Preparation and purification of canthinone and β-carboline alkaloids from Picrasma quassioides based on bioautography and mass-spectrometry-directed autopurification system

J Sep Sci. 2018 Aug;41(15):3014-3021. doi: 10.1002/jssc.201800127. Epub 2018 Jul 3.

Abstract

Picrasma quassioides (D. Don) Benn. is a widely used traditional Chinese medicine for anti-inflammation and antibiosis. Canthinone and β-carboline alkaloids are the main characteristic constituents that possess diverse pharmacological effects, such as anti-inflammatory and anti-infectious properties. In this study, bioautography in thin-layer chromatography indicated that the antiradical activity compound may be alkaloids. Then, a simple, fast, and efficient method was established for the separation and purification of two types of alkaloids from P. quassioides by mass-spectrometry-directed autopurification system. Eight alkaloids were isolated and purified in this one-step methodology. Among them, five compounds (3, 95.1%, 58.8 mg; 4, 98.4%, 71.7 mg; 6, 97.8%, 365.4 mg; 7, 97.7%, 172.7 mg; 8, 98.2%, 180.3 mg) were obtained in large amounts with extremely high purities. Then, the antiradical activities of the isolates showed that 4-methoxy-5-hydroxycanthin-6-one (6) exhibited obvious 1,1-diphenyl-2-picryl-hydrazyl free radical scavenging activity with an IC50 value of 84.037 μM. This study offers a new method for the preparation of targeted bioactive alkaloids in P. quassioides. This work also provides a reference for the separation of other targeted chemical components with potential activities from traditional Chinese herbal medicines.

Keywords: autopurification; bioautography; carboline alkaloids; traditional Chinese medicine; β-canthinone alkaloids.

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification
  • Antibiosis
  • Carbolines / chemistry
  • Carbolines / isolation & purification*
  • Chromatography, Thin Layer
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Mass Spectrometry
  • Medicine, Chinese Traditional
  • Molecular Structure
  • Picrasma / chemistry*
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification*

Substances

  • Alkaloids
  • Anti-Inflammatory Agents
  • Carbolines
  • Drugs, Chinese Herbal
  • Plant Extracts
  • canthinone