Bromophenols from the red alga Rhodomela confervoides

Six new bromophenols, 3-bromo-4,5-bis(2,3-dibromo-4,5-dihydroxybenzyl)pyrocatechol (1), 2,2',3-tribromo-3',4,4',5-tetrahydroxy-6'-hydroxymethyldiphenylmethane (2), 2,2',3-tribromo-3',4,4',5-tetrahydroxy-6'-ethyloxymethyldiphenylmethane (3),(+/-)-2-methyl-3-(2,3-dibromo-4,5-dihydroxyphenyl)propylaldehyde (4), (+/-)-2-methyl-3-(2,3-dibromo-4,5-dihydroxyphenyl)propylaldehyde dimethyl acetal (5), and 3-bromo-4,5-dihydroxybenzoic acid methyl ester (6), together with eight known bromophenols, 3-bromo-4,5-dihydroxybenzaldehyde (7), 2,3-dibromo-4,5-dihydroxybenzyl alcohol (lanosol, 8), 2,3-dibromo-4,5-dihydroxybenzyl methyl ether (9), 2,3-dibromo-4,5-dihydroxybenzyl ethyl ether (10), 2,3-dibromo-4,5-dihydroxybenzylaldehyde (11), bis(2,3-dibromo-4,5-dihydroxybenzyl) ether (12), 3-bromo-4-(2,3-dibromo-4,5-dihydroxybenzyl)-5-methoxymethylpyrocatechol (13), and 2,2',3,3'-tetrabromo-4,4',5,5'-tetrahydroxydiphenyl methane (14), were isolated from the red alga Rhodomela confervoides. Their structures were elucidated by chemical and spectroscopic methods including IR, HRFABMS, and 1D and 2D NMR techniques.

Bromophenols coupled with methyl gamma-ureidobutyrate and bromophenol sulfates from the red alga Rhodomela confervoides

Four new bromophenols C-N coupled with methyl gamma-ureidobutyrate (1-4), a phenylethanol bromophenol (5), and three phenylethanol sulfate bromophenols (6-8) have been isolated from polar fractions of an ethanolic extract of the red alga Rhodomela confervoides. On the basis of spectroscopic evidence including HRMS and 2D NMR data, the structures of the new compounds were determined as methyl N'-(2,3-dibromo-4,5-dihydroxybenzyl)-gamma-ureidobutyrate (1), methyl N,N'-bis(2,3-dibromo-4,5-dihydroxybenzyl)-gamma-ureidobutyrate (2), methyl N'-[3-bromo-2-(2,3-dibromo-4,5-dihydroxybenzyl)-4,5-dihydroxybenzyl]-gamma-ureidobutyrate (3), methyl N'-(2,3-dibromo-4,5-dihydroxybenzyl)-A7-[3-bromo2-(2,3-dibromo-4,5-dihydroxybenzyl)-4,5-dihydroxybenzyl]-gamma-ureidobutyrate (4), 2,3-dibromo-4,5-dihydroxyphenylethanol (5), 2,3-dibromo-4,5-dihydroxyphenylethanol Sulfate (6), 3-bromo-4,5-dihydroxyphenylethanol sulfate (7), and 3-bromo2-(2,3-dibromo-4,5-dihydroxybenzyl)-4,5-dihydroxyphenylethanol sulfate (8). The cytotoxicity of all compounds was evaluated against several human cancer cell lines including human colon cancer (HCT-8), hepatoma (Bel7402), stomach cancer (BGC-823), lung adenocarcinoma (A549), and human ovarian cancer (A2780). Among them, the phenylethanol and the phenylethanol sulfate bromophenols (5-8) showed moderate cytotoxicity against all tested cell lines.

