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1.
Four bromophenols were isolated from the extract of marine red alga,Rhodomela confervoides by column chromatography and HPLC methods. By means of spectroscopic methods inclding IR, MS, 1D, and 2D-NMR techniques, their structures were elucidated as (1) 3-bromo-4,5-dihydroxy benzoic acid methyl ester; (2) bis (2,3-dibromo-4,5-dihydroxybenzyl) ether; (3) 3,4-dibromo-5-(methoxymethyl)-1,2-benzenediol and (4) 3-bromo-4,5-dihydroxy-benzaldehyde. Compound 1 was first isolated from the algae in nature, and 1, 4 were found to have selective cytotoxic activities against KB, Bel 7402 and A549 cells, 2 showed powerful antibacterial activities againstStaphylococcus aurens andPseudomonas aeruginosa. Supported by National “863” Program (No. 2004AA625030, 2001AA620503), Quingdao marine sciences project (No. 04-2-NN-26) and Key Knowledge Innovative Project of the Chinese Academy of Sciences (KZCX3-SW-215).  相似文献   

2.
3-bromo-4,5-bis(2,3-dibromo-4,5-dihydroxybenzyl)-1,2-benzenediol (1) is a natural bromophenol isolated from the red algae Rhodomela confervoides that exhibits significant inhibition against protein tyrosine phosphatase 1B (PTP1B). Based on its activity, we synthesized two new synthetic bromophenols and their methoxy derivatives from vanillin using the structure of natural bromophenol 1 as a scaffold. The structures of these bromophenols were elucidated from 1H NMR, 13C NMR, and high resolution electron ionization mass spectrometry as 2,3-dibromo-1-(2p-bromo-6p-(3q,4q-dimethoxybenzyl)- 3p,4p-dimethoxybenzyl)-4,5-dimethoxybenzene(2),2,3-dibromo-1-(2p-bromo-6p-(2q-bromo-4q,5q-dimethoxy-benzyl)-3p,4p-dimethoxybenzyl)-4,5-dimethoxybenzene(3),3,4-dibromo-5-(2p-bromo-6p-(2q-bromo-4q,5q-dihydroxybenzyl)-3p,4p-dihydroxybenzyl)pyrocatechol(4)and 3,4-dibromo-5-(2p-bromo-6p-(3q,4q-dihydroxybenzyl)-3p,4p-dihydroxybenzyl)pyrocatechol (5).PTP1B inhibition activities of these compounds were evaluated using a colorimetric assay,and compounds 3 and 4 demonstrated interesting activity against PTP1B.  相似文献   

3.
To investigate the antitumor effect of bromophenol derivatives in vitro and Leathesia nana extract in vivo, six bromophenol derivatives 6-(2,3-dibromo-4,5-dihydroxybenzyl)-2,3-dibromo-4,5-dihydroxy benzyl methyl ether (1), (+)-3-(2,3-dibromo-4,5-dihydroxyphenyl)-4-bromo-5,6-dihydroxy-1,3-dihydroisobenzofuran (2), 3-bromo-4-(2,3-dibromo-4,5-dihydroxybenzyl)-5-methoxymethyl-pyrocatechol (3),2,2',3,3'-tetrabromo-4,4',5,5'-tetrahydroxy-diphenylmethane (4), bis(2,3-dibromo-4,5-dihydroxybenzyl) ether (5), 2,2',3-tribromo-3',4,4',5-tetrahydroxy-6'-ethyloxymethyldiphenylmethane (6) were isolated from brown alga Leathesia nana, and their cytotoxicity were tested by MTr assays in human cancer cell lines A549, BGC-823, MCF-7, B16-BL6, HT-1080, A2780, Bel7402 and HCT-8. Their inhibitory activity against protein tyrosine kinase (PTK) with over-expression of c-kit was analyzed also by ELISA. The antitumor activity of ethanolic extraction of Leathesia nana (EELN) was evaluated on S180-bearing mice.All compounds showed very potent cytotoxicity against all of the eight cancer cell lines with IC50 below 10 μg/mL. In PTK inhibition study, all bromophenol derivatives showed moderate inhibitory activity and compounds 2, 5 and 6 showed significant bioactivity with the inhibition ratio of 77.5%, 80.1% and 71.4%,respectively. Pharmacological studies reveal that EELN could inhibit the growth of Sarcoma 180 tumor and increase the indices of thymus and spleen to improve the immune system remarkably in vivo. Results indicated that the bromophenoi derivatives and EELN can be used as potent antitumor agents for PTK over-expression of c-kit and considered in a new therapeutic strategy for treatment of cancer.  相似文献   

