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Marine Drugs | Free Full-Text | Isolation of Araguspongine M, a New Stereoisomer of an Araguspongine/Xestospongin alkaloid, and Dopamine from the Marine Sponge Neopetrosia exigua Collected in Palau

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Volume 2, Issue 4

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× Open AccessArticle Mar. Drugs 2004, 2(4), 154-163; [doi.org]

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 Full-Text   |   PDF [106 KB, uploaded 24 February 2015] No

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. View Full-Text Keywords: Marine sponge; Neopetrosia exigua; araguspongine/xestospongin alkaloid; cytotoxicity; HL-60 Marine sponge; Neopetrosia exigua; araguspongine/xestospongin alkaloid; cytotoxicity; HL-60 This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Liu, H.; Mishima, Y.; Fujiwara, T.; Nagai, H.; Kitazawa, A.; Mine, Y.; Kobayashi, H.; Yao, X.; Yamada, J.; Oda, T.; Namikoshi, M. Isolation of Araguspongine M, a New Stereoisomer of an Araguspongine/Xestospongin alkaloid, and Dopamine from the Marine Sponge Neopetrosia exigua Collected in Palau. Mar. Drugs 2004, 2, 154-163.

AMA Style

Liu H, Mishima Y, Fujiwara T, Nagai H, Kitazawa A, Mine Y, Kobayashi H, Yao X, Yamada J, Oda T, Namikoshi M. 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. 2004; 2(4):154-163.

Chicago/Turabian Style

Liu, Hongwei; Mishima, Yuri; Fujiwara, Takeshi; Nagai, Hiroshi; Kitazawa, Akira; Mine, Yuji; Kobayashi, Hisayoshi; Yao, Xinsheng; Yamada, Junko; Oda, Taiko; Namikoshi, Michio. 2004. "Isolation of Araguspongine M, a New Stereoisomer of an Araguspongine/Xestospongin alkaloid, and Dopamine from the Marine Sponge Neopetrosia exigua Collected in Palau." Mar. Drugs 2, no. 4: 154-163.

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