Abstract
Based on profiles of secondary metabolites produced by marine bacteria obtained using LC/MS, succinilenes A–D (1–4), new triene polyols, were discovered from a culture of a Streptomyces strain SAK1, which was collected in the southern area of Jeju Island, Republic of Korea. The gross structures of 1–4 were primarily determined through analysis of NMR spectra. The double bond geometries of the succinilenes, which could not be established from conventional 1H NMR spectra because of the highly overlapped olefinic signals, were successfully deciphered using the recently developed quantum-mechanics-driven 1H iterative full spin analysis (QM-HiFSA). Succinilenes A–C (1–3) displayed inhibitory effects against lipopolysaccharide (LPS)-induced nitric oxide (NO) production, indicating their anti-inflammatory significance. These three compounds (1–3) commonly bear a succinic acid moiety, although succinilene D (4), which did not inhibit NO production, does not have this moiety in its structure. The absolute configurations of succinilenes A–D (1–4) were established through J-based configuration analysis, the modified Mosher’s method following methanolysis, and CD spectral analysis.
Highlights
Precise interpretation of the spectroscopic data of molecules is the critical step in natural product research for drug discovery
Novel bioactive secondary metabolites by were analysis. Based on this approach and focusing on actinobacterial chemical profiles, we mainly identified through the chemical profiling of bacterial secondary metabolites by LC/MS
Dulbecco’s modified Eagle’s medium (DMEM), fetal bovine serum (FBS), sodium pyruvate, L-glutamine, antibiotics-antimycotics solution, and trypsin-EDTA were purchased from Invitrogen Co. (Grand Island, NY, USA)
Summary
Precise interpretation of the spectroscopic data of molecules is the critical step in natural product research for drug discovery. Based on this approach and focusing on actinobacterial chemical profiles, we mainly identified through the chemical profiling of bacterial secondary metabolites by LC/MS have continuously isolated actinomycete strains from the southern area of Jejuprofiles, Island, Republic analysis Based on this approach and focusing on actinobacterial chemical we have of. The gross structures of activities against lipopolysaccharide (LPS)‐induced nitric oxide (NO) production were obtained The these new compounds were elucidated by conventional 1D and 2D NMR spectroscopy. Their gross structures of these new compounds were elucidated by conventional 1D and 2D NMR overlapped 1 H NMR signals, especially in the olefinic region, required the application of QM-HiFSA to spectroscopy Their overlapped 1H NMR signals, especially in the olefinic region, required determine the geometries of their triene moieties.
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