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Mar. Drugs 2004, 2(4), 154-163; doi:10.3390/md204154

Article

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 ^1,4 , Yuri Mishima ¹ , Takeshi Fujiwara ¹ , Hiroshi Nagai ¹ , Akira Kitazawa ¹ , Yuji Mine ¹ , Hisayoshi Kobayashi ² , Xinsheng Yao ^3,4 , Junko Yamada ⁵ , Taiko Oda ⁵  and Michio Namikoshi ^1,*

¹ Department of Ocean Sciences and T/R Vessel Shin’yo Maru, Tokyo University of Marine Science and Technology, Minato-ku, Tokyo 108-8477, Japan ² Institute of Molecular and Cellular Biosciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-0032, Japan ³ Department of Natural Products, Shenyang Pharmaceutical University, Wenhua Road 103, Shenyang 110016, People’s Republic of China ⁴ Traditional Chinese Medicines and Natural products Research Center, Tsinghua Campus, The University Town, Shenzhen 518055, People’s Republic of China ⁵ Kyoritsu College of Pharmacy, Minato-ku, Tokyo 105-8512, Japan

* Author to whom correspondence should be addressed.

Received: 3 August 2004 / Accepted: 22 September 2004 / Published: 25 November 2004

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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.

Keywords: Marine sponge; Neopetrosia exigua; araguspongine/xestospongin alkaloid; cytotoxicity; HL-60

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