Periglaucines A-D, anti-HBV and -HIV-1 alkaloids from Pericampylus glaucus

J Nat Prod. 2008 May;71(5):760-3. doi: 10.1021/np070479+. Epub 2008 Apr 9.

Abstract

Four new hasubanane-type alkaloids, periglaucines A-D (1-4), and three known alkaloids, norruffscine (5), (-)-8-oxotetrahydropalmatine (6), and (-)-8-oxocanadine (7), were isolated from the aerial parts of Pericampylus glaucus. Their structures were elucidated on the basis of extensive NMR and EIMS data, and that of periglaucine A (1) was confirmed by single-crystal X-ray diffraction. Alkaloids 1-4 inhibited hepatitis B virus (HBV) surface antigen (HBsAg) secretion in Hep G2.2.15 cells. (-)-8-Oxotetrahydropalmatine (6) possessed a high selectivity index (SI = 22.4) for HBsAg secretion of the Hep G2.2.15 cell line with an IC(50) value of 0.14 mM. Norruffscine (5) and (-)-8-oxotetrahydropalmatine (6) exhibited inhibitory activity against human immunodeficiency virus (HIV-1) with EC(50) values of 10.9 and 14.1 microM in C8166 cells (SI = 45.7 and 18.8), respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology*
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / isolation & purification*
  • Anti-HIV Agents / pharmacology*
  • Antiviral Agents / chemistry
  • Antiviral Agents / isolation & purification*
  • Antiviral Agents / pharmacology*
  • Crystallography, X-Ray
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology*
  • HIV-1 / drug effects
  • Hepatitis B virus / drug effects
  • Humans
  • Inhibitory Concentration 50
  • Menispermaceae / chemistry*
  • Molecular Conformation
  • Molecular Structure
  • Plants, Medicinal / chemistry*

Substances

  • Alkaloids
  • Anti-HIV Agents
  • Antiviral Agents
  • Drugs, Chinese Herbal