Schistosomiasis has been controlled for more than 40 years with a single drug, praziquantel, and only one molluscicide, niclosamide, raising concern of the possibility of the emergence of resistant strains. However, the molecular targets for both agents are thus far unknown. Consequently, the search for lead compounds from natural sources has been encouraged due to their diverse structure and function. Our search for natural compounds with potential use in schistosomiasis control led to the identification of an algal species, Laurencia dendroidea, whose extracts demonstrated significant activity toward both Schistosoma mansoni parasites and their intermediate host snails Biomphalaria glabrata. In the present study, three seaweed-derived halogenated sesquiterpenes, (−)-elatol, rogiolol, and obtusol are proposed as potential lead compounds for the development of anthelminthic drugs for the treatment of and pesticides for the environmental control of schistosomiasis. The three compounds were screened for their antischistosomal and molluscicidal activities. The screening revealed that rogiolol exhibits significant activity toward the survival of adult worms, and that all three compounds showed activity against S. mansoni cercariae and B. glabrata embryos. Biomonitored fractioning of L. dendroidea extracts indicated elatol as the most active compound toward cercariae larvae and snail embryos.

Coral community patterns on some Indonesian reefs influenced by CO2 from underwater volcanic vents and nutrients from eutrophication pressures were examined. The overall aim of the study was to provide an insight into the significance of future ocean acidification compared to eutrophication pressures on tropical coral communities. Coral cover and seawater characteristics at acidified sites (with varied levels of eutrophication), i.e., moderate acidification (pH: 7.87 +/- 0.04), low acidification (pH: 8.01 +/- 0.04) and reference (pH: 8.2 +/- 0.02), were observed at reefs associated with Minahasa Seashore, and Mahengetang and Gunung Api Islands. Results showed that coral community patterns varied among locations and acidified sites, e.g., domination of families such as Alcyoniidae, Acroporidae, Poritidae and Heliporidae, and with different levels of abiotic cover. Surprisingly, pH was not detected as the major determining factor. This finding probably relates to tropical seawater temperatures being high enough to still allow for aragonite deposition even at pH values down to 7.8. Nutrients (phosphate and dissolved inorganic nitrogen) were shown to be the main determining factors that influenced community patterns on the observed coral reefs. Overall, the results indicate that tropical coral reef community patterns will continue to vary as pH decreases to the predicted oceanic value of pH 7.8 over the next 100 years, and bio-geo-ecological characteristics and anthropogenic pressures will be the major factors determining Indonesian tropical coral community structure, compared to pH.

The following review covers the primary literature concerning marine natural products isolated for the first time from organisms collected around the islands of Hawaii published in the 51-year period 1964 to July 2015. The review is divided into seven main sections based on major taxonomic groupings; algae, sponges, mollusks, miscellaneous invertebrates, cyanobacteria, bacteria, and fungi. The aim of the review is to discuss the compounds and information concerning their original biological activity and other potentially interesting properties. The majority of the 320 structures of isolated compounds are not shown directly in the review but are contained in the Supporting Information section in 22 figures, Figs. 1 S-22 S. The Supporting Information section also contains Table 1 S that has information relating to the taxonomic identification of the source organism of each compound, collection location of the source organism, a trivial or semi-systematic name for each compound, as well as its general structural class. The authors hope that this review will be the spawning ground for other reviews and the basis for a great deal more research into the marine life found in Hawaiian waters.

Fish serum albumin (FSA) is an aquatic resource that has potential to be developed as nutraceutical. Therefore, research was undertaken to assess albumin levels in the aqueous extract of muscle tissue of several Perciformes commonly available at a local fish market in Indonesia. Three random replicates for each of 17 Perciformes species were collected and assessed for their FSA content by application of a reversed-phase (C4) HPLC analytical method. Results of these analyses showed that the albumin concentration of the extracts was in the range 3.49-12.61 g/L, and that they varied significantly (P < 0.05) between species and families. This finding may mean that FSA levels are species and family dependent, something that could be investigated in future studies. As fishes from the family Scrombidae showed the highest concentration (12.61 g/L) of FSA, they would likely have the most value as a source for production of albumin-based nutritional and/or clinical products.

