One-step purification of palmatine and its derivative dl-tetrahydropalmatine from Enantia chlorantha using high-performance displacement chromatography.
Palmatine and its reduced form, dl-tetrahydropalmatine are a group of isoquinoline alkaloids that have been reported to display a variety of biological and pharmacological activities. Both drugs are hydrophilic and are difficult to be purified by conventional purification methods of natural products. A high-performance displacement chromatography (HPDC) method successfully purified palmatine and its semi-synthetic derivative dl-tetrahydropalmatine from crude extract of the African medicinal plant Enantia chlorantha. The crude extract from the root bark of E. chlorantha was fractionated on an analytical reversed-phase C(18) column by using 0.1% trifluoroacetic acid (TFA) or acetic acid/H2O as a carrier and cetylpyridinium trifluoroacetate (or acetate) (1.9mg/mL) in 0.1% TFA (or acetic acid)/H2O as a displacer. Palmatine was quantitatively purified at >98% purity in the fully developed displacement mode. dl-Tetrahydropalmatine was semi-synthesized by NaBH4 reduction from crude palmatine and directly purified by HPDC. Both palmatine and dl-tetrahydropalmatine were identified by high-resolution electrospray tandem mass spectrometry, (1)H NMR and (13)C NMR. This is the first report of one-step HPDC purification of natural and semi-synthetic products from a complex crude extract.
Gao
Jin-Ming
JM
Research Centre for Natural Medicinal Chemistry, College of Science, Northwest A & F University, Yangling, Shaanxi 712100, China.
Kamnaing
Pierre
P
Kiyota
Taira
T
Watchueng
Jean
J
Kubo
Takahiro
T
Jarussophon
Suwatchai
S
Konishi
Yasuo
Y
D029061:Annonaceae / Q000737:chemistry*; D001600:Berberine Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D010946:Plants, Medicinal / Q000737:chemistry
D001600:Berberine Alkaloids; C014215:tetrahydropalmatine; C005413:palmatine