Chemical constituents from the stems of Acanthopanax senticosus with their cytotoxic activities.

A new coumestan named 7,5'-dihydroxy-4'-(3''-hydroxy-3''-methyl-trans-isobut-1''-enyl) coumestan (1), together with five known compounds (2-6), was isolated from the EtOAc-soluble extract of the stems of Acanthopanax senticosus. Their structures were elucidated based on extensive spectroscopic analyses. All the isolates were evaluated for in vitro cytotoxic activities against four human cancer cells including HepG2, A549, HeLa and MCF-7. Among them, the new compound 1 was found to exhibit significant cytotoxic activity on HeLa cells with IC50 value of 6.5 µM.

Two new prenylated isoflavones from Hedysarum multijugum.

Chemical investigation on the ethyl acetate extract of the roots of Hedysarum multijugum resulted in the isolation of two new prenylated isoflavonoids: 5, 7, 2'-trihydroxy-4'-methoxy-3'-(γ, γ-dimethylallyl) isoflavone (hedysarimisoflavone A, 1) and 5, 7, 2'-trihydroxy-4'-methoxy-6, 8-di-(γ, γ-dimethylallyl) isoflavone (hedysarimisoflavone B, 2). Their structures were elucidated on the basis of spectroscopic analyses, especially, 1H and 13C NMR spectra in conjunction with their 2D experiments, 1H-1H COSY, HMQC, HMBC, and NOESY.

[Study on HPLC-fingerprint-based identification of dao-di herb and non dao-di herb of scutellariae radix].

OBJECTIVE: To compare the discrepancies between chemical constituents in Dao-di herb and non Dao-di herb of Huangqin (the root of Scutellaria baicalensis), study the impact of habitat and growth pattern (including cultivated and wild Huangqin) on chemical substances of Huangqin, and then provide evidence for the identification of Dao-di herb and quality evaluation of Huangqin. METHOD: The chemical constituents in Huangqin collected from different habitats and under different growth patterns, were analyzed using HPLC fingerprint. The fingerprints obtained were then evaluated by hierarchical clustering analysis, principal component analysis and components peak area pattern. RESULT: The fingerprints' chemical profiles of Dao-di herb and non Dao-di Huangqin had significant disparity. The fingerprints of modem Dao-di herb Huangqin samples originated from Chengde (Hebei Province) were significantly different from those from other habitats, though the fingerprints of the non Dao-di Huangqin collected from Chifeng (Inner Mongolia) and Chengde had high similarity to each other. The chemical characteristics of Huangqin samples collected from the habitats recorded in ancient herbals, such as Qingyang (Gansu Province), Yan'an (Shaanxi Province), Linyi (Shangdong Province), Changzhi and Jinzhong (Shanxi Province) were similar. The fingerprints of modern non Dao-di samples collected from Dingxi and Longnan (Gansu Province) and Shangluo (Shaanxi Province) had high similarity. In addition, the content of acteoside in wild Huangqin was higher than that in cultivated Huangqin. CONCLUSION: Dao-di herb and non Dao-di herb of Huangqin could be distinguished using the developed HPLC fingerprints. The results obtained may provide evidence for the quality control and pharmcodynamical research of Dao-di herb and non Dao-di Huangqin.

Characterization of flavonoids in Millettia nitida var. hirsutissima by HPLC/DAD/ESI-MS n.

Millettia nitida var. hirsutissima is a Chinese herbal medicine used for the treatment of gynecological diseases. An HPLC/DAD/ESI-MS n method was established for the rapid separation and characterization of bioactive flavonoids in M. nitida var. hirsutissima. A total of 32 flavonoids were detected, of which 14 compounds were unambiguously characterized by comparing their retention time, UV, and MS spectra with those of the reference standards, and the others were tentatively identified based on their tandem mass spectrometry fragmentation data obtained in the negative ionization mode on line. Nineteen of these compounds characterized were reported from this plant for the first time.

[Phenolic acid derivatives from Bauhinia glauca subsp. pernervosa].

To study the chemical constituents of Bauhinia glauca subsp. pernervosa, eleven phenolic acids were isolated from a 95% ethanol extract by using a combination of various chromatographic techniques including column chromatography over silica gel, ODS, MCI, Sephadex LH-20, and semi-preparative HPLC. By spectroscopic techniques including 1H NMR, 13C NMR, 2D NMR, and HR-ESI-MS, these compounds were identified as isopropyl O-beta-(6'-O-galloyl)-glucopyranoside (1), ethyl O-beta-(6'-O-galloyl)-glucopyranoside (2), 3, 4, 5-trimethoxyphenyl-(6'-O-galloyl)-O-beta-D-glucopyranoside (3), 3, 4, 5-trimethoxyphenyl-beta-D-glucopyranoside (4), gallic acid (5), methyl gallate (6), ethyl gallate (7), protocatechuic acid (8), 3, 5-dimethoxy-4-hydroxybenzoic acid (9), erigeside C (10) and glucosyringic acid (11). Among them, compound 1 is a new polyhydroxyl compound; compounds 2, 10, and 11 were isolated from the genus Bauhinia for the first time, and the other compounds were isolated from the plant for the first time. Compounds 6 and 8 showed significant protein tyrosine phosphatase1B (PTP1B) inhibitory activity in vitro with the IC50 values of 72.3 and 54.1 micromol x L(-1), respectively.

