title: Lignans from the Australian Endemic Plant Austrobaileya scandens.
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.
authors.affiliation: Eskitis Institute for Drug Discovery, Griffith University , Brisbane, Queensland 4111, Australia.
authors.forename: Trong D
authors.initials: TD
authors.lastname: Tran
authors.affiliation: Eskitis Institute for Drug Discovery, Griffith University , Brisbane, Queensland 4111, Australia.
authors.forename: Ngoc B
authors.initials: NB
authors.lastname: Pham
authors.affiliation: Queensland Herbarium, DSITI, Brisbane Botanic Gardens , Mt. Coot-tha Road, Brisbane, Queensland 4066, Australia.
authors.forename: Ron
authors.initials: R
authors.lastname: Booth
authors.affiliation: Queensland Herbarium, DSITI, Brisbane Botanic Gardens , Mt. Coot-tha Road, Brisbane, Queensland 4066, Australia.
authors.forename: Paul I
authors.initials: PI
authors.lastname: Forster
authors.affiliation: Eskitis Institute for Drug Discovery, Griffith University , Brisbane, Queensland 4111, Australia.
authors.forename: Ronald J
authors.initials: RJ
authors.lastname: Quinn
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001315:Australia; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D019684:Magnoliopsida / Q000737:chemistry*; D008297:Male; D015394:Molecular Structure; D011471:Prostatic Neoplasms / Q000188:drug therapy*; D016196:S Phase / Q000187:drug effects
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D017705:Lignans