Ancistrotanzanine A, the first 5,3'-coupled naphthylisoquinoline alkaloid, and two further, 5,8'-linked related compounds from the newly described species Ancistrocladus tanzaniensis

J Nat Prod. 2003 Sep;66(9):1159-65. doi: 10.1021/np030077b.

Abstract

The first phytochemical investigation of the recently discovered East African liana Ancistrocladus tanzaniensis is described, resulting in the isolation and structural elucidation of two new naphthylisoquinoline alkaloids, ancistrotanzanines A (5) and B (6), and the known compound ancistrotectoriline A (7). Ancistrotazanine A (5) represents a hitherto unprecedented 5,3'-coupling type between the naphthalene and isoquinoline portions, while 6 and 7 are 5,8'-coupled. The structures of the compounds were determined by spectroscopic, chemical, and chiroptical methods. Compounds 5 and 6 showed good activities against the pathogens of leishmaniasis and Chagas' disease, Leishmania donovani and Trypanosoma cruzi, while 5-7 displayed moderately potent antiplasmodial activities against Plasmodium falciparum parasites.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology
  • Animals
  • Antiprotozoal Agents / chemistry
  • Antiprotozoal Agents / isolation & purification*
  • Antiprotozoal Agents / pharmacology
  • Isoquinolines / chemistry
  • Isoquinolines / isolation & purification*
  • Isoquinolines / pharmacology
  • Leishmania donovani / drug effects
  • Magnoliopsida / chemistry*
  • Molecular Structure
  • Naphthalenes / chemistry
  • Naphthalenes / isolation & purification*
  • Naphthalenes / pharmacology
  • Nuclear Magnetic Resonance, Biomolecular
  • Plasmodium falciparum / drug effects
  • Stereoisomerism
  • Tanzania
  • Trypanosoma cruzi / drug effects

Substances

  • Alkaloids
  • Antiprotozoal Agents
  • Isoquinolines
  • Naphthalenes
  • ancistrotanzanine A