4.
Bromophenols are a set of natural products widely distributed in seaweed, most of which exhibit interesting and useful biological activities. To develop a reliable and efficient synthetic route to these natural bromophenols, three of them, 3,4-dibromo-5-(2′-bromo-3′,4′-dihydroxy-6′-methoxymethyl-benzyl)-benzene-1,2-diol (compound 9), 3,4-dibromo-5-(2′-bromo-6′-ethoxy methyl-3′,4′-dihydroxybenzyl)-benzene-1,2-diol (compound 10), and 3-bromo-4-(3′-bromo-4′,5′-dihydroxy benzyl)-5-(ethoxymethyl)-benzene-1,2-diol (compound 14), isolated from red marine algae, have been synthesized in eight steps with an overall yield of 14.4%, 14.4%, and 18.2% respectively, via a practical approach employing bromination, Wolff-Kishner-Huang reduction and a Friedel-Crafts reaction as key steps. The protein tyrosine phosphatase 1B (PTP1B) inhibitory activities of the synthetic compounds were evaluated by the colorimetric assay. The results show that these compounds are moderate PTP1B inhibitors. The synthesis of these bromophenol derivatives makes in vivo studies of their structure-activity relationships and inhibition activity against PTP1B possible.  相似文献   

5.
To investigate the antitumor effect of bromophenol derivatives in vitro and Leathesia nana extract in vivo, six bromophenol derivatives 6-(2,3-dibromo-4,5-dihydroxybenzyl)-2,3-dibromo-4,5-dihydroxy benzyl methyl ether (1), (+)-3-(2,3-dibromo-4,5-dihydroxyphenyl)-4-bromo-5,6-dihydroxy-1,3-dihydroisobenzofuran (2), 3-bromo-4-(2,3-dibromo-4,5-dihydroxybenzyl)-5-methoxymethyl-pyrocatechol (3), 2,2′,3,3′-tetrabromo-4,4′,5,5′-tetrahydroxy-diphenylmethane (4), bis(2,3-dibromo-4,5-dihydroxybenzyl) ether (5), 2,2′,3-tribromo-3′,4,4′,5-tetrahydroxy-6′-ethyloxymethyldiphenylmethane (6) were isolated from brown alga Leathesia nana, and their cytotoxicity were tested by MTT assays in human cancer cell lines A549, BGC-823, MCF-7, B16-BL6, HT-1080, A2780, Bel7402 and HCT-8. Their inhibitory activity against protein tyrosine kinase (PTK) with over-expression of c-kit was analyzed also by ELISA. The antitumor activity of ethanolic extraction of Leathesia nana (EELN) was evaluated on S180-bearing mice. All compounds showed very potent cytotoxicity against all of the eight cancer cell lines with IC50 below 10 μg/mL. In PTK inhibition study, all bromophenol derivatives showed moderate inhibitory activity and compounds 2, 5 and 6 showed significant bioactivity with the inhibition ratio of 77.5%, 80.1% and 71.4%, respectively. Pharmacological studies reveal that EELN could inhibit the growth of Sarcoma 180 tumor and increase the indices of thymus and spleen to improve the immune system remarkably in vivo. Results indicated that the bromophenol derivatives and EELN can be used as potent antitumor agents for PTK over-expression of c-kit and considered in a new therapeutic strategy for treatment of cancer. Supported by the National High Technology Research and Development Program of China (863 Program, No. 2007AA09Z410) and Knowledge Innovation Program of Chinese Academy of Sciences (No. KZCX2-YW-209)  相似文献   

