Proof of Learning Outcome by the Advanced Clinical Competency Examination Trial after the Long-term Student's Practice in Pharmaceutical Education.

At Setsunan University, a debrief session (a poster session) is commonly performed by the students who have completed the long-term students' practice. Since the valuable changes in practical competency of the students cannot be evaluated through this session, we specified items that can help evaluate and methods that can help estimate the students' competency as clinical pharmacists. We subsequently carried out a trial called the "Advanced Clinical Competency Examination". We evaluated 103 students who had concluded the students' practice for the second period (Sep 1, 2014, to Nov 16, 2014): 70 students (called "All finish students") who had completed the practice in a hospital and pharmacy, and 33 students (called "Hospital finish students") who had finished the practice at a hospital only. The trial was executed in four stages. In the first stage, students drew pictures of something impressive they had learned during the practice. In the second stage, students were given patient cases and were asked, "What is this patient's problem?" and "How would you solve this problem?". In the third stage, the students discussed their answers in a group. In the fourth stage, each group made a poster presentation in separate rooms. By using a rubric, the teachers evaluated each student individually, the results of which showed that the "All finish students" could identify more problems than the "Hospital finish students".

The absolute configurations of hydroxy fatty acids from the royal jelly of honeybees (Apis mellifera).

9-Hydroxy-2E-decenoic acid (9-HDA) is a precursor of the queen-produced substance, 9-oxo-2E-decenoic acid (9-ODA), which has various important functions and roles for caste maintenance in honeybee colonies (Apis mellifera). 9-HDA in royal jelly is considered to be a metabolite of 9-ODA produced by worker bees, and it is fed back to the queen who then transforms it into 9-ODA. Recently we found that 9-HDA is present in royal jelly as a mixture of optical isomers (R:S, 2:1). The finding leads us to suspect that chiral fatty acids in royal jelly are precursors of semiochemicals. Rather than looking for semiochemicals in the mandibular glands of the queen bee, this study involves the search for precursors of pheromones from large quantities of royal jelly. Seven chiral hydroxy fatty acids, 9,10-dihydroxy-2E-decenoic, 4,10-dihydroxy-2E-decenoic, 4,9-dihydroxy-2E-decenoic, 3-hydroxydecanoic, 3,9-dihydroxydecanoic, 3,11-dihydroxydodecanoic, and 3,10-dihydroxydecanoic acids were isolated. The absolute configurations of these acids were determined using the modified Mosher's method, and it was revealed that, similar to 9-HDA, five acids are present in royal jelly as mixtures of optical isomers.

Compositions of royal jelly II. Organic acid glycosides and sterols of the royal jelly of honeybees (Apis mellifera).

Two organic acid glycosides (1, 2) and 16 sterols were isolated from the royal jelly of honeybees (Apis mellifera). The former two were monoglucosides of 10-hydroxy-2E-decenoic and 10-hydroxydecanoic acids. They are the first examples of glycosides isolated from royal jelly. The latter 16 were sterols mainly composed of 28 or 29 carbons. Among them, four compounds were new isofucosterol derivatives, and their structures were characterized as (24Z)-stigmasta-5,24(28)-dien-3beta-ol-7-one (3), (24Z)-stigmasta-5,24(28)-diene-3beta,7beta-diol (4), (24Z)-stigmasta-5,24(28)-diene-3beta,7alpha-diol (5), and (24Z)-stigmast-24(28)-ene-3beta,5alpha,6beta-triol (6) on the basis of various NMR spectroscopic data.

Cantharimide dimers from the Chinese blister beetle, Mylabris phalerate PALLAS.

Five cantharidin-related compounds were isolated from the Chinese blister beetle, Mylabris phalerate PALLAS (Meloidae). Their structures were determined based on spectroscopic and chemical evidence. Three of them were identified as cantharimide dimers, which consist of two units of cantharimide combined with a tri-, tetra-, or penta-methylene group.

Two isoindoline alkaloids from the crude drug, the ant lion (the larvae of Myrmeleontidae species).

Two compounds having an isoindoline skeleton were isolated from the ant lion (the larvae of Myrmeleontidae species). They were characterized as 4-hydroxyisoindolin-1-one and 2-(2-hydroxyethyl)-4-hydroxyisoindolin-1-one on the basis of spectroscopic data.

Isolation and characterization of some hydroxy fatty and phosphoric acid esters of 10-hydroxy-2-decenoic acid from the royal jelly of honeybees (Apis mellifera).

The present work characterizes novel FA in the royal jelly of honeybees (Apis mellifera). TLC analysis showed that the chloroform/methanol extract obtained from royal jelly consists mainly of FA. The FABMS spectrum of this extract gave several ion peaks due to compounds with higher M.W. than those of the FA so far reported. The methanol extract was found to contain unknown phospholipids. By means of reversed-phase HPLC with various solvent systems, 13 compounds were obtained in pure state. Their structures including absolute configurations were determined by chemical, NMR, and MS spectral analysis. Six compounds were identified as novel mono- or di-esters of 10-hydroxy-2E-decenoic acid in which the hydroxyl group was esterified by another FA unit, and one was hydroxy-2E-decenoic acid 10-phosphate. In addition, we demonstrated that 9-hydroxy-2E-decenoic acid exists as a mixture of optical isomers.

Three novel cantharidin-related compounds from the Chinese blister beetle, Mylabris phalerata Pall.

Three novel cantharidin analogues were isolated from the Chinese blister beetle, Mylabris phalerata PALL. (Meloidae), which has been used in traditional Chinese medicine for the treatment of cancer. Their structures were determined on the basis of heteronuclear multiple-bond connectivity and nuclear Overhauser effect spectroscopy experiments, and chemical data confirmed them to be so-called cantharimides, in which the anhydride oxygen atoms are replaced by the basic amino acid L-lysine, L-ornithine, and L-arginine moieties.