Verbascum thapsus or common mullein has a history of use in Europe that stretches back over 2000 years. It is commonly found in Asia, Africa and Europe and has found its way to Australia, North and South America and Hawaii, where it is classified as a weed. We became interested in this plant since it is only commonly found on the Big Island of Hawaii in areas where the ground has been recently disturbed at higher elevations, 1500 m, and because of its reported antimycobacterial (anti-TB) activity. Although the anti-TB activity of the methanol extract of the leaves proved to be negative we did find it to have some antimicrobial and antioxidant activty. On this basis we undertook fractionation of the extract and isolated and characterized the main components; apigenin (1), luteolin (2), aucubin (3), 6-epiaucubin (4) and verbascocide (5). All of these isolates were determined to have antioxidant properties and apigenin (1), luteolin (2) and verbascoside (5) to have antimicrobial activity towards Staphylococcus aureus.

In this review the reported effects of shade levels on the amounts of reputed biologically active potential key chemical markers l -theanine and caffeine, and the four catechin-polyphenols, (−)-epicatechin (EC), (−)-epicatechin gallate (ECG), (−)-epigallocatechin (EGC), and (−)-epigallocatechin gallate (EGCG) found in the bud and first two leaves during development of tea ( Camellia sinensis ) grown on a Hawaiian plantation are discussed. Also discussed is the antioxidant activity of the overall extract of the tea leaf bud, and first and second leaves, together with the importance of employing 1 H NMR spectroscopy as an analytical tool for the determination of the validity of reference materials.

Antioxidant activity of symbiotic organisms known as lichens is an intriguing field of research because of its strong contribution to their ability to withstand extremes of physical and biological stress (e.g. desiccation, temperature, UV radiation and microbial infection). We present a comparative study on the antioxidant activities of 76 Icelandic and 41 Hawaiian lichen samples assessed employing the DPPH- and FRAP-based antioxidant assays. Utilizing this unprecedented sample size, we show that while highest individual sample activity is present in the Icelandic dataset, the overall antioxidant activity is higher for lichens found in Hawaii. Furthermore, we report that lichens from the genus Peltigera that have been described as strong antioxidant producers in studies on Chinese, Russian and Turkish lichens also show high antioxidant activities in both Icelandic and Hawaiian lichen samples. Finally, we show that opportunistic sampling of lichens in both Iceland and Hawaii will yield high numbers of lichen species that exclusively include green algae as photobiont.

The Nene bush (Coprosma ernodeoides) or 'Aiakanene in Hawaiian is a rambling perennial prostrate shrub endemic to Hawaii. Worldwide, mainly the Pacific Islands, there are around 110 species in the genus the majority of which (55) are to be found in New Zealand. The plant has very small leaves (2 – 3 mm) that grow densely along branches that can be up to three meters long. At various times of the year the bush produces shiny black edible berries (5 – 8 mm dia) that were and are used by native Hawaiians as laxatives. Our interest was drawn to this plant because of its distinctive berries, the fact that it is endemic to Hawaii and finally because there are no reported natural products investigation of any parts of the plant. The data presented on this poster result from investigations of methanol extracts made from the leaves and from the berries that both demonstrated antioxidant properties in DPPH and FRAP assays. From the berries the three known iridoid glycosides 1 – 3 were isolated and from the leaves the known iridoid glycoside 4.

Marine algae belonging to the genus Laurencia are the most prolific producers of secondary metabolites compared to any other marine genus. The secondary metabolites produced by these plants are typically halogenated and have a wide variety of biological properties. The most common structural classes encountered being sesquiterpenes, diterpenes, triterpenes, sterols, C15 acetogenins and long-chain hydrocarbons. Sphingosines are among the lesser reported compounds isolated from this genus, with only one, (+)-N-(2S, 3R)-2-acetamido-3-acetoxyoctadecan-l-ol, being reported to date. In this poster presentation we report the isolation of additional sphingosines, including 1 and 2, from the genus Laurencia, this time from a new species collected in Brazil.