6.
Thrombin,the ultimate proteinase of the coagulation cascade,is an attractive target for the treatment of a variety of cardiovascular diseases.A bromophenol derivative named (+)-3-(2,3-dibromo-4,5-dihydroxy-phenyl)-4-bromo-5,6-dihydroxy-1,3-dihydroiso-benzofuran 1,isolated from the brown alga Leathesia nana exhibited significant thrombin inhibitory activity.In this study,we investigated the inhibition of human thrombin in vitro with this bromophenol derivative,and its antithrombotic efficacy in vivo using th...  相似文献   

7.
Previously, we had characterized several structurally interesting brominated phenols from the marine red alga Symphyocladia latiuscula collected from various sites. However, Phytochemical investigations on this species collected from the Weihai coastline of Shandong Province remains blank. Therefore, we characterized the chemical constituents of individuals of this species collected from the region. Eight bromophenols were isolated and identified. Using detailed spectroscopic techniques and comparisons with published data, these compounds were identified as 2,3-dibromo-4,5-dihydroxybenzyl methyl ether (1), 3,5-dibromo-4-hydroxybenzoic acid (2), 2,3,6-tribromo-4,5-dihydroxymethylbenzene (3), 2,3,6-tribromo-4,5-dihydroxybenzaldehyde (4), 2,3,6-tribromo-4,5-dihydroxybenzyl methyl ether (5), bis(2,3,6-tribromo-4,5-dihydroxyphenyl)methane (6), 1,2-bis(2,3,6-tribromo-4,5-dihydroxyphenyl)-ethane (7), and 1-(2,3,6-tribromo-4,5-dihydroxybenzyl)-pyrrolidin-2-one (8). Among these compounds, 1 and 2 were isolated for the first time from S. latiuscula. Each compound was evaluated on the ability to inhibit protein tyrosine phosphatase 1B (PTP1B), which is a potential therapeutic target in the treatment of type 2 diabetes. Bromophenols 5, 6, and 7 showed strong activities with IC50 values of 3.9, 4.3, and 3.5 μmol/L, respectively. This study provides further evidence that bromophenols are predominant among the chemical constituents of Symphyocladia, and that some of these compounds may be candidates for the development of anti-diabetes drugs.  相似文献   

8.
Thrombin, the ultimate proteinase of the coagulation cascade, is an attractive target for the treatment of a variety of cardiovascular diseases. A bromophenol derivative named (+)-3-(2,3-dibromo-4, 5-dihydroxy-phenyl)-4-bromo-5,6-dihydroxy-1,3-dihydroiso-benzofuran 1, isolated from the brown alga Leathesia nana exhibited significant thrombin inhibitory activity. In this study, we investigated the inhibition of human thrombin in vitro with this bromophenol derivative, and its antithrombotic efficacy in vivo using the arteriovenous shunt model and the ferric chloride-induced arterial thrombosis model in rats. The results show that the bromophenol derivative is a potential inhibitor of thrombin (IC50=1.03 nmol/L). In antithrombotic experiments in vivo, the bromophenol derivative also shows good effect comparing with the control group. These data indicate that the bromophenol derivative is a potential drug for prophylaxis and the treatment of thrombotic diseases.  相似文献   

