Amphimedosides, 3-alkylpyridine glycosides from a marine sponge Amphimedon sp.
Five 3-alkylpyridine alkaloids, amphimedosides A-E (1-5), have been isolated from a marine sponge Amphimedon sp. The structures of 1-5 have been determined by analysis of NMR and FABMS data and chiral GC analyses of the acid hyrolyzates. In particular, the site of glycosylation in 1 was confirmed by the 1H-15N HMBC experiment, and the location of the double bond in 5 was assigned on the basis of tandem FABMS data. Amphimedosides are the first examples of beta-D-glucosylated 3-alkylpyridine alkaloids and exhibited cytotoxic activities comparable with those of the nonglycosylated congeners.
Takekawa
Yoshihiko
Y
Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-8657, Japan.
Matsunaga
Shigeki
S
van Soest
Rob W M
RW
Fusetani
Nobuhiro
N
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D007941:Leukemia P388; D008386:Marine Biology; D051379:Mice; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D006027:Glycosides