Sesquiterpenoid and phenolic glucoside gallates from Lagerstroemia balansae.

Three new compounds, including a sesquiterpenoid glucoside gallate, 2 Z,4 E,1' R,2' S,4' R,6' S-dihydrophaseic acid 4'-O-(6''-O-galloyl)-ß-D-glucopyranoside (1), two new phenolic glucoside gallates, 4-hydroxy-3,5-dimethoxybenzoic acid 4-O-(6'-O-galloyl)-ß-D-glucopyranoside (2) and 3,4-dimethoxyphenol 1-O-(6'-O-galloyl)-ß-D-glucopyranoside (3), together with eight known compounds (4-11), have been isolated from the stems of Lagerstroemia balansae. Their structures were elucidated on the basis of chemical and spectroscopic evidences.

Neuroprotective xanthone glycosides from Swertia punicea.

Two new dimeric xanthone O-glycosides, puniceasides A (1) and B (2), a new trimeric O-glycoside, puniceaside C (3), and two new trimeric C-glycosides, puniceasides D (4) and E (5), together with 12 known xanthones were isolated from the entire plant of Swertia punicea. The structures of 1-5 were determined by HRESIMS and NMR spectroscopic methods. Compounds 2, 6, and 7 exhibited potent neuroprotective activity against H(2)O(2)-induced PC12 cell damage.

Hypnotic effect of jujubosides from Semen Ziziphi Spinosae.

ETHNOPHARMACOLOGICAL SIGNIFICANCE: Semen Ziziphi Spinosae, the seed of Ziziphus jujuba Mill. var. spinosa (bunge) Hu ex H.F. Chow has been widely used in treating insomnia and anxiety. AIM OF THE STUDY: In this study, we investigated the hypnotic effect of jujubosides, one of the major components (saponin) of Semen Ziziphi Spinosae, in both day and night period. MATERIALS AND METHODS: After the administration of jujubosides (9 mg/kg once per day for 3 days), sleep parameters were examined by EEG and EMG analysis in normal rats and the action of jujubosides on pentobarbital-induced sleep assessed by the loss-of righting reflex. RESULTS: During daytime (9:00-15:00), jujubosides significantly increased the total sleep and rapid eye movement (REM) sleep without significant influence on non-REM (NREM) sleep. During nighttime (21:00-3:00), jujubosides significantly increased the total sleep and NREM sleep especially the light sleep while showed no significant effect on REM sleep and slow wave sleep (SWS). In pentobarbital-treated mice, jujubosides significantly augmented the hypnotic effect of pentobarbital (45 mg/kg, i.p.), proved by increasing sleep time and this augmentative effect was potentiated by 5-hydroxytryptophan (2mg/kg, i.p.). Furthermore, jujubosides inhibited the para-chlorophenylalanine-induced suppression of pentobarbital-induced hypnosis. CONCLUSIONS: These results suggested that the hypnotic effect of jujubosides on normal rats may be influenced by circadian rhythm and the serotonergic system may involve in the hypnotic effect of jujubosides. Jujubosides may be good source of lead compounds for novel hypnotics.

[Isoflavones from Millettia nitida var. hirsutissima].

To study the chemical constituents of Millettia nitida var. hirsutissima, the constituents were isolated by chromatographic techniques, and structures were identified by spectroscopic methods. Eight isoflavones were isolated and identified, including a new compound, hirsutissimiside F (1), and seven known compounds, formononetin (2), ononin (3), odoratin 7-O-beta-D-glucopyranoside (4), lanceolarin (5), afromosin (6), sphaerobioside (7), and hirsutissimiside B (8). Compounds 3, 4, 5 and 7 were isolated from the genus Millettia for the first time, 2 was obtained from this plant for the first time.

Metabolism of hibifolin by human intestinal bacteria.

Hibifolin, the highest-content bioactive flavonoid of the flowers of Abelmoschus manihot, was incubated with human intestinal bacteria, and four metabolites (1-4) were obtained from the incubated solution by chromatographic methods. The structures of the four metabolites were elucidated as gossypetin 8-O-beta-D-4''-deoxy- Delta(4'')-glucuropyranoside (1), gossypetin (2), quercetin (3), and 8-methoxy-quercetin (4), respectively, on the basis of UV, NMR, and MS data. Metabolite 1 was obtained as a new compound with a specific beta-D-4''-deoxy-Delta(4'')-glucuropyranosyl moiety, which was formed through a unique and novel metabolic pathway that has not been reported previously.

