Ircinia

Pawlik, J. R., McFall, G., and Zea, S. (2002). Does the odor from sponges of the genus Ircinia protect them from fish predztors Journal of Chemical Ecology 28 1103-1115. 

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. 

Wright, A.E. McCarthy, P.J. Schulte, G.K. (1989) Sulfircin a new sesterterpene sulfate from a deep-water sponge of the genus Ircinia. J. Org. Chem., 54, 3472-4. 

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. 

Suvanine (358), an acetyl cholinesterase inhibitor was first isolated from species of Ircinia [316] and then later from a Coscinoderma species from Fiji and Palau when the structure was revised [317]. 

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]. 

Sulfircin (369), an antifungal sesterterpene sulfate was isolated as the iV,iV-dimethylguanidinium salt from a deepwater Ircinia species and its structure was determined by X-ray analysis [324]. Two sesterterpene sulfates, hipposulfates A (370) and B (371), were isolated from Hippospongia cf. metachromia from Okinawa and their structures were elucidated by interpretation of spectroscopic data. Both compounds possess an enolsulfate functionality [325]. 

Four unstable sulfate esters (373-376) of known furanosesterterpenes were obtained from Ircinia variabilis and from /. or os from the northern Adriatic Sea [328], The 22-O-sulfates of palinurin (377) and fasiculatin (378) were isolated from 7. variabilis and from /. fasiculata respectively. Both were toxic to brine shrimp [329]. Ircinianin sulfate (379) was isolated from /. (Psammocinia) wistarii from the Great Barrier Reef as a very unstable metabolite [330]. 

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]. 

The cyclic hexapeptide, waiakeamide (447) was isolated from an Indonesian collection of Ircinia dendroides [373]. Haliclona nigra from Papua New Guinea contained two cyclic hexapeptides, haligramides A (448) and B (449). They showed an unusual activity pattern in the National Cancer Institute (NCI) 60 cell-line panel [374],... 

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]. 

Fused tetracyclic and pentacyclic alkaloids constitute a relatively new class of natural products isolated mostly from ascidians and sponges. Cytotoxic, antimicrobial and antiviral activities have been reported for many of these compounds. The manzamine alkaloids, Fig. (33) are characterized by a complex pentacyclic diamine linked to C-l of P-carboline moiety. Manzamine have been isolated mainly from six different genera of marine sponges Haliclona, Pellina, Xestospongia, Ircinia, Pachypellin and Amphimedon. 

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... 

Psymberin (irciniastatin A), a cytotoxin of the pederin family, has been isolated from the marine sponges Psammocinia sp. and Ircinia ramosa. Its highly cytostatic... 

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-... 

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