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1.
China Journal of Chinese Materia Medica ; (24): 4438-4445, 2021.
Article in Chinese | WPRIM | ID: wpr-888144

ABSTRACT

The chemical constituents from the stems and leaves of Clausena excavata were isolated and purified by column chromatography with silica gel, ODS, Sephadex LH-20 and RP-HPLC. The chemical structures of the isolated compounds were identified on the basis of physicochemical properties, spectroscopic analysis, as well as the comparisons with the data reported in literature. Nineteen compounds were isolated from the 90% ethanol extract of the stems and leaves of C. excavata, which were identified as methyl orsellinate(1), syringaresinol(2), lenisin A(3), scopoletin(4), osthenol(5), N-benzoyltyrarnine methyl ether(6), N-p-coumaroyltyramine(7), aurantiamide acetate(8), 1H-indole-3-carboxaldehyde(9), furostifoline(10), clausenalansine E(11), 3-formylcarbazole(12), clausine L(13), clausine E(14), methyl carbazole-3-carboxylate(15), glycosinin(16), murrayafoline A(17), clausine H(18) and 2,7-dihydroxy-3-formyl-1-(3'-methyl-2'-butenyl)carbazole(19). Among these isolated compounds, compounds 1-11 were isolated from C. excavata for the first time, and compounds 1, 2 and 10 were isolated from the genus Clausena for the first time. In addition, this study evaluated the anti-rheumatoid arthritis activities of compounds 1-19 by measuring their anti-proliferative effects on synoviocytes in vitro according to MTS method. Compounds 10-19 displayed remarkable anti-rheumatoid arthritis activities, which exhibited the inhibitory effects on the proliferation of MH7 A synovial fibroblast cells with the IC_(50) values ranging from(27.63±0.18) to(235.67±2.16) μmol·L~(-1).


Subject(s)
Cell Proliferation , Chromatography, Reverse-Phase , Clausena , Plant Leaves , Synoviocytes
2.
Asian Pacific Journal of Tropical Biomedicine ; (12): 232-238, 2020.
Article in Chinese | WPRIM | ID: wpr-950304

ABSTRACT

Objective: To investigate the anti-inflammatory properties of methanolic extract of Clausena excavata in lipopolysaccharide (LPS)-activated macrophages (J774A.1) and the effect on skin wound in a rat model through determining cytokine levels and gene expressions. Methods: The effects of methanolic extract of Clausena excavata on in vitro viability and TNF-α, IL-6, IL-10, and nitric oxide release by LPS-activated J774A.1 cells were determined. In addition, relative expressions of BAX, BCL-2 and COX-2 genes were examined in healed wounds of rats. Results: The methanolic extract of Clausena excavata was not toxic to J774A.1 cells at the highest dose of 400 μg/mL. It decreased levels of TNF-α and IL-6, while increasing IL-10 level in LPS-activated J774A.1 cells and in the healed wounds of rats. The methanolic extract of Clausena excavata also inhibited nitric oxide production in LPS-activated J774A.1 cells. The BAX and COX-2 genes were downregulated while the BCL-2 gene was upregulated in the healed wound of rats. Conclusions: The methanolic extract of Clausena excavata promotes wound healing via its anti-inflammatory and anti-apoptotic activities.

3.
Chinese Traditional and Herbal Drugs ; (24): 1825-1830, 2020.
Article in Chinese | WPRIM | ID: wpr-846488

ABSTRACT

Objective: To study the coumarins and alkaloids from the stems of Clausena lenis. Methods: The chemical constituents from the stems of C. lenis were separated and purified by silica gel, ODS, Sephadex LH-20 gel column chromatographies and preparative HPLC. Their structures were identified by physicochemical properties, spectroscopic analysis, as well as the comparisons with the data reported in literatures. Results: A total of 18 compounds were isolated from the 90% ethanol extract of the stems of C. lenis, which were identified as 6,8-diprenylumbelliferone (1), byakangelicin (2), tert-O-methylheraclenol (3), pabularinone (4), isogosferol (5), heraclenol (6), imperatorin (7), decursinol (8), xanthyletin (9), marmesin (10), skimmianine (11), kokusaginine (12), N-metilatanina (13), clausine Z (14), murrayanine (15), 2-methoxy-1-(3-methyl-buten-1-yl)-9H-carbazole-3-carbaldehyde (16), claulansine I (17) and clausehainanine A (18). Among them, compounds 1-10 were coumarins and 11-18 were alkaloids. Conclusion: All compounds are isolated from C. lenis for the first time, compounds 2, 3 and 8 are separated from the genus Clausena for the first time.