The wealth of marine sponges and soft corals in Indonesian waters represents a rich source of natural products. However, anthropogenic pressures potentially decrease diversity in coral reefs. Presented here are trends for tropical sponge and soft coral biodiversity and their bioactivity potential under the influence of increasing anthropogenic pressures. Samples were collected along transects (near, mid, and far) at Karimunjawa and Seribu Islands Marine National Parks and environmental parameters (salinity, pH, dissolved oxygen (DO), phosphate, nitrate, and ammonia), sponge and soft coral biodiversity, and the bioactivity potential of those organisms (50% Growth Inhibition (GI50) of cancer cell lines H460-Lung, MCF7-Breast, and SF268-CNS) are compared. The environmental conditions and biodiversity were found to be significantly different between groups of sampling sites (P<0.05). Canonical Discriminant Analysis (CDA) revealed DO was the discriminant factor driving the separation between groups (90.1%). Diversity tended to be higher in the Far group with strong and significant relation to DO (R= 0.611, P<0.05) and ammonia (R = -0.812, P<0.05). The CDA also showed that an increase in bioactivity (low % GI50) of sponge and soft coral extracts was related to a canonical function (57.21%) consisting of high DO, high pH, and low nutrients. These findings indicate the production of bioactive compounds is related to diversity and complexity of coral reef systems. Therefore, strategies for marine protection by mitigating the impacts of anthropogenic pressures needs to be optimized in order to conserve the overall environment and sustain its natural bioactivity potential indefinitely.

Over a decade ago Wright et al., proposed a putative antiplasmodial mechanism of action for marine isonitriles (1, and 3-6) and isothiocyanate (2) that involved interference in heme detoxification by Plasmodium falciparum thus inhibiting the growth of the parasite. In the current paper we describe the successful down scaling of Egan's P-hematin inhibition assay for analyses of small quantities of marine natural products as potential beta-hematin inhibitors. The modified assay revealed for the first time that the most active antiplasmodial marine isonitrile 4 (IC50 13 nM) totally inhibited beta-hematin crystallization while 5 (IC50 31 nM) and 6 (IC50 81 nM) showed inhibition at lower levels. A cursory ab initio molecular dynamics investigation into the relative stabilities of bonded complexes between isocyanate, isothiocyanate and isonitrile groups with the iron center of heme supported our findings that these marine metabolites do indeed interfere with biocrystallization of heme. (C) 2015 Elsevier Masson SAS. All rights reserved.

Oroidin (1), (E)-N-(3-(2-amino-1H-imidazol-4-yl)allyl)-4,5-dibromo-1H-pyrrole-2-carboxamide, is a pyrrole alkaloid isolated from the marine sponge Agelas oroides. Routine screening in a panel of twelve cancer cell lines revealed 1 to be poorly cytotoxic with the 50% growth inhibition concentration (GI50) of 42 μM in MCF-7 (breast) cells and 24 μM in A2780 (ovarian) cells and >50 μM in all other cell lines tested. The development of eight focused libraries comprising thirty compounds total identified N-(biphenyl-4-ylmethyl)-1H-pyrrole-2-carboxamide (4l), N-benzyl-4,5-dibromo-1H-pyrrole-2-carboxamide (5a) and N-(biphenyl-4-ylmethyl)-4,5-dibromo-1H-pyrrole-2-carboxamide (5l) as potent inhibitors of cell growth in our panel of cell lines. Of these compounds GI50 values of <5 μM were observed with 4l against HT29 (colon) and SW480 (colon); 5a against HT29; and 5l against HT29, SW480, MCF-7, A431 (skin), Du145 (prostate), BE2-C (neuroblastoma) and MIA (pancreas) cell lines. As a cancer class, colon cancer appears to be more sensitive to the oroidin series of compounds, with analogue 5l being the most active.

