A new carbazole alkaloid from the stems of Clausena lansium / 药学学报

A new carbazole alkaloid was isolated from the aqueous extract of the stems of Clausena lansium (Lour.) Skeels by various chromatographic methods, including HPD-100, PRP-512A, silica gel, and reverse phase C18. Its structure was determined by spectroscopic and chemical methods, including UV, IR, HR-ESI-MS, 1D/2DNMR and ECD. Compound 1, named as Claulamine F, showed no antimicrobial activity on Staphylococcus aureus, Escherichia coli or Pseudomonas aeruginosa. In addition, compound 1 exhibited no cytotoxicity on five kinds of cancer cells through MTT methods.

Chemical constituents and their bioactivities from seeds of Clausena lansium / 中草药

Objective To study the chemical constituents and their biological activities of the seeds of Clausena lansium. Methods The compounds were isolated by various column chromatographic techniques including silica gel, Sephadex LH-20, semi-preparative HPLC, et al., and their structures were identified through a combined analysis of physicochemical properties, as well as NMR and MS data. The in vitro α-glucosidase inhibitory activity and nematicidal activity against Panagrellus redivivusl were screened by PNPG and Berman funnel methods, respectively. Results Eleven compounds were isolated and identified as (4R*,6R*)-6-hydroxypiperitone (1), (4S*,6R*)-6-hydroxypiperitone (2), (1S*,2S*,4R*)-1-methyl-4-(prop-l-en-2-yl) cyclohexane-1,2-diol (3), subamone (4), methyl (1R*,2R*,2’Z)-2-(5’-hydroxy-pent-2’-enyl)-3-oxo-cyclopentane acetate (5), 5-hydroxy-4-phenyl-5H-furan-2-one (6), loliolide (7), xylogranatinin (8), 2,6-dihydroxyhumula-3(12),7(13),9(E)-triene (9), xanthoxol (10), and ligballinol (11). Conclusion Compounds 1-8 are isolated from the genus for the first time, and compound 9 is first isolated from this species. Compound 8 showed strong α-glucosidase inhibitory activity, and compound 5 exhibited potent nematicidal activity.

Isolation and Identification of the Coumarins from the Seeds of Clausena lansium and Study on Their Inhibitory Activity of α-glucosidase and Nematicidal Activity against Panagrellus redivivus / 中国药房

OBJECTIVE： To isolate and identify the coumarins from the seeds of Clausena lansium， and to study their inhibitory activity of α-glucosidase and nematicidal activity against Panagrellus redivivus. METHODS： Column chromatography， reversed phase silica gel column chromatography and HPLC method were used to separate and purify the coumarins from the seeds of C. lansium. The structures of compounds were identified according to physicochemical properties， 1H-NMR and 13C-NMR spectral data. Using acarbose and avermectin as positive control， PNPG and Berman funnel methods were used to investigate the α-glucosidase inhibitory activity and nematicidal activity against P. redivivus， respectively. RESULTS： Seven coumarins compounds were isolated from the seeds of C. lansium， and were identified as 7-hydroxy-1-benzopiran-2-one （Ⅰ）， Wampetin （Ⅱ）， Lansiumarin-C （Ⅲ）， Claucoumarin A （Ⅳ）， Clausenalansimin A （Ⅴ）， （E，E）-8-（7-hydroxy-3，7-dimethylocta-2，5-dienyloxy） psoralen （Ⅵ）， Dihydroindicolactone （Ⅶ）. Under 0.25 mg/mL， the α-glucosidase inhibitory rates of compounds Ⅰ， Ⅲ， Ⅴ were （32.4±1.9）％，（37.1±6.0）％， （39.5±1.1）％， respectively. Under 2.5 mg/mL， corrected mortality of compounds Ⅰ， Ⅳwere 50.5％ and 47.9％. CONCLUSIONS： Compounds Ⅰ， Ⅲ， Ⅴ show α-glucosidase inhibitory activity， and compounds Ⅰ，Ⅳ display nematicidal activity against P. redivivus.  α-Glucosidase inhibitory activity of compounds Ⅲ， Ⅴ， and nematicidal activity of compound Ⅳ are found for the first time.

