Halogenated metabolites from the new Okinawan red alga Laurencia yonaguniensis.
A novel brominated diterpene based on the rare neoirieane skeleton, named neoirietetraol (1), has been isolated along with a halogenated C15 acetogenin, (3Z)-laurenyne (2), from a new Laurencia species, L.yonaguniensis Masuda et Abe, species inedita, collected at Yonaguni Island, Okinawa Prefecture, Japan. The structures of these metabolites were elucidated by spectroscopic data (IR, 1H NMR, 13C NMR, 2D NMR, and MS). Neoirietetraol (1) was toxic to the brine shrimp (Altemia salina; LC50, 40.1 microM) and also showed weak antibacterial activities against two marine bacteria, Alcaligenes aquamarinus and Escherichia coli.
Takahashi
Yoshinori
Y
Division of Material Science, Graduate School of Environmental Earth Science, Hokkaido University, Sapporo 060-0810, Japan.
Daitoh
Motonari
M
Suzuki
Minoru
M
Abe
Tsuyoshi
T
Masuda
Michio
M
D000421:Alcaligenes / Q000187:drug effects; D020591:Alteromonas / Q000187:drug effects; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001156:Artemia / Q000187:drug effects; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004885:Erwinia / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D019625:Halococcus / Q000187:drug effects; D006573:Heterocyclic Compounds, 1-Ring / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007564:Japan; D013058:Mass Spectrometry; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011548:Pseudomonadaceae / Q000187:drug effects; D000461:Rhodophyta / Q000737:chemistry*; D013055:Spectrophotometry, Infrared
D000900:Anti-Bacterial Agents; D004224:Diterpenes; D006573:Heterocyclic Compounds, 1-Ring; D006843:Hydrocarbons, Chlorinated; C455739:laurenyne; C455740:neoirietetraol