Contemporary Gathering Practice and Antioxidant Benefit of Wild Seaweeds in Hawai’i. Wild-gathered seaweeds (limu) are a prominent component of Native Hawaiian diet and culture, but are understudied for their nutritional benefits and contemporary cultural use. This study uses a combination of ethnographic, pharmacological, and ecological approaches to document contemporary levels of wild seaweed gathering and consumption, and it explores the impact of cultivation and eutrophication on the disease-preventive benefits wild seaweeds may provide. Levels of gathering and consumption of seaweed were assessed with surveys of high school students and interviews with adult limu gatherers on O’ahu island, Hawai’i. Antioxidant activity was assessed with laboratory-based assays. Almost all students surveyed reported consuming cultivated seaweeds, one-third reported having consumed wild seaweeds, and one-fifth had gathered them, confirming that gathering practice and traditional diet have persisted in Hawai’i despite major social and environmental change. Wild gathering was three times as high and consumption 60% more prevalent among Native Hawaiians compared to non-Hawaiian students. Further, students with a parent who gathered limu were six times more likely to have gathered limu themselves, asserting the importance of within-family transmission to cultural continuity. A larger proportion of male than female Hawaiian students reported gathering wild seaweeds, indicating a cultural shift from pre-Contact Hawai’i, when women were the predominant gatherers and consumers of limu. The wild seaweeds assessed demonstrated higher levels of antioxidant activity than did cultivated seaweeds. Eutrophication was correlated with a decline in antioxidant activity, indicating that changing ocean conditions may alter the nutritional quality of this traditional food. Today, nearly all students are receiving some antioxidant benefits from seaweed, with Native Hawaiian youth from families that gather seaweed most likely to receive this health benefit. Conservation and restoration of near-shore environments to promote native edible seaweeds in pollution-free areas would provide greater opportunities for Native Hawaiian gathering practice and would support Native Hawaiian health.

Antioxidant and proton nmr screening of extracts derived from sponges found growing in the twilight zone around Hawaiian Island of Maui yielded an unusual compound that appears to be a conjugation between a terpene (1) and a small alkaloid (2). DOSY spectroscopy revealed that in solution the two entities exist free from one another.

The presented study looked in a preliminary and speculative way for a correlation between production by a single soft coral species, Nephthea sp., of two secondary metabolites and local environmental stresses, pollution, around the Seribu Islands, Indonesia. The study region was selected because of the significant land-based run-off from the heavily populated Indonesian capital, Jakarta. A Nephthea sp., was chosen based on the well known bioactive cembranoid diterpene content of animals of the genus that is often involved in protecting them from predation. For the study, levels of the recently reported 3,4-epoxy-nephthenol acetate (1) and the previously known 15-hydroxycembrane (2) were monitored. Results showed levels of 1 and 2 to decrease as pollutants increased. A contour map of levels of 1 and 2 showed a likely different pattern of their occurrence, with 2 being found more in polluted, higher stress, areas and 1 likely only to occur in areas with low environmental stresses. It is postulated that low levels of anthropogenic stress, pollution, in the reef environment result in no inhibition of biodiversity and number of fishes that prey on Nephthea sp., likely causing enhanced secondary metabolite production in these species in order to protect them from predation. This may mean levels and/or presence or absence of 1 might be indicators of pollution entering a coral reef area, with the resultant threat to a reef’s potential biopotency. Results also show where anthropogenic pollution increases in a reef system the overall level of biodiversity drops, as a consequence so does chemical diversity and with it the chance of discovering new and biological active secondary metabolites.