Carbazole alkaloids isolated from the branch and leaf extracts of Clausena lansium / 中国天然药物

The present study carried out a phytochemical investigation of the methanol extract of the branches and leaves of Clausena lansium and afforded nine carbazole alkaloids (compounds 1-9) including two new carbazole alkaloids, claulansiums A and B (compounds 1 and 2). The new compounds were elucidated on the basis of extensive spectroscopic data (MS, NMR, IR, and UV) and the known compounds were identified by comparing spectroscopic data with those reported in literature. All the isolated compounds were tested for their cytotoxic activity against A549 and Hela cancer cell lines. Our results showed that compounds 2-6 exhibited varying degrees of cytotoxicity to cancer cells, with IC values ranging from 8.67 to 98.89 μmol·L.

Analysis and identification of volatile components of different parts of Clausena lansium in Hainan by HS-SPME-GC-MS / 中草药

Objective A headspace-solid phase microextraction-gas chromatography-mass spectrometry method (HS-SPME-GC-MS) was adopted for analyzing the volatile components of different parts of Clausena lansium in Hainan Province. Methods Five different fibers were investigated and optimized. Other five experimental parameters such as volume of water, extraction temperature, equilibrium time, extraction time, and salt concentration had been evaluated and optimized by means of the orthogonal design with L16(45) table. Finally, the volatile components of C. lansium leaves, pericarps, and seeds in Hainan were analyzed and identified by GC-MS combined with retention index (RI). Results The optimum extraction conditions were as follows: a 50/30 μm DVB/CAR/PDMS fiber, 10 mg sample powders, 2.0 mL water, 0.2 g NaCl, extraction temperature 80 ℃, equilibrium time 30 min, extraction time 60 min. A total of 83 chemical components were identified from leaves, 96 from pericarps, and 106 from seeds, representing the relative contents of 95.24%, 92.15%, and 95.92% of the total composition. The highest contents were sesquiterpenes in all of the parts, but there were obviously different both in components and contents. Conclusion The HS-SPME-GC-MS method is rapid and sensitive, with a small sample size, without any organic solvents. GC-MS combined with RI has improved the accuracy of analysis and identification. The results may provide experimental basis for further exploitation of C. lansium in Hainan. This method can be used to perform enrichment analysis of the components with high-boiling point and micro-components, which can comprehensively and scientifically characterize and evaluate the quality of Chinese materia medica.

Carbazole alkaloids isolated from the branch and leaf extracts of Clausena lansium / 中国天然药物

The present study carried out a phytochemical investigation of the methanol extract of the branches and leaves of Clausena lansium and afforded nine carbazole alkaloids (compounds 1-9) including two new carbazole alkaloids, claulansiums A and B (compounds 1 and 2). The new compounds were elucidated on the basis of extensive spectroscopic data (MS, NMR, IR, and UV) and the known compounds were identified by comparing spectroscopic data with those reported in literature. All the isolated compounds were tested for their cytotoxic activity against A549 and Hela cancer cell lines. Our results showed that compounds 2-6 exhibited varying degrees of cytotoxicity to cancer cells, with IC values ranging from 8.67 to 98.89 μmol·L.

Chemical constituents from the stems of Clausena lansium / 中成药

AIM To study the chemical constituents from the stems of Clausena lansium (Lour.) Skeels.METHODS The n-butanol fraction of Clausena lansium stems' 95％ ethanol extract and herb residue's 50％ ethanol extract were isolated and purified by silica,RP-MPLC and PHPLC column,then the structures of obtained compounds were identified by spectral data.RESULTS Eight compounds were isolated and identified as marmesinin (1),nodakenin (2),decuroside Ⅳ (3),3,4-dimethoxyphenyl-β-D-glucopyranoside (4),glucosyringic acid (5),2-(3-methoxy-4-hydroxyphenyl)-ethanol-1-O-β-D-glucopyranoside (6),4-hydroxy-2-methoxy-phenyl-β-D-glucopyranoside (7),4-hydroxy-2,6-dimethoxyphenyl-β-D-glucopyranoside (8).CONCLUSION Compounds 4-6 and 8 are isolated from genus Clausena for the first time.

Chemical Composition of Clausena lansium (Lour.) Skeels Leaves and Antifungal Activity

The first study on chemical constituents and biological activities of Clausena lansium (Lour.) Skeels (Rutaceae) growing in Vietnam has been done. Phytochemical investigation of n-hexane extract led to the isolation of five compounds: dihydroindicolactone (1), 8-geranyloxy psoralen (2), imperatorin (3), heraclenol (4) and indicolactone (5), in which this is the first report on the presence of dihydroindicolactone (1). Their structures were elucidated based on LC/MS/NMR hyphenated techniques as well as comparison with those of literature data. The n-hexane extract and its subfractions, ethanol 95% extract and several isolated compounds were evaluated for antifungal activity.

