The first total synthesis of （+）-5α-hydroxy-isopterocarpolone （1）, an oxygenated eudesmane isolated from Chinese folk medicine Artemisia eriopoda, starting from （+）-dihydrocarvone（2） was described. Compound 4...The first total synthesis of （+）-5α-hydroxy-isopterocarpolone （1）, an oxygenated eudesmane isolated from Chinese folk medicine Artemisia eriopoda, starting from （+）-dihydrocarvone（2） was described. Compound 4 was stereoselectively prepared from compound 2 in three steps according to reference-. The treatment of tosylhydrazone 5, which was formed via the reaction of compound 4 and TsNHNH2 catalyzed by BF3-5Et2O, with an excess of n-butyllithium gave triene 6. Oxidation of triene 6 with singlet oxygen afforded the desired endo-peroxide 7 as a single product. Reductive cleavage of peroxide 7 with K2CO3 gave α-rotunol 3, a natural eudesmane firstly isolated in 1969. Hydrolysis of α-rotunol 3 with 10% sulfuric acid afforded （+）-5α-hydroxy-isopterocarpolone （1）. The structures of all the compounds were confirmed by IR, MS and NMR spectra.展开更多
3-Oxo-11,12,13-trihydroxyeudesm-4-ene(1) was a highly oxygenated natural eudesmane isolated from traditional herbal medicine with an antiphlogostic and spasmolytic activity.For the purpose of pharmacological activity ...3-Oxo-11,12,13-trihydroxyeudesm-4-ene(1) was a highly oxygenated natural eudesmane isolated from traditional herbal medicine with an antiphlogostic and spasmolytic activity.For the purpose of pharmacological activity research on natural product 1 and its derivatives,a facile total synthesis of compound 1 starting from(+)-dihydrocarvone(2) was completed in an overall yield of 24%.The structures of all intermediates and product 1 were confirmed via 1H NMR,13C NMR,MS and IR techniques.The NMR data of compound 1 are in agreement with those of natural products.展开更多
A facile and efficient diastereoselective synthesis of methyl 3β-hydroxyeudesmane-4,11(13)-dien-12-oicate starting from (+)-dihydrocarvone has been carried out in 9 steps at the first time.
目的初步探讨血镉及胎盘11β-羟基类固醇脱氢酶2(11β-hydroxysteroid dehydrogenase type 2,11β-HSD2)与重度子痫前期的相关性及镉与11β-HSD2参与重度子痫前期发生的机制。方法选取32例重度子痫前期妊娠孕妇为研究组及同期孕检正常孕...目的初步探讨血镉及胎盘11β-羟基类固醇脱氢酶2(11β-hydroxysteroid dehydrogenase type 2,11β-HSD2)与重度子痫前期的相关性及镉与11β-HSD2参与重度子痫前期发生的机制。方法选取32例重度子痫前期妊娠孕妇为研究组及同期孕检正常孕妇32例为正常妊娠组,测定2组孕妇血镉水平和胎盘中11β-HSD2表达水平。结果与正常妊娠组相比,研究组重金属镉水平升高,11β-HSD2表达降低(P<0.05)。结论血镉与11β-HSD2可能参与了重度子痫前期的发生发展。展开更多