[Chemical constituents of Momordica charantia L].

Momordica charantia L. is a vegetable widely cultivated around the world. Its fruits have been used in Asian countries as a folk medicine for the treatment of non-insulin-dependent diabetes mellitus. Here we report eight compounds isolated from the fruits of M. charantia. On the basis of NMR and MS spectroscopic analyses, these compounds were identified as momordicolide ((10E)-3-hydroxyl-dodeca-10-en-9-olide, 1), monordicophenoide A (4-hydroxyl-benzoic acid 4-O-beta-D-apiofuranosyl (1 --> 2)-O-beta-D-glucopyranoside, 2), dihydrophaseic acid 3-O-beta-D-glucopyranoside (3), 6,9-dihydroxy-megastigman-4,7-dien-3-one (blumenol, 4), guanosine (5), adenosine (6), uracil (7) and cytosine (8). Among them, 1 and 2 are new compounds. Compounds 3-5 were isolated from this plant for the first time.

[Effect of supplemented Taoren Chengqi decoction on NIT-1, a pancreatic beta-cell from a transgenic NOD/Lt mouse].

OBJECTIVE: To study the effect of Supplemented Taoren Chengqi decoction (STCD) on the secretion of insulin and proliferation of NIT-1. METHOD: The effect of STCD and the serum of rat after orally administrating of STCD on the secretion of insulin and proliferation of NIT-1 were studied. The proliferation of NIT-1 was measured by 3H-TdR incorporation and cell counting methods, while the secretion of insulin was measured from the cultured medium by the ultra sensitive rat insulin ELISIA kit. RESULT: Both the STCD and the serum of rat after orally administrating of STCD significantly could increased the secretion of insulin and proliferation of NIT-1. CONCLUSION: The treatment of the diabetic patients by STCD might be through with its improvement of secretion of insulin and proliferation on pancreatic beta-cell.

[Studies on chemical constituents from seed of Psoralea corylifolia].

OBJECTIVE: To study the chemical constituents of Psoralea corylifolia. METHOD: Chromatographic methods were used to separate compounds, and spectroscopic methods were used to determine the structures. RESULT: Five compounds were isolated and identified as furano (2", 3", 7, 6)-4'-hydroxyflavanone (1), psoralidin (2), genistein (3), psoralen (4), isopsoralen (5). CONCLUSION: Compounds 1 was a new compound named psoraleflavanone. And 13C-NMR data of compound 2 were assined for the first time.

[Main flavonoids from Sophora flavescenes].

Radix Sophorae Flavescentis is a traditional Chinese medicine, which is the roots of Sophora flavescens and is used to treat abscess, dysentery, eczema and skin itch. The main active compounds of the roots of Sophora flavescens are alkaloids and flavonoids. To provide reference compounds for HPLC-DAD qualitification analysis of flavanonoids and for study on the bioactivities of flavanonoids, six main flavanonoids were isolated from the roots of Sophora flavescens. They are 5-methoxy-7, 2', 4'-trihydroxy-8-[3,3-dimethylallyl] -flavanone (1), isoxanthohumol (2), 3/beta, 7, 4'-trihydroxy-5-methoxy-8-[3,3-dimethylallyl] -flavanone (3), nor-kurarinone [(2S) -sophoraflavanone G] (4), kurarinone (5) and kushenol I (6). Compound 1 is a new compound, and compound 3 is obtained from Sophora flavecens for the first time. The 13C NMR data of compounds 3 and 5 are reported for the first time.

[Chemical constituents from Spatholobus sinensis].

Spatholobus sinensis is a plant of the Spatholobus genus (Leguminosae family). Its caulis are used as "ji-xue-teng" regionally. However, to our knowledge, no phytochemical investigation on S. sinensis has been reported to date. In this study, eight compounds were isolated from the ethanol extract of the caulis of S. sinensis, by solvents extraction and column chromatography methods. By analysis of their physic-chemical constants and spectral data, the structures of 8 compounds were identified as spatholosineside A (1), 2',4',5,7-tetrahydroxyisoflavone (2), isoliquiritigenin (3), lupinalbin A (4), coumestrol (5), naringenin (6), protocatechuic acid (7), leonuriside A (8). Compound 1 is a new compound.

Pedicularioside A from Buddleia lindleyana inhibits cell death induced by 1-methyl-4-phenylpyridinium ions (MPP+) in primary cultures of rat mesencephalic neurons.

