Antibacterial Neurymenolides from the Fijian Red Alga Neurymenia fraxinifolia

Author:

Stout E. Paige1,Hasemeyer Adam P.1,Lane Amy L.1,Davenport Theresa M.1,Engel Sebastian1,Hay Mark E.1,Fairchild Craig R.1,Prudhomme Jacques1,Le Roch Karine1,Aalbersberg William1,Kubanek Julia1

Affiliation:

1. School of Chemistry & Biochemistry and School of Biology, Georgia Institute of Technology, Atlanta, Georgia, 30332, Bristol-Myers Squibb Pharmaceutical Research Institute, Princeton, New Jersey 08543, Department of Cell Biology and Neuroscience, University of California, Riverside, California 92521, and Institute of Applied Sciences, University of the South Pacific, Suva, Fiji

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Reference10 articles.

1. 2-Pyrone natural products and mimetics: isolation, characterisation and biological activity

2. Macrocyclic enol-ethers containing an acetylenic group from the red alga Phacelocarpus labillardieri

3. New macrocyclic - and -pyrones from the marine red alga

4. Neurymenolide A (1): clear oil (2.9 mg, 0.098% plant dry mass); [α]24D−150 (c0.02 g/100 mL, MeOH); UV (ACN) λmax295 nm (log ε = 3.39); IR (NaCl) νmax3350 (br), 3010, 2860, 2660, 1680, 1570, 1440, 1280, 1160, 970 cm−1;1H and13C NMR (CDCl3, 500 MHz) data see Table1; COSY, HMBC, and NOE data, see theSupporting Information; HR ESI-MS [M + H]+m/z369.2428 (calcd for C24H33O3, 369.2429). Neurymenolide B (2): clear oil (1.0 mg, 0.013% plant dry mass); [α]24D−240 (c0.02 g/100 mL, MeOH); UV (ACN) λmax295 nm (log ε = 3.41);1H and13C NMR (CDCl3, 500 MHz) data, see Table1; COSY, HMBC, and NOE data, see theSupporting Information; HR ESI-MS [M + H]+m/z397.2756 (calcd for C26H37O3, 397.2743).

5. Spectra as a Guide to Structure in the Hydroxypyrone and Hydroxypyridone Series

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