Dataset Information

Meroterpene-Like ?-Glucosidase Inhibitors Based on Biomimetic Reactions Starting from ?-Caryophyllene.

ABSTRACT: BACKGROUND:Natural meroterpenes derived from phloroglucinols and ?-caryophyllene have shown high inhibitory activity against ?-glucosidase or cancer cells, however, the chemical diversity of this type of skeletons in Nature is limited. METHODS:To expand the chemical space and explore their inhibitory activities against ?-glucosidase (EC 3.2.1.20), we employed ?-caryophyllene and some natural moieties (4-hydroxycoumarins, lawsone or syncarpic acid) to synthesize new types of meroterpene-like skeletons. All the products (including side products) were isolated and characterized by NMR, HR-MS, and ECD. RESULTS:In total, 17 products (representing seven scaffolds) were generated through a one-pot procedure. Most products (12 compounds) showed more potential activity (IC50 < 25 ?M) than the positive controls (acarbose and genistein, IC50 58.19, and 54.74 ?M, respectively). Compound 7 exhibited the most potent inhibition of ?-glucosidase (IC50 3.56 ?M) in a mixed-type manner. The CD analysis indicated that compound 7 could bind to ?-glucosidase and influence the enzyme's secondary structure. CONCLUSIONS:Compound 7 could serve as a new type of template compound to develop ?-glucosidase inhibitors. Full investigation of a biomimic reaction can be used as a concise strategy to explore diverse natural-like skeletons and search for novel lead compounds.

SUBMITTER: Yan DW

PROVIDER: S-EPMC7024386 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Publications

Meroterpene-Like α-Glucosidase Inhibitors Based on Biomimetic Reactions Starting from β-Caryophyllene.

Yan Da-Wei DW Huang Cheng-Di CD Zheng Hang-Hang HH Zhao Na N Feng Xiao-Lan XL Ma Shuang-Jiang SJ Zhang An-Ling AL Zhang Qiang Q

Molecules (Basel, Switzerland) 20200108 2

<h4>Background</h4>Natural meroterpenes derived from phloroglucinols and β-caryophyllene have shown high inhibitory activity against α-glucosidase or cancer cells, however, the chemical diversity of this type of skeletons in Nature is limited.<h4>Methods</h4>To expand the chemical space and explore their inhibitory activities against α-glucosidase (EC 3.2.1.20), we employed β-caryophyllene and some natural moieties (4-hydroxycoumarins, lawsone or syncarpic acid) to synthesize new types of merote ...[more]

PMID: 31936396

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Project description:The formation of atmospheric cloud droplets due to secondary organic aerosol (SOA) particles is important for quantifying the Earth's radiative balance under future, possibly warmer, climates, yet is only poorly understood. While cloud activation may be parametrized using the surface tension depression that coincides with surfactant partitioning to the gas-droplet interface, the extent to which cloud activation is influenced by both the chemical structure and reactivity of the individual molecules comprising this surfactant pool is largely unknown. We report herein considerable differences in the surface tension depression of aqueous pendant droplets that contain synthetically prepared ozonolysis products derived from α-pinene and β-caryophyllene, the most abundant of the monoterpenes and sesquiterpenes, respectively, that are emitted over the planet's vast forest ecosystems. Oxidation products derived from β-caryophyllene were found to exhibit significantly higher surface activity than those prepared from α-pinene, with the critical supersaturation required for cloud droplet activation reduced by 50% for β-caryophyllene aldehyde at 1 mM. These considerable reductions in the critical supersaturation were found to coincide with free energies of adsorption that exceed ∼25 kJ/mol, or just one hydrogen bond equivalent, depending on the ammonium sulfate and oxidation product concentration in the solution. Additional experiments showed that aldehyde-containing oxidation products exist in equilibrium with hydrated forms in aqueous solution, which may modulate their bulk solubility and surface activity. Equilibration time scales on the order of 10-5 to 10-4 s calculated for micrometer-sized aerosol particles indicate instantaneous surface tension depression in the activation processes leading to cloud formation in the atmosphere. Our findings highlight the underlying importance of molecular structure and reactivity when considering cloud condensation activity in the presence of SOA particles.

Dataset Information

Meroterpene-Like ?-Glucosidase Inhibitors Based on Biomimetic Reactions Starting from ?-Caryophyllene.

Publications

Meroterpene-Like α-Glucosidase Inhibitors Based on Biomimetic Reactions Starting from β-Caryophyllene.

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