Chemical Defenses: From Compounds to Communities

Paul, Valerie J.; Arthur, Karen E.; Ritson‐Williams, Raphael; Ross, Cliff; Sharp, Koty

doi:10.2307/25066642

Cited by 173 publications

(157 citation statements)

References 288 publications

(331 reference statements)

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“…1 While marine cyanobacteria are common inhabitants of tropical and subtropical coastal waters worldwide, under favorable environmental conditions they can grow rapidly and form harmful algal blooms. 2 Grounding of the M/V Wellwood on Molasses Reef in Key Largo, Florida Keys National Marine Sanctuary (FKNMS), on August 4, 1984, resulted in massive destruction to living corals and underlying reef framework. Further injury to this restoration site was caused during the 1998 storm season.…”

mentioning

confidence: 99%

Molassamide, a Depsipeptide Serine Protease Inhibitor from the Marine Cyanobacterium Dichothrix utahensis

et al. 2009

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A new dolastatin 13 analogue, molassamide (1), was isolated from cyanobacterial assemblages of Dichothrix utahensis collected from the Molasses Reef, Key Largo, Florida, and from Brewer's Bay, St. Thomas, U.S. Virgin Islands. This is the first peptide reported from the cyanobacterial genus Dichothrix and the first natural product isolated from marine Dichothrix spp. Its planar structure was determined by NMR spectroscopic techniques, and the configurations of the asymmetric centers were assigned after chiral HPLC analysis of the hydrolysis products. The depsipeptide 1 exhibited protease-inhibitory activity, with IC 50 values of 0.032 and 0.234 µM against elastase and chymotrypsin, respectively. There was no apparent inhibition of trypsin at 10 µM, the highest concentration tested.Marine cyanobacteria have emerged as a rich source of biologically and ecologically active secondary metabolites, in particular peptides and depsipeptides. 1 While marine cyanobacteria are common inhabitants of tropical and subtropical coastal waters worldwide, under favorable environmental conditions they can grow rapidly and form harmful algal blooms. 2 Grounding of the M/V Wellwood on Molasses Reef in Key Largo, Florida Keys National Marine Sanctuary (FKNMS), on August 4, 1984, resulted in massive destruction to living corals and underlying reef framework. Further injury to this restoration site was caused during the 1998 storm season. Artificial reef structures were placed at the Wellwood grounding site in 2002 as a restoration action by FKNMS. National Oceanic and Atmospheric Administration scientists have attempted to settle larval corals in situ on these Wellwood restoration structures (WRS) for several years, and from 2003-2005, Southeast Fisheries Science Center and academic partners "seeded" tens of thousands of reef-building coral larvae and out-planted a few thousand newly settled coral polyps to the WRS for restoration purposes. They have identified only two survivors from this effort. The WRS has an obvious algal mat cover dominated by the cyanobacterium Dichothrix utahensis, which appears as "black puff balls". The cyanobacterial mat was 14 times more abundant on the WRS than on adjacent natural reef surfaces at similar depth (5-7 m). Preliminary experiments conducted using the cyanobacterial mat exudates with swimming coral larvae indicated significant reduction of larval settlement, 3 leading NOAA scientists to hypothesize that algal mat exudates inhibit coral success on the WRS and possibly other nearby restoration structures. 4 Therefore, we selectively collected a cyanobacterial assemblage of D. utahensis from the WRS and investigated the natural products chemistry of this bloom-forming cyanobacterium to better understand the chemical ecology of this species.Here we report the isolation, structure elucidation, and proteaseinhibitory studies of a new dolastatin 13 analogue, trivially named molassamide (1), as a component of the polar n-BuOH-soluble fraction. Molassamide contains the six common amino acid residues Val,...

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Molassamide, a Depsipeptide Serine Protease Inhibitor from the Marine Cyanobacterium Dichothrix utahensis

et al. 2009

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“…Many of these compounds have been discovered through prospecting for natural products with biomedical applications, particularly in soft-bodied anthozoans (e.g., zoanthids, gorgonians and alycyonaceans). These animals are benthic as adults and lack the physical defense of a mineralized skeleton, so secondary metabolites often serve as chemical defenses against predation, fouling, or infection (Paul et al, 2007;Paul and Puglisi, 2004). While some metabolites have been experimentally demonstrated to play a defensive role, the functions of others are unknown, and some compounds are likely to be physiologically important within the animals.…”

Section: Steroid Metabolism In Cnidariansmentioning

confidence: 99%

Steroid metabolism in cnidarians: Insights from Nematostella vectensis

Tarrant

Reitzel

Blomquist

et al. 2009

Molecular and Cellular Endocrinology

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Cnidarians occupy a key evolutionary position as a sister group to bilaterian animals. While cnidarians contain a diverse complement of steroids, sterols, and other lipid metabolites, relatively little is known of the endogenous steroid metabolism or function in cnidarian tissues. Incubations of cnidarian tissues with steroid substrates have indicated the presence of steroid metabolizing enzymes, particularly enzymes with 17β-hydroxysteroid dehydrogenase (17β-HSD) activity. Through analysis of the genome of the starlet sea anemone, Nematostella vectensis, we identified a suite of genes in the short chain dehydrogenase/reductase (SDR) superfamily including homologs of genes that metabolize steroids in other animals. A more detailed analysis of Hsd17b4 revealed complex evolutionary relationships, apparent intron loss in several taxa, and predominantly adult expression in N. vectensis. Due to its ease of culture and available molecular tools N. vectensis is an excellent model for investigation of cnidarian steroid metabolism and gene function. KeywordsEvolution, hydroxysteroid dehydrogenase, short chain dehydrogenase/reductase Abbreviations CYP HSD AKR 3

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“…(4) Âòîðè÷íыå ìåòàбîëèòы, пðåäíàзíà÷åííыå äëÿ зàщèòы îò ðàñòèòåëüíîÿäíых îðгàíèзìîâ è èх ëè÷èíîê. К пðîÿâëåíèю èх àêòèâíîñòè îòíîñèòñÿ èíгèбèðîâàíèå пèòàíèÿ, пëîäî-âèòîñòè, пîäâèжíîñòè è ñíèжåíèå óðîâíÿ âыжèâàåìîñòè âîäíых ÷ëåíèñòîíîгèх [11,12]. Тàêèå жå эффåêòы ìы íàбëюäàëè â îпыòàх íà ìîäåëüíых òåñò-îбъåêòàх, ÷òî пîзâîëÿåò ñäåëàòü зàêëю÷åíèå î зàщèòíîì хàðàêòåðå äåéñòâèÿ íåòîêñè÷íых ìåòàбîëèòîâ öèàíîбàêòåðèé (â ÷àñòíîñòè, эòèìè ñâîéñòâàìè îбëàäàюò ëèпèäíыå è òåðпåíîâыå ñîåäèíåíèÿ [4,9]).…”

Section: ìікробіоëоãія і біотеõноëоãія ¹ 8/2009unclassified

Cyanobacteria and Herbivorous Organisms: The Properties of Interspecific Interactions

Гольдiн¹

2009

Microbiology&Biotechnology

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Chemical Defenses: From Compounds to Communities

Cited by 173 publications

References 288 publications

Molassamide, a Depsipeptide Serine Protease Inhibitor from the Marine Cyanobacterium Dichothrix utahensis

Molassamide, a Depsipeptide Serine Protease Inhibitor from the Marine Cyanobacterium Dichothrix utahensis

Steroid metabolism in cnidarians: Insights from Nematostella vectensis

Cyanobacteria and Herbivorous Organisms: The Properties of Interspecific Interactions

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