Three new coumarins, integmarins A-C (1-3), and a new coumarin glycoside, integmaside A (4) were isolated from the leaves and stems of Micromelum integerrimum. Their structures were elucidated on the basis of 1D and 2D NMR and MS data, and their absolute configurations were assigned according to the ECD data of the in situ formed transition metal complexes and comparison of experimental and calculated ECD data. Compounds 1 and 2 are two rare coumarins with butyl and propyl moieties at the C-6 position; compound 3 is a novel coumarin with a highly oxidized prenyl group, and compound 4 is a rare bisdihydrofuranocoumarin glycoside.
Coumarins/isolation & purification* ; Glycosides/isolation & purification* ; Molecular Structure ; Plant Leaves/chemistry* ; Plant Stems/chemistry* ; Rutaceae/chemistry*

OBJECTIVEThe multiple levels fragmentations of five furocoumarine (psoralen, xanthotoxin, bergapten, oxypeucedanin, and byakangelicol) in Angelica dahurica have been demonstrated using LTQ-Orbitrap mass spectrometry with high resolution and high mass accuracy to discover the possible,fragmentation regularity.

METHODDuringcollsion-induced dissociation (CID), the MS(n) data of the five compoundswhich were gained in the positive ion mode at 35ev collision energy by direct injection syrings method were analyzed using Xcalibar 2.0 Software to infer the formula of these fragmentations.

RESULTThe results indicated that the five compounds have similar fragmentation process with CO meutral lost at C5,C8-subsituents and furan ring, meanwhile the meutralloss of CO2 occurred easily at lactone group.

CONCLUSIONThis method is helpful in identifying the structures of other furocoumarinein Angelica dahuricaand their metabolites in vivo.

Angelica ; chemistry ; Chemical Phenomena ; Coumarins ; chemistry ; isolation & purification ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; Mass Spectrometry ; methods ; Molecular Structure

Tyrosol, crenulatin and salidroside are the main active constituents of Rhodiola crenulata, with extensive pharmacological activities. In the study, grams of high purity tyrosol, crenulatin and salidroside were simultaneously separated from R. crenulata by the first time. Firstly, R. crenulata was extracted by 70% alcohol. Then, with the yields of three compounds as the index, the macroporous resin was optimized. At last, grams of high purity tyrosol, crenulatin and salidroside were isolated by D-101 macroporousresin, purified by column chromatography. Detected by HPLC, the purity of three compounds were higher than 98%. This method has the advantages of simple process and operation, less dosage of organic solvent, highly yield and reproducibility, suitable for the simultaneously preparation of tyrosol, crenulatin and salidroside.
Chemical Fractionation ; methods ; Chemistry, Pharmaceutical ; Chromatography, High Pressure Liquid ; Coumarins ; analysis ; isolation & purification ; Drugs, Chinese Herbal ; analysis ; isolation & purification ; Glucosides ; analysis ; isolation & purification ; Phenols ; analysis ; isolation & purification ; Phenylethyl Alcohol ; analogs & derivatives ; analysis ; isolation & purification ; Rhodiola ; chemistry

This study is to study is to investigate the coumarins from Fruit of Cnidium monnieri and their cytotoxic activities. The constituents were separated by column chromatography, and their structures were elucidated by spectroscopic data analyses. The isolated compounds were evaluated for their cytoxic activities by MTT method. Eleven compounds were isolated and identified as osthole (1), bergaptan (2), xanthotoxol (3), xanthotoxin (4), imperatorin (5), isopimpinellin (6), osthenol (7), psoralen (8), 5,7-dimethoxycoumarin (9), oxypeucedaninhydrate (10), and swietenocoumarin F (11). Compounds 7, 9-11 were isolated from the Cnidium genus for the first time. Compounds 1,5,10 and 11 showed significant cytotoxic activities against L1210 cell lines at a concentration of 1 x 10(-5) mol x L(-1) with inhibitory rates of were 70.13, 63.10, 55.77, and 75.08% respectively.
Animals ; Cell Line, Tumor ; Cell Proliferation ; drug effects ; Cnidium ; chemistry ; toxicity ; Coumarins ; chemistry ; isolation & purification ; toxicity ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; toxicity ; Fruit ; chemistry ; toxicity ; Mice ; Molecular Structure

