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1.
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
2.
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
3.
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
4.
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
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 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
6.
Four bromophenols were isolated from the extract of marine red alga, Rhodomela confervoides by column chromatography and HPLC methods. By means of spectroscopic methods including IR, MS, 1D, and 2D-NMR techniques, their structures were elucidated as (1) 3-bromo-4,5-dihydroxy benzoic acid methyl ester; (2) his (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 against Staphylococcus aurens and Pseudomonas aeruginosa. 相似文献
7.
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
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.
Effects of alginate gel at different concentrations on rheological properties of hair-tail (Trichiurus lepturus) surimi were investigated. Alginate gel (1% - 3%) exhibited enhanced effects, especially when alginate gel concentration increased. The rheological properties of mixture samples were studied by the time sweep, frequency sweep and temperature sweep. The critical strain values of the mixture samples for the onset of non-linear viscoelasticity were about 5%. The storage modulus G’ of the mixture samples increased with time for 4 h. The frequency sweep showed that G’ was greater than G" for all the mixture gels with different alginate gel concentrations, and values of both n’ and n" for all samples were low (<0.2), these constants corresponding to G’ and G", and indicating the elasticity of mixture gels. The values of storage modulus G’ decreased during heating process and increased with decreasing temperature. 相似文献
10.
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 first 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.
Supported by the National Natural Science Foundation of China (No. 30770234); Knowledge Innovation Program of Chinese Academy
of Sciences (KZCX2-YW-211-04); Department of Science and Technology of Shandong Province (No.2006GG2205023) 相似文献
11.
Little has been done in measurement and research of the flux of CH4 emission from paddy fields in Changchun area, Jilin Province, China before 1994. So the purpose of the study is to offer
available regional data of CH4 emission flux and to discuss the factors which affect CH4 emission from paddy fields. Experimental paddy fields are chosen using TM pictures respectively in Xinlicheng (43°49′N, 125°20′E)
of the Yitong River’s and in Wanchang (43°44′10″N, 125°53′11″E) of the Yinma River’s alluvial plain. The fluxes of CH4 emission from paddy fields are measured by the method of static chamber in Changchun area in 3 consecutive years. The research
results show that the peak of CH4 emission from paddy fields occurs during the booting stage. The mean fluxes of CH4 emission are 7.056 mg/m(2 · h) and 0.489 mg/(m2 · h) in the paddy fields of flood and discontinuous irrigation respectively. The contrastive study holds that climate condition,
the way of water management and fertilizer variation have significant influence on fluxes of CH4 emission from paddy fields. The difference of climatic conditions causes the interannual change of the flux of CH4 emission from paddy fields. In general, the flux of CH4 emission from paddy fields of flood irrigation is greater than that from paddy fields of discontinuous irrigation. To change
the way of water management perhaps in an available way to reduce CH4 emission flux from paddy fields.
Foundation item: Under the auspices of Jilin Commttee of Science and Technology (grant 963416 - 1), and Changchun Jingyuetan
Remote Sensing Test Site of the Chinese Academy of Sciences (grant 9504).
Biography: YAN Min-hua (1964 -), female, a native of Liaoning Province, master, associate professor. Her research interests
include climate change, greenhouse gases and wetland climate. 相似文献
12.
沈志良 《中国海洋湖沼学报》1996,14(4):303-307
The distributions of SiO_3-Si, PO_4-P, NO_3-N and NO_2-N concentrations in the seawater, iceand snow from 82°45′21″W, 88°01′20″N to the North Pole are reported and the exchange of thenutrients among the seawater, ice and snow are discussed. The average concentrations of the nutrients inthe seawater near the North Pole were 4.9±2.4μmol/L for SiO_3-Si; 0.60±0.10μmol/L for PO_4-P,3.4±1.7μmol/L for NO_3-N and 0.13±0.04μmol/L for NO_2-N. The nutrient concentrations inthe ice and snow in the North Pole were 0.20 and 0.65μmol/L for SiO_3-Si; 0.22 and 0.25μmol/L forPO_4-P; 1.6 and 5.8μmol/L for NO_3-N, 0.19 and 0.15μmol/L for NO_2-N. 相似文献
13.
The total organic carbon (TOC) content series from the lake sediment of Minqin Basin (100°57′–104°57′E, 37°48′–39°17′N) in northwestern China, which has a 10 000-year-long paleo-climatic proxy record, was used to analyze the Holocene climate changes in the local region. The proxy record was established in the Sanjiaocheng (SJC), Triangle Town in Chinese, Section (103°20′25″E, 39°00′38″N), which is located at the northwestern boundary of the present Asian summer monsoon in China, and is sensitive to global environmental and climate changes. Applying singular spectrum analysis (SSA) to the TOC series, principal climatic oscillations and periodical changes were studied. The results reveal 3 major patterns of climate change regulated by reconstructed components (RCs). The first pattern is natural long-term trend of climatic change in the local area (Minqin Basin), indicating a relatively wetter stage in early Holocene (starting at 9.5 kaBP), and a relatively dryer stage with a strong lake desiccation and a declined vegetation cover in mid-Holocene (during 7–6 kaBP). From 4.0 kaBP to the present, there has been a gradually decreasing trend in the third reconstructed component (RC3) showing that the local climate changed again into a dryer stage. The second pattern shows millennial-centennial scale oscillations containing cycles of 1 600 and 800 years that have been present throughout almost the entire Holocene period of the last 10 000 years. The third pattern is a millennial-centennial scale variation with a relatively smaller amplitude and unclear cycles showing a nonlinear interaction within the earth’s climate systems. 相似文献
14.
