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1.
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
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.
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
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.
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
6.
7.
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
8.
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
9.
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
10.
Zhang Yujiang Zhan Songmei Cao Pengli Liu Ning Chen Xuehong Wang Yuejun Wang Chunbo 《中国海洋湖沼学报》2005,23(3):357-362
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
11.
In vitro acute cytotoxicity of neonicotinoid insecticide imidacloprid (IMI) to the gill cell line of flounder (FG) that collected in the gill of Paralichthys olivaceus, was examined by 3 widely used endpoint bioassays: NR (neutral red), MTT (3-(4,5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide) and TCP (total cell protein). The result shows that the IMI increased at concentrations ≥0.5 μg/ml. The IC50 value of NR, MTT, and TCP was 41.86, 38.46, and 39.08 μg/ml, respectively. The ultrastructural observation revealed that the mitochondria of the cells exposed to 60 μg/ml IMI for 48 h were severely damaged, swollen or disrupted, while their nuclei and rough endoplasmic reticulum (RER) remained normal. This would suggest that the mitochondria are probably the primary target of IMI. 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 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
13.
PHYSIOLOGICAL INHIBITORY EFFECT OF OCS IN ARACHIDONIC ACID-RICH PARIETOCHLORIS INCISA （TREBOUXIOPHYCEAE, CHLOROPHYTA） 总被引：2，自引：0，他引：2
Parietochloris incisa is an arachidonic acid-rich snow green alga. The main physiological profiles, such as ash free dry weight (AFDW), chlorophyll, carotenoid, protein and total fatty acids (TFA), in this alga exposed to old culture supernatant (OCS) at the decline phase or its crude ethyl acetate extracts (CEAE) were investigated by using tubular photobioreactors of different diameters. Results showed that both OCS and CEAE had strong inhibitory effect on the above physiological parameters. The longer the culture was exposed to OCS and the more CEAE were added into the algal culture, the more the above physiological properties were inhibited. Arachidonic acid (AA), the dominant component of fatty acids in this alga, was also seriously inhibited with respect to total TFA, AFDW of cell mass, or culture volume, due to a prebable reduction of enzymes activities catalyzing chain elongation from C18:1ω9 to AA. These results incontestably evidenced that some CEAE dissolving substances existing in OCS, like auto-inhibitors, inhibited P. incisa growth through feedback. Hence, any efficient removal of auto-inhibitors from algal culture to decrease their bioactivity could be good for maximal production of desired products like AA. 相似文献
14.
Totally more than 500 yeast strains were isolated from seawater, sea sediments, mud of sea salterns, marine fish guts and
marine algae. The results of routine and molecular biology identification methods show that nine strains among these marine
yeasts belong to Aureobasidium pullulans, although the morphologies of their colonies are very different. The marine yeasts isolated from different marine environments
indicate that A. pullulans is widely distributed in different environmental conditions. These Aureobasidium pullulans strains include A. pullulans 4#2, A. pullulans N13d, A. pullulans HN3-11, A. pullulans HN2-3, A. pullulans JHSc, A. pullulans HN4.7, A. pullulans HN5.3, A. pullulans HN6.2 and A. pullulans W13a. A. pullulans 4#2 could produce cellulase and single cell protein. A. pullulans N13d could produce protease, lipase, amylase and cellulase. Both A. pullulans HN3-11 and A. pullulans HN2-3 were able to produce protease, lipase and cellulase. A. pullulans JHSc could secrete cellulase and killer toxin. Both A. pullulans HN4.7 and A. pullulans HN5.3 could yield lipase and cellulase. A. pullulans W13a was able to secrete extracellular amylase and cellulase while A. pullulans HN4.7 and A. pullulans N13d could produce siderophores. This means that different A. pullulans strains from different marine environments have different physiological characteristics, which may be applied in many different
biotechnological industries. 相似文献
15.
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
16.
REN Hong GU Qianqun CUI Chengbin ZHU Weiming 《中国海洋大学学报(英文版)》2006,5(1):75-81
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
17.
Du Zongjun Li Yun Yu Dehua Wang Xianghong Chen Jixiang P. A. W. Robertson B. Austin Xu Huaishu 《中国海洋大学学报(英文版)》2002,1(1):59-62
From Oct. 1999 to Oct. 2000, the heterotrophic bacterial floras in the industrial marine environment around the Qingdao Power
Plant (QPP) and in the unpolluted marine environments were investigated. The results showed that the numbers of the heterotrophic
bacteria around QPP were much higher than those in unpolluted environments, and the average numbers in QPP Seawater, QPP Sediment,
Unpolluted Seawater and Unpolluted Sediment were 5.4×104cfu(mL)−1, 5.0×105cfug−1, 3.0×102cfu(mL)−1 and 1.3×105cfug−1 respectively. Totally, 118 strains were isolated from QPP and 99 of them were Gram-negative. One hundred and twenty one strains
were isolated from the unpolluted environments and 104 of them were Gram-negative. All the Gram-negative bacteria belonged
to 13 genera. The distribution of the bacteria was varied in different marine environments. The results showed that the unpolluted
marine environments contained much more Vibrio than seawater and sediment around QPP. 相似文献
18.
The auxin concentration in sixteen Chinese marine algae 总被引：1，自引：0，他引：1
韩丽君 《中国海洋湖沼学报》2006,24(3):329-332
1 INTRODUCTION Auxins are plant hormones. They play impor- tant roles in regulating plant activities, including phototropism, fruit development, root initiation and so on. In early 1940, Thirmann and Scoog (1940) found that auxin was present in more than … 相似文献
19.
Pavlova viridis sp. nov. is described on the basis of light and electron microscope observations. The material was collected from the coast
of haiyang county of Shandong, China. It is characterized by 1) yellowish green to green chloroplast, 2) rudimentary short
flagellum 0.3 μm long and hook-shaped, 3) long flagellum with small spherical knob-scales, 4) absence of pyrenoid and stigma,
and 5) marine habitat. This new species andP. salina seem to be most closely related to each other but their colour, the insertion of their three appendages, the shape of their
knob scales, and their cell periplasts are quite different from one another.
Contribution No. 1879 from the Institute of Oceanology, Academia Sinica 相似文献