Laurendecumallenes A-B and laurendecumenynes A-B, halogenated nonterpenoid C(15)-acetogenins from the marine red alga Laurencia decumbens.
Four new halogenated nonterpenoid C(15)-acetogenins, 4:7,6:13-bisepoxy-9,10-diol-1,12-dibromopentadeca-1,2-diene (1, laurendecumallene A), 4:7,6:12-bisepoxy-9,10-diol-1,13-dibromopentadeca-1,2-diene (2, laurendecumallene B), (3Z)-6:10,7:13-bisepoxy-12-bromo-9-hydroperoxylpentadeca-3-en-1-yne (3, laurendecumenyne A), and (3Z)-6:10,9:13-bisepoxy-12-bromo-7-chloropentadeca-3-en-1-yne (4, laurendecumenyne B), together with one known halogenated C(15)-acetogenin elatenyne (5) were isolated and identified from the organic extract of the marine red alga Laurencia decumbens. Their structures and relative stereochemistry were established by means of spectroscopic analysis including UV, IR, high-resolution electrospray ionization mass spectrometry (HRESIMS), and 1D and 2D NMR techniques. All these metabolites were submitted for the cytotoxic assay against tumor cell line A549 (human lung adenocarcinoma), but all of them were found inactive (IC(50) > 10 microg/mL).
Ji
Nai-Yun
NY
Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Qingdao, People's Republic of China.
Li
Xiao-Ming
XM
Li
Ke
K
Wang
Bin-Gui
BG
D054378:Acetogenins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002681:China; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D006842:Hydrocarbons, Brominated / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D044722:Laurencia / Q000737:chemistry*; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular
D054378:Acetogenins; D006842:Hydrocarbons, Brominated; C524236:laurendecumallene A; C524237:laurendecumallene B; C524238:laurendecumenyne A; C524239:laurendecumenyne B