Aim To investigate more efficient synthetic method of the nitrogen analogue 4 of salacinol (1) for searching new antidiabetic agents. Methods The synthesis of the key intermediate 2,4-O-isopropylidene-L-erythritol 1,3-cyclic sulfate (2a) was accomplished by modification of reports from Dglucose via seven steps in much more less expensive. Using this method, an efficient synthesis of 4 was carried out. The glycosidase inhibitory activity of 4 was tested for the intestinal α-glucosidase in vitro and compared with that of salacinol. Results A nitrogen analogue 4 of salacinol (1) was synthesized by the coupling reaction between the cyclic sulfate 2a and an azasugar 3b. Conclusion Substitution of the sulfur atom in 1 with a nitrogen reduced the activity considerably.

AIMTo study the chemical composition of Opuntia dillenii Haw.

METHODSMany kinds of chromatography methods were used to separate the chemical constituents. Their structures were determined by NMR and MS spectral analysis.

RESULTSA new compound, together with five known compounds, were isolated from the 80% ethanolic extract of the stems.

CONCLUSIONThe new compound was identified as 4-ethoxyl-6-hydroxymethyl-alpha-pyrone. Compounds 1, 3, 4 and 5 were obtained for the first time from the genus of Opuntia, and they were: 3-O-methyl isorhamnein, 1-heptanecanol, vanillic acid, isorhamnetin-3-O-beta-D-rutinoside. Ruin was isolated from this plant for the first time.

Molecular Structure ; Opuntia ; chemistry ; Plant Stems ; chemistry ; Plants, Medicinal ; chemistry ; Pyrones ; chemistry ; isolation & purification ; Rutin ; chemistry ; isolation & purification ; Vanillic Acid ; chemistry ; isolation & purification

OBJECTIVETo study the chemical composition of Opuntia dillenii.

METHODMany kinds of chromatography methods were used in the isolation procedure, while the structures of isolated compounds were determined on the aids of NMR and MS spectral analysis.

RESULTA new compound, together with five known compounds, was isolated form the 80% ethanolic extract of its stems.

CONCLUSIONThe new compound was characterized as opuntioside. Four compounds were obtained for the first from the genus Opuntia, and they were daucosterol, p-hydroxybenzoicacid, L-(-)-malic acid, (E)-ferulic acid. Opuntiol was also separated for the first from the plant.

Coumaric Acids ; chemistry ; isolation & purification ; Molecular Structure ; Monosaccharides ; chemistry ; isolation & purification ; Opuntia ; chemistry ; Plant Stems ; chemistry ; Plants, Medicinal ; chemistry ; Sitosterols ; chemistry ; isolation & purification

AIMTo investigate more efficient synthetic method of the nitrogen analogue 4 of salacinol (1) for searching new antidiabetic agents.

METHODSThe synthesis of the key intermediate 2, 4-O-isopropylidene-L-erythritol 1,3-cyclic sulfate (2a) was accomplished by modification of reports from D-glucose via seven steps in much more less expensive. Using this method, an efficient synthesis of 4 was carried out. The glycosidase inhibitory activity of 4 was tested for the intestinal alpha-glucosidase in vitro and compared with that of salacinol.

RESULTSA nitrogen analogue 4 of salacinol (1) was synthesized by the coupling reaction between the cyclic sulfate 2a and an azasugar 3b.

CONCLUSIONSubstitution of the sulfur atom in 1 with a nitrogen reduced the activity considerably.

Animals ; Enzyme Inhibitors ; chemical synthesis ; chemistry ; pharmacology ; Glycoside Hydrolase Inhibitors ; Intestinal Mucosa ; drug effects ; enzymology ; Molecular Structure ; Nitrogen Compounds ; chemical synthesis ; pharmacology ; Rats ; Structure-Activity Relationship ; Sugar Alcohols ; chemical synthesis ; chemistry ; pharmacology ; Sulfates ; chemical synthesis ; chemistry ; pharmacology ; alpha-Glucosidases ; metabolism

Purpose: Primary tumor location of colon cancer has been reported to affect the prognosis after curative resection. However, some reports suggested the impact was varied by tumor stage. This study analyzed the prognostic impact of the sidedness of colon cancer in stages II, III, and liver metastasis after curative resection using propensity-matched analysis. Methods: Right-sided colon cancer was defined as a tumor located from cecum to splenic flexure, while any more distal colon cancer was defined as left-sided colon cancer. Patients who underwent curative resection at Nara Medical University hospital between 2000 and 2016 were analyzed. Results: There were 110 patients with stage II, 100 patients with stage III, and 106 patients with liver metastasis. After propensity matching, 28 pairs with stage II and 32 pairs with stage III were identified. In the patients with stage II, overall survival (OS) and recurrence-free survival (RFS) were not significantly different for right- and left-sided colon cancers. In the patients with stage III, OS and RFS were significantly worse in right-sided colon cancer. In those with liver metastasis, OS of right-sided colon cancer was significantly worse than left-sided disease, while RFS was similar. Regarding metachronous liver metastasis, the difference was observed only in the patients whose primary colon cancer was stage III. In each stage, significantly higher rate of peritoneal recurrence was found in those with right-sided colon cancer. Conclusion Sidedness of colon cancer had a significant and varied prognostic impact in patients with stage II, III, and liver metastasis after curative resection.

Background/Aims: Bispectral index (BIS) monitors process and display electroencephalographic data are used to assess the depth of anesthesia. This study retrospectively evaluated the usefulness of BIS monitoring during endoscopic ultrasonography (EUS). Methods: This study included 725 consecutive patients who underwent EUS under sedation with propofol. BIS monitoring was used in 364 patients and was not used in 361. The following parameters were evaluated: (1) median dose of propofol; (2) respiratory and circulatory depression; (3) occurrence of body movements; (4) awakening score >8 at the time; and (5) awakening score 2 hours after leaving the endoscopy room. Results: The BIS group received a significantly lower median dose of propofol than the non-BIS group (159.2 mg vs. 167.5 mg; p=0.015) in all age groups. For patients aged ≥75 years, the reduction in heart rate was significantly lower in the BIS group than in the non-BIS group (1.2% vs. 9.1%; p=0.023). Moreover, the occurrence of body movements was markedly lower in the BIS group than in the non-BIS group (8.5% vs. 39.4%; p<0.001). Conclusions During EUS examination, BIS monitoring is useful for maintaining a constant depth of anesthesia, especially in patients 75 years of age or older.