4.
Acta Pharmaceutica Sinica ; (12): 110-112, 2020.
Article in Chinese | WPRIM | ID: wpr-780575

ABSTRACT

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.

5.
Asian Pacific Journal of Tropical Biomedicine ; (12): 232-238, 2020.
Article in Chinese | WPRIM | ID: wpr-823937

ABSTRACT

Objective: To investigate the anti-inflammatory properties of methanolic extract of Clausena excavata in lipopolysaccharide (LPS)-activated macrophages (J774A.1) and the effect on skin wound in a rat model through determining cytokine levels and gene expressions.Methods: The effects of methanolic extract of Clausena excavata on in vitro viability and TNF-α, IL-6, IL-10, and nitric oxide release by LPS-activated J774A.1 cells were determined. In addition, relative expressions of BAX, BCL-2 and COX-2 genes were examined in healed wounds of rats. Results: The methanolic extract of Clausena excavata was not toxic to J774A.1 cells at the highest dose of 400 μg/mL. It decreased levels of TNF-α and IL-6, while increasing IL-10 level in LPS-activated J774A.1 cells and in the healed wounds of rats. The methanolic extract of Clausena excavata also inhibited nitric oxide production in LPS-activated J774A.1 cells. The BAX and COX-2 genes were downregulated while the BCL-2 gene was upregulated in the healed wound of rats. Conclusions: The methanolic extract of Clausena excavata promotes wound healing via its anti-inflammatory and anti-apoptotic activities.

6.
Chinese Traditional and Herbal Drugs ; (24): 324-329, 2019.
Article in Chinese | WPRIM | ID: wpr-851401

ABSTRACT

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.

7.
China Pharmacy ; (12): 518-522, 2019.
Article in Chinese | WPRIM | ID: wpr-817098

ABSTRACT

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.

8.
China Pharmacy ; (12): 677-680, 2019.
Article in Chinese | WPRIM | ID: wpr-817073

ABSTRACT

OBJECTIVE: To analyze the difference of volatile oil components from the leaves of Clausena lansium and Clausena excavata. METHODS: The volatile oil was extracted from the leaves of C. lansium and C. excavata by steam distillation. GC-MS method was adopted to analyze volatile oil to obtain TIC. After mass spectra scanning of the chromatographic peaks in the TIC diagram by HPMSD chemical workstation, chemical components of volatile oil in 2 kinds of samples were identified by retrieving and comparing mass spectrum database NIST Version 1.7. The peak area normalization method was used to calculate the relative mass fraction of each component. RESULTS: A total of 43 and 31 kinds of components were identified in volatile oil from the leaves of C. lansium and C. excavata; total relative mass fractions were 97.59% and 98.57%. Relative mass fractions of 19 and 18 components in volatile oil from the leaves of C. lansium and C. excavata were more than 1%, mainly being sesquiterpenoids. Relative mass fractions of 7 and 5 components in volatile oil from the leaves of C. lansium and C. excavata were more than 5%; the volatile components in volatile oil from the leaves of C. lansium were mainly (-)-spatol (12.35%) and (E)-5-{(1R,3R,6S)-2,3-dimethyltricyclic [2.2.1.02,6] heptane-3-yl}-2-methyl pentane-2-enol (14.70%); those from the leaves of C. excavata were mainly (E)-sesquihydrated betuline (24.94%) and 1-(1, 5-dimethy-4-hexenyl)-4-methyl-benzene (16.15%). A total of 4 components were found in volatile oil from the leaves of C. lansium and C. excavata, mainly being α-humulene, (E)-5-{(1R,3R,6S)-2,3-dimethyltricyclic [2.2.1.02,6] heptane-3-yl}-2-methylpentaeryl-2-enol, caryophyllene oxide and (-)-spatol; the content differences of them were not significant. CONCLUSIONS: The components of volatile oils from the leaves of C. lansium and C. excavata are basically similar However, the composition and comtent of specific components are quiet different and can not substituted for each other.