Bromophenols coupled with nucleoside bases and brominated tetrahydroisoquinolines from the red alga Rhodomela confervoides

Three new bromophenols C-N coupled with nucleoside base derivatives (1-3) and three new brominated 1,2,3,4-tetrahydroisoquinolines (5-7, together with a new brominated tyrosine derivative (4, have been isolated from polar fractions of an ethanolic extract of the red alga Rhodomela confervoides. By spectroscopic and chemical methods including HRMS and 2D NMR data, their structures were determined as 7-[3-bromo-2-(2,3-dibromo-4,5-dihydroxybenzyl)-4,5-dihydroxybenzyl]-3,7-dihydro-1H-purine-2,6-dione (1), 7-(2,3-dibromo-4,5-dihydroxybenzyl)-3,7-dihydro-1H-purine-2,6-dione (2, 9-[3-bromo-2-(2,3-dibromo-4,5-dihydroxybenzyl)-4,5-dihydroxybenzyl]adenine (3), (-)-8S-(3-bromo-5-hydroxy-4-methoxy)phenylalanine (4), (-)-3S-8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (5), methyl (-)-3S-8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (6), and methyl (-)-3S-6-bromo-8-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (7). Compounds 5-7 were semisynthesized by using 4 as the starting material.

Sesquiterpenes from the red alga Laurencia tristicha

Seven new sesquiterpenes (1-7), together with seven known sesquiterpenes, aplysin (8), aplysinol (9), gossonorol (10), 7,10-epoxy-ar-bisabol-11-ol (11), 10-epi-7,10-epoxy-ar-bisabol-11-ol (12), johnstonol (13), and laurebiphenyl (14), have been isolated from the red alga Laurencia tristicha. The structures of new compounds were established as laur-11-en-2,10-diol (1), laur-11-en-10-ol (2), laur-11-en-1,10-diol (3), 4-bromo-1,10-epoxylaur-11-ene (4), cyclolauren-2-ol (5), laurentristich-4-ol (6), and ar-bisabol-9-en-7,11-diol (7) by means of spectroscopic methods including IR, HRMS, and ID and 21) NMR techniques. Compound 6 possessed a novel rearranged skeleton. All compounds were tested against several human cancer cell lines including lung adenocarcinoma (A549), stomach cancer (BGC-823), hepatoma (Bel 7402), colon cancer (HCT-8), and HELA cell lines. Laurebiphenyl (14) showed moderate cytotoxicity against all tested cell lines, with IC50 values of 1.68, 1.22, 1.91, 1.77, and 1.61 mu g/mL, respectively. Other compounds were inactive (IC50 > 10 mu g/mL).

Bromophenol derivatives from the red alga Rhodomela confervoides

Eight new bromophenol derivatives, 2,3-dibromo-4,5-dihydroxybenzyl methyl sulfoxide (1), 4-(2,3-dibromo-4,5-dihydroxyphenyl)-3-butene-2-one (2), 2-(3-bromo-5-hydroxy-4-methoxyphenyl)-3-(2,3-dibromo-4,5-dihydroxyphenyl)propionic acid (3), 2-(3-bromo-5-hydroxy-4-methoxyphenyl)-3-(2,3-dibromo-4,5-dihydroxyphenyl)propionic acid methyl ester (4), 2-phenyl-3-(2,3-dibromo-4,5-dihydroxyphenyl)propionic acid (5), 4'-methoxy-2",3',3"-tribromo-4",5',5"-trihydroxydiphenylacetic acid (6), and 3-bromo-5-hydroxy-4-methoxyphenylacetic acid (7) and its methyl ester (8), together with a known bromophenol, 3-bromo-5-hydroxy4-methoxybenzoic acid (9), were isolated from the red alga Rhodomela confervoides. Their structures were elucidated by spectroscopic methods including IR, EIMS, FABMS, ESIMS, HRFABMS, HRESIMS, 1D and 2D NMR, and single-crystal X-ray structure analysis. Compounds 1-4, 8, and 9 were found inactive against several human cancer cell lines and microorganisms.

