Isolation, structure elucidation and cytotoxic evaluation of endiandrin B from the Australian rainforest plant Endiandra anthropophagorum.
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 IC(50) value of 7.49 microM.
Davis
Rohan A
RA
Eskitis Institute for Cell and Molecular Therapies, Griffith University, Brisbane, QLD 4111, Australia. r.davis@griffith.edu.au
Barnes
Emma C
EC
Longden
James
J
Avery
Vicky M
VM
Healy
Peter C
PC
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D001315:Australia; D045744:Cell Line, Tumor; D018360:Crystallography, X-Ray; D003503:Cyclobutanes / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D006139:Guaiacol / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000633:toxicity; D006801:Humans; D020128:Inhibitory Concentration 50; D019770:Lauraceae / Q000737:chemistry*; D017705:Lignans / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D009682:Magnetic Resonance Spectroscopy; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry
D000972:Antineoplastic Agents, Phytogenic; D003503:Cyclobutanes; D017705:Lignans; C447287:cinbalansan; C522142:endiandrin A; C539862:endiandrin B; C015816:dihydroguaiaretic acid; D006139:Guaiacol