The extracting technology of salidroside, tyrosol, crenulatin and gallic acid from Rhodiolae Crenulatae Radix et Rhizoma was optimized. With extraction rate of salidroside, tyrosol, crenulatin and gallic acid as indexes, orthogonal test was used to evaluate effect of 4 factors on extracting technology, including concentration of solvent, the dosage of solvent, duration of extraction, and frequency of extraction. The results showed that, the best extracting technology was to extract in 70% alcohol with 8 times the weight of herbal medicine for 2 times, with 3 hours once. High extraction rate of salidroside, tyrosol, crenulatin and gallic acid were obtained with the present technology. The extracting technology was stable and feasible with high extraction rate of four compounds from Rhodiolae Crenulatae Radix et Rhizoma, it was suitable for industrial production.
Chemical Fractionation ; methods ; Chemistry, Pharmaceutical ; methods ; Coumarins ; isolation & purification ; Drugs, Chinese Herbal ; isolation & purification ; Gallic Acid ; isolation & purification ; Glucosides ; isolation & purification ; Phenols ; isolation & purification ; Phenylethyl Alcohol ; analogs & derivatives ; isolation & purification ; Rhizome ; chemistry ; Rhodiola ; chemistry

The chemical constituents from lipophilic parts in the roots of Angelica dahurica var. formosana cv. Chuanbaizhi were studied in this paper. The compounds were separated and purified by repeated column chromatographic methods on silica gel and HPLC, and the chemical structures of compounds were determined by spectral data analyses. Twenty-nine compounds were obtained and identified as isoimperatorin (1), β-sitosterol (2), imperatorin (3), bergapten (4), osthenol (5), xanthotoxin (6), isoimpinellin (7), dehydrogeijerin (8), phellopterin (9), isodemethylfuropinarine (10), 7-demethylsuberosin (11), alloimperatorin (12), xanthotoxol (13), isooxypeucedanin (14), alloisoimperatorin (15), demethylfuropinarine (16), 5-hydroxy-8-methoxypsoralen (17), oxypeucedanin methanolate (18), pabulenol (19), byakangelicin (20), marmesin (21), (+) -decursinol (22), heraclenol (23), oxypeucedanin hydrate (24), marmesinin (25), ulopterol (26), erythro-guaiacylglycerol-β-ferulic acid ether (27), threo-guaiacylglycerol-β-ferulic acid ether (28), and uracil (29). Compounds 5, 8, 11, 18, 21-23, and 26-28 were obtained from the roots of title plant for the first time.
Angelica ; chemistry ; Coumarins ; chemistry ; isolation & purification ; Furocoumarins ; chemistry ; isolation & purification ; Methoxsalen ; chemistry ; isolation & purification ; Phytochemicals ; analysis ; chemistry ; Plant Roots ; chemistry

The chemical consituents from Psychotria straminea were separated and purified by column chromatographies on silica gel, Sephadex LH-20, ODS and RP-HPLC. The strictures of the isolated compounds were identified on the basis of physicochemical properties and spectroscopic analysis, as well as comparisons with the data in literature. Sixteen compounds were isolated and elucidated as tectochrysin (1), apigenin (2), kaempferol (3), luteolin (4), diosmetin (5), quercetin (6), kaempferol-4'-O-methylether (7), rhamnetin (8), 7-hydroxycoumarin (9), 7-methoxycoumarin (10), scopoletin (11), lupeol (12), 30-oxo-lupeol (13), lupenyl acetate (14), α-amyrin (15), and ursolic acid (16). This is the first study on the chemical composition of P. Straminea, and all compounds were isolated from P. straminea for the first time. In addition to compounds 6 and 9, the other compounds were isolated from the genus Psychotria for the first time.
Coumarins ; chemistry ; isolation & purification ; Flavonoids ; chemistry ; isolation & purification ; Phytochemicals ; chemistry ; isolation & purification ; Psychotria ; chemistry ; Triterpenes ; chemistry ; isolation & purification