Bromophenols coupled with derivatives of amino acids and nucleosides from the red alga Rhodomela confervoides

Three new bromophenols coupled with pyroglutamic acid derivatives and one bromophenol coupled with deoxyguanosine were obtained from the red alga Rhodomela confervoides. By spectroscopic methods including 2D NMR and single-crystal X-ray structure analysis their structures were elucidated as N-(2,3-dibromo-4,5-dihydroxybenzyl)methyl pyroglutamate (1), N-(2,3-dibromo-4,5-dihydroxybenzyl)pyroglutamic acid (2), N-[3-bromo-2-(2,3-dibromo-4,5-dihydroxybenzyl)-4,5-dihydroxybenzyllmethyl pyroglutamate (3), and 2-N-(2,3-dibromo-4,5-dihydroxybenzylamino)deoxyguanosine (4), respectively. Compounds 1-4 were evaluated against several microorganisms and human cancer cell lines, but found inactive. To our knowledge this is the first report of bromophenols coupled with amino acid or nucleoside derivatives through the C-N bond.

Biosorption of Cr(VI) from aqueous solutions by nonliving green algae Cladophora albida

Biosorption of Cr(VI) from aqueous solutions by nonliving green algae Cladophora albida was investigated in batch experiments. The influence of pH, algal dosage, initial Cr(VI) concentration, temperature and coexisting anions on removal efficiencies of C. albida was studied. Cr(VI) removal process was influenced significantly by the variation of pH, and the optimum pH was chosen at a range of 1.0-3.0. The optimum algal dosage 2 g/L was used in the experiment. The removal rate of Cr(VI) was relatively rapid in the first 60 min, but then the rate decreased gradually. Removal mechanism was studied by analyzing Cr(VI) and total Cr in the solution. Biosorption and bioreduction were involved in the Cr(VI) removal. Biosorption of Cr(VI) was the first step. followed by Cr(VI) bioreduction and Cr(III) biosorption on the algal biomass. Actual industrial wastewater was used to evaluate the practicality of the biomass C. albida. From a practical viewpoint, the abundant and economic biomass C. albida could be used for removal of Cr(VI) from wastewater by the reduction of toxic Cr(VI) to less toxic Cr(III). (C) 2008 Elsevier Ltd. All rights reserved.

Sesquiterpenes from the Marine Red Alga Laurencia saitoi

Together with five known sesquiterpenes, EtOH extraction of Laurencia saitoi yielded four new compounds, including three sesquiterpenes and one norsesquiterpene derivative. Their structures and relative configurations were elucidated by spectroscopic methods, including 1D- and 2D-NMR (H-1,H-1-COSY, HMQC, HMBC, and NOESY), as well as low- and high-resolution mass-spectrometric analyses.

Two new bromoindoles from red alga Laurencia similis

Two new bromoindole alkaloids have been isolated from the ethanolic extract of the red alga Laurencia similis. On the basis of chemical and spectroscopic methods (including 1D and 2D NMR technique), their structures have been elucidated as 2,2',5,5',6,6'-sixibromo-3, 3'-bi-1H-indole and 3, 5-dibromo-1-methylindole, respectively. (C) 2008 Xiao Bin Zhu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

A NOVEL BROMOPHENOL FROM MARINE RED ALGA Symphyocladia latiuscula

2,3,6-Tribromo-4,5-dihydroxybenzyl ethyl ether (1), a new bromophenol, was isolated from the ethanol extract of marine red alga Symphyocladia latiuscula, with a known compound, 2,3,6-tribromo-4,5-dihydroxybenzyl methyl ether ( 2). Their structures were elucidated by spectroscopic analysis, including high-resolution mass spectroscopy, and 1 and 2-dimensional NMR techniques. Compounds 1 and 2 showed inhibitory activity against Staphyloccocus aureus with IC50 102 and 50 mu g/mL, respectively.

