Anti-inflammatory and antiproliferative prenylated chalcones from Hedysarum gmelinii.

Five new prenylated chalcones hedysarumines C-G (1-5), along with eight known chalcones (6-13) all of which were isolated from the genus Hedysarum for the first time, were isolated from the roots of Hedysarum gmelinii by chromatographic methods. Their structures were determined by extensive spectroscopic techniques. The isolated chalcones (2-13) and previously isolated prenylated chalcones (14-16) were evaluated for antiproliferative activity against five human cancer cell lines (HepG2, A549, Du145, BGC823, and HCT116) and in vitro anti-inflammatory activity. Compounds 5, 10, and 15 inhibited NO production induced by lipopolysaccharide in BV-2 cells, with IC50 values ranging from 3.25 to 8.48 µM. Compounds 4 and 11 showed moderate antiproliferative activity to selective human cancer cell lines, with the IC50 values of 4 and 11 against A549 cell line being 7.79 and 9.67 µM, respectively, and the IC50 value of 11 against HCT116 cell line being 8.85 µM.

3-Hydroxy-3-methylglutaryl flavonol glycosides from Oxytropis falcata.

Five new 3-hydroxy-3-methylglutaryl (HMG) flavonol 3-O-glycosides, named oxytroflavosides A-E (1-5), and two new rhamnocitrin 3-O-glycosides, oxytroflavosides F and G (6 and 7) were isolated from the n-BuOH-soluble fraction of an EtOH extract of Oxytropis falcata together with seven known kaempferol glycosides (8-14), of which six were isolated from the genus Oxytropis for the first time. The structures of these compounds were elucidated by spectroscopic techniques and chemical methods. The absolute configuration of HMG in compounds 1-5 was determined to be S through spectroscopic analysis of the mevalonamide obtained by amidation and reduction of the HMG moiety. Compounds 1-10 were evaluated for anti-inflammatory activities using lipopolysaccharide-induced RAW 264.7 cells, but none of them showed inhibitory effects on NO production.

Triterpenoid saponins from Dipsacus asper and their activities in vitro.

Two new triterpenoid saponins 1 and 2, along with six known saponins 3-8, were isolated from the roots of Dipsacus asper. The structures of new compounds were established as 3-O-ß-d-glucopyranosyl-(1 â†’ 4)-[α-l-rhamnopyranosyl-(1 â†’ 3)]-ß-d-glucopyranosyl-(1 â†’ 3)-α-l-rhamnopyranosyl-(1 â†’ 2)-α-l-arabinopyranosyl-hederagenin-28-O-ß-d-glucopyranoside (dipsacus saponin J, 1) and 3-O-α-l-arabinopyranosyl-hederagenin-28-O-ß-d-glucopyranosyl-(1 â†’ 6)-ß-d-glucopyranosyl-(1 â†’ 6)-ß-d-glucopyranoside (dipsacus saponin K, 2). The structures were determined by extensive analysis of their spectroscopic data. Compounds 6 and 7 could significantly stimulate UMR106 cell proliferation and increase alkaline phosphatase activities in UMR106 cell at the concentration of 4 µM.

[A study on the NMR spectrum of methyl-ofloxacin].

