Journal article
Lignans from the Australian Endemic Plant Austrobaileya scandens
Journal of Natural Products, Vol.79(6), pp.1514-1523
2016
Abstract
The sole species of the vascular plant family Austrobaileyaceae, Austrobaileya scandens, is endemic to the tropical rainforest of northeastern Queensland, Australia. A single lead-like enhanced fraction of A. scandens showed potent inhibition against human prostate cancer PC3 cells. Chemical investigation of this plant resulted in the isolation of two new aryltetralin lignans, austrobailignans 8 and 9 (1 and 2), and the synthetic compound nicotlactone B (3), newly identified as a natural product together with nine known lignans (4-12). Their structures were established on the basis of spectroscopic analyses. Absolute configurations of the new compounds were determined by quantum chemical electronic circular dichroism (ECD) calculations employing time-dependent density functional theory. The ECD calculations were also used to assign the absolute configuration of marphenol K (4) and revise the absolute configuration of kadsurindutin C (20). Ten out of the 12 isolated compounds inhibited the growth of PC3 cells with IC50 values ranging from micromolar to nanomolar. Marphenol A (5) was found for the first time to induce apoptosis and arrest the S cell cycle phase of PC3 cells. © 2016 The American Chemical Society and American Society of Pharmacognosy.
Details
- Title
- Lignans from the Australian Endemic Plant Austrobaileya scandens
- Authors
- Trong D Tran (Author) - Griffith UniversityN B Pham (Author) - Griffith UniversityR Booth (Author) - Griffith UniversityP I Forster (Author) - Griffith UniversityR J Quinn (Author) - Griffith University
- Publication details
- Journal of Natural Products, Vol.79(6), pp.1514-1523
- Publisher
- American Chemical Society
- Date published
- 2016
- DOI
- 10.1021/acs.jnatprod.5b00988
- ISSN
- 0163-3864
- Organisation Unit
- School of Science and Engineering - Legacy; University of the Sunshine Coast, Queensland; School of Science, Technology and Engineering; Centre for Bioinnovation
- Language
- English
- Record Identifier
- 99450576002621
- Output Type
- Journal article
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- Web Of Science research areas
- Chemistry, Medicinal
- Pharmacology & Pharmacy
- Plant Sciences
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Source: InCites