1.Alkaloids from Macleaya cordata and their cytotoxicity assay.
Hui-liang ZOU ; Hong-yu LI ; Shao-fu YU ; Miao CHENG ; Xing-dong ZHOU ; Ying ZHANG ; Bai-lian LIU ; Guang-xiong ZHOU
China Journal of Chinese Materia Medica 2015;40(3):458-462
OBJECTIVETo study the alkaloids of Macleaya cordata and their anti-tumor activities.
METHODAlcohol and liquid-liquid extraction were used methods were used to extract the alkaloids constituents, and silica gel, reverse-phase octadecylsilyl (ODS), sephadex LH-20 chromatographic methods and HPLC were applied to isolate and purify compounds. MS, NMR spectroscopic methods were used to determine their structures. Furthermore, the cytotoxicity of these chemical components for MCF-7 and SF-268 cell lines was measured by MTT method.
RESULTTwelve alkaloids were isolated from the fruits of M. cordata, and their structures were identified as: maclekarpine E (1), 6-acetonyldihyrochelerythrine (2), cavidilinine (3), 6-acetonyldihyrosanguinnarine (4), O-methylzanthoxyline (5), 6-methoxy-dihydrosanguinarine (6), spallidamine (7), 6-hydroxyldihydrochelerythrine (8), arnotianamida (9), dihydrosanguinarine (10), protopine (11), and cryptopine (12).
CONCLUSIONCompounds 1, 3, 7-9 were isolated from M. cordata for the first time, and compound 5 is a new natural product. The results of cytotoxic assay indicated that compound 6 showed strong cytotoxicity against MCF-7 and SF-268 cell lines with IC50 values of 0.61 μmol · L(-1) and 0.54 μmol · L(-1), respectively.
Alkaloids ; isolation & purification ; pharmacology ; Antineoplastic Agents, Phytogenic ; isolation & purification ; Cell Line, Tumor ; Humans ; Papaveraceae ; chemistry
2.Components of myrsinane-type diterpenes from Euphorbia prolifera.
Jie LI ; Wei ZHAO ; Liang DENG ; Xiang-Rong LI
Journal of Zhejiang University. Medical sciences 2011;40(4):380-383
OBJECTIVETo extract and isolate the component from myrsinane-type diterpenes of Euphorbia prolifera.
METHODSPetroleum extraction and chromatography on the silica gel were used to extract and isolate the diterpenes of Euphorbia prolifera.
RESULTSEight components of myrsinol diterpenes were isolated, namely: Proliferin A(1), Proliferin B (2), Proliferin C(3), Proliferin D(4), Euphorprolitherin B(5), Euphorprolitherin D(6), SPr5(7) and 14-desoxo-3-O-prorionyl-5, 15-di-O-acetyl-7-O-nicotinoyl-myrsinol-14β-acetate(8). Their structures were identified with mass-spectroscopic methods and NMR techniques. The cytotoxicity of compounds 1, 2, and 4 against cancer cells was evaluated, with compound 1 being active against A2780 cancer cells (IC(50) 7.7 μmol/L).
CONCLUSIONMyrsinane-type diterpene Proliferin A from Euphorbia prolifera shows cytotoxic effect against human ovarian cancer cell line A2780.
Antineoplastic Agents, Phytogenic ; pharmacology ; Cell Line, Tumor ; Diterpenes ; isolation & purification ; pharmacology ; Euphorbia ; chemistry ; Humans
3.Chemical constituents from twigs of Euonymus alatus.
