| Identification | More | [Name]
Peiminine | [CAS]
18059-10-4 | [Synonyms]
PEIMININE
PEINININE
RADDEANINE
3beta,20-Dihydroxy-5alpha-cevan-6-one
Cevan-6-one,3,20-dihydroxy-, (3β,5α)-
Fritillarine
Osnovanine | [Molecular Formula]
C27H43NO3 | [MDL Number]
MFCD00210542 | [Molecular Weight]
429.64 | [MOL File]
18059-10-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
267° | [alpha ]
D22 -38.5° (c = 1.5 in chloroform) | [Boiling point ]
567.1±50.0 °C(Predicted) | [density ]
1.18±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C Freezer, Under inert atmosphere | [solubility ]
Chloroform (Slightly), Ethanol (Slightly, Sonicated) | [form ]
Solid | [pka]
14.56±0.70(Predicted) | [color ]
White to Off-White | [InChIKey]
IQDIERHFZVCNRZ-MYFUJZFTNA-N | [CAS DataBase Reference]
18059-10-4(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Description]
Corydalis ochotensis var. raddeana also yields this alkaloid which must not be
confused with the two bases of the same name previously isolated from
Fritillaria raddeana. The structure has been determined from chemical analysis
and the ultraviolet, infrared, NMR and mass spectra. | [Chemical Properties]
Peiminine is an alkaloid isolated from the Chinese drug 'Pei-Mu', the 'Szechuan' variety of which is stated to be obtained from the corms of Fritillaria RoyZei Hook. This base was first prepared by Chou and Chen who gave it the formula C18H22O2N. Other formulae assigned to the alkaloid are C26H43O2N and C25H41O3N. Peiminine yields colourless needles from EtOH and is laevorotatory having [a]D18 - 67.3° (EtOH). It forms a hydrochloride, m.p. 295-8°C; hydrobromide, m.p. 292°C; oxime, m.p. 10SoC (dec.); semicarbazone, m.p. 255-6°C and the phenylhydrazone hydrochloride, m.p. 266°C. The acetyl derivative yields colourless needles from Me2CO, m.p. 174°C, giving a hydrochloride, m.p. 268°C. Chi and his co-workers have found that the free base sinters at 140°C, melts at 147- 8°C and again at 225-6°C after intermediate solidification. These authors consider the alkaloid to be identical with verticilline (q.v.). | [Uses]
Peiminine is a derivative of Peimine (P218375) a steroidal alkaloid compound extracted from the Fritillaria species of medicinal plants. | [Definition]
ChEBI: Imperialine is an alkaloid. | [in vivo]
Peiminine (3mg/kg, intraperitoneal injection, single dose) alleviates inflammatory manifestations and mitigates intestinal tissue damage in an experimental model of ulcerative colitis[2].
Peiminine (10 mg/kg, Intraperitoneal injection, once every 2 days for 6 weeks) prevents bone loss and fat formation in OVX-induced rat model[3].
Peiminine (1-5 mg/kg, are applied to the dorsal skin, once daily for 16 days) inhibits serum IL-6 and TNF-α in the dinitrochlorobenzene (DNCB)-induced Allergic dermatitis animal model[4].
Peiminine (2-5 mg/kg, Intraperitoneal injection, once a day for 4 weeks) has a cardioprotective effect against myocardial infarction-induced myocardial injury and fibrosis in myocardial infarction rat model[5].
Peiminine (1-5 mg/kg, Intraperitoneal injection, single dose) can reduce the damage of inflammatory response to the body and the possibility of pulmonary edema in LPS-induced Acute lung injury model mice[6]. | Animal Model: | ulcerative colitis model[2] | | Dosage: | 3mg/kg | | Administration: | Intraperitoneal injection (i.p.) | | Result: | Reduced inflammation, mucosal ulcers, involvement of digestive system layers, and infltration of inflammatory cells.
Reduced the levels of MPO and NO generated in the rectal tissue.
Reduced cell proliferation in spleen cell.
Decreased the production of f IL-1β, IL-6, and TNF-α cytokines.
Reduced expression levels of genes IL-1β, IL-6, TNF-α, iNOS, and COX2. |
| Animal Model: | Ovariectomized (OVX) rat model[3] | | Dosage: | 10 mg/kg | | Administration: | Intraperitoneal injection (i.p.) | | Result: | Alleviated the bone loss caused by surgical castration.
Improved the expression of COL1A1 and β-catenin and reduced the increase expression of PPAR-γ in trabecular bone. |
| Animal Model: | Allergic dermatitis model[4] | | Dosage: | 1 mg/kg, 5 mg/kg | | Administration: | were applied to the dorsal skin | | Result: | Alleviated the bone loss caused by surgical castration.
Improved the expression of COL1A1 and β-catenin and reduced the increase expression of PPAR-γ in trabecular bone. |
| [IC 50]
Caspase 3; Caspase-8; Caspase-9; PARP-1; ERK1; ERK2; Bcl-2; p65 | [References]
Kametani et al., Heterocycles, 4, 723 (1976) |
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