9.
China Journal of Chinese Materia Medica ; (24): 2096-2101, 2019.
Article in Chinese | WPRIM | ID: wpr-773122

ABSTRACT

The chemical constituents from the stems and leaves of Clausena emarginata were separated and purified by column chromatographies on silica gel,ODS,Sephadex LH-20,and PR-HPLC. The structures of the isolated compounds were identified on the basis of physicochemical properties and spectroscopic analysis,as well as comparisons with the data reported in the literature. Sixteen compounds were isolated from the 90% ethanol extract of the stems and leaves of C. emarginata,which were identified as siamenol( 1),murrastanine A( 2),3-formyl-1,6-dimethoxycarbazole( 3),3-methoxymethylcarbazole( 4),3-methylcarbazole( 5),murrayafoline A( 6),3-formylcarbazole( 7),3-formyl-1-hydroxycarbazole( 8),3-formyl-6-methoxycarbazole( 9),murrayanine( 10),murrayacine( 11),girinimbine( 12),nordentatin( 13),chalepin( 14),8-hydroxy-6-methoxy-3-pentylisocoumarin( 15) and ethyl orsellinate( 16). Compounds 1-4,14-16 were isolated from C. emarginata for the first time. Among them,compounds 1,2,15 and 16 were isolated from the genus Clausena for the first time. All isolated compounds were evaluated for their cytotoxic activities against five human cancer cell lines: HL-60,SMMC-7721,A-549,MCF-7 and SW480 in vitro. Compounds 12 and 14 showed significant inhibitory effects against various human cancer cell lines with IC_(50) values comparable to those of doxorubicin.


Subject(s)
Humans , Antineoplastic Agents, Phytogenic , Pharmacology , Cell Line, Tumor , Clausena , Chemistry , Doxorubicin , Phytochemicals , Pharmacology , Plant Leaves , Chemistry , Plant Stems , Chemistry
10.
Chinese Traditional and Herbal Drugs ; (24): 4241-4249, 2018.
Article in Chinese | WPRIM | ID: wpr-851684

ABSTRACT

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.

11.
Chinese Traditional and Herbal Drugs ; (24): 4494-4499, 2018.
Article in Chinese | WPRIM | ID: wpr-851648

ABSTRACT

Objective To investigate the lignans from the stems of Clausena emarginata. Methods The compounds were isolated and purified by chromatography on kieselguhr, silica gel, MPLC, and preparative HPLC. Their structures were identified on the basis of spectral data and physicochemical properties. Inhibitory activities on LPS-induced NO production of the lignans were initially investigated. Results Sixteen lignans were isolated from the CHCl3 fractions of 95% ethanol extract of the stems of C. emarginata, and their structures were identified as buddlenol C (1), hedyotol D (2), hedyotol C (3), 3-(2,4-dihydroxy-3-methoxybenzyl)-4- (4-hydroxy-3-methoxybenzyl) tetrahydrofuran (4), tripterygiol (5), busaliol (6), 2,3-bis [(4-hydroxy-3,5-dimethoxyphenyl)-methyl]- 1,4-butanediol (7), polystachyol (8), syringaresinol (9), nitidanin (10), 4-[3-hydroxymethyl-5-((E)-3-hydroxypropenyl)-7-methoxy- 2,3-dihydrobenzofuran-2-yl]-2,6-dimethoxy-phenol (11), erythro-guaiacylglycerol-β-O-4’-sinapyl ether (12), erythro-guaiacylglycerol- 8-O-4’-(coniferyl alcohol) ether (13), erythro-1-(4-hydroxy-3-methoxyphenyl)-2-(4-formyl-2-methoxyphenoxy)-propane-1,3-diol (14), rosalaevin B (15), and dehydroconiferyl alcohol (16). Conclusion Compounds 1-15 are isolated from this plant for the first time. Compounds 8 and 16 show inhibitory effects against LPS-induced NO production in microglia BV2 Cell.

