A green chemical oligomerization of phloroglucinol induced by plasma as novel α-glucosidase inhibitors

Abstract

A new facile method was developed for simple green synthesis of methylene-bridged phloroglucinol oligomers using nonthermal dielectric barrier discharge (DBD) plasma in methanolic solution. The chemical structures of these newly generated oligomers 2-5 were determined by interpretation of the spectroscopic data, and the inhibitory activity toward α-glucosidase of all isolates was evaluated. The unusual phloroglcuinol pentamer 5 connected by four methylene linkages showed a much higher potential inhibitory effect against α-glucosidase than the other generated oligomers 2-4 and appeared to be a promising lead for development as a potential antidiabetic agent. Abbreviations: T2DM, type2 diabetes mellitus; DBD, dielectric barrier discharge; HPLC, high-performance liquid chromatography; IC50, 50% inhibition concentration; NMR, nuclear magnetic resonance; FABMS, fastatom bombardment mass spectrometry.

Plasma-Polymerized Phlorotannins and Their Enhanced Biological Activities

“…These chromatograms indicate that CP treatment induced structural changes in phloroglucinol that were closely associated with an enhancement in biological activities. Choi et al also showed that the degree of oligomerization increased with increasing CP treatment time on phloroglucinol. In addition, the oligomerization of phloroglucinol induced by CP increased the antidiabetic activities measured by α-glucosidase inhibitory activity .…”

“…Choi et al also showed that the degree of oligomerization increased with increasing CP treatment time on phloroglucinol. In addition, the oligomerization of phloroglucinol induced by CP increased the antidiabetic activities measured by α-glucosidase inhibitory activity . However, there may be an appropriate range of polymerization for optimum bioactivities. , …”

“…In addition, the oligomerization of phloroglucinol induced by CP increased the antidiabetic activities measured by α-glucosidase inhibitory activity. 43 However, there may be an appropriate range of polymerization for optimum bioactivities. 32,33 MS analyses (Figure 4) of peaks 1, 2, 5, 6, 7, and 8 revealed [M − H] − ion at m/z 263.1, 401.1, 539.1, 677.2, 815.2, and 953.2, respectively.…”

Plasma-Induced Oxidation Products of (–)-Epigallocatechin Gallate with Digestive Enzymes Inhibitory Effects

“…A recent study reported the development of newly generated products induced by the DBD plasma irradiation of natural polyphenolic compounds. In addition, a DBD plasma treatment under alcoholic solution conditions was readily converted to methylene-linked dimeric products ( trans -resveratrol, sesamol, and phloridzin), which showed improved pharmacological activity compared with the parent compounds [ 10 , 11 , 12 , 13 ]. On the other hand, its influences on plasma-induced oxidation under aqueous conditions, associated with changes in the chemical structure and biological activities, are not completely understood.…”

Novel Hybrid Molecules Based on (−)-Epigallocatechin Gallate as Potent Anti-adipogenic Agents

“…13) A recent exploration presented that non-thermal plasma irradiation is a characteristic green chemical technique for creation of structurally modified natural products with improved biological efficacy and yields. 14,15) Therefore, some novel hybridization approaches develop to clear these problems on the basis of increasing environmental and economic problem. However, the beneficial use of plasma irradiation technique for induction of specific chemical reactions during hybridization of pharmacological active molecules with each different frameworks is still very limited.…”