Ircinia sponges

Bifiilco, G. Bruno, I. Minale, L. Riccio, R. Debitus, C. Bourdy, G. Vassas, A. Lavayre, J. (1995B) Bioactive prenyIhydroquinone sulfates and a novel C3 j furanoterpene alcohol sulfate from the marine sponge Ircinia sp. J. Nat. Prod., 58, 1444-9. 

The chemistry of fiiians and benzofurans was a Held of lively research in the last year. There are a number of reasons for this activity. The furan ring system - both in its native as well as in its reduced form - occurs in a great number of natural products and a wide variety of these compounds has been isolated from natural sources. This subject is treated regularly with care and accuracy in Heterocycles and will not be repeated here. Therefore only a few examples will be given in this chapter. Several new furan derivatives were isolated from natural sources (-)-wistarin 1 from the marine sponge Ircinia sp. <99TA3869>,... 

Pallela, R., Bojja, S., and Janapala, V. R. (2011). Biochemical and biophysical characterization of collagens of marine sponge, Ircinia fusca (Porifera Demospongiae Irciniidae). Int. J. Biol. Macromol. 49, 85-92. 

The medicinal terrestrial plant Turraea pubescens has yielded turrapubesin A (637) (742), and the Okinawan sponge Ircinia sp. contains the new furanoses-terterpenes 638 and 639 (743). An Aspergillus sp. culture has yielded ICM0301C (640) and ICM0301D (641), along with several nonchlorinated analogs (744, 745). 

Issa HH, Tanaka J, Higa T (2003) New Cytotoxic Furanosesterterpenes from an Okinawan Marine Sponge, Ircinia sp. J Nat Prod 66 251... 

Takada N, Sato H, Suenaga K, Arimoto H, Yamada K, Ueda K, Uemura D (1999) Isolation and Structures of Haterumalides NA, NB, NC, ND, and NE, Novel Macrolides from an Okinawan Sponge Ircinia sp. Tetrahedron Lett 40 6309... 

Marin, A., Lopez Belluga, M.D., Scognamiglio, G., and Cimino, G., Morphological and chemical camouflage of the Mediterranean nudibranch Discodoris indecora on the sponges Ircinia variabilis and Ircinia fasciculata, J. Moll. Stud., 63, 431, 1997. 

The sponge Ircinia fefix from Columbia has yielded ten fatty acid esters (18R)-variabilin-l 1-methyloctadecanoate, (7 , 12 , 18R,20Z)-variabilin (5Z,9Z)-22-mclhyllricosadienoate, (7 ,12 ,18R,20Z)-variabilin (5Z,9Z)-tetra-... 

HexaprenyIhydroquinone Onchidium sp. Sponge, Ircinia sp. HlV-1, -2, murine leukemia virus HIV-RT [226]... 

Ircinal B (70) and Ircinol B (71). The tetracyclic precursors of 65-69, ircinal B (70) [65] and ircinol B (71) [68], were isolated from two different Okinawan sponges, Ircinia sp. and Amphimedon sp., respectively. Surprisingly, the alcohol congener possessed the opposite absolute configuration to that of ircinal B and the aforementioned manzamine related alkaloids. Halicyclamines A (72) and B (73), halyclonacyclamines A... 

Ircinals A and B from the Okinawan Marine Sponge Ircinia sp. Plausible Biogenetic Precursors of Manzamine Alkaloids. Kondo, K. Shigemori, H. Kikuchi, Y. Ishibashi, M. Sasaki, T. and Kobayashi, J. J. Org. Chem. 1992, 57, 2480. 

Alkaloid from the Okinawan marine sponge Ircinia sp. Exhibits cytotoxicity against HeLa cells in vitro. Powder. [a]2i + 15.0 (c, 0.27 in MeOH). 

Ircinin-4 is part of a family of furanoterpenes, produced by the Mediterranean sponges Ircinia oros and /. fasciculata, that exhibit high activity in the brine shrimp assay and turn out to be selective inhibitors of phospholipase A2. The first total synthesis was recently described by Furstner et al. and was based on the Pd-catalyzed opening of vinyloxirane (Scheme 21) employing the Tsuji-Trost conditions. Treatment of the epoxide 108, obtained from the reaction of 3-furyl-acetaldehyde with a sulfur ylide, with catalytic amounts of... 

Isol. from the sponge Ircinia strobilina and a Sarcotragus sp. Plant phytoalexin with antibiotic props. Oil. [a]u -4° (c, 1 in CHCI3). 255 nm (MeOH). 20E-Isomer [114761-90-9]. 

Cafieri, F., E. Fattorusso, C. Santacroce, and L. Minale Fasciculatin, a Novel Sesterterpene from the Sponge Ircinia fasciculata. Tetrahedron 28, 1579 (1972). 

CiMiNO, G., S. DE Stefano, L. Minale, and E. Fattorusso Ircinin-1 and -2, Linear Sesterterpenes from the Marine Sponge Ircinia oros. Tetrahedron 28, 333 (1972). 

Faulkner, D. J. Variabilin, an Antibiotic from the Sponge, Ircinia variabilis. Tetrahedron Letters 3821 (1973). 

Rothberg, I., and P. Shubiak The Structure of some Antibiotics from the Sponge Ircinia strobilina. Tetrahedron Letters 769 (1975). 

Gregson, R.P., and D. Ouvrier Wistarin, a Tetracyclic Furanosesterterpene from the Marine Sponge Ircinia wistarii. J. Nat. Prod. 45, 412 (1982). 

Pettit, G.R. etal. Antineoplastic agents. 520. Isolation and structure of irciniastatins A and B from the Indo-Pacific marine sponge Ircinia ramosa. J. Med. Chem. 47, 1149-1152(2004). 

Bacillus pumilus Sponge Ircinia sp. Bacircins 1-5 (cyclic depsipeptides) Cytotoxins Kalinovskaya eta/., 1995... 

Pseudomonas sp. (IM-1) Sponge, Ircinia muscarum Italy Cyclopeptides Mitova, Tommonaro, and De Rosa, 2003... 

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