Isolation and biological activity of a novel cadinane-type sesquiterpenoid from the essential oil of Alangium salviifolium.

The components of the essential oil from the roots of Alangium salviifolium were analyzed by capillary gas chromatography-mass spectrometry (GC-MS). Ninety compounds, representing 74.5% of the total oil, were identified; the main components of the oil were epi-α-cadinol, followed by trans-2-hydroxycalamenene, cadalene, and cadina-4,10(15)-dien-3-one. A further unknown component comprised 5.5% of the oil. Therefore, the essential oil was purified by flash column chromatography to isolate this component. Its structure was established using extensive spectroscopic data analyses, including NMR, HR-EI-MS, and IR. The results showed that this isolated compound was (-)-7, 8-dihydroxycalamenal, which is a novel cadinane-type sesquiterpenoid. This compound was tested for its antioxidant activity and inhibition of tyrosinase, and showed particularly strong inhibition effects.

New compounds, 6-hydroxykarahanaenone and 10-hydroxykarahanaenone, from biotransformation of karahanaenone by CYP2A6.

The in vitro biotransformation of karahanaenone was examined in cytochrome P450 (CYP) 2A6. The biotransformation of karahanaenone by CYP2A6 was investigated by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). Karahanaenone was found to be oxidized to two metabolites by CYP2A6. In order to produce large quantity of metabolites by CYP2A6, the biotransformation of karahanaenone by Salmonella typhimurium OY1002/2A6 was investigated. Similarly, two metabolites were confirmed by GC and GC-MS. The structure of metabolites was determined by 1D NMR, 2D NMR, and infrared, as a result there were new compounds, (6R)-hydroxykarahanaenone and 10-hydroxykarahanaenone.

Biotransformation of (+)-fenchone by Salmonella typhimurium OY1002/2A6 expressing human CYP2A6 and NADPH-P450 reductase.

In this study, biotransformation of (+)-fenchone (compound 1) by Salmonella typhimurium OY1002/2A6 expressing human CYP2A6 and NADPH-P450 reductase yielded two oxidized metabolites, namely, (+)-(1S,6R)-6-endo-hydroxyfenchone (compound 2) and (+)-(1S,6S)-6-exo-hydroxyfenchone (compound 3). The conversion rate of compound 1 to compound 2 and 3 was 2.4% and 5.2%, respectively. This is the first study that succeeded in metabolizing compound 1 to obtain large amounts of metabolite 2 and 3 by using S. typhimurium OY1002/2A6 expressing human CYP2A6 and NADPH-P450 reductase.

Characteristic chemical components of the essential oil from white kwao krua (Pueraria mirifica).

The components of the essential oil from the roots of Pueraria mirifica were analyzed by capillary gas chromatography-mass spectrometry (GC-MS). Eighty-two components, representing 88.5% of the total oil, were identified by GC-MS. The main component of the oil was 2-pentylfuran, followed by hexanal and hexadecanol. With regard to the odor components from the essential oil of P. mirifica as determined by gas chromatography-olfactometry and aroma extract dilution analysis, it was revealed that phenylacetaldehyde and (2E)-nonenal imparted the green odor of the oil, and geraniol contributed to the sweet odor.

Tyrosinase inhibitory constituents from the bark of Peltophorum dasyrachis (yellow batai).

Tyrosinase inhibitory activity-guided fractionation of the bark of Peltophorum dasyrachis (yellow batai) led to the isolation of the six active compounds which were characterised as six flavonoids: apigenin (1), (+)-2,3-trans-dihydrokaempferol (2), (+)-2,3-trans-dihydrokaempferol-3-O-α-L-rhamnoside (3), (+)-4',7-dimethoxy-2,3-trans-dihydroquercetin (4), (+)-2,3-trans-dihydroquercetin (5) and (-)-2,3-trans-dihydroquercetin-3-O-α-L-rhamnoside (6). All compounds were isolated for the first time from the bark of P. dasyrachis. Moreover, all compounds were evaluated for tyrosinase activities towards L-DOPA as the substrate. We observed that compounds 2 and 5 showed potent inhibitory effects (IC50 values were 126 ± 3.2 and 210 ± 5.8 µM, respectively). In general, for flavonoids the 3',4'-dihydroxy group's substituent is a more potent inhibitor than the 4'-hydroxy group substituent, i.e. quercetin > kaempferol. Interestingly, our result in the oxidation of L-DOPA showed that the 4'-hydroxy group substituent (compound 2) is a more potent inhibitor than the 3',4'-dihydroxy group substituent (compound 5). This result showed a new relationship between tyrosinase inhibitory activities and flavonoids. The kinetic analyses by Lineweaver-Burk plots showed that both the compounds 2 and 5 behaved as competitive inhibitors of L-DOPA oxidation.

Biotransformation of turmerones by Aspergillus niger.

