The Hantzsch synthesis has been used for the preparation of the 1,4-Dihydropyridines compounds with different pharmacophore groups. The use of a designed glycosylated compound in Hantzsch synthesis would lead to a nov...The Hantzsch synthesis has been used for the preparation of the 1,4-Dihydropyridines compounds with different pharmacophore groups. The use of a designed glycosylated compound in Hantzsch synthesis would lead to a novel Dihydropyridines C-Glycosylated compound. We used the 6-methoxy-2, 2-dimethyltetrahydrofuro [3, 4-d] [1, 3] dioxole-4-carbaldehyde as a glycosylated-based aldehydes. The 4-(3,4-Dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxy-lic acid 3-ethyl ester 5-methyl ester was synthesized. The structure of compounds was determined by NMR spectroscopy, FTIR and mass spectroscopy methods. We synthesized this 1,4-Dihydropyridines compound by ionic liquid under ultrasound irradiation as a green chemistry synthesis.展开更多
C-glycosides have been demonstrated to have distinct biological functions and therefore display notable pharmacological values,whereas the access to the versatile structural analog of C-glycosides is a significant cha...C-glycosides have been demonstrated to have distinct biological functions and therefore display notable pharmacological values,whereas the access to the versatile structural analog of C-glycosides is a significant challenge to their advancement as therapeutic agents.We herein disclose a facial and efficient catalytic C-glycosylation using a glycosyl ortho-2,2-dimethoxycarbony lcyclopropylbenzoate(CCBz)as the donor.The trailblazing glycosyl donor can be simply activated by a non-toxic and easily accessible Sc(Ⅲ)catalyst.The ring-strain release of the incorporated donor-acceptor cyclopropane(DAC)serves as a powerful driving force of the glycosylation system.The adaptability of current methods to different types of donors and acceptors was exemplified.Examinations on the synthetic potential were done with the one-pot synthesis of free C-indolyl-glycosides and the subsequent biological studies,unlocking the antibacterial potentials of these compounds.展开更多
Passiflora incarnata L.is known to contain abundant C-glycosyl flavones,which exhibit various biological activities;however,its anti-obesity effects have not yet been investigated.To this end,herein,we conducted UPLC-...Passiflora incarnata L.is known to contain abundant C-glycosyl flavones,which exhibit various biological activities;however,its anti-obesity effects have not yet been investigated.To this end,herein,we conducted UPLC-MS/MS to identify flavonoids in Passiflora incarnata L.aqueous and 60% ethanol extracts(denoted as PAE and PEE,respectively)and HPLC to quantify five major C-glycosyl flavones(vitexin,isovitexin,orientin,isoorientin,and vicenin-2).PEE contained most of the C-glycosyl flavones compared to PAE.The analysis of the inhibitory effect on lipid accumulation of these extracts and the five C-glycosyl flavones were conducted using differentiated 3T3-L1 and oleic acid(OA)-treated HepG2 cells.PEE more effectively inhibited lipid accumulation than PAE.Among C-glycosyl flavones,vicenin-2 showed the strongest lipid accumulation inhibitory effect in both cells and significantly inhibited lipid-metabolism-related FAS,PPARγ,FABP4,and SREBP1c.Moreover,we fed a high-fat diet(HFD)containing PEE to C57BL/6 mice for eight weeks and measured the body weight,serum lipid,hepatic lipid,and adipocyte size.The results showed that PEE reduced body weight gain and serum lipids in HFD-fed mice.PEE suppressed hepatic lipid accumulation and adipocyte size by suppressing adipogenesis and lipogenesis.Our results demonstrated that C-glycosyl-flavone-rich PEE can be used as an anti-obesity agent.展开更多
文摘The Hantzsch synthesis has been used for the preparation of the 1,4-Dihydropyridines compounds with different pharmacophore groups. The use of a designed glycosylated compound in Hantzsch synthesis would lead to a novel Dihydropyridines C-Glycosylated compound. We used the 6-methoxy-2, 2-dimethyltetrahydrofuro [3, 4-d] [1, 3] dioxole-4-carbaldehyde as a glycosylated-based aldehydes. The 4-(3,4-Dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxy-lic acid 3-ethyl ester 5-methyl ester was synthesized. The structure of compounds was determined by NMR spectroscopy, FTIR and mass spectroscopy methods. We synthesized this 1,4-Dihydropyridines compound by ionic liquid under ultrasound irradiation as a green chemistry synthesis.
基金Ministry of Education(MOE-T2EP30120-0007,Tier-1 RG107/23)of Singapore for the financial support.
文摘C-glycosides have been demonstrated to have distinct biological functions and therefore display notable pharmacological values,whereas the access to the versatile structural analog of C-glycosides is a significant challenge to their advancement as therapeutic agents.We herein disclose a facial and efficient catalytic C-glycosylation using a glycosyl ortho-2,2-dimethoxycarbony lcyclopropylbenzoate(CCBz)as the donor.The trailblazing glycosyl donor can be simply activated by a non-toxic and easily accessible Sc(Ⅲ)catalyst.The ring-strain release of the incorporated donor-acceptor cyclopropane(DAC)serves as a powerful driving force of the glycosylation system.The adaptability of current methods to different types of donors and acceptors was exemplified.Examinations on the synthetic potential were done with the one-pot synthesis of free C-indolyl-glycosides and the subsequent biological studies,unlocking the antibacterial potentials of these compounds.
基金supported by the Ministry of Trade,Industry and Energy(GN201800)the Korea Food Research Institute(E0210100).
文摘Passiflora incarnata L.is known to contain abundant C-glycosyl flavones,which exhibit various biological activities;however,its anti-obesity effects have not yet been investigated.To this end,herein,we conducted UPLC-MS/MS to identify flavonoids in Passiflora incarnata L.aqueous and 60% ethanol extracts(denoted as PAE and PEE,respectively)and HPLC to quantify five major C-glycosyl flavones(vitexin,isovitexin,orientin,isoorientin,and vicenin-2).PEE contained most of the C-glycosyl flavones compared to PAE.The analysis of the inhibitory effect on lipid accumulation of these extracts and the five C-glycosyl flavones were conducted using differentiated 3T3-L1 and oleic acid(OA)-treated HepG2 cells.PEE more effectively inhibited lipid accumulation than PAE.Among C-glycosyl flavones,vicenin-2 showed the strongest lipid accumulation inhibitory effect in both cells and significantly inhibited lipid-metabolism-related FAS,PPARγ,FABP4,and SREBP1c.Moreover,we fed a high-fat diet(HFD)containing PEE to C57BL/6 mice for eight weeks and measured the body weight,serum lipid,hepatic lipid,and adipocyte size.The results showed that PEE reduced body weight gain and serum lipids in HFD-fed mice.PEE suppressed hepatic lipid accumulation and adipocyte size by suppressing adipogenesis and lipogenesis.Our results demonstrated that C-glycosyl-flavone-rich PEE can be used as an anti-obesity agent.
