ABSTRACT
In screening experiments for rat intestinal alpha-glucosidase (sucrase and maltase) inhibitors in 325 plants cultivated in Japan's southern island, of Tanegashima, marked inhibition against both sucrase and maltase was found in the extract of the fruit of Solanum torvum. Enzyme-assay guided fractionation of the extract led to the isolation of methyl caffeate (1) as a rat intestinal sucrase and maltase inhibitor. We examined 13 caffeoyl derivatives for sucrase- and maltase-inhibitory activities. The results showed that methyl caffeate (1) had a most favorable structure for both sucrase and maltase inhibition, except for a higher activity of methyl 3,4,5-trihydroxycinnamate (14) against sucrase. Its moderate inhibitory action against alpha-glucosidase provides a prospect for antidiabetic usage of S. torvum fruit.
Subject(s)
Fruit/enzymology , Glycoside Hydrolase Inhibitors , Solanum/enzymology , Animals , Caffeic Acids , Enzyme Assays , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/pharmacology , Hypoglycemic Agents/antagonists & inhibitors , Hypoglycemic Agents/pharmacology , Intestines/drug effects , Japan , Rats , Sucrase/antagonists & inhibitorsABSTRACT
Three novel chalcone derivatives, mallotophilippens C (1), D (2) and E (3) were isolated from the fruits of Mallotus philippinensis MUELL. ARG. These compounds were identified, using chemical and spectral data, as 1-[6-(3,7-dimethyl-octa-2,6-dienyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl]-3-(4-hydroxy-phenyl)-propenone, 3-(3,4-dihydroxy-phenyl)-1-[6-(3,7-dimethyl-octa-2,6-dienyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl]-propenone and 1-[5,7-dihydroxy-2-methyl-6-(3-methyl-but-2-enyl)-2-(4-methyl-pent-3-enyl)-2H-chromen-8-yl]-3-(3,4-dihydroxy-phenyl)-propenone, respectively. They inhibited nitric oxide (NO) production and inducible NO synthase (iNOS) gene expression by a murine macrophage-like cell line (RAW 264.7), which was activated by lipopolysaccharide (LPS) and recombinant mouse interferon-gamma (IFN-gamma). Furthermore, they downregulated cyclooxygenase-2 (COX-2) gene, interleukin-6 (IL-6) gene and interleukin-1beta (IL-1beta) gene expression. These results suggest that they have anti-inflammatory and immunoregulatory effects.
Subject(s)
Anti-Allergic Agents/pharmacology , Chalcones/pharmacology , Mallotus Plant , Nitric Oxide/antagonists & inhibitors , Anti-Allergic Agents/chemistry , Anti-Allergic Agents/isolation & purification , Chalcones/chemistry , Chalcones/isolation & purification , Nitric Oxide/biosynthesis , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Plant Extracts/pharmacologyABSTRACT
Two phenylpropanoid sucrose esters were isolated from dry rhizomes of Canna edulis Ker Gawl., along with a known phenylpropanoid sucrose ester and four known phenylpropanoids. On the basis of analysis of spectroscopic data and chemical evidence, these two phenylpropanoid sucrose esters were shown to be 3-O-p-coumaroyl-6-O-feruloyl-beta-D-fructofuranosyl 6-O-acetyl-alpha-D-glucopyranoside and 3,6-di-O-p-coumaroyl-beta-D-fructofuranosyl 6-O-acetyl-alpha-D-glucopyranoside.
Subject(s)
Esters/chemistry , Marantaceae/chemistry , Phenylpropionates/chemistry , Sucrose/chemistry , Benzofurans/chemistry , Benzofurans/isolation & purification , Caffeic Acids/chemistry , Caffeic Acids/isolation & purification , Chromatography, High Pressure Liquid , Cinnamates/chemistry , Cinnamates/isolation & purification , Depsides , Esters/isolation & purification , Magnetic Resonance Spectroscopy , Molecular Structure , Optical Rotation , Rosmarinic AcidABSTRACT
Two new phloroglucinol derivatives, mallotophilippen A (1). and B (2). were isolated from the fruits of Mallotus philippensis. These compounds were identified, using chemical and spectral data, as 1-[5,7-dihydroxy-2,2-dimethyl-6-(2,4,6-trihydroxy-3-isobutyryl-5-methyl-benzyl)-2H-chromen-8-yl]-2-methyl-butan-1-one and 1-[6-(3-Acetyl-2,4,6-trihydroxy-5-methyl-benzyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl]-2-methyl-butan-1-one, respectively. They inhibited nitric oxide (NO) production and inducible NO synthase (iNOS) gene expression by a murine macrophage-like cell line (RAW 264.7), which was activated by lipopolysaccharide (LPS) and recombinant mouse interferon-gamma (IFN-gamma). Furthermore, they inhibited histamine release from rat peritoneal mast cells induced by Compound 48/80. These results suggest that the novel phloroglucinol derivatives have anti-inflammatory effects.