9.
The Cytotoxic Constituents from Marine-derived Streptomyces 3320^#   总被引：2，自引：0，他引：2  
The present work studies the chemical constituents from marine-derived streptomyces 3320^# and their antitumor activities. The n-BuOH extract of the ferment broth of 3320^# was chromatographed on silica gel, Sephadex LH-20, ODS columns and HPLC to separate the compounds with antitoumor activities. Their structures were identified using IR, UV, NMR, MS spectroscopic techniques and compared with published data. The antitumor activities of the isolates were assayed using SRB method and flow cytometry assay, accompanied with the morphological observation of the cells under light micro- scope against mammalian tsFT210 cells. Ten compounds, cyclo-（Ala-Leu） 1, cyclo-（Ala-Ile） 2, cyclo-（Ala-Val） 3, cyclo- （Phe-Pro） 4, cyclo-（Phe-Gly）5, cyclo-（Leu-Pro）6, 1-methyl-1, 2, 3, 4-tetrahydro-β-carboline-3-carboxylic acid 7, N-（4- hydroxyphenethyl） acetamide 8, 4-methyoxy-l-（2-hydroxy） ethylbenzene 9 and uridine 10, were isolated from the ferment broth of streptomyces 3320^# . Among them, compounds 6, 7, 8 and 10 showed potent cytotoxicity against the tsFT210 cell with the IC50 values of 3.6, 7.2, 5.2 and 1.6 mmol L-1, respectively. Compounds 8, 10 also exhibited apoptosis inducing activity under 2.0 mmol L-1. Compounds 6, 7, 8 and 10 are the principle bioactive constituents responsible for the antitumor activities of marine streptomyces 3320^#. Compound 7 was isolated from this species for the first time.  相似文献   

10.
Eight known compounds were isolated from a marine-derived bacterium Streptoverticillium luteoverticillatum 11014 using bioassay-guided fractionations. Their structures were identified by spectral analysis as bis （4-hydroxybenzyl） ether （1）, p-hydroxyphenylethyl alcohol （2）, N-（4-hydroxyphenethyl） acetamide （3）, indole-3 carboxylic acid methyl ester （4）, dibenzo[b,e] [1,4]dioxine （5）, thymine （6）, cytosine deoxyribonucleoside （7） and 2, 3-butanediol （8）. These compounds were evaluated for their cytotoxic activities against K562 cell line with the SRB method for the first time. Compounds 2 and 4 showed cytotoxcities with IC50 values of 101.1 and 165.3 μolL^-1, respectively. All compounds were isolated from S. luteoverticillatum 11014 for the first time.  相似文献   

11.
Two phenylquinolinones, including one new compound (1) and a previously isolated compound (2), were isolated from the ethyl acetate extracts of the fungus Aspergillus versicolor Y31-2, which was obtained from seawater samples collected from the Indian Ocean. The structures of these compounds were established by spectroscopic analyses. 4-(3-Hydroxyphenyl)-3-methoxyquinolin-2(1H)-one (1) exhibited moderate cytotoxicity against MCF-7 (human breast carcinoma cell line) and SMMC-7721 (human liver cancer cell line) cells with IC50 values of 16.6 and 18.2 μmol/L, respectively. To the best of our knowledge, this study represents the first reported account of the isolation of compounds 1 and 2 as the secondary metabolites of the seawater derived fungus Aspergillus versicolor from the Indian Ocean.  相似文献   

12.
Twenty-four compounds including eight steroids (1-8), nine triterpenoids (9-16, 24), three flavonoids (20-22), and four benzenecarboxylic derivatives (17-19, 23) were isolated and identified from stems and twigs of medicinal mangrove plant Sonneratia caseolaris. The structures of the isolated compounds were determined by extensive analysis of their spectroscopic data. Among these metabolites, compounds 1, 4-20 and 22-24 were isolated and identified for the f'urst time from S. caseolaris. In the in vitro cytotoxic assay against SMMC-7721 human hepatoma cells, compound 21 (3',4',5,7-tetrahydroxyflavone)exhibited significant activity with IC50 2.8 μg/mL, while oleanolic acid (14), 3,3'-di-O-methyl ether ellagic acid (18), and 3,3',4-O-tri-O-methyl ether ellagic acid (19) showed weak activity. None of these compounds displayed significant antibacterial activites.  相似文献   