Ofloxacin ((+/-)-9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2, 3-dihydro-7H-pyrido[1,2,3-de]-1, 4-benzoxazine-6-carboxylic acid) is a totally synthetic fluoroquinolone antimicrobial agent with a broad spectrum of activity against Gram-positive and Gram-negative bacteria and atypical pathogens such as Mycoplasma, Chlamydia and Legionella. Even though it is widely used for the treatment of gastrointestinal, pulmonary, urinary, and other infections, the comprehensive mechanism of action at molecular level has not been known so far. It is very important to understand the structural characteristics of the drug and the effects that are caused by the environments. With the purpose of deeply investigating the structure of Ofloxacin, an analog of Ofloxacin, Methyl-Ofloxacin (Me-OFL), was synthesized by methylation of 4'N in piperazine ring from Ofloxacin with CH3I. Then appropriate Me-OFL was dissolved in DC1/D2O and NaOH/D2O to prepare corresponding acidic and alkaline solutions. Systematic NMR spectroscopic investigation on Me-OFL in both acidic and alkaline solution was conducted using quantitative 1H and 13C spectra, DEPT, HSQC together with HMBC techniques. The spectra were recorded with Bruker AM-300 spectrometer and DRX500 spectrometer. Chemical shifts have been given in values referred to dioxane (deltaJ = 3.7, deltac = 67.8). Complete assignments on 1H and 13C signals of Me-OFL were obtained in different pH environments where the coupling constant between 13 C and 19F was found to be very helpful for the assignment of aromatic 13C signals. A comprehensive comparison between the 1H, 13C chemical shifts, together with the structural transformation in acidic and alkaline solutions was made and discussed in details. Due to the formation of hydrogen bond between COOH and C==O, the COOH and aromatic ring are in the same plane. As a result, a weak O...H--C hydrogen bond forms between C==O from the carboxyl group and 5-H from aromatic ring. In alkaline solution, the deprivation of H+ from COOH destroys not only the hydrogen bond between COOH and carbonyl group but also the weak hydrogen between the C==O from COOH and 5H. As a result, the 5H exhibited remarkable shift toward high field (1.02). Meanwhile, the chemical shift of 6C, 13C, 7C, 15C also exhibited remarkable shift to low field at 12. 04, 7.46, 4.33, 2.88 respectively. Such variations were related to the changes of p electrons from carboxyl group caused by the transformation between the carboxyl group and the carboxylate group in different pH environments. Comparison of deltaH, deltac data between Me-OFL and OFL in acidic solution and OFL in alkaline was made. In Me-OFL acidic solution, the chemical shift of 3'C, 5'C, 7'C, 8'C also exhibited remarkable shift to low field at 6.66-7.32 respectively, the chemical shift of 2'C and 6'C also exhibited remarkable shift to high field 6.04. In OFL acidic solution, the chemical shift of 2'C, 3'C, 5'C, 6'C, 7'C, 8'C also exhibited remarkable shift to high field within 2.39, Comparison between the protonation and the methylation on the 4'N atom from the piperazine ring was also made. The distribution of positive charge also showed difference. When protonation occurred on the piperazine ring, the positive charge was on the proton connected with 4'N. However, if methylation occurred, the positive charge is on the 4'-N atom.

[A novel triterpenoid saponin from Prunella vulgaris].

To study the constituents of the Prunella vulgaris L, the constituents were isolated by various column chromatography and the structures were identified on the basis of chemical and spectral analysis. One saponin compound (I) and one flavone glycoside compound (II) were obtained from Prunella vulgaris L. Their structures were elucidated as 16-oxo-17-demethyl-3beta,24-dihydroxylolean-12-en-3-O-beta-D-glucuronoside (I), and acacetin-7-O-beta-D-glucopyranoside (II). Compound I is a novel triterpenoid saponin and named as prunelloside A. Compound II was obtained for the first time from the Prunella genus.

[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.

[Isolation and structure identification of chemical constituents from Saposhnikovia divaricata (Turcz.) Schischk].

Fourteen compounds were isolated from the ethanol extraction of Saposhnikovia divaricata (Turcz.) Schischk using column chromatographic methods after enrichment by macroporous adsorptive resins. They were identified as fangfengalpyrimidine (1), clemiscosin A (2), 5-hydroxy-8-methoxypsoralen (3), sec-O-glucosylhamaudol (4), hamaudol (5), nodakenetin (6), prim-O-glucosylcimifugin (7), cimifugin (8), 4'-O-beta-D-glucosyl-5-O-methylvisamminol (9), 5-O-methylvisamminol (10), marmesin (11), adenosine (12), daucosterol (13) and beta-sitosterol (14) by physico-chemical properties and spectral data. Compound 1 is a new compound. Compounds 2 and 3 were isolated from umbelliferae plants and Saposhnikovia divaricata (Turcz.) Schischk for the first time respectively.

Cyclolanostane triterpene glycosides from Souliea vaginata.

