title: QM-HiFSA-Aided Structure Determination of Succinilenes A-D, New Triene Polyols from a Marine-Derived Streptomyces sp.
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 aStreptomycesstrain SAK1, which was collected in the southern area of Jeju Island, Republic of Korea. The gross structures of1-4were 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 throughJ-based configuration analysis, the modified Mosher's method following methanolysis, and CD spectral analysis.
authors.affiliation: Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, Korea. baemoon89@snu.ac.kr.
authors.forename: Munhyung
authors.initials: M
authors.lastname: Bae
authors.affiliation: Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, Korea. hanirela@snu.ac.kr.
authors.forename: So Hyun
authors.initials: SH
authors.lastname: Park
authors.affiliation: Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, Korea. kisi2016@snu.ac.kr.
authors.forename: Yun
authors.initials: Y
authors.lastname: Kwon
authors.affiliation: Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, Korea. sklee61@snu.ac.kr.
authors.forename: Sang Kook
authors.initials: SK
authors.lastname: Lee
authors.affiliation: Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, Korea. shinj@snu.ac.kr.
authors.forename: Jongheon
authors.initials: J
authors.lastname: Shin
authors.affiliation: College of Pharmacy, Yeungnam University, Gyeongsan, Gyeongbuk 38541, Korea. jwnam@yu.ac.kr.|Department of Medicinal Chemistry & Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, USA. jwnam@yu.ac.kr.
authors.forename: Joo-Won
authors.initials: JW
authors.lastname: Nam
authors.affiliation: Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, Korea. dongchanoh@snu.ac.kr.
authors.forename: Dong-Chan
authors.initials: DC
authors.lastname: Oh
mesh_terms: D000893:Anti-Inflammatory Agents / Q000737:chemistry*; D059001:Aquatic Organisms / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D015394:Molecular Structure; D009569:Nitric Oxide / Q000378:metabolism; D011108:Polymers / Q000737:chemistry*; D056910:Republic of Korea; D013302:Streptomyces / Q000378:metabolism*; D019802:Succinic Acid / Q000737:chemistry
chemical_list: D000893:Anti-Inflammatory Agents; D011108:Polymers; C024617:polyol; D009569:Nitric Oxide; D019802:Succinic Acid
keywords: NMR; QM-HiFSA; anti-inflammatory; marine actinomycete