Ircinia sp.

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>,... 

A Californian sponge of the Halichondriidae family contained a sulfated sesterterpene hydroquinone and five sulfated sesterterpenes. The structures of the halisulfates 1-5 (359-363) were determined by interpretation of spectral data and a structure was proposed for halisulfate 6 (364). The halisulfates are antimicrobial and antiinflammatory [318]. The absolute configuration of halisulfate 3 (361), which was also isolated from Ircinia sp. from the Philippines, has been determined by application of the chiral amide method and by chemical degradation techniques [319]. Halisulfate 7 (365) is a sesterterpene sulfate from a Coscinoderma sp. from Yap, Micronesia [320]. 

A heptaprenylhydroquinone derivative (402) was isolated from an Indian sample of Ircinia fasciculata [341]. Ircinia spinulosa from the Adriatic contained three sulfated 2-prenylhydroquinones (403-405) that are toxic to brine shrimp [342]. An Ircinia sp. from New Caledonia contained a sulfated 2-prenylhydroquinone (406) and a sulfated furanoterpene (407) [343]. An Australian Sarcotragus sp. contained octaprenylhydroquinone sulfate (408) and nonaprenylhydroquinone sulfate (409) as inhibitors of al,3 fucosyltransferase VH [344]. 

Irciniasulfonic acid (629) was obtained from Ircinia sp. from Japanese waters. Spectroscopic and chemical analyses revealed it to consist of three different kinds of acids common fatty acids, a novel unsaturated branched CIO fatty acid and an isethionic acid. Irciniasulfonic acid (629) reverses multidrug resistance in human carcinoma cells caused by overexpression of membrane glycoprotein [498]. 

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... 

Genus Ircinia Nardo Ircinia sp. Undetermined Palau 17, 18 [46]... 

Ircinamine Ircinia sp. Activity is expected based on the reactivity of the thioester moiety... 

Strobel and co-workers isolated haterumalide NA/oocydin A (2) from bacteria Sermtia marcescens [10]. Haterumalide NA was also obtained from a soil bacterium [11]. The isolation of similar compounds from two unrelated invertebrates such as the ascidian Lissoclinum sp. and the sponge of Ircinia sp., and the microorganisms, supports the potential microbial origin of haterumalides [12-15]. Although more than 200 marine macrolides have been recorded since the first isolation of the aplysiatoxins, halogenated marine macrolides are rarely found [16, 17]. 

Less common are those examples of this class of compound in which the tetronic acid moiety is nonconjugated. Palinurin (10a) was the first example of this class of compound, isolated from I. variabilis [37]. Subsequently, from an Australian Ircinia sp. was isolated a hydro derivative (11) of palinurin, which inhibits the growth of B. subtilis [38]. 

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

Ingeniously, Baldwin and Whitehead proposed a hypothetical pathway for the biosynthesis of manzamine alkaloids. According to this scheme the compound is formed by the condensation of three different building blocks ammonia, acrolein and two equivalents of a ten carbon unsaturated dialdehyde. Several aspects of this proposed route have been supported by the discovery of a precursor called ircinal A, a constituent of Ircinia sp. 

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). 

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