Lei ZHANG ; Yan ZOU ; Xian-sheng YE ; Jia ZHANG ; Wei-ku ZHANG ; Ping LI
China Journal of Chinese Materia Medica 2015;40(13):2612-2616
To investigate the chemical compounds from the twigs of Euonymus alatus, nine compounds were isolated and identified as(+)-delta(2,11)-enaminousnic acid(1), 11-keto-beta-boswellic acid(2), acetyl 11-keto-beta-boswellic acid(3), camaldulenic acid(4), betulinic acid(5), 6beta-hydroxy-stigmast-4-en-3-one(6), 5-hydroxy-6,7-dimethoxyflavone(7), ethyl 2,4-dihydroxy-6-methylbenzoate(8), 4,4'-dimethoxy-1,1'-biphenyl(9). Their structures were elucidated by extensive spectroscopic analysis. Among them, compound 1 was a new natural product. Compounds 2-4 and 7-9 were obtained from the Euonymus genus for the first time. In vitro study showed that compounds 2 and 3 showed significant anti-tumor activities to BEL-7402 and HCT-8 at the concentration of 10 mg x L(-1). The inhibition rate of compound 2 was 61.78% and 68.29%, whereas the inhibition rate of compound 3 had reached to 70.91% and 84.07%.
Antineoplastic Agents, Phytogenic
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chemistry
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isolation & purification
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pharmacology
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Cell Line, Tumor
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Euonymus
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chemistry
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Humans
4.Anti-tumor metastatic constituents from Rhodiola wallichiana.
Ya-qing CHAI ; Guo-hua ZHAO ; Ren-jiu WANG ; Ming-guang CAO ; Hai-bo WU ; Sheng-an TANG ; Hong-quan DUAN
China Journal of Chinese Materia Medica 2015;40(2):258-263
To study the anti-tumor metastatic constituents in Rhodiola wallichiana (HK) S H Fu var Cholaensis (Praeg) S H Fu, chemical constituents were isolated and purified by repeated column chromatography (silica gel, Toyopearl HW-40C and preparative HPLC). Their structures were elucidated on the basis of spectral data analysis. The anti-tumor metastasis assay was applied to evaluate the activities of the isolated compounds. Ten compounds (1-10) were isolated and their structures were identified by comparison of their spectral data with literature as follows: syringic acid (1), salidroside (2), tyrosol (3), scaphopetalone (4), berchemol (5), 2,6-dimethoxyacetophenone (6), rhobupcyanoside A (7), miyaginin (8), chavicol-4-O-β-D-apiofuranosyl-(1 --> 6)-O-β-D-glucopyranoside (9), eugenyol-O-β-D-apiofuranosyl-(1 --> 6)-O-β-D-glucopyranoside (10). Compounds 4-6 and 8-10, were isolated from this genus for the first time, while compound 7 was isolated from this plant for the first time. Compounds 2, 6-8 showed positive anti-tumor metastatic activities, and compounds 2 and 8 showed significant anti-tumor metastatic activities.
Antineoplastic Agents, Phytogenic
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isolation & purification
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pharmacology
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Cell Line, Tumor
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Humans
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Neoplasm Metastasis
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prevention & control
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Rhodiola
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chemistry
5.Analysis of the chemical constituents of Hedyotis diffusa.
Journal of Southern Medical University 2008;28(1):127-128
OBJECTIVETo analyze the chemical constituents of Hedyotis diffusa.
METHODSColumn chromatographies were used to isolate and purify the chemical constituents of this plant, and their structures were identified by spectral analysis and physicochemical properties.
RESULTS AND CONCLUSIONSeven compounds were isolated and identified as p-coumaric acid (I), methyl-p-coumarate (II), 2-formyl-5- hydroxymethylfuran (III), quercetin (IV), kaempferol (V), beta-sitosterol(VI) and daucosterol(VII), respectively, among which the compounds II and III were isolated from Hedyotis diffusa for the first time.
Antineoplastic Agents, Phytogenic ; isolation & purification ; Cinnamates ; isolation & purification ; Coumaric Acids ; isolation & purification ; Furans ; isolation & purification ; Hedyotis ; chemistry ; Kaempferols ; isolation & purification ; Propionates ; Quercetin ; isolation & purification
6.Extraction, purification technology and antineoplastic effects of solamargine.
Zhaohui TANG ; Yan ZHANG ; Na LI ; Lianming XU ; Binjiang ZHAO ; Wei XIAO ; Zhenzhong WANG ; Yu'an BI
China Journal of Chinese Materia Medica 2011;36(16):2192-2195
OBJECTIVETo extract and purify of solamargine from Solanum nigrum, and to research its antineoplastic effects.
