Monomeric, Dimeric, and Trimeric Tropane Alkaloids from Pellacalyx saccardianus

J Nat Prod. 2021 Aug 27;84(8):2272-2281. doi: 10.1021/acs.jnatprod.1c00374. Epub 2021 Aug 3.

Abstract

Seven new tropane alkaloids, including five monomeric (1-5), one dimeric (6), and one trimeric (7) 3α-nortropane ester, along with two known monomeric nortropane alkaloids (8 and 9), were isolated from the leaves and bark of Pellacalyx saccardianus. Their structures, including the absolute configuration of the enantiomeric pair of (±)-6, were elucidated by comprehensive spectroscopic analyses. Alkaloids 6 and 7 showed cytotoxicity toward human pancreatic cancer cell lines (AsPC-1, BxPC3, PANC-1, and SW1990). Alkaloids 1, 4, and 9 induced a smooth muscle relaxation effect comparable to that of atropine (Emax 106.1 ± 7.5%, 97.0 ± 5.2%, 100.9 ± 1.4%, 111.7 ± 1.7%, respectively) on isolated rat tracheal rings.

MeSH terms

  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Animals
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Line, Tumor
  • Humans
  • In Vitro Techniques
  • Malaysia
  • Male
  • Molecular Structure
  • Muscle, Smooth / drug effects*
  • Phytochemicals / isolation & purification
  • Phytochemicals / pharmacology
  • Plant Bark / chemistry
  • Plant Leaves / chemistry
  • Rats
  • Rats, Sprague-Dawley
  • Rhizophoraceae / chemistry*
  • Trachea / drug effects
  • Tropanes / isolation & purification
  • Tropanes / pharmacology*

Substances

  • Alkaloids
  • Antineoplastic Agents, Phytogenic
  • Phytochemicals
  • Tropanes