Parkinson's disease is characterized by the progressive degeneration of midbrain dopaminergic neurons. Buddleia lindleyana is a traditional Chinese herb, commonly called Zui Yu Cao. The purification and identification of pedicularioside A and other phenylethanoid glycosides from this plant have been reported. However, their neuroprotective effects on the 1-methyl-4-phenylpyridinium ion (MPP(+))-induced death of rat mesencephalic neuron primary cultures and the precise mechanism of this protection remains unclear. We used the 3-(4, 5-dimethylthiozol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) assay for cellular growth to examine the effects of five phenylethanoid glycosides isolated from B. lindleyana, including pedicularioside A, leucosceptoside A, isoacteoside, acteoside, and arenariside, on the viability of mesencephalic neurons treated with MPP(+). Of the compounds tested, pedicularioside A exhibited the greatest degree of protection from MPP(+)-induced cell death. We also observed a marked increase in the number of tyrosine hydroxylase immunoreactive neurons. Pedicularioside A inhibited expression of the caspase-3 gene and cleavage of poly (ADP-ribose) polymerase (PARP) in cultures exposed to MPP(+). Our results suggest that pedicularioside A has a neuroprotective effect to improve the survival of mesencephalic neurons (dopaminergic neurons and non-dopaminergic neurons). The mode of action appears to be the inhibition of caspase-3 gene expression, thereby protecting mesencephalic neurons from MPP(+)-induced cell death.

[Study on biligustilides from Angelica sinensis].

OBJECTIVE: To study the chemical constituents of Angelica sinensis. METHOD: The constituents were separated by chromatographic methods, and their structures were identified on the basis of spectroscopic analysis. RESULT: Eight compounds were isolated and identified as levistolide A (1), senkyunolide O (2), (3Z, 3Z')-6.8', 7.3'-diligustilide (3), tokinolide B (4), isotokinolide B (5), (3'Z)-(3R, 8S, 3a'R, 6'S)-3, 3a': 8, 6'-biligustilide (6), E, E'-3. 3', 8. 8'-diligustilide (7) and E, E'-3. 3', 8. 8'-isodiligustilide (8), which are all diligustilides. CONCLUSION: Compound 7 was obtained from the plant for the first time; compounds 6 and 8 are new compounds.

[Studies on chemical constituents of Tibetan medicine Caryopteris toroetii].

OBJECTIVE: To study the chemical constituents of the Tibetan medicine Caryopteris toroetii. METHOD: The crude drug was extracted with 95% EtOH and isolated by repeatedly chromatographic methods. The structures of the isolated compounds were elucidated by spectral analysis. RESULT: Six compounds were yielded and identified as: phenethyl cinnamide (1), 1-hydroxy-2, 3, 4, 5-tetramethoxy-xanthone (2), 1-hydroxy-2, 3, 5-trimethoxy-xanthone (3), (2S)-5-hydroxy-7-methoxyflavanone (4), 2', 4'-dihydroxydihydrochalcone (5) and rutin (6). CONCLUSION: All the above compounds were obtained from C. toroetii for the first time.

Simultaneous determination and pharmacokinetic studies of dihydromyricetin and myricetin in rat plasma by HPLC-DAD after oral administration of Ampelopsis grossedentata decoction.

A simple and sensitive high-performance liquid chromatographic method was developed for the simultaneous determination of dihydromyricetin (1) and myricetin (2) in rat plasma after orally administrating the decoction of Ampelopsis grossedentata. Plasma samples were acidified with 0.375% phosphoric acid and extracted with ethyl acetate. Analysis of the extract was performed on reversed-phase C(18) column with a gradient eluent composed of acetonitrile and 0.04% phosphoric acid. The flow rate was kept at 1 ml/min and the detection wavelength was set at 290 and 370 nm for 1 and 2, respectively. The calibration curves were linear in the range of 0.247-4.114 microg/ml and 0.150-2.501 microg/ml for 1 and 2, respectively. The intra-day and inter-day precisions were better than 4.9 and 6.2%, respectively. The limits of detection (LOD) for 1 and 2 in plasma were 21.600 and 52.530 ng/ml, and the limits of quantification (LOQ) were 0.247 and 0.150 microg/ml, respectively. The mean recoveries for 1 and 2 were 92.0 and 93.3%, respectively. The accuracy and precision were well within the acceptable range and R.S.D. of measured rat samples was less than 7.5%. This validated method has been successfully applied in the pharmacokinetics study of dihydromyricetin and myricetin in vivo after orally administrating the decoction of A. grossedentata to rats.

[Determination of constituents of polysaccharide and contents of saccharide from Mongolian medicine Agari-8].

The water soluble polysaccharide was extracted from Agari-8, and the contents of the water soluble polysaccharide were determined by phenyl hydrate-sulfuric acid method. The average recovery was 101.80%. The RSD was 0. 92Y. The components of the water soluble polysaccharide were identified by gas chromatography with: arabinose, xylose, mannose and glucose in the molar ratio of 0.40 : 0.10 : 5.67 : 22.78. Their IR and UV spectra were studied.