Molecular evidence of cryptic speciation in the "cosmopolitan" excavating sponge Cliona celata (Porifera, Clionaidae).

Over the past several decades molecular tools have shown an enormous potential to aid in the clarification of species boundaries in the marine realm, particularly in morphologically simple groups. In this paper we report a case of cryptic speciation in an allegedly cosmopolitan and ecologically important species-the excavating sponge Cliona celata (Clionaidae, Hadromerida). In the Northeast Atlantic and Mediterranean C. celata displays a discontinuous distribution of its putative growth stages (boring, encrusting, and massive) leading us to investigate its specific status. Phylogenetic reconstructions of mitochondrial (COI, Atp8) and nuclear (28S) gene fragments revealed levels of genetic diversity and divergence compatible with interspecific relationships. We therefore demonstrate C. celata as constituting a species complex comprised of at least four morphologically indistinct species, each showing a far more restricted distribution: two species on the Atlantic European coasts and two on the Mediterranean and adjacent Atlantic coasts (Macaronesian islands). Our results provide further confirmation that the different morphotypes do indeed constitute either growth stages or ecologically adapted phenotypes as boring and massive forms were found in two of the four uncovered species. We additionally provide an overview of the cases of cryptic speciation which have been reported to date within the Porifera, and highlight how taxonomic crypsis may confound scientific interpretation and hamper biotechnological advancement. Our work together with previous studies suggests that overconservative systematic traditions but also morphological stasis have led to genetic complexity going undetected and that a DNA-assisted taxonomy may play a key role in uncovering the hidden diversity in this taxonomic group.

New terpenoids from two Indonesian marine sponges.

A C16 norsesterterpenoid (euplectellodiol, 1) and a norditerpenoid (2) have been isolated from the marine sponges Mycale euplectelloides and Diacarnus megaspinorhabdosa, respectively. Their structures have been determined by spectroscopic methods. Compounds 1 and 2 are new natural products.

Speculation with spiculation?--Three independent gene fragments and biochemical characters versus morphology in demosponge higher classification.

Demosponge higher-level systematics is currently a subject of major changes due to the simplicity and paucity of complex morphological characters. Still, sponge classification is primarily based on morphological features. The systematics of the demosponge order Agelasida has been exceptionally problematic in the past. Here, we present the first molecular phylogenetic analysis based on three partially independent genes in demosponges in combination with a comprehensive search for biochemical synapomorphies to indicate their phylogenetic relationships. We show how sponges with fundamentally different skeletons can be in fact closely related and discuss examples of the misleading nature of morphological systematics in sponges.

A new C-20 polyacetylene from the sponge Callyspongia pseudoreticulata.

The Indonesian marine sponge Callyspongia pseudoreticulata was found to contain (3S,18S,4E,16E)-eicosa-1,19-diyne-3,18-diol-4,16-diene (1), the structure of which was determined by detailed spectroscopic analysis. Its absolute configuration was established using the modified Mosher's method after esterification of the secondary alcohols with Mosher's reagent.

Cellular location of (2R, 3R, 7Z)-2-aminotetradec-7-ene-1, 3-diol, a potent antimicrobial metabolite produced by the Caribbean sponge Haliclona vansoesti.

The Caribbean sponge Haliclona vansoesti has been found to contain large amounts of a new sphingosine derivative, (2R, 3R, 7Z)-2-aminotetradec-7-ene-1, 3-diol (compound 1). To determine the localization of this compound within the organism, cell distribution and quantitative determination of the aminodiol content of cell fractions obtained by differential centrifugation have been performed. Results show that choanocytes and archaeocytes are the major sponge cell types and that H. vansoesti harbour small photosynthetic symbionts (cyanobacteria) and few heterotrophic bacteria. Reverse-phase HPLC analyses of the cell fractions reveal that the aminodiol 1 is not associated with the prokaryotic endobionts but with the sponge cells, in particular the archaeocytes. This is clearly established by the positive significant correlation existing between the numbers of archaeocytes and the amounts of aminodiol 1. The mean aminodiol concentration is estimated to be 2 microg/10(5) archaeocytes. The aminodiol 1 is also found in substantial amounts in primary cell cultures, so that cell culture can be envisaged as an option for its production. Sponge cell suspensions display potent antibacterial and antiyeast activities, in correlation with their aminodiol content, indicating that this compound is at least in part responsible for these activities in the sponge. The release of the aminodiol I into the external medium suggests that this substance may be involved in the defence mechanisms of the sponge.

New antifeedant bromopyrrole alkaloid from the Caribbean sponge Stylissa caribica.

In this first report on the chemistry of the sponge Stylissa caribica, two known bromopyrrole metabolites and a new compound, N-methyldibromoisophakellin (1), were isolated and identified. The structure of 1 was determined using spectroscopic methods and the computer program COCON. N-Methyldibromoisophakellin (1) was shown to be the only secondary metabolite in Stylissa caribica that, at its natural concentration, is active as a feeding deterrent against a common omnivorous reef fish.

Dactyloquinones A and B, new sesquiterpenoid quinones from the Okinawan marine sponge Dactylospongia elegans.

Structurally unique new sesquiterpenoid quinones dactyloquinone A (1) and B (2), each possessing a dihydropyran moiety, were isolated from an Okinawan sponge Dactylospongia elegans, along with known sesquiterpenoid quinones. The structures of these compounds were determined by spectroscopic analysis.

