A mass spectrometry (MS)-guided isolation has led to the purification of a new cyanobactin, wewakazole B (1), along with known compound curacin D from Red Sea Moorea producens. The planar structure 1 was elucidated using combination NMR and MS techniques. After ozonolysis acid hydrolysis, absolute configurations amino components were determined by chiral-phase LC-MS HPLC analyses. Notably, exhibited cytotoxic activity toward human MCF7 breast cancer cells (IC50 = 0.58 μM) H460 lung 1.0 also...

Barnacle (Balanus amphitrite) settlement on synthetic hydrogels with various chemical structures was tested in laboratory assays. The results demonstrated that cyprids settle less or not at all and PDMS elastomer compared the polystyrene control. low gels is most likely due to 'easy release' of initially attached from gel surfaces. This adhesion independent surface hydrophilicity hydrophobicity, charge. also revealed can be categorized into two groups. One group showed an extremely strong...

Abstract Natural antifouling products have been the subject of considerable attention. We screened marine algae for activity and discovered omaezallenes, new bromoallene‐containing natural isolated from red alga Laurencia sp. Described is isolation, structure elucidation, total syntheses omaezallenes. The relative absolute configurations omaezallenes were unambiguously established through synthesis. activities ecotoxicity also evaluated.

Six new compounds, omaezol, intricatriol, hachijojimallenes A and B, debromoaplysinal, 11,12-dihydro-3-hydroxyretinol have been isolated from four collections of Laurencia sp. These structures were determined by MS NMR analyses. Their antifouling activities evaluated together with eight previously known compounds the same samples. In particular, omaezol hachijojimallene showed potent (EC50 = 0.15-0.23 µg/mL) against larvae barnacle Amphibalanus amphitrite.

NMR- and MS-guided fractionation of an extract Okeania sp. marine cyanobacterium, collected from the Red Sea, led to isolation four new metabolites, including serinolamides C (1) D (2) lyngbyabellins O (3) P (4), together with three known substances F (5) G (6) dolastatin 16 (7). The planar structures compounds were determined using NMR MS analyses. absolute configurations 1 2 by Marfey's analysis their hydrolysates. configuration 3 was ascertained chiral-phase chromatography degradation...

Larval development and settlement of whale barnacles have not previously been described, unlike intertidal barnacles. Indeed, the mechanisms association between whales studied. Here we describe larval barnacle, Coronula diadema , possible involvement a cue from host in inducing settlement. Eight-cell stage embryos were collected C. on stranded humpback whale, incubated filtered seawater for 7 days, nauplius larvae hatched out. When fed with Chaetoceros gracilis nauplii developed to VI,...

The first enantioselective total synthesis of 10-isocyano-4-cadinene, a marine sesquiterpene isolated from nudibranchs the family Phyllidiidae, was achieved. cadinene is expected to be novel nontoxic antifouling agent. In synthesis, an intermolecular Diels−Alder reaction and SmI2-induced Barbier-type were employed as key steps. absolute configuration 10-isocyano-4-cadinene determined (1S, 6S, 7R, 10S) on basis synthesis. Antifouling activities against Balanus amphitrite with both enantiomers...

Isocyanide is a potential antifouling compound in marine environments. In this study, we investigated its mode of action three aquatic organisms. Two them, the bryozoan Bugula neritina and barnacle Balanus amphitrite, are major fouling invertebrates, other organism non-target species zebrafish Danio rerio. swimming larvae B. neritina, isocyanide did not affect total attachment rate (≤50 µg ml−1), but it change site by increasing percentage on bottom container rather than wall or air-water...

Cyanobacteria are reported as rich sources of secondary metabolites that provide biological activities such enzyme inhibition and cytotoxicity. Ten depsipeptide derivatives (lyngbyabellins) were isolated from a Malaysian Moorea bouillonii Red Sea Okeania sp.: lyngbyabellins G (1), O (2), P (3), H (4), A (7), 27-deoxylyngbyabellin (5), homohydroxydolabellin (6). This study indicated displayed cytotoxicity, antimalarial, antifouling activities. The compounds tested for cytotoxic effect against...

A new synthesis of 3-isocyanotheonellin, a marine sesquiterpene with potent antifouling activity against the larvae barnacle Balanus amphirite, and its analogues is described. The highlight synthetic strategy one-step construction tertiary isocyanide from an alcohol using trimethylsilyl cyanide silver salt. activities 3-isocyanotheonellin are also reported.

Twelve simple linear isocyanides were synthesized and examined for antifouling activity toxicity against cyprid larvae of the barnacle, Balanus amphitrite. Larval settlement was inhibited, with EC50 values 0.046-1.90 microg ml(-1), they much less toxic (LD50 ranging over 21.28 ml(-1)) than CuSO4 (EC50 0.30 ml(-1) LD50 2.95 ml(-1)). The data indicate that are promising non-toxic agents.

