TY - JOUR
T1 - Manoalide derivatives from a marine sponge Luffariella sp. collected in Palau
AU - Namikoshi, Michio
AU - Suzuki, Shigeo
AU - Meguro, Shiori
AU - Nagai, Hiroshi
AU - Koike, Yoshio
AU - Kitazawa, Akira
AU - Kobayashi, Hisayoshi
AU - Oda, Taiko
AU - Yamada, Junko
PY - 2004/2/1
Y1 - 2004/2/1
N2 - Two diastereomers of 24-O-methylmanoalide (1 and 2) and (6Z)-neomanoalide-24,25-diacetate (3) were isolated together with manoalide (4), seco-manoalide (5), (4E,6E)-dehydromanoalide (6) and manoalide-25-acetate (7) from a marine sponge Luffariella sp. collected in Palau. Two methyl ethers of manoalide (1 and 2) were revealed to be derived from manoalide, the main component of the extract, during the separation procedure. The stereochemistries of 1 (24R) and 2 (24S) were assigned based on the NOESY data for 2 and two 24,25-di-O-methylmanoalides (8 and 9), synthesized from 1 and 2. Although 3 has been chemically transformed from (6Z)-neomanoalide, this is the first report of the isolation of this compound from a marine sponge. Compounds 1, 2, 4, 5 and 7 showed an antibacterial activity against Staphylococcus aureus at 5-10 μg, while 3, 8 and 9 were not active at 50 μg.
AB - Two diastereomers of 24-O-methylmanoalide (1 and 2) and (6Z)-neomanoalide-24,25-diacetate (3) were isolated together with manoalide (4), seco-manoalide (5), (4E,6E)-dehydromanoalide (6) and manoalide-25-acetate (7) from a marine sponge Luffariella sp. collected in Palau. Two methyl ethers of manoalide (1 and 2) were revealed to be derived from manoalide, the main component of the extract, during the separation procedure. The stereochemistries of 1 (24R) and 2 (24S) were assigned based on the NOESY data for 2 and two 24,25-di-O-methylmanoalides (8 and 9), synthesized from 1 and 2. Although 3 has been chemically transformed from (6Z)-neomanoalide, this is the first report of the isolation of this compound from a marine sponge. Compounds 1, 2, 4, 5 and 7 showed an antibacterial activity against Staphylococcus aureus at 5-10 μg, while 3, 8 and 9 were not active at 50 μg.
KW - (6Z)-neomanoalide-24,25-diacetate
KW - 24-O-methylmanoalide
KW - Luffariella sp.
KW - Manoalide
KW - Marine sponge
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U2 - 10.1111/j.1444-2906.2003.00783.x
DO - 10.1111/j.1444-2906.2003.00783.x
M3 - Article
AN - SCOPUS:1542321221
SN - 0919-9268
VL - 70
SP - 152
EP - 158
JO - Fisheries Science
JF - Fisheries Science
IS - 1
ER -