12.
Chinese Journal of Natural Medicines (English Ed.) ; (6): 509-512, 2018.
Article in English | WPRIM | ID: wpr-812378

ABSTRACT

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.


Subject(s)
Humans , A549 Cells , Alkaloids , Chemistry , Toxicity , Antineoplastic Agents , Chemistry , Toxicity , Carbazoles , Chemistry , Toxicity , Cell Line, Tumor , Cell Survival , Clausena , Chemistry , HeLa Cells , Molecular Structure , Plant Extracts , Chemistry , Toxicity , Plant Leaves , Chemistry , Plant Stems , Chemistry , Plants, Medicinal , Chemistry
13.
Chinese Journal of Natural Medicines (English Ed.) ; (6): 509-512, 2018.
Article in English | WPRIM | ID: wpr-773589

ABSTRACT

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.


Subject(s)
Humans , A549 Cells , Alkaloids , Chemistry , Toxicity , Antineoplastic Agents , Chemistry , Toxicity , Carbazoles , Chemistry , Toxicity , Cell Line, Tumor , Cell Survival , Clausena , Chemistry , HeLa Cells , Molecular Structure , Plant Extracts , Chemistry , Toxicity , Plant Leaves , Chemistry , Plant Stems , Chemistry , Plants, Medicinal , Chemistry
14.
Chinese Traditional Patent Medicine ; (12): 1203-1206, 2017.
Article in Chinese | WPRIM | ID: wpr-618512

ABSTRACT

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.

15.
Chinese Traditional and Herbal Drugs ; (24): 2761-2770, 2017.
Article in Chinese | WPRIM | ID: wpr-852695

ABSTRACT

The genus Clausena Burm.f. (family Rutaceae) concerns 25 species all over the world, and 13 species are native to China especially in the southwest and south of China, Yunnan Province has 11 species. The chemical composition from Clausena Burm.f. included carbazole alkaloids, coumarins, sesquiterpenes, benzene derivatives, tetranortriterpenoids, flavonoids and so on. The carbazole alkaloids have attracted much attention in recent years. The recent research progress on carbazole alkaloids from Clausena Burm.f. was reviewed in this paper about the structures, isolation, structure elucidation, and biological activities.

16.
Chinese Traditional and Herbal Drugs ; (24): 4388-4393, 2017.
Article in Chinese | WPRIM | ID: wpr-852410

ABSTRACT

Objective To study the chemical constituents of the stems and leaves of Clausena hainanensis. Methods The chemical constituents of C. hainanensis were separated and purified by silica gel, ODS, Sephadex LH-20 gel column chromatographies, and preparative HPLC. Their structures were identified by physicochemical properties, spectroscopic analysis, as well as comparisons with the data reported in literature. Results Eighteen compounds were isolated from the 90% ethanol extract of the stems and leaves of C. hainanensis, which were identified as mukonine (1), methyl carbazole-3-carboxylate (2), lansine (3), murrayanine (4), 3-formylcarbazole (5), 3-formyl-6-methoxycarbazole (6), lansamide 4 (7), 4-methoxy-N-methyl-2-quinolone (8), (E)-N- (4-methoxyphenethyl)-2-methylbut-2-enamide (9), (E)-N-methyl cinnamon amide (10), N-(2-hydroxy-2-phenylethyl) cinnamamide (11), N-benzoyltyramine (12), aurantiamide (13), N-methyl-2-pyrolidinone (14), coumaric acid (15), 6,8-dimethoxy-4,5-dimethyl-3- methyleneisochromanl-one (16), 8-methoxypsoralen (17), and isololiolide (18). Conclusion This is the first time reporting the chemical constituents from C. hainanensis, all compounds are isolated from C. hainanensis for the first time, and compounds 12-16 are isolated from the genus Clausena for the first time.

