Bioactive alkaloids from the aerial parts of Houttuynia cordata

J Ethnopharmacol. 2017 Jan 4:195:166-172. doi: 10.1016/j.jep.2016.11.013. Epub 2016 Nov 11.

Abstract

Ethnopharmacological relevance: Houttuynia cordata is an important traditional Chinese medicine used in heat-clearing and detoxifying, swelling and discharging pus, promoting diuresis and relieving stranguria which recorded in Pharmacopoeia of the people's Republic of China (2015 Edition). H. cordata has been recorded in the book Bencaogangmu which was written by Shizhen Li for the treatment of pyretic toxicity, carbuncle swelling, haemorrhoids, and rectocele diseases.

Aim of the study: Phytochemical investigation of the aerial parts of H. cordata and evaluation of their PTP1B inhibitory activities and hepatoprotective activities.

Materials and methods: The dried aerial parts of H. cordata were fractionated by liquid-liquid extraction to obtain CHCl3, ethyl acetate, and n-butanolic fractions. The CHCl3 fraction was confirmed active fraction by the bioactivity-guided investigation, which was isolated and purified by chromatographing over silica gel, Sephadex LH-20, MPLC, and preparative HPLC. The chemical structures of the purified compounds were identified by their spectroscopic data and references.

Results: Eight new compounds (1-8), together with fourteen known compounds (9-22) were isolated from the aerial parts of H. cordata. The known compounds (9-22) were obtained from this plant for the first time. Among them, some compounds exhibited moderate bioactivities.

Conclusion: Compounds (1-8) were identified as new alkaloids, and the known alkaloids (9-22) were isolated from this plant for the first time. Compounds 1, 4, 14, and 19 showed significant PTP1B inhibitory activities with IC50 values of 1.254, 2.016, 2.672, and 1.862µm, respectively. Compounds 1, 3, 6, 11, 17, and 20 (10µm) exhibited moderate hepatoprotective activities against D-galactosamine-induced WB-F344 cells damage.

Keywords: Alkaloid; Atherospermidine (PubChem CID: 77514); Cepharanone B (PubChem CID: 162739); Hepatoprotective activity; Houttuynia cordata; Liriodenine (PubChem CID: 10144). Ouregidione (PubChem CID: 11958181). Cepharadione B (PubChem CID: 189151); Lysicamine (PubChem CID: 122691); PTP1B inhibitory activity; Piperolactam C (PubChem CID: 10881419); Piperolactam D (PubChem CID: 14039008); Sauristolactam (PubChem CID: 131002).

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Cell Line
  • Chemical and Drug Induced Liver Injury / etiology
  • Chemical and Drug Induced Liver Injury / pathology
  • Chemical and Drug Induced Liver Injury / prevention & control*
  • Cytoprotection
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification
  • Drugs, Chinese Herbal / pharmacology*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification
  • Enzyme Inhibitors / pharmacology*
  • Galactosamine / toxicity
  • Hepatocytes / drug effects*
  • Hepatocytes / pathology
  • Houttuynia / chemistry*
  • Liver / drug effects*
  • Liver / pathology
  • Molecular Structure
  • Phytotherapy
  • Plant Components, Aerial / chemistry*
  • Plants, Medicinal
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors*
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / metabolism
  • Structure-Activity Relationship

Substances

  • Alkaloids
  • Drugs, Chinese Herbal
  • Enzyme Inhibitors
  • Houttuynia cordata extract
  • Galactosamine
  • PTPN1 protein, human
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1