Seven compounds (1–7) were identified from the cultivation of the endophytic fungus Exophiala oligosperma (EN-21) that was isolated from the inner tissue of the marine red alga Laurencia similis. Their structures were identified with spectroscopic and chemical methods as 2-phenoxynaphthalene (1), (2S, 3R, 4E, 8E)-1-O-β-D-glucopyranosyl-3-hydroxy-2-[(R)-2′-hydroxyoctadecanoyl] amino-9-methyl-4, 8-octadeca-diene (2), (22E,24R)-ergosta-7,22-dien-3β,5α,6β-triol (3), (22E, 24R)-3β, 5α, 9α-trihydroxy- ergosta-7, ... 相似文献
15.
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
16.
Reversible protein phosphorylation, catalyzed by protein kinases and phosphatases, is an important and versatile mechanism by which eukaryotic cells regulate almost all the signaling processes. Protein phosphatase 1 （PP1） is the first and well-characterized member of the protein serine/threonine phosphatase family. In the present study, a full-length cDNA encoding the beta isoform of the catalytic subunit of protein phosphatase l（PPlcb）, was for the first time isolated and sequenced from the skin tissue of flatfish turbot Scophthalmus maximus, designated SmPPlcb, by the rapid amplification of cDNA ends （RACE） technique. The cDNA sequence of SmPPlcb we obtained contains a 984 bp open reading frame （ORF）, flanked by a complete 39 bp 5＇ untranslated region and 462 bp 3＇ untranslated region. The ORF encodes a putative 327 amino acid protein, and the N-terminal section of this protein is highly acidic, Met-Ala-Glu-Gly-Glu-Leu-Asp-Val-Asp, a common feature for PP1 catalytic subunit but absent in protein phosphatase 2B （PP2B）. And its calculated molecular mass is 37 193 Da and pI 5.8. Sequence analysis indicated that, SmPPlcb is extremely conserved in both amino acid and nucleotide acid levels compared with the PPlcb of other vertebrates and invertebrates, and its Kozak motif contained in the 5＇UTR around ATG start codon is GXXAXXGXXATGG, which is different from mammalian in two positions A6 and G3, indicating the possibility of different initiation of translation in turbot, and also the 3＇UTR of SmPPlcb is highly diverse in the sequence similarity and length compared with other animals, especially zebraf＇lsh. The cloning and sequencing of SmPPlcb gene lays a good foundation for the future work on the biological functions of PP1 in the flatfish turbot. 相似文献
17.
The fatty acid compositions of seston and Calanus sinicus were investigated to study trophic relationships in Jiaozhou Bay. Principal component analysis was carried out to ordinate the fatty acid patterns of seston in stations and months. The results showed that diatoms were most abundant in the phytoplankton at station A5 (located in the northwest of the bay:36°9′N, 120°20′E) and least abundant at station D7 (located outside of the bay: 35°59′N, 120°26′E). By contrast, dinoflagellates were most abundant at station D7 and least abundant at station A5. According to the annual variations of 16:1ω7 and 18:4ω3/ 16:1ω7, diatoms flourished mainly in spring and summer, while dinoflagellates bloomed exclusively in summer. A distinctive feature of the fatty acid composition of C. sinicus was the prevalence of 20:5ω3 and 22:6ω3. The higher content of 16:1ω7 over 18:4ω3 in females indicated that diatoms contributed more than dinoflagellates to the diet of C. sinicus. The feeding intensity of C. sinicus on diatoms was higher in spring and autumn than in other seasons. The herbivorous indicators 20:1 and 22:1 were comparatively low, suggesting that besides phytoplankton, C. sinicus might feed on a wider range of particles including organic detritus, bacteria and small copepods. 相似文献
18.
AncientLoulanTOWnwasafamoustownontheSilkROadinthehistory,butsuddenlydisappearedfromthehistoricalrecords1400yearsago.Untilthespringof1900,Aierdeke,theUygurguideoftheexploringpartyledbyMr.SVehHedin,aSWedishexplorer,discoveredthismystery,whichmadeasensationintheworld.Afterwards,alotofexplorersathomeandabroad,E.NuntingtrnfromAmerica(1905),SirAureSteinfromEngland(1906,Igl4),azureOtanietal.fromJapan(1908--1911)wentthereoneafteranotherandthelastinvestigationofwidescopewasdonebyanarchaeologi… 相似文献
19.
The Antitumor Components from Marine-derived Bacterium Streptoverticillium luteoverticillatum 11014 Ⅱ 总被引：2，自引：0，他引：2
LI Dehai ZHU Tianjiao FANG Yuchun LIU Hongbing GU Qianqun ZHU Weiming 《中国海洋大学学报(英文版)》2007,6(2):193-195
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
20.
ＲＥＬＡＴＩＯＮＳＨＩＰＢＥＴＷＥＥＮＱＩＮＧＨＡＩＬＡＫＥＬＥＶＥＬＤＥＳＣＥＮＤＩＮＧＡＮＤＡＲＴＩＦＩＣＩＡＬＷＡＴＥＲ－ＣＯＮＳＵＭＰＴＩＯＮ￥ＰｅｎｇＭｉｎ（彭敏）ＣｈｅｎＧｕｉｃｈｅｎ（陈桂琛）ＺｈｏｕＬｉｈｕａ（周立华）（Ｎｏｒｔｈｗｅ... 相似文献