Feeding-deterrent bromophenols from Odonthalia corymbifera

Synthesis and paroxonase activities of novel bromophenols

“…By applying the same procedure, acylation of veratrole (4) with 2,3-dimethoxybenzoic acid (5) in PPA at 80°C furnished 6 18 with a yield of 85%. As it is known, bromination of aromatic compounds can be achieved by either N-bromosuccinimide (NBS) 25 , and LiBr/Ceric ammonium nitrate 8 , or molecular bromine (Br 2 ) 26 .…”

“…These compounds have attracted much attention in the field of functional food and pharmaceutical agents 2 . It has been reported that naturally occurring bromophenol 1 shows enzyme inhibition 3 , cytotoxicity 4 , feeding deterrent 5 , anti-microbial 6 , anti-cancer 7 and anti-oxidant 8 activities. Aldose reductase 9 and carbonic anhydrase 10 inhibitory properties of natural products 2-3 have also been noted ( Figure 1).…”

Synthesis and carbonic anhydrase inhibitory properties of novel bromophenols including natural products

“…Of these natural compounds, 5,5′-methylenebis(3,4-dibromobenzene-1,2-diol) (1) and 3,4-dibromo-5-(2-bromo-3,4-dihydroxy-6-(methoxymethyl)benzyl)benzene-1,2-diol (2) exhibit enzyme inhibition, e.g. isocitrate lyase 3 cytotoxicity 4 , feeding deterrent 5 , and microbial 6,7 activities, while 3,4,6-tribromo-5-(2,5-dibromo-3,4-dihydroxybenzyl) benzene-1,2-diol (3) and 5,5′-methylenebis(3,4,6-tribromo-benzene-1,2-diol) (4) exhibit significant aldose reductase inhibitory activity 8 . Additionally, it was reported that bromophenol 1 is an inhibitor of protein tyrosine phosphatase 9 .…”

Sulfated bromophenols from Osmundaria obtusiloba (C. Agardh) R. E. Norris (Rhodophyta, Ceramiales)

“…These compounds are considered a chemical defense mechanism against marine herbivorous animals ( Kurata et al 1997) but only few of them were isolated, unequivocally identified and evaluated for biological Corresponding author: lretz@uol.com.br activities (Carvalho & Roque 2000, Smit 2004). Of these substances that have been studied, lanosol shows antialgal and anti-inflammatory properties, it influences growth and morphology of marine macroalgae and stimulates seeds growth (Carvalho & Roque 2000); the diarylmethane-type bromophenol of Odonthalia corymbifera has potent feeding-deterrent activity, and from the same species, two oligomeric bromophenols were found to be inactivators of α-glycosidase (Kurata et al 1997, Kuhiraha et al 1999.…”

“…Of these substances that have been studied, lanosol shows antialgal and anti-inflammatory properties, it influences growth and morphology of marine macroalgae and stimulates seeds growth (Carvalho & Roque 2000); the diarylmethane-type bromophenol of Odonthalia corymbifera has potent feeding-deterrent activity, and from the same species, two oligomeric bromophenols were found to be inactivators of α-glycosidase (Kurata et al 1997, Kuhiraha et al 1999. Vidalol A and vidalol B are two anti-inflammatory oligobromophenols from Osmundaria obtusiloba (Wiemer et al 1991).…”