Penasins A-E, long-chain cytotoxic sphingoid bases, from a marine sponge Penares sp.
Five sphingoid bases, penasin A (1), penasin B (2), and a mixture of penasins C-E (3-5), were identified from a marine sponge Penares sp. as cytotoxic constituents. The structure of the common polar head part was assigned by analysis of the NMR data, whereas the structures of the long aliphatic chains including the locations of double bond(s) and a branched methyl group were determined by analysis of tandem FABMS and (13)C NMR data together with the GC-MS analysis of ozonolysis products. The absolute configuration of the headgroup was defined for the mixture of 3-5 by the modified Mosher method. Penasins exhibit moderate cytotoxicity against HeLa and P388 cells.
Ando
Hideki
H
Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo, 113-8657, Japan.
Ueoka
Reiko
R
Okada
Shigeru
S
Fujita
Tsuyoshi
T
Iwashita
Takashi
T
Imai
Takaaki
T
Yokoyama
Tomoya
T
Matsumoto
Yuji
Y
van Soest
Rob W M
RW
Matsunaga
Shigeki
S
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D037341:Fumonisins; D008401:Gas Chromatography-Mass Spectrometry; D006367:HeLa Cells; D006801:Humans; D007941:Leukemia P388; D008386:Marine Biology; D051379:Mice; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
D000970:Antineoplastic Agents; D037341:Fumonisins; C554488:penasin A; C554489:penasin B; D013110:Sphingosine