Isolation, structure elucidation and cytotoxic evaluation of endiandrin B from the Australian rainforest plant Endiandra anthropophagorum

Rohan A. Davis*, Emma C. Barnes, James Longden, Vicky M. Avery, Peter C. Healy

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

Chemical investigations of the DCM extract from the roots of Endiandra anthropophagorum resulted in the isolation of a new cyclobutane lignan endiandrin B (1), together with the known natural products, endiandrin A (2), and (-)-dihydroguaiaretic acid (3). The structure of 1 was determined by extensive spectroscopic analyses, and confirmed by single crystal X-ray crystallography. Methylation of 1 using diazomethane afforded the previously reported natural product, cinbalansan (4). All compounds were evaluated for their cytotoxicity towards human lung carcinoma cells (A549) using high-content screening. (-)-Dihydroguaiaretic acid (3) was found to be the most potent cytotoxin against the A549 lung carcinoma cell line, with an IC50 value of 7.49 μM.

Original languageEnglish
Pages (from-to)1387-1392
Number of pages6
JournalBioorganic and Medicinal Chemistry
Volume17
Issue number3
DOIs
Publication statusPublished - 1 Feb 2009
Externally publishedYes

Keywords

  • (-)-Dihydroguaiaretic acid
  • A549
  • Cinbalansan
  • Cytotoxicity
  • Endiandrin A
  • Endiandrin B
  • High content screening
  • Natural products
  • NMR
  • Structure elucidation
  • X-ray

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