Abibalsamins A and B, two new tetraterpenoids from Abies balsamea oleoresin

Org Lett. 2012 Mar 16;14(6):1504-7. doi: 10.1021/ol300237f. Epub 2012 Mar 7.

Abstract

Abibalsamins A (1) and B (2), two unprecedented tetraterpenoids featuring a 3,4-seco-rearranged lanostane system fused with a β-myrcene lateral chain via a [4 + 2] Diels-Alder cycloaddition, were isolated from the oleoresin of Abies balsamea. Their structures were elucidated by means of extensive 2D NMR, IR, and MS spectroscopy analyses. The absolute configuration of 1 was determined by single-crystal X-ray diffraction. Both compounds exhibited significant cytotoxic activity against cancer cell lines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Abies / chemistry*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Humans
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plants, Medicinal / chemistry*
  • Spiro Compounds
  • Terpenes / chemistry
  • Terpenes / isolation & purification*
  • Terpenes / pharmacology

Substances

  • Antineoplastic Agents, Phytogenic
  • Spiro Compounds
  • Terpenes
  • abibalsamin A
  • abibalsamin B