New naphthalene derivatives and isoquinoline alkaloids from Ancistrocladus cochinchinensis with their anti-proliferative activity on human cancer cells

Bioorg Med Chem Lett. 2016 Aug 15;26(16):3913-7. doi: 10.1016/j.bmcl.2016.07.014. Epub 2016 Jul 5.

Abstract

Five new compounds, named ancistronaphtosides A and B (1 and 2), anciscochine (3), anciscochine 6-O-β-d-glucopyranoside (4), and 4'-methoxy-5-epi-ancistecrorine A1 (5), together with tortoside A (6) and 4-hydroxy-2-methoxyphenyl-6-O-syringoyl-β-d-glucopyranoside (7) were isolated from the methanolic extract of Ancistrocladus cochinchinensis. Their chemical structures were established using HR-ESI-MS, NMR spectroscopic, and chiroptical methods. Compound 5 significantly exhibited anti-proliferation against HL-60, LU-1, and SK-MEL-2 cells with IC50 values of 5.0±1.2, 6.5±1.6, and 6.8±2.0μg/mL, respectively.

Keywords: Ancistrocladus cochinchinensis; Anti-proliferation; Isoquinoline alkaloid; Naphthalene derivative.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / isolation & purification
  • Alkaloids / toxicity
  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / toxicity
  • Apoptosis / drug effects
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • HL-60 Cells
  • Humans
  • Isoquinolines / chemistry*
  • Magnetic Resonance Spectroscopy
  • Magnoliopsida / chemistry*
  • Magnoliopsida / metabolism
  • Molecular Conformation
  • Naphthalenes / chemistry*
  • Naphthalenes / isolation & purification
  • Naphthalenes / toxicity
  • Neoplasms / metabolism
  • Neoplasms / pathology
  • Plant Extracts / chemistry
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Alkaloids
  • Antineoplastic Agents, Phytogenic
  • Isoquinolines
  • Naphthalenes
  • Plant Extracts
  • isoquinoline