A mass spectrometry (MS)-guided isolation has led to the purification of a new cyanobactin, wewakazole B (1), along with the known compound curacin D from a Red Sea Moorea producens. The planar structure of 1 was elucidated using a combination of NMR and MS techniques. After ozonolysis and acid hydrolysis, the absolute configurations of the amino acid components of 1 were determined by chiral-phase LC-MS and HPLC analyses. Notably, compound 1 exhibited cytotoxic activity toward human MCF7 breast cancer cells (IC50 = 0.58 μM) and human H460 lung cancer cells (IC50 = 1.0 μM) and was also found to be inactive in a siderophore assay.
A previously undescribed larval settlement-inducing protein was purified from adult extracts of the barnacle, Balanus amphitrite (=Amphibalanus amphitrite). Results of SDS-PAGE indicated that the relative molecular mass of the protein in reduced and denatured form is 31,600 +/- 500 kDa, and that it is distinct from the Settlement Inducing Protein Complex (SIPC) which has previously been determined as a larval settlement-inducing pheromone. The N-terminal 33-residue sequence of the intact protein showed no similarity with previously reported proteins in the EMBL/Genbank/DDBJ databases. The purified protein at a concentration of 10 microg ml(-1) induced approximately four times more larval settlement than the control (filtered natural seawater). In addition, results of the assay using both 24-well polystyrene plates and agarose gels indicated that this protein is probably released into seawater and attracts cypris larvae. These results suggest that the purified protein is a waterborne type pheromone which induces settlement of larvae of B. amphitrite.
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 on hydrogels and PDMS elastomer compared with the polystyrene control. The low settlement on gels is most likely due to the 'easy release' of initially attached cyprids from the gel surfaces. This low adhesion of cyprids is independent of surface hydrophilicity or hydrophobicity, and of surface charge. The results also revealed that hydrogels can be categorized into two groups. One group showed an extremely strong antifouling (AF) performance that was independent of the elasticity (E) or swelling degree (q) of the gels. The second group showed relatively less strong AF performance that was E- or q-dependent. In the latter case, E, rather than the q, may be the more important factor for cyprid settlement.
Natural antifouling products have been the subject of considerable attention. We screened marine algae for antifouling activity and discovered omaezallenes, the new bromoallene-containing natural products isolated from the red alga Laurencia sp. Described is the isolation, structure elucidation, and total syntheses of omaezallenes. The relative and absolute configurations of natural omaezallenes were unambiguously established through total synthesis. The antifouling activities and ecotoxicity of omaezallenes were also evaluated.
In this paper, settlement, metamorphosis, and long term growth of barnacle on soft substrates with a wide elasticity range (modulus 0.01-0.47 MPa) as well as with the variation of wettability were investigated for the first time in vitro, in the laboratory environment. Tough double-network (DN) hydrogels and polydimethylsiloxane (PDMS) were used as the soft hydrophilic substrates and hydrophobic substrates, respectively, and polystyrene (PS), a hard and hydrophobic substrate, was used as a control. It was observed that 1) the initial settlement and metamorphosis of cyprid larvae dramatically increases with the substrate elastic modulus while does not show an explicit dependence on the substrate wettability; 2) the growth rate of barnacles on both DN gels and PDMSs does not show an explicit dependence on the elasticity of the soft substrates, while it shows a slightly higher value on the hydrophobic PDMSs than on the hydrophilic DN gels; 3) the growth rate on these soft substrates is explicitly lower than that on the rigid PS substrate at the late state of the growth; 4) the "selfrelease" phenomenon of barnacles was observed for PDMS substrate with modulus higher than 0.01 MPa. Based on these observations, the antifouling effects of the soft substrates on barnacles were discussed.
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