Because of the eutrophication resulting from increasing anthropogenic activities, hypoxia (i.e. dissolved oxygen < 2.8 mg O2 L-1) is on the rise globally. The objective of this research was to understand more about the effects of hypoxia on the marine benthic communities. Particularly, it focused on the latent effects and indirect effects of hypoxia by investigating how early exposure to hypoxia affect the later life stage of a marine gastropod Crepidula onyx, and how hypoxia alter the bacterial composition of biofilms and the subsequent larval settlement of marine invertebrates. In the first study, the larvae of C. onyx were exposed to 2, 3, and 6 mg O2 l-1. Under low food concentration (Isochrysis galbana at 1 × 105 cells l-1), larvae in both hypoxic treatments (2 and 3 mg O2 l-1) required a longer time to become competent to metamorphose. But when they did, they had a similar size and total lipid content to the control larvae. Moreover, the latent effects of early hypoxic exposure on the juvenile growth were evident. After 2 weeks development in field, the growth rate, mean dry weight and filtration rate of juveniles were significantly reduced in the hypoxic treatments. However, there was no discernible effect on larvae or juveniles when the food concentration during the larval stage was doubled (I. galbana at 2 × 105 cells l-1), suggesting that the latent effects of hypoxia can be offset by larval access to high algal concentration. In the second study, the biofilms were exposed to hypoxia and normoxia in microcosms for up to 7 days, and their bacterial community composition was analysed by terminal-restriction fragment length polymorphism (T-RFLP). The results suggested that hypoxia altered the bacterial community structure within biofilms, and the difference between the hypoxia and normoxia treatments increased through the length of exposure period. The resulting changes in biofilms did not alter the larval settlement response of a model species (i.e. C. onyx) in laboratory assays. Nevertheless, when the biofilms were deployed in the field to allow natural larval settlement and recruitment, biofilms that had been exposed to hypoxia altered the overall larval settlement pattern of different marine invertebrates, potentially leading to a shift in the benthic invertebrate community. This research suggested that periodic hypoxic events and the resulting exposure of organisms to hypoxia during their early development might have effects that persist across the life history. Moreover, it highlighted the possibility that the effects of hypoxia on species composition and structure of benthic invertebrate communities might be mediated through changes in biofilms and subsequently larval settlement and recruitment. To conclude, this research demonstrated that hypoxia could affect the growth in the later life stages of marine invertebrates and the recruitment of the benthic communities. / published_or_final_version / Biological Sciences / Master / Master of Philosophy

Bibliography: leaves 278-288. / Microfiche. / xvii, 288 leaves, bound ill. (some col.), plates 29 cm

Thesis (M.S.)--Oregon State University, 2009. / Printout. Includes bibliographical references (leaves 48-51). Also available on the World Wide Web.

Thesis (Ph. D.)--Duke University, 2007. / Includes bibliographical references.

Thesis (Ph. D.)--Auburn University. / Abstract. Includes bibliographical references.

A study of the secondary metabolism of two nudibranchs and one soft coral has led to the isolation of eighteen new and two known secondary metabolites. The structures of all compounds were determined by a combination of the interpretation of spectral data, chemical degradations and interconversions, and single crystal x-ray diffraction analysis. The British Columbian dorid nudibranch Diaulula sandiegensis yielded two new steroidal metabolites, diaulusterols A (41) and B (42). The 25-(3-hydroxybutanoate) residue of diaulusterol A (41) and the 2α,3α-diol array of both 41 and 42 are not commonly encountered in naturally occurring steroids. Both metabolites exhibited considerable antibacterial and antifungal activity. Steroid 41 exhibited fish antifeedant activity. The relative concentration of 4.1 and 42 in the skin extracts of D. sandiegensis appears to be related to the animals' seasonal abundance. Extracts of the British Columbian soft coral Gersemia rubiformis yielded a series of ten diterpenes possessing cembrane (170-175), pseudopterane (167-169) and gersolane (176) carbon skeletons. The structure of an eleventh diterpene remains unresolved. In addition, the structure of a degraded diterpene possessing a 13-membered ring (177) is tentatively proposed. G. rubiformis represents the first example of a soft coral to yield pseudopterane diterpenes. The organism is the first to contain cembrane, pseudopterane and gersolane metabolites, a fact which has biogenetic implications. Two new sesquiterpenes were also isolated. Tochuinyl acetate (165) and dihydrotochuinyl acetate (166) represent the first examples of cuparane sesquiterpenes to be isolated from a soft coral. A biogenesis is proposed. Metabolite 166 exhibited fish antifeedant activity. Investigations of Gersemia rubiformis collected in Newfoundland waters revealed that the secondary metabolism differed from west coast specimens. The isolation of the new unstable sesquiterpene (+)-β-cubebene-3-acetate (178) resulted. Skin extracts of the dendronotoid nudibranch Toquina tetraquetra were examined in an attempt to correlate its feeding dependency and lack of predation to the presence of allomones. Metabolites 165, 166, 170, 179 and the new butanoate diterpene 180 could be traced to the coelenterates which make up the animal's diet. Tochuinyl acetate (165), dihydrotochuinyl acetate (166) and rubifolide (170) were previously found in extracts of Gersemia rubiformis. Ptilosarcenone (179) has been reported as one of the major metabolites of the sea pen Ptilosarcus gurneyi²¹³. The exact origin of a sixth metabolite, pukalide (63), remains unknown. It is proposed that Tochuina tetraquetra selectively sequesters dietary metabolites for defensive purposes. / Science, Faculty of / Chemistry, Department of / Graduate

