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-dihydroxybenzyl]methyl 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.
Zhao
Jielu
J
Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Bejing 100050, People's Republic of China.
Ma
Ming
M
Wang
Sujuan
S
Li
Shuai
S
Cao
Peng
P
Yang
Yongchun
Y
Lü
Yang
Y
Shi
Jiangong
J
Xu
Nianjun
N
Fan
Xiao
X
He
Lan
L
D000596:Amino Acids; D002681:China; D003849:Deoxyguanosine / Q000737:chemistry; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D006842:Hydrocarbons, Brominated / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011761:Pyrrolidonecarboxylic Acid / Q000737:chemistry; D000461:Rhodophyta / Q000737:chemistry*; D014407:Tumor Cells, Cultured
D000596:Amino Acids; D006842:Hydrocarbons, Brominated; D003849:Deoxyguanosine; D011761:Pyrrolidonecarboxylic Acid