A new 2-(2-phenylethyl)chromone derivative in Chinese agarwood 'Qi-Nan' from Aquilaria sinensis.

Phytochemical analysis of the high quality Chinese agarwood 'Qi-Nan' originating from Aquilaria sinensis (Lour.) Glig led to the isolation of a new 2-(2-phenylethyl)chromone derivative, qinanones G (1), and four known 2-(2-phenylethyl)chromones (2-5). Their structures were elucidated by spectroscopic techniques (UV, IR, 1D and 2D NMR) and MS analyses. The NMR data of chromones 1-3 were first reported, and chromones 2 and 3 showed weak inhibitory activity against acetylcholinesterase.

2-(2-phenylethyl)chromone derivatives in Chinese agarwood "Qi-Nan" from Aquilaria sinensis.

Five new 2-(2-phenylethyl)chromone derivatives, qinanones A-E (1-5), together with eight known 2-(2-phenylethyl)chromone derivatives (6-13), were isolated from the Et2O extract of high-quality Chinese agarwood "Qi-Nan" originating from Aquilaria sinensis. The structures of the new 2-(2-phenylethyl)chromones were elucidated by spectroscopic techniques (UV, IR, 1D and 2D NMR) and MS analyses. In the bioassay for acetylcholinesterase inhibitors, compounds 1-6, 10, and 12 exhibited weak inhibitory activities (inhibition percentage ranged from 10 % to 24 % at the concentration of 50 µg/mL). Compared with other agarwoods, "Qi-Nan" was different in containing 2-(2-phenylethyl)chromones with unsubstituted chromone rings.

A new antibacterial denitroaristolochic acid from the tubers of Stephania succifera.

A new denitroaristolochic acid, demethylaristofolin C (1), together with six known alkaloids, crebanine N-oxide (2), (-)-sukhodianine-ß-N-oxide (3), palmatine (4), corydalmine (5), dehydrocorydalmine (6), and corynoxidine (7), was isolated from the tubers of Stephania succifera. The structure of demethylaristofolin C was elucidated by spectroscopic techniques (UV, IR, 1D, and 2D NMR) and HR-ESI-MS analyses. These compounds exhibited antibacterial activities against Staphylococcus aureus and methicillin-resistant S. aureus strains in different degrees.

Characterization and determination of 2-(2-phenylethyl)chromones in agarwood by GC-MS.

Agarwood is the fragrant resinous heartwood obtained from certain trees in the genus Aquilaria belonging to the family Thymelaeaceae. 2-(2-Phenylethyl)chromones and characteristic sesquiterpenes are the main classes of aromatic compounds isolated from agarwood. Although there are many sesquiterpenes, relatively few 2-(2-phenylethyl)chromones have been determined in agarwood by GC-MS. After analysis of the MS spectra of eighteen 2-(2-phenylethyl)chromone derivatives isolated from agarwood and identified by NMR spectroscopy, together with the reported MS data and characteristic of structures of 2-(2-phenylethyl)chromones, the MS characterization, fragmentation patterns and characteristic fragment peaks for the compounds were deduced and a table summarizing MS characterization of 2-(2-phenylethyl)chromones in agarwood is presented. All the 2-(2-phenylethyl)chromones previously reported in agarwood are substituted by methoxy or/and hydroxy groups, except for one compound. Due to the fact they all possess the same basic skeleton (molecular weight: 250) and similar substituent groups (methoxy or hydroxy groups), a formula (30m + 16n = MW - 250) is provided to calculate the number of methoxy (m) or hydroxy (n) groups according to molecular ion peak or molecular weight (MW). We deduced that the characteristic fragmentation behaviors of the 2-(2-phenylethyl)chromones are the cleavages of the CH2-CH2 bond between chromone moiety and phenyl moiety. Thus, characteristic fragment ions, such as m/z 91 [C7H7], 107 [C7H6+OH], 121 [C7H6+OCH3], 137 [C7H5+OH+OCH3] are formed by different substituted benzyl moieties, while characteristic fragment ions such as m/z 160 [C10H8O2], 176 [C10H7O2+OH], 190 [C10H7O2+OCH3], 220 [C10H6O2+OCH3×2] are formed by different substituted chromone moieties. Furthermore, rules regarding to the relationship between the positions of hydroxy or methoxy groups and the relative abundances of benzyl and chromone fragment ions have been deduced. Elucidation of how the positions of hydroxy or methoxy groups affect the relative abundances of benzyl and chromone fragment peaks is also provided. Fifteen unidentified compounds of an artificial agarwood sample analyzed by GC-MS, were preliminary determined as 2-(2-phenylethyl)chromones by analysis of their MS characterization and by comparison of their MS spectra with those of 18 standard compounds or 2-(2-phenylethyl)chromones reported in literature according to the above-mentioned methods and rules. This report will be helpful for the analysis and structural elucidation of 2-(2-phenylethyl)chromones in agarwood by GC-MS, and provides fast and reliable characterization of the quality of agarwood.

