Brominated metabolites from an Okinawan Laurencia intricata.
Two halogenated C(15) acetogenins, itomanallenes A and B, with a terminal bromoallene moiety along with a halogenated sesquiterpene, itomanol, have been isolated from the red alga Laurencia intricata collected in Okinawan waters. Their structures were deduced from 1D and 2D NMR experiments including (1)H-(1)H COSY, HSQC, HMBC, and NOESY methods. The alcohol corresponding to itomanallene B seems to be a plausible precursor of itomanallene A, which has an unusual 2,10-dioxabicyclo[7.3.0]dodecene skeleton. Itomanol was found to be a selinane-type bromosesquiterpenoid, and is the first example of a selinane to be isolated from Japanese Laurencia species.
Suzuki
Minoru
M
Division of Material Science, Graduate School of Environmental Earth Science, Hokkaido University, Sapporo 060-0810, Japan. misu@ees.hokudai.ac.jp
Takahashi
Yoshinori
Y
Mitome
Yasuko
Y
Itoh
Taiji
T
Abe
Tsuyoshi
T
Masuda
Michio
M
D001966:Bromine / Q000378:metabolism*; D006574:Heterocyclic Compounds, 2-Ring / Q000737:chemistry / Q000302:isolation & purification*; D015394:Molecular Structure; D000461:Rhodophyta / Q000378:metabolism*; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification*; D013057:Spectrum Analysis
D006574:Heterocyclic Compounds, 2-Ring; D012717:Sesquiterpenes; C470776:itomanallene A; C470774:itomanallene B; C470775:itomanol; D001966:Bromine