Five new cyclolanostane triterpene glycosides, 12-deacetyloxy-15alpha-hydroxy-23-epi-26-deoxyactein, 12-deacetyloxy-23-epi-26-deoxyactein, 24-O-acetyldahurinol-3-O-beta-D-xylopyranoside, 12beta-hydroxycimigenol-3-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranoside, 25-anhydrocimicigenol-3-O-beta-D-(2'-O-acetyl)xylopyranoside, were isolated from the rhizome of Souliea vaginata collected in China. Their structures were elucidated by spectroscopic techniques, including 2D NMR spectra, and in the case of 5, by chemical correlation.

[Studies on the chemical constituents in root of Gentiana macrophylla from Shaanxi].

OBJECTIVE: To in vestigate the constituents in root of Gentiana macrophylla. METHOD: Various column chromatographic techniques were used for isolation and purification of the principles. The structures were elucidated on the basis of spectral data (UV, IR, MS, 1H-, 13C-NMR etc.) and identified by comparing with standard substance. RESULT: Eight compounds were identified. Four compounds isolated from the chloroform fraction are: 5-carboxyl-3,4-dihydrogen-1H-2-benzopyran-1-one (1), erythrocentauric acid (2), roburic acid (3), oleanolic acid (4). Water fraction gave four known secoiridoid glucosides. They were: gentiopicroside (5), swertiamarine (6), sweroside (7), 6'-O-beta-D-glucosylgentiopicroside (8). CONCLUSION: 1 is a novel compound. It was named as erythrocentauric acid. 2 was isolated from genus Gentiana and 8 was isolated from G. macrophylla for the first time.

[A new natural product from the roots of Hedysarum multijugum].

OBJECTIVE: To study the chemical constituents of the roots of Hedysarum multijugum Maxim. METHODS: Compounds were isolated and purified by solvent and column chromatographic methods, and their structures were determined on the basis of physico-chemical properties and spectroscopic data. RESULTS: Seven compounds warangalone-4'-methyl ether (1), afrormosin (2), sissotrin (3) and ononin (4), naringenin-5, 7-di-O-beta-D-glucopyranoside (5), apigenin (6) and narcissin (7) were obtained from the roots of Hedysarum multijugum. CONCLUSION: Compound 1 is a new natural product, and other compounds; are obtained from the plant for the first time.

[Studies on lignan glycosides from the roots of Bupleurum scorzonerifolium].

AIM: To study the lignan glycosides from the roots of Bupleurum scorzonerifolium. Chromatography methods was used to isolate compounds and chemical and spectral methods were used to identify the structures of isolated compounds. RESULTS: Two lignan glycosides were isolated from the roots of B. scorzonerifolium and their structures were identified as 2, 3-E-2,3-dihydro-2-(3'-methoxy-4'-O-beta-D-glucopyranosyl-phenyl)-3-hydroxymethyl-5-(3"-hydroxypropenyl )-7-methoxy-1-benzo [b] furan (1) and 2, 3-E-2, 3-dihydro-2-( 3'-methoxy-4'-hydroxy-phenyl)-3-hydroxymethyl-5-( 3"-hydroxypropenyl)-7-O-beta-D-glucopyranosyl-1-benzo[b]furan (2), both of them which were the mixture of (+)2S,3R- and (-)2R,3S-type diastereoisomer and in both of them the amount of (+)2S,3R-type was a little more than that of the (-)2R,3S-type. CONCLUSION: Compounds 1 and 2 were isolated from B. scorzonerifolium for the first time. (+)2S, 3R-2, 3-Dihydro-2-(3'-methoxy-4'-hydroxy-phenyl)-3-hydroxymethyl-5-(3"-hydroxypropenyl)-7-O-beta-D-glucopyranosyl-1-benzo[b] furan is a new compound.

An antitumor compound julibroside J28 from Albizia julibrissin.

A new triterpenoid saponin, julibroside J(28) (1), was isolated from the stem bark of Albizia julibrissin Durazz (Leguminosae) by using chromatographic method. The structure of 1 was established by spectroscopic methods. 1 displayed significant antitumor activity in vitro against PC-3M-1E8, Bel-7402, and HeLa cancer cell lines at 10 microM assayed by SRB method.

