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

doi:10.3390/md204154

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

Research output: Contribution to journal › Article › peer-review

32 Citations (Scopus)

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 language	English
Pages (from-to)	154-163
Number of pages	10
Journal	Marine Drugs
Volume	2
Issue number	4
DOIs	https://doi.org/10.3390/md204154
Publication status	Published - 2004
Externally published	Yes

Keywords

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

ASJC Scopus subject areas

Drug Discovery

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.3390/md204154

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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, vol. 2, no. 4, pp. 154-163. https://doi.org/10.3390/md204154

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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.",

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

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AU - Liu, Hongwei

AU - Mishima, Yuri

AU - Fujiwara, Takeshi

AU - Nagai, Hiroshi

AU - Kitazawa, Akira

AU - Mine, Yuji

AU - Kobayashi, Hisayoshi

AU - Yao, Xinsheng

AU - Yamada, Junko

AU - Oda, Taiko

AU - Namikoshi, Michio

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N2 - 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.

AB - 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.

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

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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