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2003, Australian Journal of Chemistry
Journal of the American Chemical Society
Macromolecular Engineering: Precise Synthesis, Materials Properties, Applications. Volumes 1−4 Edited by Krzysztof Matyjaszewski (Carnegie Mellon University, Pittsburgh, PA, USA), Yves Gnanou (Université Bordeaux I, Pessac, France), and Ludwik Leibler (Ecole Supérieure de Physique et Chimie Indu...2007 •
2013 •
Chemical investigations into solid phase cultivations of an Australian sheep station pasture plant-derived Streptomyces sp. CMB-PB042, yielded the rare enamine naphthopyranoquinones BE-54238A (1) and BE-54238B (2), together with four new analogues, glenthenamines B–D (4–6) and F (8), and two handling artifacts, glenthenamines A (3) and E (7). Single crystal X-ray analyses of 1–2 resolved configurational ambiguities in the scientific literature, while detailed spectroscopic analysis and biosynthetic considerations assigned structures inclusive of absolute configuration to 3–8. We propose a plausible sequence of biosynthetic transformations linking structural and configurational features of 1–8, and apply a novel Schiff base "fishing" approach to detect a key deoxyaminosugar precursor. These enamine naphthopyranoquinone disclose a new P-gp inhibitory pharmacophore capable of reversing doxorubicin resistance in P-gp overexpressing colon carcinoma cells.
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