Biotransformation studies conducted on (+)-(S)-ar-turmerone (1) and (+)-(S)-dihydro-ar-turmerone (2) by the fungus Aspergillus niger have revealed that 1 was metabolized to give four oxidized metabolites, (+)-(7S)-hydroxydehydro-ar-todomatuic acid (3), (+)-(7S,10E)-12-hydroxydehydro-ar-todomatuic acid (4), (+)-(7S,10E)-7,12-dihydroxydehydro-ar-todomatuic acid (5), and (+)-(7S)-15-carboxy-9,13-epoxy-7-hydroxy-9,13-dehydro-ar-curcumene (6), and (+)-(S)-dihydro-ar-turmerone (2) was metabolized to (+)-7,11-dihydroxy-ar-todomatuic acid (7). Metabolites 3-7 were characterized using spectroscopic techniques. Metabolites 3-7 inhibited acetylcholinesterase (AChE) although less so than the parent substrates.

Successful diagnosis of diaphragmatic solitary fibrous tumor of the pleura by preoperative ultrasonography.

The diaphragm is an uncommon site for solitary fibrous tumors of the pleura (SFTPs). Diaphragmatic SFTPs are usually found as pedunculated tumors with a clear margin with their surrounding structures. However, preoperative diagnosis of the tumor is difficult because their morphological features are not well detected on radiological images. We presented a case of diaphragmatic SFTP that was successfully diagnosed by ultrasonography (US). The US revealed a well-circumscribed mass with the feeding arteries leading from the diaphragm. Subsequently, this finding was confirmed histopathologically after resection. US can be less invasive and more sensitive than radiological examinations for diagnosing diaphragmatic SFTPs. To our knowledge, this is the first report of a preoperative diagnosis of diaphragmatic SFTP by US.

Acetylcholinesterase inhibitory activity of volatile oil from Peltophorum dasyrachis Kurz ex Bakar (yellow batai) and Bisabolane-type sesquiterpenoids.

In this study, the chemical compositions and acetylcholinesterase (AChE) inhibitory activitiy of the volatile oil from the bark of Peltophorum dasyrachis Kurz ex Bakar (yellow batai) were evaluated. As a result, 68 compounds, accounting for 88.0% of the total oil, were identified. The main characteristic constituent in P. dasyrachis was isolated by silica gel column chromatography and found to be a sesquiterpenoid, (+)-(S)-ar-turmerone (1). In the AChE inhibitory assay, the volatile oil showed potent inhibitory activity with the IC(50) value of 83.2 +/- 2.8 microg/mL. Among the volatile oil components and characteristic sesquiterpenoids, (+)-(S)-ar-turmerone (1) and (+)-(S)-dihydro-ar-turmerone (2) were potent compounds, inhibiting AChE in a dose-dependent manner, with IC(50) values of 191.1 +/- 0.3 and 81.5 +/- 0.2 microM, respectively. (+)-(S)-Dihydro-ar-turmerone (2), in particular, was found to be the most potent AChE inhibitor. Also, bisabolane-type sesquiterpenoid derivatives, (+)-(7S,9S)-ar-turmerol (3), (+)-(7S,9R)-ar-turmerol (4), (+)-(7S,9S)-dihydro-ar-turmerol (5), (+)-(7S,9R)-dihydro-ar-turmerol (6), (+)-(S)-ar-curcumene (7), and (+)-(S)-dihydro-ar-curcumene (8), were synthesized and tested for their AChE inhibitory effect, and their structure-activity relationships were evaluated. All sesquiterpenoids exhibited AChE inhibitory activity. The order of AChE inhibitory potency by bisabolane-type sesquiterpenoids was as follows: ketones > alcohols > hydrocarbons. Furthermore, the inhibition kinetics analyzed by Dixon plots indicated that (+)-(S)-ar-turmerone (1) is a competitive inhibitor, with a K(i) value of 882.1 +/- 2.1 microM, whereas (+)-(S)-dihydro-ar-turmerone (2) is a non-competitive inhibitor.

[A patient with sarcoidosis needed differential diagnosis from motor neuron disease].

A 50-year-old woman lost about 10 kg of body weight within two months. Thereafter, she developed dysphagia and dysphonia. She visited our hospital and presented with a weak elevation of the soft palate, fasciculation of the tongue, hoarseness of voice, muscle weakness of the neck and extremities, and a decrement in vital capacity. She was admitted with a provisional diagnosis of motor neuron disease. The results of laboratory examinations showed an elevation in serum lysozyme and liquor protein levels, and pleocytosis in the liquor. Needle electromyography showed neurogenic changes, and bilateral hilar lymphadenopathy was revealed by computerized tomography. A biopsy specimen was excised from lymph nodes near the right anterior scalene muscle, which showed noncaseating granulomas consistent with sarcoidosis. All her symptoms improved after steroid administration. Such patients can be treatable with steroids. Moreover, the differential diagnosis from motor neuron disease is important.