Abstract
Two new indole derivatives, 5-hydroxy-1H-indole-3-carboxylic acid ethyl ester (1) and 5-hydroxy-1H-indole-3-glyoxylate ethyl ester (2), and seven known indole alkaloids, dragmacidonamine B (3), gesashidine A (4), hyrtiosulawesine (5), hyrtiomanzamine (6), hyrtimomine D (7), hyrtiosine A (8), and 5-hydroxy-1H-indole-3-carbaldehyde (9), were isolated from a marine sponge Ircinia sp., Irciniidae, collected at Iriomote Island. The structures of 1 and 2 were elucidated on the basis of their spectroscopic data. Compound 1 has previously been reported as a synthetic intermediate and this is the first time that it has been obtained from a natural source.
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References
Blunt JW, Copp BR, Keyzers RA, Munro MH, Prinsep MR (2014) Marine natural products and previous reports in this series. Nat Prod Rep 31:160–258
Faulkner DJ (2002) Marine natural products and previous reports in this series. Nat Prod Rep 19:1–48
Skropeta D, Wei L (2014) Recent advances in deep-sea natural products. Nat Prod Rep 31:999–1025
Mehbub MF, Lei J, Franco C, Zhang W (2014) Marine sponge derived natural products between 2001 and 2010: trends and opportunities for discovery of bioactives. Mar Drugs 12:4539–4577
Pedpradab S, Edrada R, Ebel R, Wray V, Proksch P (2004) New β-carboline alkaloids from the Andaman Sea sponge Dragmacidon sp. J Nat Prod 67:2113–2116
Iinuma Y, Kozawa S, Ishiyama H, Tsuda M, Fukushi E, Kawabata J, Fromont J, Kobayashi J (2005) Gesashidine A, a β-carboline alkaloid with an imidazole ring from a Thorectidae sponge. J Nat Prod 68:1109–1110
Salmoun M, Devijver C, Daloze D, Braekman JC, van Soest RW (2002) 5-Hydroxytryptamine-derived alkaloids from two marine sponges of the genus Hyrtios. J Nat Prod 65:1173–1176
Bourguet-Kondracki ML, Martin MT, Guyot M (1996) A new β-carboline alkaloid isolated from the marine sponge Hyrtios erecta. Tetrahedron Lett 37:3457–3460
Tanaka N, Momose R, Takahashi Y, Kubota T, Takahashi-Nakaguchi A, Gonoi T, Fromont J, Kobayashi J (2013) Hyrtimomines D and E, bis indole alkaloids from a marine sponge Hyrtios sp. Tetrahedron Lett 54:4038–4040
Kobayashi J, Murayama T, Ishibashi M, Kosuge S, Takamatsu M, Ohizumi Y, Kobayashi H, Ohta T, Nozoe S, Sasaki T (1990) Hyrtiosins A and B, new indole alkaloids from the Okinawan marine sponge Hyrtios erecta. Tetrahedron Lett 46:7699–7702
Sauleau P, Martin MT, Dau ME, Youssef DT, Bourguet-Kondracki ML (2006) Hyrtiazepine, an azepino-indole-type alkaloid from the Red Sea marine sponge Hyrtios erectus. J Nat Prod 69:1676–1679
Bao B, Zhang P, Lee Y, Hong J, Lee CO, Jung JH (2007) Monoindole alkaloids from a marine sponge Spongosorites sp. Mar Drugs 5:31–39
Harriman GC, Kolz CN, Luly JR, Roth BD, Song Y, Trivedi BK (2000) Functionalized heterocycles as chemokine receptor modulators. PCT Int. Appl, WO (2000042045)
Lee YJ, Lee DG, Rho HS, Krasokhin VB, Shin HJ, Lee JS, Lee HS (2013) Cytotoxic 5-hydroxyindole alkaloids from the marine sponge Scalarispongia sp. J Heterocyclic Chem 50:1400–1404
Bu YY, Yamazaki H, Ukai K, Namikoshi M (2014) Anti-mycobacterial nucleoside antibiotics from a marine-derived Streptomyces sp. TPU1236A. Mar Drugs 12:6102–6112
Acknowledgments
This work was supported in part by the Foundation for Japanese Chemical Research to H.Y. We express our thanks to Dr. K. Ogawa of Z. Nakai Laboratory for identification of the marine sponge and to Mr. T. Matsuki and S. Sato for measurement of mass and NMR spectra.
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Abdjul, D.B., Yamazaki, H., Ukai, K. et al. Two new indole derivatives from a marine sponge Ircinia sp. collected at Iriomote Island. J Nat Med 69, 416–420 (2015). https://doi.org/10.1007/s11418-015-0891-y
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DOI: https://doi.org/10.1007/s11418-015-0891-y