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Oxypeoniflorin

[(1aR,2S,5R,5aR,5bS)-1a-(beta-D-glucopyranosyloxy)-5-hydroxy-2-methyltetrahydro-1H-2,5-methano-3,4-dioxacyclobuta[cd]pentalen-5b(3aH)-yl]methyl 4-hydroxybenzoate

CAS: 39011-91-1

Molecular Formula: C23H28O12

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Oxypeoniflorin - Names and Identifiers

Name [(1aR,2S,5R,5aR,5bS)-1a-(beta-D-glucopyranosyloxy)-5-hydroxy-2-methyltetrahydro-1H-2,5-methano-3,4-dioxacyclobuta[cd]pentalen-5b(3aH)-yl]methyl 4-hydroxybenzoate
Synonyms Nsc258310
Oxypeoniflorin
oxypaeoniflora
oxypaeoniflorin
[1a-(hexopyranosyloxy)-5-hydroxy-2-methyltetrahydro-1H-2,5-methano-3,4-dioxacyclobuta[cd]pentalen-5b(3aH)-yl]methyl 4-hydroxybenzoate
[(1aR,2S,5R,5aR,5bS)-1a-(beta-D-glucopyranosyloxy)-5-hydroxy-2-methyltetrahydro-1H-2,5-methano-3,4-dioxacyclobuta[cd]pentalen-5b(3aH)-yl]methyl 4-hydroxybenzoate
β-D-Glucopyranoside, (1aR,2S,3aR,5R,5aR,5bS)-tetrahydro-5-hydroxy-5b-[[(4-hydroxybenzoyl)oxy]methyl]-2-methyl-2,5-methano-1H-3,4-dioxacyclobuta[cd]pentalen-1a(2H)-yl
[[(1aR)-3aβ,5,5aβ,5b-Tetrahydro-5β-hydroxy-5bβ-[[(4-hydroxybenzoyl)oxy]methyl]-2-methyl-2α,5-methano-3,4-dioxa-1H-cyclobuta[cd]pentalen]-1aβ(2H)-yl]β-D-glucopyranoside
((2S,2aR,2a1S,3aR,4R,5aR)-4-hydroxy-2-methyl-2a-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-1,5-dioxa-2,4-methanocyclobuta[cd]pentalen-2a1-yl)methyl 4-hydroxybenzoate
CAS 39011-91-1
InChI InChI=1/C23H28O12/c1-20-8-22(30)13-6-23(20,33-18-16(28)15(27)14(26)12(7-24)32-18)21(13,19(34-20)35-22)9-31-17(29)10-2-4-11(25)5-3-10/h2-5,12-16,18-19,24-28,30H,6-9H2,1H3/t12-,13-,14-,15+,16-,18+,19?,20+,21+,22-,23+/m1/s1

Oxypeoniflorin - Physico-chemical Properties

Molecular FormulaC23H28O12
Molar Mass496.46
Density1.71±0.1 g/cm3(Predicted)
Melting Point>162°C (dec.)
Boling Point737.1±60.0 °C(Predicted)
Specific Rotation(α)-17.1(C=1.0,甲酸)
Flash Point254.6°C
Solubility DMSO : 100 mg/mL (201.43 mM; Need ultrasonic)
Vapor Presure8.22E-23mmHg at 25°C
AppearanceWhite moisture-absorbing amorphous powder
ColorWhite to Pale Yellow
pKa8.16±0.15(Predicted)
Storage ConditionHygroscopic, -20°C Freezer, Under inert atmosphere
StabilityHygroscopic
Refractive Index1.707
MDLMFCD00869478
Physical and Chemical PropertiesWhite crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, from peony bark, peony, peony root.
In vitro study Oxypaeoniflorin (OPA; 0.1-10 µM; 8 hours) obviously reversed the hypoxia/reoxygenation (H/R)-induced decrease in cell activity and increase in apoptosis of H9c2 cells. Oxypaeoniflorin inhibits apoptosis by activating the Sirt1 (silent information regulator factor 2 related enzyme 1)/Foxo1(forkhead transcription factor FKHR) signaling pathway in myocardial tissues and H9c2 cells. Oxypaeoniflorin (0-30 μM) attenuates inflammatory effects via regulation of the toll-like receptor (TLR), extracellular signal-related kinase (ERK) and p38 mitogen-activated protein (MAP) kinases signaling pathways in LPS-stimulated RAW264.7 cells.

Oxypeoniflorin - 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. Shi Suying, Yu Nianjun, Peng Daiyin, etc. Study on characteristic Atlas of different parts of root of Paeonia lactiflora [J]. Journal of Yunnan College of Traditional Chinese Medicine, 202043 volumes 1, 12-18 pages, ISTIC, 2020.
3. 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.
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. 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.
7. Zhang Jiajia, Ma Chi, Zhu Zhiling, Zhang Songbai, Zhang Xun. Simultaneous determination of five components in Radix Paeoniae Alba by HPLC [J]. Fujian traditional Chinese medicine 2019 50(01):66-67 70.
8. Wang Hua, He Danyu, Zhu Liangyu, etc. Simultaneous determination of nine active components in Radix Paeoniae rubra by HPLC [J]. Chinese herbal medicine, 2018, 049(003):708-711.
9. 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.
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. Xu Chao, Lin Jie, Jin Chuanshan, Liu Junling. Comparison of chemical constituents of Paeonia lactiflora pall with different growth years by HPLC fingerprint combined with Chemometrics [J]. Chinese herbal medicine, 2021,52(08):2408-2413.
14. Li-Mei Feng, Yan-Yan Chen, Ding-Qiao Xu, Rui-Jia Fu, Shi-Jun Yu, 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 reduction for treating neuropa
15. 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
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=5.645] Zhang-Zhen Bai et al."Comparative investigation on metabolites and biological activities of Paeonia ostii stamens from different geographical regions of China."Ind Crop Prod. 2021 Nov;172:114038
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
20. [IF=1.902] Ting Zhang et al."The influence of essential oils from ZhaLi NuSi Prescription on the pharmacokinetics of its non-volatile components in normal rats."Biomedical Chromatography. 2021 Oct 21
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