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Sortase A-Inhibitory Coumarins from the Folk Medicinal Plant Poncirus trifoliata
Journal of Natural Products ( IF 3.3 ) Pub Date : 2020-09-30 , DOI: 10.1021/acs.jnatprod.0c00551 Jae-Sung Park 1 , Beomkoo Chung 2 , Won-Hee Lee 1 , Jayho Lee 2 , Youngbae Suh 1 , Dong-Chan Oh 1 , Ki-Bong Oh 2 , Jongheon Shin 1
Journal of Natural Products ( IF 3.3 ) Pub Date : 2020-09-30 , DOI: 10.1021/acs.jnatprod.0c00551 Jae-Sung Park 1 , Beomkoo Chung 2 , Won-Hee Lee 1 , Jayho Lee 2 , Youngbae Suh 1 , Dong-Chan Oh 1 , Ki-Bong Oh 2 , Jongheon Shin 1
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Thirteen coumarins (1–13), including five new compounds (1–5), were isolated from the folk medicinal plant Poncirus trifoliata. Combined spectroscopic analyses revealed that coumarins 1–4 are bis-isoprenylated coumarins with diverse oxidation patterns, while 5 is an enantiomeric di-isoprenylated coumarin. The absolute configurations of the stereogenic centers in the isoprenyl chains were assigned through MTPA and MPA methods, and those of the known compounds triphasiol (6) and ponciol (7) were also assigned using similar methods. These coumarins inhibited significantly Staphylococcus aureus-derived sortase A (SrtA), a transpeptidase responsible for anchoring surface proteins to the peptidoglycan cell wall in Gram-positive bacteria. The present results obtained indicated that the bioactivity and underlying mechanism of action of these coumarins are associated with the inhibition of SrtA-mediated S. aureus adhesion to eukaryotic cell matrix proteins including fibrinogen and fibronectin, thus potentially serving as SrtA inhibitors.
中文翻译：
来自民间药用植物枳实的分选酶 A 抑制香豆素
十三香豆素（1 - 13），包括五个新化合物（1 - 5），从该民间药用植物中分离枸橘。合并的分光分析表明，香豆素1 - 4是双- isoprenylated与不同的氧化图案香豆素，而5是对映异构体的二isoprenylated香豆素。异戊二烯链中立体中心的绝对构型通过MTPA和MPA方法确定，已知化合物triphasiol( 6 )和ponciol( 7 )的绝对构型也用类似方法确定。这些香豆素显着抑制金黄色葡萄球菌衍生的分选酶 A (SrtA)，一种转肽酶，负责将表面蛋白锚定到革兰氏阳性菌的肽聚糖细胞壁上。目前获得的结果表明，这些香豆素的生物活性和潜在作用机制与抑制 SrtA 介导的金黄色葡萄球菌对真核细胞基质蛋白（包括纤维蛋白原和纤连蛋白）的粘附有关，因此可能用作 SrtA 抑制剂。
更新日期：2020-10-26
中文翻译：
来自民间药用植物枳实的分选酶 A 抑制香豆素
十三香豆素（1 - 13），包括五个新化合物（1 - 5），从该民间药用植物中分离枸橘。合并的分光分析表明，香豆素1 - 4是双- isoprenylated与不同的氧化图案香豆素，而5是对映异构体的二isoprenylated香豆素。异戊二烯链中立体中心的绝对构型通过MTPA和MPA方法确定，已知化合物triphasiol( 6 )和ponciol( 7 )的绝对构型也用类似方法确定。这些香豆素显着抑制金黄色葡萄球菌衍生的分选酶 A (SrtA)，一种转肽酶，负责将表面蛋白锚定到革兰氏阳性菌的肽聚糖细胞壁上。目前获得的结果表明，这些香豆素的生物活性和潜在作用机制与抑制 SrtA 介导的金黄色葡萄球菌对真核细胞基质蛋白（包括纤维蛋白原和纤连蛋白）的粘附有关，因此可能用作 SrtA 抑制剂。
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