目的:探讨微小RNA-144-3p(microRNA-144-3p,miR-144-3p)在卵巢癌细胞对顺铂耐药中的作用并分析其作用机制与溶质载体家族7成员11(solute carrier family 7 member 11,SLC7A11)和铁死亡是否有关。方法:将miR-144-3p mimic转染入耐顺铂人...目的:探讨微小RNA-144-3p(microRNA-144-3p,miR-144-3p)在卵巢癌细胞对顺铂耐药中的作用并分析其作用机制与溶质载体家族7成员11(solute carrier family 7 member 11,SLC7A11)和铁死亡是否有关。方法:将miR-144-3p mimic转染入耐顺铂人卵巢癌细胞株A2780/DDP和SKOV3/DDP后,RT-qPCR法检测miR-144-3p的表达丰度;CCK-8法检测细胞对顺铂的敏感性;集落形成实验测定细胞增殖情况;试剂盒法评估细胞内丙二醛(malondialdehyde,MDA)和谷胱甘肽(glutathione,GSH)的水平;Fe^(2+)探针及活性氧簇(reactive oxygen species,ROS)荧光探针检测细胞内Fe^(2+)含量及ROS水平;透射电子显微镜观察线粒体形态;双萤光素酶报告基因实验验证miR-144-3p与SLC7A11之间的靶向结合。建立耐药细胞株A2780/DDP异种移植瘤模型,体内评估miR-144-3p对肿瘤生长的影响。结果:耐药细胞株A2780/DDP和SKOV3/DDP中的miR-144-3p表达显著低于亲本细胞株A2780和SKOV3(P<0.05)。转染miR-144-3p mimic可抑制细胞增殖,增强耐药细胞株对顺铂的敏感性(P<0.01)。双萤光素酶报告基因实验结果显示SLC7A11是miR-144-3p的作用靶点。过表达SLC7A11可通过铁死亡途径逆转miR-144-3p对细胞增殖及化疗敏感性的作用(P<0.05)。异种移植瘤实验结果表明miR-144-3p可显著抑制瘤体生长,抑制SLC7A11及谷胱甘肽过氧化物酶4(glutathione peroxidase 4,GPX4)蛋白表达(P<0.01),提高4-羟基壬烯醛(4-hy-droxynonenal,4-HNE)水平(P<0.01)。结论:miR-144-3p通过靶向SLC7A11而增强耐药卵巢癌细胞对顺铂的敏感性,其作用机制可能涉及铁死亡过程。展开更多
文摘The first total synthesis of （+）-5α-hydroxy-isopterocarpolone （1）, an oxygenated eudesmane isolated from Chinese folk medicine Artemisia eriopoda, starting from （+）-dihydrocarvone（2） was described. Compound 4 was stereoselectively prepared from compound 2 in three steps according to reference-. The treatment of tosylhydrazone 5, which was formed via the reaction of compound 4 and TsNHNH2 catalyzed by BF3-5Et2O, with an excess of n-butyllithium gave triene 6. Oxidation of triene 6 with singlet oxygen afforded the desired endo-peroxide 7 as a single product. Reductive cleavage of peroxide 7 with K2CO3 gave α-rotunol 3, a natural eudesmane firstly isolated in 1969. Hydrolysis of α-rotunol 3 with 10% sulfuric acid afforded （+）-5α-hydroxy-isopterocarpolone （1）. The structures of all the compounds were confirmed by IR, MS and NMR spectra.
文摘3-Oxo-11,12,13-trihydroxyeudesm-4-ene(1) was a highly oxygenated natural eudesmane isolated from traditional herbal medicine with an antiphlogostic and spasmolytic activity.For the purpose of pharmacological activity research on natural product 1 and its derivatives,a facile total synthesis of compound 1 starting from(+)-dihydrocarvone(2) was completed in an overall yield of 24%.The structures of all intermediates and product 1 were confirmed via 1H NMR,13C NMR,MS and IR techniques.The NMR data of compound 1 are in agreement with those of natural products.
文摘A facile and efficient diastereoselective synthesis of methyl 3β-hydroxyeudesmane-4,11(13)-dien-12-oicate starting from (+)-dihydrocarvone has been carried out in 9 steps at the first time.
文摘目的初步探讨血镉及胎盘11β-羟基类固醇脱氢酶2(11β-hydroxysteroid dehydrogenase type 2,11β-HSD2)与重度子痫前期的相关性及镉与11β-HSD2参与重度子痫前期发生的机制。方法选取32例重度子痫前期妊娠孕妇为研究组及同期孕检正常孕妇32例为正常妊娠组,测定2组孕妇血镉水平和胎盘中11β-HSD2表达水平。结果与正常妊娠组相比,研究组重金属镉水平升高,11β-HSD2表达降低(P<0.05)。结论血镉与11β-HSD2可能参与了重度子痫前期的发生发展。
