Biosynthesis and Structural Revision of Neomarinone

Organic Letters

Volumn 5, Issue 23, 2003, Pages 4449-4452

  Kalaitzis, John A ^a   Hamano, Yoshimitsu ^a   Nilsen, George ^a   Moore, Bradley S ^a,b  

^a UNIVERSITY OF ARIZONA   (United States)

^b University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON 13; NEOMARINONE; TERPENOID; UNCLASSIFIED DRUG;

ACTINOMYCETES; ARTICLE; BIOSYNTHESIS; DRUG STRUCTURE; ISOTOPE LABELING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ASCOMYCOTA; FURANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NAPHTHOQUINONES;

EID: 0344065639     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035748b     Document Type: Article

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10. 6 neomarinone showed moderate antibiotic activities (MIC): Staphylococcus aureus ATCC29213 (MSSA), 4 μg/mL; S. aureus ATCC43300 (MRSA), >32 μg/mL; Streptococcus pneumonia ATCC 49619, >32 μg/mL; Enterococcus faecalis ATCC29212, 8 μg/mL; Haemophilus influenzae ATCC49766, >32 μg/mL; Pseudomonas aeruginosa ATCC27853, >32 μg/mL.
11. 18 (YMC, 20 mm x 250 mm, 10 μm) reversed-phase HPLC employing gradient elution from 30% MeCN in 0.15% TFA to 100% MeCN over 30 min at a flow rate of 9.5 mL/min with monitoring by UV at 254 nm. Neomarinone (∼7 mg/L) and debromomarinone (∼10 mg/L) eluted at 26 and 28 min, respectively.
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14. 6) δ (multiplicity, assignment, coupling constants in Hz, COSYs, HMBCs): 0.73 (s, H23, C15, C16, C17, C21), 0.77 (d, H24, 6.5 Hz, H17, C16, C17, C18), 1.13 (s, H25, C6, C12, C13, C14), 1.14 (m, H14a, H15b), 1.16 (m. H15a, H14a, H14b, C16, C21), 1.30 (d, H11, 6.0 Hz, H12, C12, C13), 1.32 (m, H15b, H14a, H14b, C16, C23), 1.36 (m, H18, H17, H19a, H19b, C17, C19), 1.51 (s, H22, C16, C20, C21), 1.69 (m, H17, H18, H24, C16, C18, C23, C24), 1.82 (s, H26, C1, C9, C10), 1.84 (m, H19a, H18, H20), 1.86 (m, H14b, H15a, H15b, C12, C13, C15, C25), 1.90 (m, H19b, H18, C20), 4.65 (q, H12, 6.0 Hz, H11, C6, C7, C13, C14, C25) 5.35 (brs, H20, H19a, C16, C18, C22), 7.04 (s, H4, C2, C3, C5, C6, C8, C13).
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