AIM: To investigate the chemical and bioactive constituents from the stems and leaves of Micromelum integerrimum. METHOD: The chemical constituents were isolated and purified by silica gel, Sephadex LH-20, and HPLC. Their structures were mainly elucidated on the basis of extensive 1D- and 2D-NMR spectroscopy and mass spectrometry. Their cytotoxicity and antimicrobial activities were tested by the SRB and turbidimetric methods, respectively. RESULTS: Two new phenylpropanoids and two known coumarins were obtained, and their structures were identified as microintegerrin A (1), microintegerrin B (2), scopoletin (3), and scopolin (4). All of the compounds were tested for their cytotoxicity against three cancer cell lines (HeLa, A549, and BGC-823) and for antimicrobial activity against the fungus Candida albicans and the bacterium Staphylococcus aureus. CONCLUSION Two new phenylpropanoids 1 and 2 were isolated and identified from the stems and leaves of M. intgerrimum. None of the compounds showed cytotoxic or antimicrobial activity at the tested concentration of 20 μg·mL(-1).
Candida albicans ; drug effects ; Coumarins ; isolation & purification ; pharmacology ; Glucosides ; isolation & purification ; pharmacology ; HeLa Cells ; Humans ; Molecular Structure ; Phenylpropionates ; chemistry ; isolation & purification ; pharmacology ; Plant Extracts ; chemistry ; pharmacology ; Plant Leaves ; Plant Stems ; Rutaceae ; chemistry ; Scopoletin ; isolation & purification ; pharmacology ; Staphylococcus aureus ; drug effects

This study is purposed to investigate the effects of praeruptorin A (PA) and praeruptorin C (PC) on UGT1A1 in HepG2 cells through hCAR pathway. PA and PC were incubated with HepG2 cells for 24 h and 48 h, mRNA and protein expressions of UGT1A1 were determined by real-time PCR and Western blotting assays. Additionally, effects of PA and PC on UGT1A1 mRNA and protein expressions were also measured after transient transfection of a specific CAR siRNA for 72 h in HepG2 cells. UGT1A1 mRNA and protein expression levels were significantly increased by PA and PC after incubation for 48 h. Moreover, the mRNA and protein up-regulations of UGT1A1 were attenuated by transient transfection of a specific CAR siRNA, suggesting the induction was mediated by CAR. The results suggest that PA and PC can significantly up-regulate UGT1A1 expression partially via the CAR-mediated pathway.
Apiaceae ; chemistry ; Coumarins ; isolation & purification ; pharmacology ; Drugs, Chinese Herbal ; pharmacology ; Glucuronosyltransferase ; genetics ; metabolism ; Hep G2 Cells ; Humans ; Plant Roots ; chemistry ; Plants, Medicinal ; chemistry ; RNA, Messenger ; metabolism ; RNA, Small Interfering ; genetics ; metabolism ; Receptors, Cytoplasmic and Nuclear ; genetics ; metabolism ; Signal Transduction ; Transfection

Angelica polymorpha Maxim. is a plant of the Angelica genus (Umbelliferae). The root and stem of this plant is a folk medicine known to have the actions of relieving rheumatism and cold and subsiding swelling and pains. To investigate the chemical constituents in the root of A. polymorpha Maxim., seven compounds were isolated from an 80% ethanol extract by column chromatography. Their structures were elucidated according to the spectroscopic analysis. Compound 1 is a new sesquiterpene, named as bisabolactone. Its absolute configuration was determined by 1D NOESY and CD analysis. The others were identified as 5-hydroxymethylfurfural (2), hycandinic acid ester 1 (3), ferulic acid (4), isooxypeucedanin (5), noreugenin (6) and cimifugin (7). Compound 2 and 3 were isolated from this genus for the first time and compound 4 was isolated from this plant for the first time.
Angelica ; chemistry ; Chromones ; chemistry ; isolation & purification ; Coumaric Acids ; chemistry ; isolation & purification ; Coumarins ; chemistry ; isolation & purification ; Furaldehyde ; analogs & derivatives ; chemistry ; isolation & purification ; Molecular Structure ; Plant Roots ; chemistry ; Plants, Medicinal ; chemistry ; Quinic Acid ; analogs & derivatives ; chemistry ; isolation & purification ; Sesquiterpenes ; chemistry ; isolation & purification