Marine organisms show potential as sources for novel, biologically and pharmacologically active, secondary metabolites. Examination of three nudibranch and one bryozoan species for biologically active metabolites has led to the isolation and structural elucidation of nine new and two known secondary metabolites. The structures of all the compounds were determined by using a combination of spectral analysis, chemical interconversion, synthesis, and single-crystal X-ray diffraction analysis. The British Columbian dorid nudibranch Acanthodoris nanaimoensis yielded three new sesquiterpenoids. The structures of nanaimoal (61) , acanthodoral (64) , and isoacanthodoral (65) represent novel sesquiterpenoid carbon skeletons. The natural mixture of aldehydes 61, 64, and 65 exhibited antibacterial and antifungal activity. From Aldisa cooperi, two ∆⁴-3-ketosteroidal acids 23 and 24, and glycerol ether 25 were isolated. Acid 23 showed feeding deterrent activity against fish. The dendronotid nudibranch Meli be leonina gave 2,6-dimethy1-5-heptenal 53 and 2,6-dimethyl-5-heptenoic acid 54. The aldehyde 53 was responsible for the "grapefruit like" odour of the nudibranch. The bryozoan Phidolopora pacifica was examined in an attempt to correlate the absence of surface fouling, in the field, with the presence of biologically active secondary metabolites. The purine alkaloids 179 and 180, which contain the rare naturally occurring nitro functionality, were responsible for much of the antifungal and antialgal activity of the crude extracts. Three nitrophenols 181, 189, and 209 were also isolated from P. pacifica. Nitrophenol 181 had been previously shown to inhibit chloroplast development both in green plants and in the unicellular algae Euglena sp. / Science, Faculty of / Chemistry, Department of / Graduate

Thesis (Ph. D.)--University of Washington, 1990. / Vita. Includes bibliographical references (leaves [215]-237).

A presente investigação teve por objetivo o isolamento de metabólitos secundários biologicamente ativos de nudibrânquios, moluscos conhecidos por produzirem ou acumularem substâncias a partir de suas presas. Foram investigados extratos de quatro espécies de nudibrânquios marinhos juntamente com suas respectivas presas. Além disso, também foi investigado o extrato ativo da esponja marinha Agelas sventres. O estudo realizado com o extrato bruto da esponja marinha Agelas sventres levou ao isolamento de uma série de alcalóides bromopirrólicos, compostos tipicamente encontrados em esponjas do gênero Agelas. Dentre os compostos isolados, a oroidina apresentou atividade inibitória frente à enzima Pdr5p de Saccharomyces cerevisiae. O estudo do nudibrânquio Tambja stegosauriformis e de sua presa, o briozoário Bugula sp., levou ao isolamento de diversos alcalóides da classe das tambjaminas. As tambjaminas C, D, K e o produto de hidrólise da tambjamina B foram observados nos dois animais; o produto de hidrólise da tambjamina A foi encontrado apenas no extrato do nudibrânquio, enquanto que a tambjamina A e um isômero da tambjamina J foram encontrados apenas no extrato do briozoário. O estudo do nudibrânquio Okenia zoobotryon e de sua presa, o briozoário Zoobotryon verticillatum, resultou no isolamento de um único alcalóide indólico conhecido, 2,5,6-tribromo-Nmetilgramina, presente nos dois animais. Resultados semelhantes foram obtidos a partir da investigação do extrato do nudibrânquio Hypselodoris lajensis e de sua presa, uma esponja do gênero Dysidea, com o isolamento de um único diterpeno, a lactona da furodisinina. Embora ambas substâncias sejam conhecidas, este foi o primeiro isolamento destes compostos a partir de espécies de nudibrânquios. Finalmente, a partir do extrato do nudibrânquio Pleurobranchus areolatus foram isoladas duas novas dicetopiperazinas modificadas, estruturalmente semelhantes às rodriguesinas A e B, outras dicetopiperazinas isoladas a partir da ascídia Didemnum sp., provável presa desta espécie de nudibrânquio. Vale ressaltar a utilização de análises por LC-UV-MS e MS/MS neste trabalho, que auxiliaram na identificação uma série de compostos presentes nos extratos estudados no presente trabalho, mesmo em quantidades muito pequenas. / Abstract The present investigation aimed the isolation of biologically active secondary metabolites from different species of nudibranchs, mollusks that can produce or accumulate substances from their preys. We investigated the extracts of four nudibranchs species and their respective preys. The active extract of the marine sponge Agelas sventres, has also been investigated. From the extract of the marine sponge Agelas sventres we could isolate a series of bromopyrrolic alkaloids, substances that are typically found in sponges of Agelas genus. Among the isolated compounds, oroidin was found to inhibit the activity and function of the Pdr5p enzyme from Saccharomyces cerevisiae. From the extract of the nudibranch Tambja stegosauriformis and its prey, the bryozoan Bugula sp., several known tambjamines alkaloids were isolated. The tambjamines C, D, K, and the aldehyde of the tambjamine B were found in both animals; aldehyde of tambjamine A was identified only in the nudibranch extract, whereas tambjamine A and an isomer of tambjamine J were found on the bryozoan. The study of the extract of the nudibranch Okenia zoobotryon and its prey, the bryozoan Zoobotryon verticillatum, resulted in the isolation of a single known brominated indole alkaloid, 2,5,6-tribromo-N-metilgramine, present on both animals. Similar results were obtained in the study of extract of the nudibranch Hypselodoris lajensis along with its prey, a Dysidea sponge, that led to the isolation of a single diterpene, the furodysinin lactone. Although both compounds are known, this is the first report on the isolation of those compounds from nudibranch species. Finally, the investigation of the extract from the nudibranch Pleurobranchus areolatus provided two new modified diketopiperazines, closely related to modified diketopiperazines, the rodriguesins A and B, isolated from the ascidian Didemnum sp. It is important to note the use of LC-UV-MS and MS/MS analysis in this work, which were important in the identification of several compounds present in the studied extracts in very small amounts.

