Bae Munhyung, Park So Hyun, Kwon Yun, Lee Sang Kook, Shin Jongheon, Nam Joo-Won, Oh Dong-Chan
Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, Korea.
College of Pharmacy, Yeungnam University, Gyeongsan, Gyeongbuk 38541, Korea.
Mar Drugs. 2017 Feb 14;15(2):38. doi: 10.3390/md15020038.
Based on profiles of secondary metabolites produced by marine bacteria obtained using LC/MS, succinilenes A-D (-), new triene polyols, were discovered from a culture of a strain SAK1, which was collected in the southern area of Jeju Island, Republic of Korea. The gross structures of - 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 (-) displayed inhibitory effects against lipopolysaccharide (LPS)-induced nitric oxide (NO) production, indicating their anti-inflammatory significance. These three compounds (-) commonly bear a succinic acid moiety, although succinilene D (), which did not inhibit NO production, does not have this moiety in its structure. The absolute configurations of succinilenes A-D (-) were established through -based configuration analysis, the modified Mosher's method following methanolysis, and CD spectral analysis.
基于使用液相色谱/质谱法获得的海洋细菌产生的次生代谢产物谱，从一株SAK1菌株的培养物中发现了新的三烯多元醇琥珀烯A - D（-），该菌株采集于大韩民国济州岛南部地区。琥珀烯A - D（-）的总体结构主要通过核磁共振谱分析确定。由于烯烃信号高度重叠，传统¹H NMR谱无法确定琥珀烯的双键几何结构，因此使用最近开发的量子力学驱动的¹H迭代全自旋分析（QM - HiFSA）成功解析了其双键几何结构。琥珀烯A - C（-）对脂多糖（LPS）诱导的一氧化氮（NO）产生具有抑制作用，表明它们具有抗炎意义。这三种化合物（-）通常含有琥珀酸部分，尽管不抑制NO产生的琥珀烯D（）在其结构中没有这个部分。通过基于圆二色光谱的构型分析、甲醇解后的改良莫舍尔方法以及圆二色光谱分析确定了琥珀烯A - D（-）的绝对构型。