METHODS. nigrum was extracted refluently with 80% alcohol, solamargine was purified with silica gel column chromatography and recrystallization, and then conducted its structure identification and purity checks. Screened the effect on human tumor cell groth inhibition in vitro by MTT assay, and researched on the features in mice with H22 liver cancer or Ehrlich ascites tumor of solamargine.
RESULTThe concent of solamargine reached 97.9%. Solamargine had significantly inhibition on 6 tumor cells in vitro, and it had significantly inhibition on mice with H22 liver cancer or ehrlich ascites tumor in the 2.4 mg x kg(-1) dose of i.v.
CONCLUSIONSolamargine have the antineoplastic effect.
Animals ; Antineoplastic Agents, Phytogenic ; isolation & purification ; Cell Line, Tumor ; Female ; Humans ; Mice ; Mice, Inbred ICR ; Solanaceous Alkaloids ; isolation & purification ; pharmacology
7.Saponins from roots of Securidaca inappendiculata with cytotoxic activities.
Hai-yan ZHA ; Xue-dong YANG ; Li-jie ZHANG ; Da-qing JIN ; Zhi WANG ; Li-zhen XU ; Shi-lin YANG
China Journal of Chinese Materia Medica 2015;40(14):2849-2853
Seven acylated triterpene saponins were isolated from the roots of Securidaca inappendiculata by means of various chromatographic techniques such as silica gel, MPLC, preparative HPLC, and semi-preparative HPLC. Their chemical structures were identified as securioside A(1), securioside B(2), 3-O-β-D-glucopyranosyl presenegenin 28-O-β-D-xylopyranosyl-(1-->4)-α-L-rhamnopyranosyl-(1-->2)-[β-D-glucopyranosyl-(1-->3)]-4-O-[(E)-3,4-dimethoxycinnamoyl]-β-D-fucopyranosyl ester(3), 3-O-β-D-glucopyranosyl presenegenin 28-O-β-D-xylopyranosyl-(1-->4)-α-L-rhamnopyranosyl-(1-->2)-[β-D-glucopyranosyl-(1-->3) ] -4-O-[(E/Z)-3, 4-dimethoxycinnamoyl]-β-D-fucopyranosyl ester(3/4), 3-O-β-D-glucopyranosyl presenegenin 28-O-α-L-arabinopyranosyl-(1-->3)-β-D-xylopyranosyl-(1-->4)-α-L-rhamnopyranosyl-(1-->2)-4-O-[(E)-3,4-dimethoxycinnamoyl]-β-D-fucopyranosyl ester(5), polygalasa- ponin XLV(6), and polygalasaponin XLVI (7) on the basis of spectroscopic data analysis and physicochemical properties. Among them, compounds 5-7 were isolated from the plants in genus Securidaca for the first time and compounds 3, 3/4 were isolated from the species for the first time. The cytotoxicity assay showed that compounds 2, 3/4, 5 have moderate cytotoxic activities against Lewis lung carcinoma LLC cells with IC50 values of 41.10, 38.17, and 48.92 µmol · L(-1), respectively; compound 2 exhibited moderate cytotoxic activities against human breast cancer MCF-7 cells with an IC50 value of 47.93 µmol · L(-1).
Antineoplastic Agents, Phytogenic
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isolation & purification
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pharmacology
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Humans
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MCF-7 Cells
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Plant Roots
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chemistry
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Saponins
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chemistry
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isolation & purification
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pharmacology
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Securidaca
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chemistry
8.Two new cyclic bisbibenzyl derivatives from Hebertus dicranus.
Chang-Long XU ; Jin-Xin WANG ; Hui-Liang LI
Chinese Journal of Natural Medicines (English Ed.) 2016;14(6):457-461
In the present study, two new cyclic bisbibenzyls (1, 2) co-occuring with a known compound, isoplagiochins C (3) were isolated from Hebertus dicranus. The structures were determined mainly by extensive 1D and 2D NMR experiments, and the absolute configurations of 1 and 2 were established by the circular dichroism spectrum. Furthermore, all these three rare compounds were tested in vitro for inhibitory activity against the growth of human cancer cell lines (A549, HCT116, MDA-MB-231, and BEL7404) by the MTT assay, and compound 2 exhibited moderately inhibitory activity with IC50 values ranging from 13.89 to 31.62 μmol·L(-1). In conclusion, our results provided a basis for future development and modification of these compounds for cancer therapy.