[Chemical constituents from stems of Aquilaria sinensis].

OBJECTIVE: To study the constituents from the stems of Aquilaria sinensis. METHOD: The chemical constituents were isolated by various column chromatographic methods. The structures were identified by spectral analysis including NMR and MS data. RESULT: Sixteen compounds were isolated and identified as threo-buddlenol C (1), thero-ficusesquilignan A (2), erythro-buddlenol C (3), (+/-) buddlenol D (4), (-) medioresinol (5), (-) pinoresinol (6), 5'-methoxy lariciresinol (7), erythro-guaiacylglycerol-beta-coniferyl ether (8), thero-guaiacylglycerol-beta-coniferyl ether (9), herpetin (10), (+) syringaresinol (11), curuilignan (12), ciwujiatone (13), coniferyl alcohol (14), 3, 4, 5-trimethoxyphenol (15) and cucurbitacin (16). CONCLUSION: All the compounds, except for 11-13 were obtained from A. sinensis for the first time.

Neurogenesis and major depression: implications from proteomic analyses of hippocampal proteins in a rat depression model.

Major depression is one of the most disabling disorders. Yet, the pathogenesis of this mental disorder is poorly understood. Hippocampus is generally believed to be associated with pathogenesis of depression. In this study, we adopted a proteomic approach to examine possible alterations of protein expression in the hippocampus of a rat depression model. Our results suggest that neurogenesis in hippocampus may play an important role in the pathogenesis of major depression.

1H magnetic resonance spectroscopy study of thalamus in treatment resistant depressive patients.

Treatment-resistant depression (TRD) is a common clinical problem, and represents a considerable challenge to treatment, however, the pathogenesis of this disease is poorly understood. Thalamus is generally believed to have a role in the pathophysiology of depression. In this study, we adopted 1.5T (1)H magnetic resonance spectroscopy ((1)H MRS) to examine possible alterations of thalamus metabolism in 20 adult TRD patients. Our results suggested there might be damage and loss of neurons, as well as membrane phospholipids associated metabolism abnormality in the TRD thalamus.

Antimicrobial glycoalkaloids from the tubers of Stephania succifera.

Three new glycoalkaloids, N-formyl-asimilobine-2-O-ß-D-glucoside (1), (-)-1-O-ß-D-glucoside-8-oxotetrahydropalmatine (2), and 1-N-monomethylcarbamate-argentinine-3-O-ß-D-glucoside (3) were isolated from tubers of Stephania succifera. The structures were established based on spectroscopic analysis, and the antimicrobial activities of the three glycoalkaloids are reported.

Two new types of bisindole alkaloid from Trigonostemon lutescens.

Six unprecedented bisindole alkaloids, trigolutesins A and B (1-2) with a unique polycyclic skeleton and trigolutes A-D (3-6) with another polycyclic skeleton, were isolated from the twigs of Trigonostemon lutescens. Their structures and relative configurations were elucidated by spectroscopic data and single-crystal X-ray diffraction crystallography. Trigolutesin A (1) showed weak AChE inhibitory activity.