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Paeoniflorin (Peoniflorin), a glycoside, is a herbal constituent extracted from the root of Paeonia albiflora Pall. Paeoniflorin has a hypoglycemic effect and has been used as an anticonvulsant. This substance activates the brain's central Adenosine A1-Rs, which reverse the hypotension brought on by guanethidine.
Physicochemical Properties
| Molecular Formula | C23H28O11 |
| Molecular Weight | 480.46 |
| Exact Mass | 480.163 |
| Elemental Analysis | C, 57.50; H, 5.87; O, 36.63 |
| CAS # | 23180-57-6 |
| Related CAS # | 1146967-98-7 (sulfate) |
| PubChem CID | 442534 |
| Appearance | White to off-white solid powder |
| Density | 1.6±0.1 g/cm3 |
| Boiling Point | 690.2±55.0 °C at 760 mmHg |
| Flash Point | 238.4±25.0 °C |
| Vapour Pressure | 0.0±2.3 mmHg at 25°C |
| Index of Refraction | 1.683 |
| LogP | -0.42 |
| Hydrogen Bond Donor Count | 5 |
| Hydrogen Bond Acceptor Count | 11 |
| Rotatable Bond Count | 7 |
| Heavy Atom Count | 34 |
| Complexity | 849 |
| Defined Atom Stereocenter Count | 11 |
| SMILES | O1[C@@]2(C[C@@]3(O[C@@]1([H])[C@@]1(COC(=O)C4C=CC=CC=4)[C@@]3(C[C@@]21[H])O[C@@]1(O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)[H])C)O |
| InChi Key | YKRGDOXKVOZESV-WRJNSLSBSA-N |
| InChi Code | InChI=1S/C23H28O11/c1-20-9-22(29)13-7-23(20,32-18-16(27)15(26)14(25)12(8-24)31-18)21(13,19(33-20)34-22)10-30-17(28)11-5-3-2-4-6-11/h2-6,12-16,18-19,24-27,29H,7-10H2,1H3/t12-,13-,14-,15+,16-,18+,19-,20+,21+,22-,23+/m1/s1 |
| Chemical Name | [(1R,2S,3R,5R,6R,8S)-6-hydroxy-8-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9,10-dioxatetracyclo[4.3.1.02,5.03,8]decan-2-yl]methyl benzoate |
| Synonyms | Paeoniflorin |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | HSP/heat shock protein |
| ln Vitro | Paeoniflorin (Pae) is extracted from the root of paeonia lactiflora which have attracted attention for anti-rheumatic and immune modulating properties. Paeoniflorin (80 μg/mL; 4–24 h) treatment can induce Hsp70, Hsp40, and Hsp27[3]. |
| ln Vivo | Paeoniflorin (intradermal injection; once daily; 25 and 100 mg/kg) exhibits positive outcomes for experimental arthritic[4].In CIA rats, the levels of anti-CII antibody, IgA, IgG and IgM in serum enhanced, BAFF, BAFF-R, PI3K, p-Akt and mTOR were highly expressed. Pae (100mg/kg) obviously decreased arthritis score, relieved ankle and paw swelling, improved spleen histopathology in CIA rats, decreased the levels of IgA, IgM, IgG and anti-CII antibody, and significantly decreased the expressions of BAFF, BAFF-R, PI3K, p-Akt and mTOR. |
| Enzyme Assay | Heat shock proteins (HSPs) are induced by various physical, chemical, and biological stresses. HSPs are known to function as molecular chaperones, and they not only regulate various processes of protein biogenesis but also function as lifeguards against proteotoxic stresses. Because it is very useful to discover nontoxic chaperone-inducing compounds, we searched for them in herbal medicines. Some herbal medicines had positive effects on the induction of HSPs (Hsp70, Hsp40, and Hsp27) in cultured mammalian cells. We next examined 2 major constituents of these herbal medicines, glycyrrhizin and paeoniflorin, with previously defined chemical structures. Glycyrrhizin had an enhancing effect on the HSP induction by heat shock but could not induce HSPs by itself. In contrast, paeoniflorin had not only an enhancing effect but also an inducing effect by itself on HSP expression. Thus, paeoniflorin might be termed a chaperone inducer and glycyrrhizin a chaperone coinducer. Treatment of cells with paeoniflorin but not glycyrrhizin resulted in enhanced phosphorylation and acquisition of the deoxyribonucleic acid-binding ability of heat shock transcription factor 1 (HSF1), as well as the formation of characteristic HSF1 granules in the nucleus, suggesting that the induction of HSPs by paeoniflorin is mediated by the activation of HSF1. Also, thermotolerance was induced by treatment with paeoniflorin but not glycyrrhizin. Paeoniflorin had no toxic effect at concentrations as high as 80 microg/ mL (166.4 microM). To our knowledge, this is the first report on the induction of HSPs by herbal medicines [3]. |
| Cell Assay |
Cell Line: HeLa and IMR-32 cells Concentration: 80 μg/mL Incubation Time: 4, 8, 12, 16, and 24 hours Result: Promoted the phosphorylation of HSF1. |
| Animal Protocol |
SD rats with collagen induced arthritis 25 and 100mg/kg Intradermal injection; 25 and 100mg/kg; once daily; 20 days CIA rats were randomly separated into different groups and treated with Pae (25, 100mg/kg) from day 18 to day 38 after immunization. The effects of Pae on B lymphocytes of CIA rats were evaluated by the levels of BAFF, anti-CII antibody, IgA, IgG and IgM, and the expressions of BAFF-R, PI3K, p-Akt and mTOR [4]. |
| References |
[1]. A review on the pharmacokinetics of paeoniflorin and its anti-inflammatory and immunomodulatory effects. Biomed Pharmacother. 2020 Oct;130:110505. [2]. Paeoniflorin: a monoterpene glycoside from plants of Paeoniaceae family with diverse anticancer activities. J Pharm Pharmacol. 2020 Apr;72(4):483-495. [3]. Paeoniflorin, a novel heat shock protein-inducing compound. Cell Stress Chaperones. 2004 Winter;9(4):378-89. Int J Oncol. 2013 Nov;43(5):1643-51. [4]. BAFF/BAFF-R involved in antibodies production of rats with collagen-induced arthritis via PI3K-Akt-mTOR signaling and the regulation of paeoniflorin. J Ethnopharmacol. 2012 May 7;141(1):290-300. |
| Additional Infomation |
Paeoniflorin is a terpene glycoside. Peoniflorin is under investigation in clinical trial NCT02878863 (Paeoniflorin Combination of Hepatoprotective Drugs Versus Hepatoprotective Drugs Only for Auto-immune Hepatitis). Paeoniflorin has been reported in Paeonia emodi, Paeonia obovata, and other organisms with data available. See also: Paeonia lactiflora root (part of); Paeonia veitchii root (part of); Paeonia X suffruticosa root bark (part of). |
Solubility Data
| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.20 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (5.20 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (5.20 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.0813 mL | 10.4067 mL | 20.8134 mL | |
| 5 mM | 0.4163 mL | 2.0813 mL | 4.1627 mL | |
| 10 mM | 0.2081 mL | 1.0407 mL | 2.0813 mL |