Bai, Mei Wang, Li-Ming Xing, Yu-Ping Tang, Jin-Ao Duan,An integrated strategy for discovering effective components of Shaoyao Gancao decoction for treating neuropa 15. [IF=1.963] Yujie Lu et al."Searching for calcium antagonists for hypertension disease therapy from Moutan Cortex using bioactivity integrated UHPLC‐QTOF‐MS."Phytochem Analysis. 2019 Jul;30(4):456-463 16. [IF=6.576] Luo Zhiqiang et al."Mechanism of Paeoniae Radix Alba in the Treatment of Non-alcoholic Fatty Liver Disease Based on Sequential Metabolites Identification Approach, Network Pharmacology, and Binding Affinity Measurement."Front Nutr. 2021 Sep;0:674 17. [IF=4.759] Xu Wang et al."A rapid and practical prediction method for the Arizona solvent system family used in high speed countercurrent chromatography."J Chromatogr A. 2020 Oct;1629:461426 18. [IF=4.36] Qiyang Shou et al."Total glucosides of peony improve ovalbumin-induced allergic asthma by inhibiting mast cell degranulation."J Ethnopharmacol. 2019 Nov;244:112136 19. [IF=4.36] Li-Mei Feng et al."An integrated strategy for discovering effective components of Shaoyao Gancao decoction for treating neuropathic pain by the combination of partial least-squares regression and multi-index comprehensive method."J Ethnopharmacol. 2020 Oc |
beta-D-Glucopyranoside, 5b-((benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta(cd)pentalen-1a(2H)-yl, 6-benzoate, (1aR-(1aalpha,2beta,3aalpha,5alpha,5aalpha,5balpha))- - Reference Information
| overview | benzoyl paeoniflorin is the main monoterpene glycoside component in radix paeoniae rubra, which has antibacterial, anti-diabetic, anti-tumor, anti-inflammatory and liver-protecting effects. Figure 1: Benzoylpaeoniflorin |
| pharmacological effects | anti-inflammatory effects: inflammation is the defensive response of the body to the stimulation of inflammatory substances and is the basis for the occurrence and development of many diseases. A variety of inflammatory cells are involved in the inflammatory response, including dendritic cells, macrophages, monocytes, T lymphocytes and B lymphocytes, which show anti-inflammatory effects by inhibiting the production of pro-inflammatory mediators, which may be related to the regulation of c AMP-dependent PGE2 receptor 2 /PGE2 receptor 4 mediated pathway. Paeoniflorin significantly reduced the levels of IL-1 and TNF-α in FLS of collagen-induced arthritis rats. Analgesic effect: Paeonia lactiflora has always been considered to be a traditional Chinese medicine that can effectively relieve various pains. Paeonia lactiflora total glycosides can dose-dependently inhibit acetic acid-induced writhing, electrical stimulation of the soles of the feet-induced hissing, and hot plate reaction in the separation of rats. The analgesic effect of paeoniflorin on visceral pain may be mediated by k-opioid receptor, α2-adrenergic receptor and theafenamine system. In addition, the results of intraventricular injection of paeoniflorin showed that paeoniflorin may have analgesic effect in the central nervous system. Antibacterial effect: It has strong growth inhibition and antibacterial activity against amoxicillin, clarithromycin, metronidazole and tetracycline-resistant strains, indicating that these components are different from the action model of antibiotics and are expected to become new antibacterial components to protect humans from Helicobacter pylori disease. In addition, Paeonia lactiflora extract not only showed antibacterial effect on bacteria, but also showed strong antibacterial effect on fungi including Aspergillus flavus, Aspergillus fumigatus, Aspergillus niger and Fusarium solani (Fusarium solani, Fusarium). Antioxidant effect: Antioxidants can reduce the risk of a variety of diseases, such as diabetes, inflammation, cancer and neurodegenerative diseases. Total glycosides increase superoxide by reducing the activity of glutamic oxaloacetic transaminase, lactate dehydrogenase and creatine kinase. The activity of dismutase reduces the level of malondialdehyde, and exerts a protective effect on isoprenaline-induced myocardial ischemia in rats. This protection may be achieved by reducing oxidative stress. Anti-cancer effect: In recent years, studies have found that Paeonia lactiflora has an inhibitory effect on tumors, and this anti-proliferation and anti-cancer activity is related to the existence of polyphenol compounds. Paeoniflorin regulates the multidrug resistance of gastric cancer cell SGC7901 to vincristine, which is at least