Isolation of araguspongine M, a new stereoisomer of an Araguspongine/ Xestospongin Alkaloid, and dopamine from the marine sponge Neopetrosia exigua collected in Palau

Hongwei Liu, Yuri Mishima, Takeshi Fujiwara, Hiroshi Nagai, Akira Kitazawa, Yuji Mine, Hisayoshi Kobayashi, Xinsheng Yao, Junko Yamada, Taiko Oda, Michio Namikoshi

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Abstract

A new stereoisomer of an araguspongine/xestospongin alkaloid, named araguspongine M (1), has been isolated together with 12 known compounds, araguspongines B (2) and D (3), dopamine, three galactosyl diacylglycerols, 24-methyl cholesterol, 5,6-dihydrocholesterol, β-sitosterol, and three 5α,8α-epidioxy sterols (11-13), from the marine sponge Neopetrosia exigua (formerly Xestospongia exigua) collected in Palau. The structure of 1 was assigned on the basis of its spectral data analysis. This is the first report on the isolation of dopamine from a marine sponge. This compound may be produced by an endosymbiotic Synechococcus-like cyanobacterium. Compounds 1-3 and 11-13 showed cytotoxicity against HL-60 at IC50's of 5.5, 5.5, 5.9, 22.4, 9.5, and 9.6 μM, respectively. The possible biosynthesis origin of the isolated metabolites is discussed.

Original languageEnglish
Pages (from-to)154-163
Number of pages10
JournalMarine Drugs
Volume2
Issue number4
DOIs
Publication statusPublished - 2004 Jan 1

Keywords

  • Araguspongine/xestospongin alkaloid
  • Cytotoxicity
  • HL-60
  • Marine sponge
  • Neopetrosia exigua

ASJC Scopus subject areas

  • Drug Discovery

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    Liu, H., Mishima, Y., Fujiwara, T., Nagai, H., Kitazawa, A., Mine, Y., Kobayashi, H., Yao, X., Yamada, J., Oda, T., & Namikoshi, M. (2004). Isolation of araguspongine M, a new stereoisomer of an Araguspongine/ Xestospongin Alkaloid, and dopamine from the marine sponge Neopetrosia exigua collected in Palau. Marine Drugs, 2(4), 154-163. https://doi.org/10.3390/md204154