The influence of phlorotannins and bromophenols on the feeding behavior of marine herbivores was determined using bioassay of Turbo cornutus. It was found that phloroglucinol and its oligomers isolated from the brown ...The influence of phlorotannins and bromophenols on the feeding behavior of marine herbivores was determined using bioassay of Turbo cornutus. It was found that phloroglucinol and its oligomers isolated from the brown alga Eisenia bicyclis (eckol, fucofuroeckol A, phlorofucofuroeckol A, dieckol, and 8,8’-bieckol) had a deterrent effect against feeding behavior of T. cornutus in the concentration of algal body, respectively. In the case of the examination of 0.1 mM concentration, although fucofuroeckol A and phlorofucofuroeckol A significantly reduced feeding by T. cornutus, phloroglucinol and 8,8’-bieckol did not show any significant influence on feeding behavior, and eckol and dieckol had stimulating activity. 2,4-Dibromophenol and 2,4,6-tribromophenol, which are major components of extracellular secretions from Eisenia and Ecklonia species, caused the death, the torpidity, and the decreased appetite of T. cornutus at the concentration of 0.1 mM. In addition, 2,4-dibromophenol had strong feeding deterrent activity at the concentration of 1 μM. These results indicate that phlorotannins and bromophenols act as chemical defense agents of brown algae against environmental stresses such as the herbivore attack.展开更多
Marine algae contain various bromophenols with a variety of biological activities, including antimicrobial, anticancer, and anti-diabetic effects. Here, we briefly review the recent progress in researches on the bioma...Marine algae contain various bromophenols with a variety of biological activities, including antimicrobial, anticancer, and anti-diabetic effects. Here, we briefly review the recent progress in researches on the biomaterials from marine algae, emphasizing the relationship between the structure and the potential anti-diabetic applications. Bromophenols from marine algae display their hyper- glycemic effects by inhibiting the activities of protein tyrosine phosphatase 1B, ct-glucosidase, as well as other mechanisms.展开更多
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 bromop...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.展开更多
文摘The influence of phlorotannins and bromophenols on the feeding behavior of marine herbivores was determined using bioassay of Turbo cornutus. It was found that phloroglucinol and its oligomers isolated from the brown alga Eisenia bicyclis (eckol, fucofuroeckol A, phlorofucofuroeckol A, dieckol, and 8,8’-bieckol) had a deterrent effect against feeding behavior of T. cornutus in the concentration of algal body, respectively. In the case of the examination of 0.1 mM concentration, although fucofuroeckol A and phlorofucofuroeckol A significantly reduced feeding by T. cornutus, phloroglucinol and 8,8’-bieckol did not show any significant influence on feeding behavior, and eckol and dieckol had stimulating activity. 2,4-Dibromophenol and 2,4,6-tribromophenol, which are major components of extracellular secretions from Eisenia and Ecklonia species, caused the death, the torpidity, and the decreased appetite of T. cornutus at the concentration of 0.1 mM. In addition, 2,4-dibromophenol had strong feeding deterrent activity at the concentration of 1 μM. These results indicate that phlorotannins and bromophenols act as chemical defense agents of brown algae against environmental stresses such as the herbivore attack.
基金supported by the State Innovative Drugs Development Program of China (2009ZX09103-661 and 2009ZX09102)
文摘Marine algae contain various bromophenols with a variety of biological activities, including antimicrobial, anticancer, and anti-diabetic effects. Here, we briefly review the recent progress in researches on the biomaterials from marine algae, emphasizing the relationship between the structure and the potential anti-diabetic applications. Bromophenols from marine algae display their hyper- glycemic effects by inhibiting the activities of protein tyrosine phosphatase 1B, ct-glucosidase, as well as other mechanisms.
基金Supported by the National Major Research Program of China (No.2009ZX09103-148)the National High Technology Research and Development Program of China (863 program) (Nos.2007AA09Z410,2007AA091604)
文摘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.
