Axinellida

Tetractinomorpha Axinellida Axinellidae Axinella Naples, Italy c15 [1]... 

Rudi, A. Yosief, T. Schl er, M. Kashman, Y. (1999B) Several new isoprenoids from two marine sponges of the family Axinellidae. Tetrahedron, 55, 5555-66. 

Over half of the compounds reported for lithistid sponges were isolated from Theonella (family Theonellidae). Theonella species have been reported to contain a wide variety of cyclic and linear peptides and polyketides, as well as 3-alkyl piperidine derivatives nearly identical to those reported from the order Haplosclerida.58 There is also a single report of cyano- and isothiocyano-sesquiter-penes similar to those isolated from Axinellidae (order Halichondrida).42 Bewley et al. performed a cellular localization study on Theonella swinhoei in which several types of microorganisms were separated from the sponge cells. Chemical analysis of the extracts from the separated cells indicated that the bicyclic peptide theopalauamide was found exclusively in filamentous bacteria while the polyketide swinholide A was localized to a mixed population of unicellular bacteria.59... 

Axinellidae Acanthella Auletta Axinella Cymbastela Dragmacidon Homaxinella Phakellia Phycopsis Pseudaxinella Ptilocaulis Stylotella Teichaxinella... 

This class of compounds is extensively described in Chapter 10. Oroidin (64) is considered the precursor in the elaboration of polycyclic CjjNs oroidin derivatives isolated from sponges belonging to the Axinellidae and Agelasidae families. These include the antiangiogenic compounds agelastatin A (65) and ageladine A (70). 

The pyrrole-imidazole alkaloids, mainly isolated from various species of the Agelasidae, Axinellidae, Dyctionellidae, and Hymeniacidonidae sponge famihes, contain characteristic pyrrole-2-carboxamide and 2-aminoimidazoline moieties or derivatives thereof. Their architectural complexity ranges from simple, achiral, monomeric oroidin to the 16-stereocenter-containing tetrameric stylissadines A and B (Fig. 9.4). Because many reviews have appeared describing these alkaloids [52-56], we provide only a short discussion of some biosynthetically and synthetically pertinent information. 

According to Hooper (2000) and Hooper and Van Soest (2002a). Previously assigned to the family Axinellidae, this genus is now assigned to Suberitidae (Hadromerida) according to Systema Porifem. 

Unlike A-nor steroids, which occur mainly in the family Axinellidae, sterols with polymethylated side chains are present in most orders, espedally Haplosderida and Ver-ongida, but also Astrophorida, Spirophorida, Halichondrida and Dictyoceratida (see below). 

The nitrogenous sesqui- and diterpenes are common in the order Axinellida, but they have also been found among Astrophorida. These are sesquiterpenoids, nor-sesquiter-penes and diterpenes associated with various types of nitrogen-containing molecules, and they may constitute a particular category of meroterpenes. 

These derivatives are interesting insofar as this category of nitrogen terpenes, which possess functional isothiocyanate and N-formylamino groups, is common in sponges of the family Axinellidae (Hahchondrida). The only notable difference is that Axinellidae almost always contain the corresponding isonitrile derivative, whereas this does not seem to have been identified so far in any member of the Lithistida. 

The incorporation of labeled histidine and proline in cell cultures of the species Teichaxinella morchella (Axinellidae, Hahchondrida) showed that the biosynthesis of certain pyrrole-imidazole alkaloids involved both of the precursors shown in Figure 19.46 (Andrade et al, 1999). These precursors, together or separately, lead to 15 different heterocyclic systems (Al Mourabit and Potier, 2001). 

In the classification of Bergquist (1978), order Halichondrida comprises the two families Halichondriidae and Hymenia-cidonidae, in that of Hooper (2000) it has four - Axinellidae, Desmoxyidae, DictyoneHidae and Halichondriidae - and in Systema Porifera, it has five - the four present in Hooper s scheme and the newfamily Bubariidae. As we have already... 

The study of the secondary metabolites of Halichondrida mainly concerns the families Axinellidae and Halichondriidae, which accormt for more than 90% of publications (850 out of 890) and isolated structures (860 out of 920). Within these two families, a few genera have been and continue to be studied, such as Axinella, Acanthella, PhakeUia and Ptilocaulis in the Axinellidae and Halichon-dria, Hymeniacidon, Axinyssa and Topsentia in the Halichondriidae. 

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