13.
Polypeptide fromChlamys farreri (PCF), a topical polypeptide isolated fromChlamys farreri, was used in this experiment aimed to investigate the photoprotective effect of PCF against chronic skin damage induced by ultraviolet A (UVA) and ultraviolet B (UVB) radiation. The chronic ultraviolet-irradiated guinea pig model was established, and visible changes in the skin including wrinkling, sagging and erythema were observed. Malondialdehyde (MDA) and antioxidant enzymes including superoxide dismutase (SOD) and glutathione peroxidase (GSH-px) in the dorsal skin were determined using biochemical methods. The results showed: (1) PCF (5 % and 20%) could greatly protect the dorsal skin of guinea pig against wrinkling, sagging and erythema induced by UV radiation in a concentration-dependent manner. (2) PCF could reduce MDA formation in the dorsal skin caused by UV irradiation, while increasing the activities of SOD and GSH-px. (3) The differences among the PCF groups and UV model group were significant (P<0.05,P<0.01). These results indicated that topical application, of PCF provided broad solar UV spectrum photoprotection; and that the antioxidant property of PCF might play a role in photoprotection. Project No. 39970638 supported by the NSFC, and the Science and Technology Bureau of Qingdao (No. 2001-28-50).  相似文献   

14.
Eight known compounds were isolated from a marine-derived bacterium Streptoverticillium luteoverticillatum 11014 using bioassay-guided fractionations. Their structures were identified by spectral analysis as bis (4-hydroxybenzyl) ether (1), p-hydroxyphenylethyl alcohol (2), N-(4-hydroxyphenethyl) acetamide (3), indole-3 carboxylic acid methyl ester (4), dibenzo[b,e] [1,4]dioxine (5), thymine (6), cytosine deoxyribonucleoside (7) and 2, 3-butanediol (8). These compounds were evaluated for their cytotoxic activities against K562 cell line with the SRB method for the first time. Compounds 2 and 4 showed cytotoxcities with IC50 values of 101.1 and 165.3 μmolL-1, respectively. All compounds were isolated from S. luteoverticillatum 11014 for the first time.  相似文献   

15.
INTRODUCTIONSolarultraviolet(UV)radiationisknowntobeamajoretiologicalriskofphotoaging.AsUVC(2 0 0nm -2 90nm)isabsorbedentirelybythestratosphericozonelayer,sunlightontheearthsur faceiscomposedofUVA (3 2 0nm -4 0 0nm)andUVB (2 90nm -3 2 0nm)only.UVAradiationenergyaccountsformorethan 90 %ofsolarUV ;andpenetratesthebasallayerofepidermismoreefficientlythanUVB (Brulsetal.,1984) .However,atsimilardosages,UVBismuchmoremuta genicthanUVA (Drobetskyetal.,1995) .Furthermore ,humanskinisexp…  相似文献   

16.
A new ketosteroid, along with six known steroids, was isolated from the ethanolic extracts of red alga Acanthophora spicifera (Vahl.) Boergesen. The structures, identified using chemical and spectroscopic methods including 2D NMR, were: (1) 22-hydroxy-5α-cholest-3,6-dione, (2) 6-hydroxycholest-4-ene-3-one, (3) cholest-4-ene-3,6-dione, (4) cholest-5-ene-3β-ol, (5) 5α-cholestane-3,6-dione, (6) β-Sitosterol and (7) Saringosterol. The MTT method was used to test the cytotoxicity of the compounds against the human cancer cell lines, HCT-8, Bel-7402, BGC-823, A549 and HELA. Compounds 1, 2, 3 and 5 showed moderate cytotoxic activity against human cancer cell lines.  相似文献   

17.
从南海海域的鱼类、贝类、海藻以及海泥样品中分离出199株海洋真菌,分属于青霉属、曲霉属和酵母属等9个属,其中以青霉属和曲霉属真菌居多,分别占28.6%和26.8%。以大肠杆菌和金黄色葡萄球菌作为指示菌,筛选出抑菌活性菌株7株,其中2株既抗大肠杆菌又抗金黄色葡萄球菌,4株抗金黄色葡萄球菌,1株抗大肠杆菌。  相似文献   

