Physicochemical Properties
| Molecular Formula | C27H43NO3 |
| Molecular Weight | 429.6352 |
| Exact Mass | 429.324 |
| CAS # | 18059-10-4 |
| PubChem CID | 167691 |
| Appearance | White to off-white solid powder |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 567.1±50.0 °C at 760 mmHg |
| Melting Point | 212-213ºC |
| Flash Point | 296.8±30.1 °C |
| Vapour Pressure | 0.0±3.5 mmHg at 25°C |
| Index of Refraction | 1.585 |
| LogP | 3.9 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 0 |
| Heavy Atom Count | 31 |
| Complexity | 755 |
| Defined Atom Stereocenter Count | 12 |
| SMILES | C[C@H]1CC[C@H]2[C@@]([C@H]3CC[C@@H]4[C@H]([C@@H]3CN2C1)C[C@H]5[C@H]4CC(=O)[C@@H]6[C@@]5(CC[C@@H](C6)O)C)(C)O |
| InChi Key | IQDIERHFZVCNRZ-YUYPDVIUSA-N |
| InChi Code | InChI=1S/C27H43NO3/c1-15-4-7-25-27(3,31)21-6-5-17-18(20(21)14-28(25)13-15)11-22-19(17)12-24(30)23-10-16(29)8-9-26(22,23)2/h15-23,25,29,31H,4-14H2,1-3H3/t15-,16-,17+,18+,19-,20-,21-,22-,23+,25-,26+,27-/m0/s1 |
| Chemical Name | (1R,2S,6S,9S,10S,11S,14S,15S,18S,20S,23R,24S)-10,20-dihydroxy-6,10,23-trimethyl-4-azahexacyclo[12.11.0.02,11.04,9.015,24.018,23]pentacosan-17-one |
| 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
| ln Vitro | In HepG2 cells, peiminine (2–6 μg/mL, 24 h) can decrease procaspase-3, procaspase-8, and procaspase-9 expression while raising caspase-3, 8, and 9 protein levels [1]. HepG2, Hela, SW480, and MCF-7 cells are clearly cytotoxically affected by periminine (2–6 μg/mL, 24-72 h) [1]. HepG2 cells are induced to arrest in the G2/M phase by peiminine (2–6 μg/mL, 24 h) [1]. |
| ln Vivo | Fritillaria (3 mg/kg, intraperitoneal injection, single dosage) can lessen intestinal tissue damage and the inflammatory symptoms of the animal model of thermally induced ductitis [2]. For six weeks, intraperitoneal fritillaria (10 mg/kg) given once every two days inhibits adipogenesis and bone loss brought on by OVX [3]. In an animal model of DNCB-induced allergic dermatitis, peiminine (1–5 mg/kg, given to the back skin once daily for 16 days) suppresses serum IL-6 and TNF-α [4]. Beminin, administered intraperitoneally once daily for four weeks at a dose of two to five mg/kg, protects against myocardial infarction damage and fibrosis [5]. In a lipopolysaccharide-induced acute lung damage model, belimine (1–5 mg/kg, i.p., single dose) may potentially reduce the response to injury and pulmonary edema [6]. |
| Cell Assay |
Cytotoxicity assay[1] Cell Types: HepG2, Hela, SW480, MCF-7 Tested Concentrations: 2 μg/. mL, 4 μg/mL, 6 μg/mL, 8 μg/mL, 10 μg/mL, 12 μg/mL and 14 μg/mL Incubation Duration: 24 hrs (hours), 48 hrs (hours), 72 hrs (hours) Experimental Results: For HepG2, Hela, SW480 and The IC50 values of MCF-7 cells after 24 hrs (hours) of survival were 4.58, 4.89, 5.07 and 5.12 μg/mL respectively. Apoptosis analysis[1] Cell Types: HepG2 Tested Concentrations: 2 μg/mL, 4 μg/mL, 6 μg/mL, 8 μg/mL Incubation Duration: 24 h Experimental Results: Dissociated chromosomes produce DNA in a dose-dependent manner fragment. Cell cycle analysis[1] Cell Types: HepG2 Tested Concentrations: 2 μg/mL, 4 μg/mL, 6 μg/mL Incubation Duration: 24 hrs (hours) Experimental Results: G1 phase percentage diminished from 65.15% ± 0.78 to 49.55% ± 0.17 Increase in concentration . As the concentration increased, the percentage of G2/M phase increased from 17.32%±0.20 to 39.99%±0.47. Western Blot Analysis[1] Cell Types: HepG2 Tested Concentrations: 2 μg/mL, 4 μg/mL, 6 μg/mL Incubation Duration: 24 h Experimental Results: diminished expression of procaspase-3, PARP |
| Animal Protocol |
Animal/Disease Models: Ulcerative colitis model [2] Doses: 3mg/kg Route of Administration: intraperitoneal (ip) injection Experimental Results: Reduce inflammation, mucosal ulceration, involvement of all layers of the digestive system, and inflammatory cell infiltration. Reduces the levels of MPO and NO produced in rectal tissue. Splenocyte proliferation is diminished. Reduces production of f IL-1β, IL-6 and TNF-α cytokines. The expression levels of IL-1β, IL-6, TNF-α, iNOS, and COX2 genes were diminished. Animal/Disease Models: Ovariectomized (OVX) rat model [3] Doses: 10 mg/kg Route of Administration: intraperitoneal (ip) injection Experimental Results: Reduce bone loss caused by surgical castration. Improved the expression of COL1A1 and β-catenin and diminished the increased expression of PPAR-γ in trabecular bone. Animal/Disease Models: allergic dermatitis model [4] Doses: 1 mg/kg, 5 mg/kg Route of Administration: Apply to the back skin Experimental Results: Reduce bone loss caused by surgical castration. Improved the expression of COL1A1 and β-catenin and r |
| References |
[1]. The effects and mechanism of peiminine-induced apoptosis in human hepatocellular carcinoma HepG2 cells . PLoS One, 2019, 14(1): e0201864. [2]. Anti-inflammatory activity of peiminine in acetic acid-induced ulcerative colitis model . Inflammopharmacology, 2023: 1-9. [3]. Peiminine regulates bone-fat balance by canonical Wnt/β-catenin pathway in an ovariectomized rat mode . Phytotherapy Research, 2023. [4]. Effect of peiminine on DNCB-induced atopic dermatitis by inhibiting inflammatory cytokine expression in vivo and in vitro . International immunopharmacology, 2018, 56: 135-142. [5]. Peiminine inhibits myocardial injury and fibrosis after myocardial infarction in rats by regulating mitogen-activated protein kinase pathway . The Korean Journal of Physiology & Pharmacology: Official Journal of the Korean Physiological Society and the Korean Society of Pharmacology, 2022, 26(2): 87-94. [6]. Peiminine attenuates acute lung injury induced by LPS through inhibiting lipid rafts formation . Inflammation, 2020, 43: 1110-1119. [7]. Peiminine ameliorates bleomycin-induced acute lung injury in rats. Mol Med Rep. 2013 Apr;7(4):1103-10. |
| Additional Infomation |
Imperialine is an alkaloid. Peiminine has been reported in Fritillaria ebeiensis, Fritillaria monantha, and other organisms with data available. |
Solubility Data
| Solubility (In Vitro) | DMSO : ≥ 100 mg/mL (~232.75 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.82 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 (5.82 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 (5.82 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 | 2.3275 mL | 11.6377 mL | 23.2753 mL | |
| 5 mM | 0.4655 mL | 2.3275 mL | 4.6551 mL | |
| 10 mM | 0.2328 mL | 1.1638 mL | 2.3275 mL |