17.
Chinese Journal of Natural Medicines (English Ed.) ; (6): 881-888, 2017.
Article in English | WPRIM | ID: wpr-812045

ABSTRACT

Pharmaceutical research has focused on the discovery and development of anticancer drugs. Clinical application of chemotherapy drugs is limited due to their severe side effects. In this regard, new naturally occurring anticancer drugs have gained increasing attention because of their potential effectiveness and safety. Fruits and vegetables are promising sources of anticancer remedy. Clausena (family Rutaceae) is a genus of flowering plants and includes several kinds of edible fruits and vegetables. Phytochemical and pharmacological studies show that carbazole alkaloids and coumarins from Clausena plants exhibit anticancer activity. This review summarizes research progresses made in the anticancer properties of plants belonging to Clausena; in particular, compounds with direct cytotoxicity, cell cycle arrest, apoptosis induction, and immune potentiation effects are discussed. This review reveals the potential use of plants from Clausena in preventing and treating cancer and provides a basis for development of relevant therapeutic agents.


Subject(s)
Humans , Alkaloids , Chemistry , Pharmacology , Therapeutic Uses , Antineoplastic Agents , Chemistry , Pharmacology , Therapeutic Uses , Apoptosis , Carbazoles , Chemistry , Pharmacology , Therapeutic Uses , Cell Cycle Checkpoints , Clausena , Chemistry , Coumarins , Chemistry , Pharmacology , Therapeutic Uses , Drugs, Chinese Herbal , Chemistry , Pharmacology , Therapeutic Uses , Plants, Medicinal , Chemistry
18.
Chinese Traditional and Herbal Drugs ; (24): 32-37, 2016.
Article in Chinese | WPRIM | ID: wpr-853778

ABSTRACT

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.

19.
Chinese Traditional and Herbal Drugs ; (24): 886-890, 2016.
Article in Chinese | WPRIM | ID: wpr-853634

ABSTRACT

Objective: To study the chemical constituents from the roots of Clausena excavata (Rutaceae). Methods: The compounds were isolated and purified by means of column chromatographies including silica gel, RP-18, and HPLC. Compound structures isolated were determined on the basis of spectroscopic data. Results: Thirteen carbazole alkaloids clausine K (1), clausine E (2), 3-formyl-7-hydroxycarbazole (3), clausine H (4), clausine M (5), mukona (6), O-demethylmurrayanine (7), clausine O (8), 3-formylcarbazole (9), 3-formyl-6-methoxy carbazole alkaloid (10), clausine C (11), 2-methoxy-3-carboxylic acid-carbazole alkaloid (12), and clausine Z (13) were isolated from the roots of C. excavata. Conclusion: Compounds 9,10, and 12 are isolated from this plant for the first time. Compounds 1,2,7,8, and 10 are tested for their cytotoxicities against A549, Hela, and BGC-823 cancer cell lines. The results show that they exhibit the cytotoxicity against A549, Hela, and BGC-823 with the IC50 values of 8.53-19.87 μg/mL.

20.
Chinese Traditional and Herbal Drugs ; (24): 1480-1485, 2016.
Article in Chinese | WPRIM | ID: wpr-853542

ABSTRACT

Objective: To investigate the chemical constituents from the stems of Clausena emarginata. Methods: The compounds were isolated by macroporous resin, silica gel, ODS column chromatography, Sephadex LH-20, reversed-phase MPLC, and then purified by preparative HPLC. Their structures were determined by the analysis of ultraviolet spectrum, mass spectrum, and NMR spectrum. Neuroprotective activities of compounds 11 and 12 were initially investigated. Results: Sixteen compounds were isolated from the petroleum ether and acetone fractions of 95% ethanol extract of the stems of Cl. emarginata, and their structures were identified as 1H-Indole-3-carboxaldehyde (1), E-N-benzoiltiramine (2), dehydrodiconiferyl alcohol (3), tortoside A (4), zhebeiresinol (5), evofolin B (6), 2,3,5,4'-tetrahydroxystilbene-2-O-β-D-glucopyranoside (7), echipuroside A (8), 3-methylcarbazole (9), murrayafoline A (10), clausine Z (11), indizoline (12), clausenaline B (13), mafaicheenamine A (14), dictamnine (15), and honokiol (16). Conclusion: Compounds 1-8 are isolated from the plants of genus Clausena L. for the first time, compounds 1-16 are isolated from this plant for the first time. Compounds 11 and 12 show the neuroprotective activity against rotenone induced PC12 cell damage.

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