18.
To investigate the effect of polypeptide fromChlamys farreri (PCF) on NHDFin vitro, we modeled oxidative damage on normal human dermal fibroblasts (NHDF) exposed to ultraviolet B (UVB). In this study, 3-[4,5-Dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) and lactate dehydrogenase (LDH) were tested to measure cell viability. Enzymes including superoxide dismutase (SOD), glutathione peroxidase (GSH-PX), catalase (CAT) and xanthine oxidase (XOD) were determined biochemically. Total antioxidative capacity (T-AOC) and anti-superoxide anion capacity (A-SAC) were also determined. Ultrastructure of fibroblasts was observed under transmission electron microscope. The results showed that: UVB (1.176×10−4 J/cm2) suppressed the growth of fibroblasts and the introduction of PCF (0.25%–1%) before UVB reduced the suppression in a concentration-dependent manner. PCF could enhance the activities of SOD, GSH-PX and T-AOC as well as A-SAC. Also PCF could inhibit XOD activity, while it did not affect CAT activity. Ultrastructure of fibroblasts were damaged after UVB irradiation, concentration-dependent PCF reduced the destructive effect of UVB on cells. These results indicated that PCF can protect human dermal fibroblasts from being harmed by UVB irradiation via its antioxidant proerty. This work was supported by the National Natural Science Foundation of China (No. 39970638) and the Science and Technology Bureau of Qingdao (No. 2001-28-50).  相似文献   

19.
Six steroids have been isolated from ethanolic extract of green alga Chaetomorpha basiretorsa Setchell by a combination of repeated normal phase silica gel and Sephadex LH-20 gel column chromatography as well as recrystallization. Using spectroscopic methods including MS and NMR, their structures were determined as β-1awsaritol （1）, saringosterol （2）, 24-hydroperoxy-24-vinyl- cholesterol （3）, β-stigmasterol （4）, stigmast-4-en-3α, 6β-diol （5）, 29-hydroxystigmasta-5, 24 （28）-dien-3β-ol （6）. All these compounds were obtained from this genus for the first time and they were inactive （IC50〉10μg/ml） against KB, Bel-7402, PC-3M, Ketr 3 and MCF-7 cell lines.  相似文献   

20.
Silva  J. Paulo  Alves  Celso  Pinteus  Susete  Silva  Joana  Valado  Ana  Pedrosa  Rui  Pereira  Leonel 《中国海洋湖沼学报》2019,37(3):825-835
Osmundea pinnatifida is a red edible seaweed known as pepper dulse. O. pinnatifida was cultivated in the farm of ALGAplus(Ilhavo, Portugal). This farm is integrated with a seabream and seabass commercial aquaculture and uses the nutrient-enriched water resultant from the fish production as its cultivation medium in the integrated multi-trophic aquaculture(IMTA) manner. Wild and IMTA-cultivated samples of O. pinnatifida were screened for antioxidant and antitumor activities. The antioxidant capacity of solvent extracts from wild and IMTA cultivated samples was assessed in two methods(2,2-diphenyl-1-picrylhydrazyl(DPPH) and oxygen radical absorbance capacity(ORAC)), and their total phenolic contents(TPC) were estimated. Antitumor activity was evaluated in three different tumor cell lines(HepG-2, MCF-7, and SH-SY5Y) through 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide(MTT)assay. Among the solvents used for extraction, dichloromethane was the most effective to extract phenolic compounds and presented higher ORAC. A significant correlation was found between TPC and ORAC,which was also sustained by the principal components analysis(PCA). Dichloromethane extracts induced a cytostatic effect on MCF-7 cells and showed weak cytotoxicity to SH-SY5Y cells and weak impact on cell proliferation. Overall, there were no statistically significant differences in the biological activities shown by the wild and IMTA-cultivated samples. Hence, O. pinnatifida can be obtained in an economical and environmentally sustainable way through IMTA, maintaining bioactive properties in a high potential for further nutraceutical purposes.  相似文献   

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