partly related to the down-regulation of multidrug resistance gene Bal-XL and Bal-2 of the target gene. In the rat bladder cancer model, the expression of Bcl-2, cyclin 1 and proliferating cell nuclear antigen in rats treated with Radix Paeoniae Alba decreased, while the expression of p-Chk2(Thr-68) ,Bax and Cip1 /p21 increased, thus inducing apoptosis and cell cycle arrest and inhibiting the growth of cancer cells. Antidepressant effect: In the rat model of chronic unpredictable stress depression, paeoniflorin significantly increased sucrose consumption, reduced serum corticosterone and adrenocorticotropic hormone levels, and attenuated the increase of norepinephrine, serotonin and 5-indoleacetic acid caused by chronic unpredictable stress. These results indicate that the regulation mechanism of hypothalamic pituitary adrenal gland and the up-regulation of serotonin and norepinephrine activation system are important mechanisms of paeoniflorin's antidepressant effect. Anti-liver fibrosis: Hepatic stellate cells play an important role in the pathogenesis of liver fibrosis. In hepatic stellate cells induced by platelet-derived growth factor BB, the migration of hepatic stellate cells induced by platelet-derived growth factor BB and the expression of α-smooth muscle actin and collagen were inhibited in a concentration-dependent manner after treatment with Paeonia lactiflora root extract. Anti-autoimmune diseases: systemic lupus erythematosus (SLE) is an autoimmune erythematosu susceptible to women. Abnormal activation of T cells plays an important role in the occurrence and development of SLE. After treating lupus erythematosus CD4T cells with paeoniflorin, it significantly increased the percentage of regulatory T cells in the cells, and increased the expression of Foxp 3 by down-regulating the methylation level of Foxp 3 motions, and increased the expression level of IFN-γ and IL-2 cells. These results indicate that paeoniflorin inhibits the autoimmunity of SLE patients may be through inducing the differentiation of regulatory T cells, modulation of Foxp 3 promoter methylation and IFN-γ and IL-2 signaling pathways. Anti-cardiovascular and cerebrovascular diseases: Cardiovascular and cerebrovascular diseases are a common disease that seriously threatens human health. The causes include hypertension, blood viscosity and abnormal metabolism of vascular wall smooth muscle. In isolated rat thoracic aortic smooth muscle cells stimulated by angiotensin Ⅱ, paeoniflorin inhibited the proliferation of angiotensin Ⅱ-induced smooth muscle cells by increasing the levels of nitric oxide and nitric oxide synthase and reducing the activity of matrix metalloproteinase 2. |
| References | [1] Jin Yingshan, Chen Manli, Tao Jun. Research Progress on Chemical Constituents and Pharmacological Effects of Paeonia lactiflora [J]. Chinese Journal of Pharmacology and Toxicology, 2013, 27(4):745-750. [2] Wang Qiao, Liu Rongxia, Bi Kaishun, etc. HPLC determination of paeoniflorin, paeoniflorin and benzoyl paeoniflorin in total glucosides of paeony capsules [J]. Chinese herbal medicine, 2005, 36(11):1630-1632. [3] he feng, mou jingli, Zhang zhirong, etc. UPLC-MS/MS method for simultaneous determination of oxidized paeoniflorin, paeoniflorin and benzoyl paeoniflorin in plasma [J]: 2617-2621. |
| biological activity | benzoylpaeoniflorin (Benzoylpaeoniflorin) is a natural compound extracted from white peony root, which can be used in the study of coronary heart disease by reducing cell apoptosis. |
| use | used for content determination/identification/pharmacological experiments, etc. Pharmacological effects: analgesic, antispasmodic, wave, detumescence, meridian, diuretic effect. |
Last Update：2024-04-10 22:29:15
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View History
beta-D-Glucopyranoside, 5b-((benzoyloxy)methyl)tetrahydro-5-hydroxy-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta(cd)pentalen-1a(2H)-yl, 6-benzoate, (1aR-(1aalpha,2beta,3aalpha,5alpha,5aalpha,5balpha))-
N-[[4-叔丁基苯基]磺酰基]-BETA-丙氨酸
N-(2-羟基乙基)氨基甲酸苄酯
1-methyl-3-propyl-1H-Imidazolium
1-甲基-4,5-二溴吡咯-2-甲酸甲酯
6-溴-2-吡啶-2-基-喹啉-4-羧酸
C.I. BASIC BLUE 53
3-(三氟甲基)苯甲醇 ,间三氟甲基苄醇, 间三氟甲基苯甲醇
CHIR258 7.7G
[1-(3-fluoro-4-methoxyphenyl)ethyl](1-methoxypropan-2-yl)amine
N-[[4-叔丁基苯基]磺酰基]-BETA-丙氨酸
N-(2-羟基乙基)氨基甲酸苄酯
1-methyl-3-propyl-1H-Imidazolium
1-甲基-4,5-二溴吡咯-2-甲酸甲酯
6-溴-2-吡啶-2-基-喹啉-4-羧酸
C.I. BASIC BLUE 53
3-(三氟甲基)苯甲醇 ,间三氟甲基苄醇, 间三氟甲基苯甲醇
CHIR258 7.7G
[1-(3-fluoro-4-methoxyphenyl)ethyl](1-methoxypropan-2-yl)amine