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Polyoxygenated Steroids from the Sponge Clathria gombawuiensis
Journal of Natural Products ( IF 3.3 ) Pub Date : 2017-11-28 00:00:00 , DOI: 10.1021/acs.jnatprod.7b00651 Jung-Kyun Woo 1 , Thi Kim Quy Ha 2 , Dong-Chan Oh 1 , Won-Keun Oh 2 , Ki-Bong Oh 3 , Jongheon Shin 1
Journal of Natural Products ( IF 3.3 ) Pub Date : 2017-11-28 00:00:00 , DOI: 10.1021/acs.jnatprod.7b00651 Jung-Kyun Woo 1 , Thi Kim Quy Ha 2 , Dong-Chan Oh 1 , Won-Keun Oh 2 , Ki-Bong Oh 3 , Jongheon Shin 1
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Six new polyoxygenated steroids (1–6) along with clathriol (7) were isolated from the Korean marine sponge Clathria gombawuiensis. Based upon the results of combined spectroscopic analyses, the structures of gombasterols A–F (1–6) were elucidated to be those of highly oxygenated steroids possessing a 3β,4α,6α,7β-tetrahydroxy or equivalent (7β-sodium O-sulfonato for 3) substitution pattern and a C-15 keto group as common structural motifs. The relative and absolute configurations of these steroids, including the rare 14β configuration of 1–4, were determined by a combination of NOESY, J-based analyses, the 2-methoxy-2-(trifluoromethyl)phenylacetic acid (MTPA) method, and X-ray crystallographic analysis. The absolute configuration of 7 was also assigned by these methods. These compounds moderately enhanced 2-deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-d-glucose (2-NBDG) uptake in differentiated 3T3-L1 adipocytes and phosphorylation of AMP-activated protein kinase (AMPK) and acetyl-CoA carboxylase (ACC) in differentiated mouse C2C12 skeletal myoblasts.
中文翻译：
海绵笼形松柏中的多氧类固醇
六个新的多氧类固醇（1 - 6）与clathriol（沿7）购自韩国海绵中分离大网gombawuiensis。基于组合分光分析的结果，gombasterols的A-F（结构1 - 6）分别鉴定为那些高度氧化的类固醇具有一个3β，4α，6α，7β四羟基或等效（7β-钠ö -sulfonato对于3）取代模式和一个C-15酮基作为常见的结构基序。这些类固醇的相对和绝对构型，包括的稀土14β配置1 - 4通过NOESY，基于J的分析，2-甲氧基-2-（三氟甲基）苯基乙酸（MTPA）方法和X射线晶体学分析的组合来确定。这些方法也分配了7的绝对配置。这些化合物中度强化2-脱氧-2 - [（7-硝基-2,1,3-苯并恶二唑-4-基）氨基] - d -葡萄糖（2-NBDG）摄取分化的3T3-L1脂肪细胞和AMP的磷酸化活化的蛋白激酶（AMPK）和乙酰辅酶A羧化酶（ACC）在分化的小鼠C2C12骨骼肌成肌细胞中。
更新日期：2017-11-28
中文翻译：
海绵笼形松柏中的多氧类固醇
六个新的多氧类固醇（1 - 6）与clathriol（沿7）购自韩国海绵中分离大网gombawuiensis。基于组合分光分析的结果，gombasterols的A-F（结构1 - 6）分别鉴定为那些高度氧化的类固醇具有一个3β，4α，6α，7β四羟基或等效（7β-钠ö -sulfonato对于3）取代模式和一个C-15酮基作为常见的结构基序。这些类固醇的相对和绝对构型，包括的稀土14β配置1 - 4通过NOESY，基于J的分析，2-甲氧基-2-（三氟甲基）苯基乙酸（MTPA）方法和X射线晶体学分析的组合来确定。这些方法也分配了7的绝对配置。这些化合物中度强化2-脱氧-2 - [（7-硝基-2,1,3-苯并恶二唑-4-基）氨基] - d -葡萄糖（2-NBDG）摄取分化的3T3-L1脂肪细胞和AMP的磷酸化活化的蛋白激酶（AMPK）和乙酰辅酶A羧化酶（ACC）在分化的小鼠C2C12骨骼肌成肌细胞中。
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