Antineoplastic Agents, Phytogenic
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chemistry
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isolation & purification
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Cell Line, Tumor
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Drugs, Chinese Herbal
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chemistry
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isolation & purification
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Hepatophyta
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chemistry
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Humans
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Molecular Structure
9.Chemical and pharmacological advances of study on Lysimachia.
Hai-tao CHANG ; Wei-liang KONG ; Peng-fei TU
China Journal of Chinese Materia Medica 2004;29(4):295-298
The progress in the research of the chemical components and pharmacological activities of Lysimachia was reviewed. Lysimachia mainly contain flavonoids, saponins and phenolic acids, and some of the plants have been used in the treatment of fever, ulcers, diarrhea and as analgesic or anti-inflammatory agents. The plants of genus Lysimachia are widespread in China, so it is a singificants work to study their chemical ingredients and pharmacological activities.
Animals
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Anti-Inflammatory Agents, Non-Steroidal
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pharmacology
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Antineoplastic Agents, Phytogenic
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pharmacology
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Drugs, Chinese Herbal
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isolation & purification
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pharmacology
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Flavonoids
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isolation & purification
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Plants, Medicinal
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chemistry
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Primulaceae
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chemistry
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Saponins
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isolation & purification
10.Preparation of magnetic molecularly imprinted polymers for selective isolation and determination of kaempferol and protoapigenone in Macrothelypteris torresiana.
Pei-shan CAI ; Yang ZHAO ; Tong-hua YANG ; Jing CHEN ; Chao-mei XIONG ; Jin-lan RUAN
Journal of Huazhong University of Science and Technology (Medical Sciences) 2014;34(6):845-855
Novel uniform-sized magnetic molecularly imprinted polymers (MMIPs) were synthesized for selective recognition of active antitumor ingredients of kaempferol (KMF) and protoapigenone (PA) in Macrothelypteris torresiana (M. torresiana) by surface molecular imprinting technique in this study. Super paramagnetic core-shell nanoparticles (γ-MPS-SiO2@Fe3O4) were used as seeds, KMF as template molecule, acrylamide (AM) as functional monomer, and N, N'-methylene bisacrylamide (BisAM) as cross-linker. The prepared MMIPs were characterized by X-ray diffraction (XRD), Fourier transform infrared spectrum (FTIR), transmission electron microscopy (TEM) and thermo-gravimetric analysis (TGA), respectively. The recognition capacity of MMIPs was 2.436 times of non-imprinted polymers. The adsorption results based on kinetics and isotherm analysis were in accordance with the pseudo-second-order model (R (2)=0.9980) and the Langmuir adsorption model (R (2)=0.9944). The value of E (6.742 kJ/mol) calculated from the Dubinin-Radushkevich isotherm model suggested that the physical adsorption via hydrogen-bonding might be predominant. The Scatchard plot showed a single line (R (2)=0.9172) and demonstrated the homogeneous recognition sites on MMIPs for KMF. The magnetic solid phase extraction (MSPE) based on MMIPs as sorbent was established for fast and selective enrichment of KMF and its structural analogue PA from the crude extract of M. torresiana and then KMF and PA were detected by HPLC-UV. The established method showed good performance and satisfactory results for real sample analysis. It also showed the feasibility of MMIPs for selective recognition of active structural analogues from complex herbal extracts.
Acrylic Resins
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chemical synthesis
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chemistry
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Antineoplastic Agents, Phytogenic
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chemistry
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isolation & purification
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Cyclohexanones
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chemistry
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isolation & purification
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Ferns
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chemistry
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Flavones
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chemistry
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isolation & purification
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Kaempferols
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chemistry
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isolation & purification
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Nanoparticles
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chemistry