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Mar. Drugs 2017, 15(2), 38; doi:10.3390/md15020038

QM-HiFSA-Aided Structure Determination of Succinilenes A–D, New Triene Polyols from a Marine-Derived Streptomyces sp.

1
Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, Korea
2
College of Pharmacy, Yeungnam University, Gyeongsan, Gyeongbuk 38541, Korea
3
Department of Medicinal Chemistry & Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, USA
*
Authors to whom correspondence should be addressed.
Academic Editors: Tadeusz Molinski and John MacMillan
Received: 14 January 2017 / Revised: 2 February 2017 / Accepted: 8 February 2017 / Published: 14 February 2017
(This article belongs to the Special Issue Structural Techniques in Natural Products Drug Discovery)
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Abstract

Based on profiles of secondary metabolites produced by marine bacteria obtained using LC/MS, succinilenes A–D (14), 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 14 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 (13) displayed inhibitory effects against lipopolysaccharide (LPS)-induced nitric oxide (NO) production, indicating their anti-inflammatory significance. These three compounds (13) 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 (14) were established through J-based configuration analysis, the modified Mosher’s method following methanolysis, and CD spectral analysis. View Full-Text
Keywords: marine actinomycete; QM-HiFSA; NMR; anti-inflammatory marine actinomycete; QM-HiFSA; NMR; anti-inflammatory
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Bae, M.; Park, S.H.; Kwon, Y.; Lee, S.K.; Shin, J.; Nam, J.-W.; Oh, D.-C. QM-HiFSA-Aided Structure Determination of Succinilenes A–D, New Triene Polyols from a Marine-Derived Streptomyces sp.. Mar. Drugs 2017, 15, 38.

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