Marine environmental resource managers and consultants require comprehensive, accurate and current data on the status of marine biodiversity in order to fully evaluate resource consent applications that involve development, impact or encroachment within the marine environment, and for identifying areas of coast appropriate for conservation. The role and efficacy of existing global, national and regional marine biodiversity databases in delivering these types of data are evaluated. Consultation with environmental consultants revealed that none regularly, if ever used any existing marine biodiversity database during their routine consulting activities. Moreover, no existing biodiversity database had appropriate data-mining tools, although each was determined to provide information of value to resource managers and environmental consultants operating at national and regional scales; none was deemed to provide the sort of information required to manage marine resources at a local scale. To achieve the objectives of this research programme, resource managers, data users and data compilers were consulted to determine their ideal data and database requirements. Existing biodiversity data sets that included New Zealand marine biodiversity then were searched or procured, and these data and that of a novel data set of species occurring at 296 intertidal and 25 fringe-saline (effectively freshwater) sites within and proximal to the Hauraki Gulf Marine Park (from Mimiwhangata Bay in the north to Tauranga Harbour in the south) were compared with species inventories from environmental consultants operating in this region. Biodiversity data from the 296 saline, comprising presence/absence data for 713 taxa recorded from the survey region were analysed in detail. Significantly different species assemblages were identified amongst these 296 sites, five intertidal habitats being recognised, each with characteristic species assemblages: marine-hard shores, marine-soft shores, brackish-hard shores, brackish-soft shores, and mangrove shores. Species richness and diversity were consistently higher in marine habitats, and greatest on hard substrata. Most sites host unique assemblages of species. A novel index of species richness is proposed, and although the spatial distribution of richness isn’t particularly revealing, as obvious patterns in the distribution of richness are not apparent, this index has value in that the richness of any shore can be compared and contrasted with that of others throughout the region. Augmenting this richness index is a novel index of species rarity. Based on the frequency of occurrence of taxa on shores throughout the survey region, very rare through to ubiquitous taxa are recognised to routinely occur on almost all shores, regardless of the total species richness. Moreover, very rare to uncommon taxa often comprise a disproportionately high percentage of the total species occurring on any given intertidal shore, in any habitat. Accordingly, alarm bells should ring for reviewers of resource consent applications wherein environmental consultants state that an area subject to development ‘hosts no rare, unique or otherwise remarkable species or ecology.’ Two applications of these novel biodiversity data are demonstrated: the relationship between species richness and regional council consented activities is described, with a negative correlation reported for the intensity of disturbance (using the number of consented activities as a proxy for disturbance) and species richness on marine hard shores; and an appraisal of four selection criteria for marine reserves (naturalness, representativeness, uniqueness and complementarities), wherein the intertidal fauna and flora of no existing or proposed marine reserve appears to be natural, unique or representative, and effort seems to have been spent duplicating certain assemblages of species in reserve networks. The former is intuitively obvious, but the latter is alarming, and the ramifications of it far reaching in terms of conservation of the marine environment. Protocols for conducting biodiversity surveys must be established and implemented to elevate the standards of environmental consultants, resulting value judgements on the composition of species, and the likely and actual effects of these developments on the marine environment to ensure that statements made in reports are based on current data rather than perceptions and client expectations. It is possible that resource consents have been issued based on spurious appraisals of the immediate and cumulative effect of discharge on the environment, or of the relative rarity (or appreciation of this) of species that occur within it. Prior to development of the novel Monalisa data set, no existing database or data set existed that provided the information routinely required by managers and consultants to make informed judgements that affect coastal development throughout the survey region. Recommendations for additional research to build on findings detailed herein are made.