Two new triterpene saponins from Lysimachia davurica.

Two new saponins, named davuricoside L (1) and davuricoside O (2), have been isolated from the whole plants of Lysimachia davurica. Their structures were determined by 1D and 2D NMR, FAB-MS techniques, and chemical methods.

Diastereoisomeric saponins from Albizia julibrissin.

The structures of four new diastereoisomeric triterpenoidal saponins Julibroside J5, J8, J12 and J13 (1-4) isolated from Albizia julibrissin Durazz. (Leguminosae) have been determined on the basis of comprehensive spectroscopic analysis and chemical degradation. Julibroside, J8 and J13 showed marked cytotoxic activities against Bel-7402 cancer cell line at 100 microg/mL.

Isolation and identification of a novel ellagitannin from Phyllanthus urinaria L.

AIM: To investigate the chemical constituents of Phyllanthus urinaria L. METHODS: Various chromatographic techniques were employed for the isolation and purification. The structure was elucidated by spectral analyses. RESULTS: A novel ellagitannin named phyllanthusiin G was isolated, its structure was established as 1-O-galloyl-2-phyllanthoyl-3,6-(R)-HHDP-beta-D-glucose. CONCLUSION: Phyllanthusiin G is a new compound.

New flavonoids from Oxytropis myriophylla.

Eight compounds were isolated from Oxytropis myriophylla. On the basis of spectral analyses, their structures were elucidated to be (6R,9R)-roseoside (1), (6R,9S)-roseoside (2), adenosine (3), myriophylloside B (4), myriophylloside C (5), myriophylloside D (6), myriophylloside E (7), and myriophylloside F (8). Five flavonoids (4-8) were new compounds, and the three known compounds were isolated from this plant for the first time.

Synthesis and hydrolysis of a phenylalanyl adenylate pentacoordinated phosphorane.

Amino acid-nucleotide conjugates have important biological functions and therapeutic applications. For example, aminoacyl adenylates are key intermediates in aminoacyl tRNA synthetase reactions. They may also be involved in the prebiotic synthesis of polypeptides. Finally, various amino acid carbomethoxy aryl phosphoramidates of nucleotide prodrugs may be activated through a mechanism involving a pentacoordinated phosphorane intermediates. In order to understand better the chemistry of these compounds, a phenylalanyl adenylate pentacoodinated phosphorane has been synthesized in 72% yield and its decomposition in aqueous solution studied. Hydrolysis gave 2('),3(')-O-isopropylidene adenosine 5(')-monophosphate, 2('),3(')-O-isopropylidene adenosine, and phenylalanine. The results provide model chemistry for the enzymatic degradation mechanism of antiviral aryl amino acid phosphodiester amidates in cells, which leads to their activation.

Two new pterocarpenes from Hedysarum multijugum.

Two new pterocarpenes were isolated from the roots of Hedysarum multijugum, and their structures were elucidated as hedysarimpterocarpene B (1) and hedysarimpterocarpene C (2) on the basis of spectroscopic data.

[Studies on chemical constituents in fruits of Tibetan medicine Phyllanthus emblica].

OBJECTIVE: To investigate the chemical constituents of Tibetan medicine Phyllanthus emblica. METHOD: Various chromatographic techniques were employed for isolation and purification of the constituents, and the structures were elucidated by chemical and spectral analyses. RESULT: 11 compounds were isolated and identified as gallic acid (I), ellagic acid (II), 1-O-galloyl-beta-D-glucose (III), 3,6-di-O-galloyl-D-glucose (IV), chebulinic acid (V), quercetin (VI), chebulagic acid (VII), corilagin (VIII), 3-ethylgallic acid (3-ethoxy-4,5-dihydroxy-benzoic acid, IX), isostrictiniin (X), 1,6-di-O-galloyl-beta-D-glucose (XI). CONCLUSION: 3-Ethylgallic acid (3-ethoxy-4,5-dihydroxy-benzoic acid) is a novel compound, and isostrictiniin was found from P. emblica for the first time.