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.
Ma
Ming
M
Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, People's Republic of China.
Zhao
Jielu
J
Wang
Sujuan
S
Li
Shuai
S
Yang
Yongchun
Y
Shi
Jiangong
J
Fan
Xiao
X
He
Lan
L
D000225:Adenine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification; D006842:Hydrocarbons, Brominated / Q000737:chemistry* / Q000302:isolation & purification*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011688:Purinones / Q000737:chemistry* / Q000302:isolation & purification*; D000461:Rhodophyta / Q000737:chemistry*; D013237:Stereoisomerism
C519240:7-(2,3-dibromo-4,5-dihydroxybenzyl)-3,7-dihydro-1H-purine-2,6-dione; C519239:7-(3-bromo-2-(2,3-dibromo-4,5-dihydroxybenzyl)-4,5-dihydroxybenzyl)-3,7-dihydro-1H-purine-2,6-dione; C519241:9-(3-bromo-2-(2,3-dibromo-4,5-dihydroxybenzyl)-4,5-dihydroxybenzyl)adenine; D006842:Hydrocarbons, Brominated; D011688:Purinones; D000225:Adenine