Manoalide derivatives from a marine sponge Luffariella sp. collected in Palau

Michio Namikoshi, Shigeo Suzuki, Shiori Meguro, Hiroshi Nagai, Yoshio Koike, Akira Kitazawa, Hisayoshi Kobayashi, Taiko Oda, Junko Yamada

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)152-158
Number of pages7
JournalFisheries Science
Volume70
Issue number1
DOIs
Publication statusPublished - 2004 Feb

Fingerprint

Palau
Porifera
sponge
chemical derivatives
diastereomers
stereochemistry
ether
ethers
Staphylococcus aureus
acetate
acetates
extracts

Keywords

  • (6Z)-neomanoalide-24,25-diacetate
  • 24-O-methylmanoalide
  • Luffariella sp.
  • Manoalide
  • Marine sponge

ASJC Scopus subject areas

  • Aquatic Science

Cite this

Namikoshi, M., Suzuki, S., Meguro, S., Nagai, H., Koike, Y., Kitazawa, A., ... Yamada, J. (2004). Manoalide derivatives from a marine sponge Luffariella sp. collected in Palau. Fisheries Science, 70(1), 152-158. https://doi.org/10.1111/j.1444-2906.2003.00783.x

Manoalide derivatives from a marine sponge Luffariella sp. collected in Palau. / Namikoshi, Michio; Suzuki, Shigeo; Meguro, Shiori; Nagai, Hiroshi; Koike, Yoshio; Kitazawa, Akira; Kobayashi, Hisayoshi; Oda, Taiko; Yamada, Junko.

In: Fisheries Science, Vol. 70, No. 1, 02.2004, p. 152-158.

Research output: Contribution to journalArticle

Namikoshi, M, Suzuki, S, Meguro, S, Nagai, H, Koike, Y, Kitazawa, A, Kobayashi, H, Oda, T & Yamada, J 2004, 'Manoalide derivatives from a marine sponge Luffariella sp. collected in Palau', Fisheries Science, vol. 70, no. 1, pp. 152-158. https://doi.org/10.1111/j.1444-2906.2003.00783.x
Namikoshi M, Suzuki S, Meguro S, Nagai H, Koike Y, Kitazawa A et al. Manoalide derivatives from a marine sponge Luffariella sp. collected in Palau. Fisheries Science. 2004 Feb;70(1):152-158. https://doi.org/10.1111/j.1444-2906.2003.00783.x
Namikoshi, Michio ; Suzuki, Shigeo ; Meguro, Shiori ; Nagai, Hiroshi ; Koike, Yoshio ; Kitazawa, Akira ; Kobayashi, Hisayoshi ; Oda, Taiko ; Yamada, Junko. / Manoalide derivatives from a marine sponge Luffariella sp. collected in Palau. In: Fisheries Science. 2004 ; Vol. 70, No. 1. pp. 152-158.
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