Sponges are relatively rare in the waters around the Big Island of Hawaii in contrast to other Hawaiian islands and other tropical costal waters around the world. This paucity probably reflects the relative geological age of the Big Island and its remoteness. In an effort to document sponges from this area a survey of waters close to Hilo was undertaken and led to the collection of 13 distinct sponge samples. To date, the majority of these samples have been identified as belonging to the genus Haliclona. For comparative purposes five mesophotic sponges were collected from depths below 80 m, employing an ocean going remotely operated vehicle (ROV), from the Au'au channel off Maui island, a much richer source of sponge biodiversity. Comparison of FRAP based antioxidant activity and antimicrobial activity of extracted samples from both the Big Island and Maui together with preliminary NMR studies, including that of a new potent antioxidant and antimicrobial meroterpenoid, puupehenol, will be presented.

Betel or areca nut is the seed of the Areca catechu palm. Depending on the reporting source, it is estimated that betel nut is chewed by 10 – 20% of the world's people. After nicotine, alcohol and caffeine it is the fourth most commonly used psychoactive substance. Studies and reports relating to betel nut are relatively common and range from analysis of their chemical content through to demographics of nut use. The quality of the data reported in these studies is highly variable and is often based on unsubstantiated facts from previous studies. For example, it is consistently reported that the four pyridine alkaloids; arecoline, arecaidine, guvacoline, and guvacine, are present in all nuts worldwide, and that these are either directly or indirectly the causative agents of addiction to chewing and of associated oral cancers. While these latter claims may or may not be true for some samples around the world there is clearly a significant likelihood that not all nuts are the same. In this respect we decided to undertake investigations of nuts from Guam and nearby islands as well as from Hawaii. In this presentation, preliminary results from some analytical and biological studies undertaken with nuts investigated from Hawaii relating to alkaloid content, their possible link to addiction and cancer formation are reported.

This paper highlights the importance of recording at least a (1)H nuclear magnetic resonance (NMR) spectrum to verify identity of standards used in analyses of organic materials irrespective of source. We show the importance of this approach with an example of a quantitative high-performance liquid chromatography (HPLC) study undertaken with green tea extracts that required the use of several polyphenols as standards. In the course of the study one of these standards [(-)-epigallocatechin, EGC], although having the physical appearance and appropriate HPLC chromatographic behavior of EGC, proved by (1)H-NMR to be a completely different class of molecule. For us, this raised significant questions concerning validity of many published pieces of research that used quantitative HPLC methods without first performing rigorous validation of the employed standards prior to their use. This paper clearly illustrates the importance of validation of all standards used in analysis of organic materials by recording at least a (1)H-NMR spectrum of them prior to their use.

The methanol extract of a Sinularia sp., collected from Bowden Reef, Queensland, Australia, yielded ten natural products. These included the new nitrogenous diterpene (4R*,5R*,9S*,10R*,11Z)-4-methoxy-9-((dimethylamino)-methyl)-12,15-epoxy-11(13)-en-decahydronaphthalen-16-ol (1), and the new lobane, (1R*,2R*,4S*,15E)-loba-8,10,13(14),15(16)-tetraen-17,18-diol-17-acetate (2). Also isolated were two known cembranes, sarcophytol-B and (1E,3E,7E)-11,12-epoxycembratrien-15-ol, and six known lobanes, loba-8,10,13(15)-triene-16,17,18-triol, 14,18-epoxyloba-8,10,13(15)-trien-17-ol, lobatrientriol, lobatrienolide, 14,17-epoxyloba-8,10,13(15)-trien-18-ol-18-acetate and (17R)-loba-8,10,13(15)-trien-17,18-diol. Structures of the new compounds were elucidated through interpretation of spectra obtained after extensive NMR and MS investigations and comparison with literature values. The tumour cell growth inhibition potential of 1 and 2 along with loba-8,10,13(15)-triene-16,17,18-triol, 14,17-epoxyloba-8,10,13(15)-trien-18-ol-18-acetate, lobatrienolide, (1E,3E,7E)-11,12-epoxycembratrien-15-ol and sarcophytol-B were assessed against three human tumour cell lines (SF-268, MCF-7 and H460). The lobanes and cembranes tested demonstrated 50% growth inhibition in the range 6.8–18.5 µM, with no selectivity, whilst 1 was less active (GI50 70–175 µM).