A previously undescribed larval settlement-inducing protein was purified from adult extracts of the barnacle, Balanus amphitrite (=Amphibalanus amphitrite). Results SDS-PAGE indicated that relative molecular mass in reduced and denatured form is 31,600 ± 500 kDa, it distinct Settlement Inducing Protein Complex (SIPC) which has been determined as a pheromone. The N-terminal 33-residue sequence intact showed no similarity with reported proteins EMBL/Genbank/DDBJ databases. at concentration 10...

A molecular based method for the quantitative detection of larvae golden mussel Limnoperna fortunei was developed. Partial nucleotide sequences mitochondrial cytochrome c oxidase subunit 1 (CO1) gene in several bivalve species including L. were analyzed. These and CO1 found habitats similar to (obtained from EMBL/Genbank/DDBJ databases) aligned. Based on these results, fortunei-specific primers designed amplification. DNA extracted subjected PCR using primers, amplification fragment...

In this paper, settlement, metamorphosis, and long term growth of barnacles on soft substrates with a wide elasticity range (modulus 0.01–0.47 MPa) as well the variation in wettability were investigated for first time vitro, laboratory environment. Tough double-network (DN) hydrogels polydimethylsiloxane (PDMS) used hydrophilic hydrophobic substrates, respectively, polystyrene (PS), hard substrate, was control. It observed that (1) initial settlement metamorphosis cyprid larvae dramatically...

The first enantioselective total synthesis of 10-isocyano-4-cadinene, a marine sesquiterpene isolated from nudibranchs the family Phyllidiidae, and determination its absolute stereochemistry were achieved. 10-Isocyano-4-cadinene is expected to be novel nontoxic antifouling agent. In synthesis, intermolecular Diels-Alder reaction samarium diiodide induced Barbier-type cyclization employed as key steps. configuration 10-isocyano-4-cadinene was determined (1S,6S,7R,10S) by comparison optical...

Twenty novel simple alkyl isocyanides derived from citronellol were synthesized and evaluated for their antifouling activity toxicity against cypris larvae of the barnacle, Balanus amphitrite. The anti-barnacle was in EC50 range 0.08–1.49 μg ml−1. Simple containing a benzoate chloro group showed most potent activity. In addition, none compounds significant LC50 values <10 LC50/EC50 ratios almost all >102. results indicate that these are promising low-toxicity agents.

The total synthesis of dolastatin 16, a macrocyclic depsipeptide first isolated from the sea hare Dolabella auricularia as potential antineoplastic metabolite by Pettit et al., was achieved in convergent manner. Dolastatin 16 reported Tan to exhibit strong antifouling activity, and thus shows promise for inhibiting attachment marine benthic organisms such Amphibalanus amphitrite ships submerged artificial structures. Therefore, is compound new, environmentally friendly material replace...

Ten novel isocyanocyclohexane compounds that possess an oxygenic functional group at the 4-position were synthesized and evaluated for their antifouling activity against larvae of barnacle Balanus amphitrite with aim exploring structure – relationships further. The anti-barnacle effect was in EC50 range 0.0096 17.0 μg ml−1. Some ester derivatives exhibited extremely high activities, none showed significant toxicity. results suggest function is one important groups expression potent isocyano...

An antifouling active natural compound, 3-isocyanotheonellin, and its analogues were synthesized evaluated for activity against the larvae of barnacle Balanus amphirite in order to explore structure-activity relationships. The anti-barnacle effect 3-isocyanotheonellin was EC 50 range 0.18-7.20 w g ml m 1 . Some exhibited potent as high 3-isocyanothoenllin, none isocyano compounds showed significant toxicity. results present study suggest that an group a hydrophobic site at suitable position...

Outbreaks of moon jellyfish Aurelia spp. are frequently reported from many parts the world's coastal areas. canonically show a metagenetic life cycle in which planulae transform into sessile polyps, can drastically increase number through asexual reproduction. Therefore, their reproduction has been recognized as one major causes outbreaks. also direct development that lacks during polyp stage, prevents us understanding mechanisms its To clarify seasonality and direct-development cycles sp....

Creation of new potent antifouling active compounds is important for the development environmentally friendly agents. Fifteen isocyanide congeners derived from proteinogenic amino acids were synthesized, and activity toxicity these against cypris larvae barnacle Balanus amphitrite investigated. All synthesized acid-isocyanides exhibited anti-barnacle with EC50 values 0.07 - 10.34 μg/ml after 120 h exposure without significant toxicity. In addition, seven showed more than 95% settlement...