Glenthenamines A–F: Enamine Pyranonaphthoquinones from the Australian Pasture Plant Derived Streptomyces sp. CMB-PB042
2区 · 生物学
Article
作者: Bernhardt, Paul V. ; Salim, Angela A. ; Cui, Hui ; Wu, Taizong ; Capon, Robert J. ; Khalil, Zeinab G.
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 and 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 naphthopyranoquinones disclose a new P-gp inhibitory pharmacophore capable of reversing doxorubicin resistance in P-gp overexpressing colon carcinoma cells.
2005-12-01·Chemical Reviews1区 · 化学
Total Synthesis of Selected Bioactive Natural Products: Illustration of Strategy and Design
1区 · 化学
Review
作者: Tatsuta, Kuniaki ; Hosokawa, Seijiro
A review of total synthesis of bioactive natural products including cochleamycin A, tetracycline, nanaomycin D, BE-54238B, sideroxylonal, lymphostin, rosmarinecine, thienamycin, trichostatin D.
2004-01-01·The Journal of Antibiotics4区 · 医学
The First Total Synthesis of a Pyranonaphthoquinone Antitumor, BE-54238B