Sesquiterpenes from red alga Laurencia tristicha

Three naturally new sesquiterpenes named 10-hydroxyepiaplysin, 10-hydroxyaplysin and 10-hydroxybromoepiaplysin have been isolated from Laurencia tristicha. On the basis of the spectroscopic techniques their structures were elucidated as (3S, 3 alpha R, 8 beta S)-(-)-2, 3, 3 alpha, 8 beta-tetrahydro-7-bromo-3-hydroxy-3, 3 alpha, 6,8 beta-tetramethyl-1H-cyclopenta[b]benzofuran, (3R, 3 alpha R, 8 beta S)(-)-2,3,3 alpha, 8 beta-tetrahydro-7-bromo-3-hydroxy-3, 3 alpha,6,8 beta-tetratnethyl-1H-cyclopenta[b]benzofuran and (3S, 3 alpha R, 8 beta S)-(-)-2, 3,3 alpha,8 beta-tetrahydro-3-hydroxy-3,3 alpha,6,8 beta-tetrainethyl-1H-cyclopenta[blbenzofuran, respectively.

Chemical characteristics of a polysaccharide from Porphyra capensis (Rhodophyta)

The structure of a polysaccharide from the red seaweed, Porphyra capensis, growing along the coast of Namibia and South Africa was investigated. Algae growing at different sites and collected at different times gave a polysaccharide extract with similar chemical components. FTIR and NMR spectral analysis showed that the polysaccharide from P. capensis had a typical porphyran structure. It has the linear backbone of alternating 3-linked beta-D-galactose and 4-linked alpha-L-galactose-6-sulfate or 3,6-anhydro-alpha- L-galactose units. The ratio of alpha-L-galactose-6-sulfate and the 3,6-anhydrogalactose is 121, as reflected by a H-1 NMR spectrum. A high degree of methylation occurred at the C-6 position of the D-galactose units. The degree of methylation was 0.64 for the D-galactose residues. (C) 2005 Elsevier Ltd. All rights reserved.

Screening marine algae from China for their antitumor activities

Thirty-nine species of marine algae collected from the coast of China were screened for their antitumor activities, and eight species Leathesia difformes, Polysiphonia urcedata, Scytosiphon lomentarius, Gloiopeliis furcata, Punctaria latifolia, Symphyocladia latiuscula, Rhodomela confervoides and Ulva pertusa showed potent cytotoxic activities. Three, Rhodomela confervoides, Scytosiphon lomentarius and Gloiopeliis furcata, were used for further investigation. More than 30 compounds were isolated and purified, and 14 bromophenols, 1 steroid and 1 carotene were identified by advanced spectroscopic methods including IR, MS, and NMR techniques. Amongst the 16 identified compounds, 7 showed vigorously selective activities against KB, Bel7402 and A549 cancer cells, and 6 bromophenols were new compounds.

A new brominated phenylpropylaldehyde and its dimethyl acetal from red alga Rhodomela confervoides

A new brominated phenylpropylaldehyde and its dimethyl acetal together with a new natural brominated phenol were isolated from Rhodomela confervoides. Their structrues were elucidated as 2-methyl-3-(2,3-dibromo-4,5-dihydroxyphenyl)propylaldehyde, 2-methyl-3-(2,3-dibromo-4,5-dihydroxyphenyl) propylaldehyde dimethyl acetal and 3-bromo-4,5-dihydroxybenzoic acid methyl ester by spectroscopic techniques including IR, HRFABMS, ID and 2DNMR experiments.

Two new bromophenols from red alga Rhodomela confervoides

Two new bromophenols were isolated from Rhodomela confervoides. Their structures were elucidated as 2, 2', 3-tribromo-3', 4, 4', 5-tetrahydroxy-6'-hydroxymethyldiphenylmethane and 2, 2', 3-tribromo-3', 4, 4', 5-tetrahydroxy-6'-ethyloxymethyldiphenylmethane by spectroscopic methods including IR, HREIMS, 1D and 2D NMR techniques.