Chemical constituents from stems of Clausena lansium / 中草药

Objective: To study the chemical constituents from the stems of Clausena lansium. Methods: The chemical constituents were separated and purified by macroporous resin, silica gel, ODS column chromatography, Sephadex LH-20, and preparative HPLC. Their structures were determined by the analyses of ultraviolet spectrum, mass spectrum, and nuclear magnetic resonance spectroscopy. Results: Fifteen compounds were isolated from the n-BuOH fractions of 95% ethanol extract from the stems of C. lansium, and their structures were identified as 1, 1', 1″, 1‴, 1″″-tricontane lactam (1), 4-hydroxy-2, 6-dimethoxyphenyl 6'-O-syringoyl-β-D- glucopyranoside (2), 4-hydroxy-2, 6-dimethoxyphenyl 6'-O-vanilloyl-β-D-glucopyranoside (3), 4-hydroxymethyl-2-methoxyphenyl- 6'-O-syringoyl-β-D-glucopyranoside (4), 4-hydroxy-2-methoxyphenyl-6-O-syringoyl-β-D-glucopyranoside (5), syingin (6), coniferin (7), 3, 4, 5-trimethoxyphenyl-O-β-D-glucopyranoside (8), tinotuberide (9), trans-isoconiferin (10), phenethyl-O-β-D-glucopuranoside (11), araliopsine (12), geibalansine (13), integriquinolone (14), and γ-fagarine (15). Conclusion: Compounds 1-14 are isolated from this plant for the first time, compounds 1-11 are isolated from the plants of genus Clausena L. for the first time, and compound 1 is a new natural product.

Effects of N-methyl-N-cis-styryl-cinnamamide on Penicillin-induced Epileptiform Discharges in Rats / 中山大学学报(医学科学版)

[Objective]To investigate the effects of the seed extract of Clausena lansium,N-methyl-N-cis-styryl-cinnamamide,on the penicillin-induced epilepsy in rats.[Methods]Thirty-two Sprague-Dawely rata were randomly divided into four groups with 8 rats in each group:normal control(20 mL/L Tween 80+Normal Saline),model control(20 mL/L Tween 80+Penicillin),low dose treatment(Cinnamamide 75 mg/kg+Penicillin),hish dose treatment(Cinnamamide 150 mg/kg+Penicillin).The epilepsy rat model was established by localized intracortical injections of penicillin.The effects of pretreatments of the rats with N-methyl-N-cis-styryl-cinnamamide(intraperitoneal injection,ip)on the penicillin-induced seizure activities and the epileptiform discharges recorded by electrocorticogram(ECoG)were observed.[Results]The penicillin-induced seizure was significantly lightened in both the pretreatment groups(75 and 150 mg/kg N-methyl-N-cis-styryl-cinnamamide),compared with the model group.N-methyl-N-cis-styryl-cinnamamide(75 and 150 mg/kg)could significantly prolonged the latency of epileptiform activities,shorten the duration of epileptiform discharges and decreased the mean spike frequency in the late stage(P＜0.05 or P＜0.01).However,there was no significant difference in the highest value or the lowest value of the epileptiform waves between the model and cinnamamide treatment groups.[Conclusion]The seed extract of Clansena lansium,N-methyl-N-cis-styryl-cinnamamide,can significantly inhibit the seizure and epileptiform discharges caused by penicillin-localized injections in the cortex of rats,suggesting that the natural substance has an anticonvulsive function.

Isolation and structure determination of compounds from Clausena lansium (Lour.) skeels

Studying on Clausena lansium (Lour.) samples collected from Pu Mat, Nghe An province in March 2004 to isolate and determine structure of some sterol compounds. Bough samples were dried and pounded leached with methanol in 20 days. Methanol extract was collected via distilling process to get solvents. Extracting with ethyl acetate, n-butanol and then distilling to get solvent we collected corresponding sediments. The corresponding solid extracts were collected by extract method with ethyl acetate, n-butanol solvents and then segment distill. A1, A2 solids were isolated by chromatographic method and segment crystallization. Using EI - MS, 1H - NMR, 13C - NMR spectroscopic methods to determine structure, A1 were identified as beta - sitosterol and A2 as stigmasterol. This is the first time these compounds isolated from Clausena lansium (Lour.) in Vietnam