Four new bioactive pyrrole-derived alkaloids from the marine sponge Axinella brevistyla.

Four new alkaloids (1-4) were isolated from the marine sponge Axinella brevistyla, and their structures were determined on the basis of spectroscopic analysis. The alkaloids 1-4 were antifungal against the yeast Saccharomyces cerevisiae at <1.0, <1.0, 30, and 100 microg/disk, respectively. Compounds 1-3 also exhibited cytotoxicity against L1210 cells with IC(50) values of 1.1, 0.66, and 2.5 microg/mL, respectively.

A new quinolizidine alkaloid from the Papua New Guinean sponge Xestospongia exigua.

A new bis-quinolizidine alkaloid, xestosin A (1), possessing cis- and trans-quinolizidine nuclei, has been isolated from the Papua New Guinean sponge Xestospongia exigua. The structure was determined by spectrometric and single-crystal X-ray analyses.

Hachijodines A-G: seven new cytotoxic 3-alkylpyridine alkaloids from two marine sponges of the genera Xestospongia and amphimedon.

Seven cytotoxic 3-alkylpyridine alkaloids, hachijodines A-G, have been isolated from two marine sponges of the genera Xestospongia and Amphimedon. Their structures were determined on the basis of spectral data. These alkaloids are moderately cytotoxic against P388 murine leukemia cells with IC(50) values of 1.0-2.3 microg/mL.

An antimicrobial C(14) acetylenic acid from a marine sponge Oceanapia species.

A C(14) acetylenic acid has been isolated as an antimicrobial principle from a marine sponge Oceanapia sp. Its structure was determined on the basis of spectral data.

New sesquiterpene/quinones from two sponges of the genus Hyrtios.

Two sponges of the genus Hyrtios have been found to contain new sesquiterpene/quinones identified by detailed spectroscopic analysis. Four new compounds with a 4,9-friedodrim-3-ene skeleton [hyrtiophenol (2), 5-epihyrtiophenol (3), 18-hydroxy-5-epihyrtiophenol (4), and 18-hydroxyhyrtiophenol (5)] were isolated from Hyrtios sp. (Seychelles Islands) along with isospongiaquinone (1). Moreover, the new compound 21-hydroxy-19-methoxyarenarone (8), which bears the 4, 9-friedodrim-4(15)-ene skeleton, was isolated from Hyrtios tubulatus (Curaçao) along with arenarol (6) and 5-epiilimaquinone (7). Assignment of the (13)C NMR signals of four types of 4, 9-friedodrimene skeletons found in sponges is presented.

Novel polycyclic guanidine alkaloids from two marine sponges of the genus Monanchora.

Two marine sponges of the genus Monanchora (Poecilosclerida, Crambeidae) have been found to contain new polycyclic guanidine alkaloids bearing the (5,6,8b)-triazaperhydroacenaphthylene skeleton. Their structures have been determined by detailed spectroscopic analysis. Dehydrobatzelladine C (1) has been isolated from M. arbuscula and crambescidins 359 (2) and 431 (3) from M. unguiculata. The chemotaxonomic implications of these findings are discussed.

New bromopyrrole alkaloids from the Indopacific sponge Agelas nakamurai.

Two new dimeric bromopyrrole alkaloids, nakamuric acid (1) and its corresponding methyl ester (2), have been isolated from the Indopacific sponge Agelas nakamurai along with the known metabolites sceptrin (3), debromosceptrin (4), and ageliferin (5). Their structures were identified by analysis of spectral data. All compounds inhibited the growth of several Gram-positive and Gram-negative bacteria in the agar plate diffusion assay.

Aurantosides D, E, and F: new antifungal tetramic acid glycosides from the marine sponge Siliquariaspongia japonica.

Aurantosides D-F (4-6), new polyene tetramic acids comprising an N-trisaccharide unit, have been isolated from the marine sponge Siliquariaspongia japonica. Their structures were determined by spectral and chemical methods. A reinvestigation of NMR data of the previously isolated aurantosides A and B led to revision of the geometry of the terminal double bond. Aurantosides exhibit potent antifungal activity against Aspergillus fumigatus and Candida albicans.

New alkaloids from the indopacific sponge Stylissa carteri.

Two samples of the marine sponge Stylissa carteri collected in Indonesia yielded two new bromopyrrole alkaloids: debromostevensine (1) and debromohymenin (2), as well as nine other known congeners (3-11). The structures of the new compounds were unambiguously established on the basis of their NMR and mass spectra.

Tokaramide A, a new cathepsin B inhibitor from the marine sponge Theonella aff. mirabilis.

A new cathepsin B inhibitor, tokaramide A (1) has been isolated from the marine sponge Theonella aff. mirabilis. Its structure was determined by spectroscopic and chemical methods. Tokaramide A inhibits cathepsin B with an IC50 value of 29.0 ng/mL.

Acanthosterol sulfates A-J: ten new antifungal steroidal sulfates from a marine sponge Acanthodendrilla sp.

Ten new steroidal sulfates, acanthosterol sulfates A-J (1-10), have been isolated from a marine sponge, Acanthodendrilla sp., collected in western Japan. Acanthosterol sulfates I and J (9 and 10) showed antifungal activity against the yeast Saccharomyces cerevisiae A364A and its mutants at 0.1 mg/disk.