Brominated labdane-type diterpenoids from an Okinawan Laurencia sp.
From an unidentified species of Laurencia collected from Okinawan waters two novel brominated metabolites, 1 and 2, along with known halogenated compounds, 2,10-dibromo-3-chloro-alpha-chamigrene (3) and microcladallene A (4), were isolated and identified. The structures of these new compounds were established as ent-labdane-type bromoditerpenes, (1S,3R,5S,6S,8S,9S,10R,13R)-1-acetoxy-3-bromo-6-hydroxy-8,13-epoxy-labd-14-ene (1) and (3R,5S,6S,8S,9S,10R,13R)-3-bromo-6-hydroxy-8,13-epoxylabd-14-en-1-one (2), by interpretation of their spectroscopic data as well as by X-ray crystallographic analysis.
Suzuki
Minoru
M
Division of Material Science, Graduate School of Environmental Earth Science, Hokkaido University, Sapporo 060-0810, Japan. misu@ees.hokudai.ac.jp
Nakano
Satoru
S
Takahashi
Yoshinori
Y
Abe
Tsuyoshi
T
Masuda
Michio
M
Takahashi
Hiroki
H
Kobayashi
Kimiko
K
D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004926:Escherichia coli / Q000187:drug effects; D006842:Hydrocarbons, Brominated / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D007564:Japan; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011549:Pseudomonas / Q000187:drug effects; D000461:Rhodophyta / Q000737:chemistry*; D012475:Salmonella / Q000187:drug effects; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013055:Spectrophotometry, Infrared; D013210:Staphylococcus / Q000187:drug effects; D013237:Stereoisomerism
C464749:1-acetoxy-3-bromo-6-hydroxy-8,13-epoxy-labd-14-ene; C464751:2,10-dibromo-3-chloro-alpha-chamigrene; C464750:3-bromo-6-hydroxy-8,13-epoxylabd-14-en-1-one; D004224:Diterpenes; D006842:Hydrocarbons, Brominated; D012717:Sesquiterpenes; C464752:microcladallene A