Bioactive Hydantoin Alkaloids from the Red Sea Marine Sponge Hemimycale arabica.

Abstract:

:In the course of our continuing efforts to identify bioactive secondary metabolites from Red Sea marine invertebrates, we have investigated the sponge Hemimycale arabica. The antimicrobial fraction of an organic extract of the sponge afforded two new hydantoin alkaloids, hemimycalins A and B (2 and 3), together with the previously reported compound (Z)-5-(4-hydroxybenzylidene)imidazolidine-2,4-dione (1). The structures of the compounds were determined by extensive 1D and 2D NMR (COSY, HSQC and HMBC) studies and high-resolution mass spectral determinations. Hemimycalins A (2) and B (3) represent the first examples of the natural N-alkylated hydantoins from the sponge Hemimycale arabica. Compounds 1-3 displayed variable antimicrobial activities against E. coli, S. aureus, and C. albicans. In addition, compound 1 displayed moderate antiproliferative activity against the human cervical carcinoma (HeLa) cell line. These findings provide further insight into the chemical diversity as well as the biological activity of this class of compounds.

journal_name

Mar Drugs

journal_title

Marine drugs

authors

Youssef DT,Shaala LA,Alshali KZ

doi

10.3390/md13116609

subject

Has Abstract

pub_date

2015-10-28 00:00:00

pages

6609-19

issue

11

issn

1660-3397

pii

md13116609

journal_volume

13

pub_type

杂志文章
  • Inhibition of bacterial quorum sensing by extracts from aquatic fungi: first report from marine endophytes.

    abstract::In our search for quorum-sensing (QS) disrupting molecules, 75 fungal isolates were recovered from reef organisms (endophytes), saline lakes and mangrove rhizosphere. Their QS inhibitory activity was evaluated in Chromobacterium violaceum CVO26. Four strains of endophytic fungi stood out for their potent activity at c...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md12115503

    authors: Martín-Rodríguez AJ,Reyes F,Martín J,Pérez-Yépez J,León-Barrios M,Couttolenc A,Espinoza C,Trigos A,Martín VS,Norte M,Fernández JJ

    更新日期:2014-11-19 00:00:00

  • Bioactive cembrane-based diterpenoids from the soft coral Sinularia triangular.

    abstract::Chemical examination of the Taiwanese soft coral Sinularia triangular led to the isolation of five cembrane-based diterpenoids 1-5, including two new metabolites, triangulenes A (1) and B (2). The structures of the new metabolites were determined on the basis of extensive spectroscopic analysis, particularly mass spec...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md9060944

    authors: Su JH,Wen ZH

    更新日期:2011-01-01 00:00:00

  • Synthesis of Pelorol and Its Analogs and Their Inhibitory Effects on Phosphatidylinositol 3-Kinase.

    abstract::There are numerous biologically active substances with novel structures and unique physiological functions in marine organisms. These substances are important sources of new lead compounds. Pelorol is a natural product isolated from marine organisms that possesses a novel structure with high bioactivity. In this paper...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md14060118

    authors: Luo Y,Chen H,Weng J,Lu G

    更新日期:2016-06-21 00:00:00

  • Pharmacokinetic Study of Bioactive Glycopeptide from Strongylocentrotus droebachiensis After Intranasal Administration to Rats Using Biomarker Approach.

    abstract::A glycopeptide fraction (GPF) from internal organs of green sea urchins (Strongylocentrotus droebachiensis Müller, Strongylocentrotidae) has been reported to be an effective bronchitis treatment. In this study, we evaluated the pharmacokinetic and tissue distribution of GPF, following single and repeated intranasal (i...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md17100577

    authors: Shikov AN,Pozharitskaya ON,Faustova NM,Kosman VM,Makarov VG,Razzazi-Fazeli E,Novak J

    更新日期:2019-10-11 00:00:00

  • The Bacterial (Vibrio alginolyticus) Production of Tetrodotoxin in the Ribbon Worm Lineus longissimus-Just a False Positive?

    abstract::We test previous claims that the bacteria Vibrio alginolyticus produces tetrodotoxin (TTX) when living in symbiosis with the nemertean Lineus longissimus by a setup with bacteria cultivation for TTX production. Toxicity experiments on the shore crab, Carcinus maenas, demonstrated the presence of a paralytic toxin, but...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md14040063

    authors: Strand M,Hedström M,Seth H,McEvoy EG,Jacobsson E,Göransson U,Andersson HS,Sundberg P

    更新日期:2016-03-25 00:00:00

  • Bacterial exopolysaccharides from extreme marine habitats: production, characterization and biological activities.

    abstract::Many marine bacteria produce exopolysaccharides (EPS) as a strategy for growth, adhering to solid surfaces, and to survive adverse conditions. There is growing interest in isolating new EPS producing bacteria from marine environments, particularly from extreme marine environments such as deep-sea hydrothermal vents ch...

    journal_title:Marine drugs

    pub_type: 杂志文章,评审

    doi:10.3390/md8061779

    authors: Poli A,Anzelmo G,Nicolaus B

    更新日期:2010-06-03 00:00:00

  • Genome Sequence of Pseudomonas stutzeri 273 and Identification of the Exopolysaccharide EPS273 Biosynthesis Locus.

    abstract::Pseudomonas stutzeri 273 is a marine bacterium producing exopolysaccharide 273 (EPS273) with high anti-biofilm activity against P. aeruginosa PAO1. Here, the complete genome of P.stutzeri 273 was sequenced and the genome contained a circular 5.03 Mb chromosome. With extensive analysis of the genome, a genetic locus co...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md15070218

    authors: Wu S,Zheng R,Sha Z,Sun C

    更新日期:2017-07-10 00:00:00

  • A Low Molecular Weight Protein from the Sea Anemone Anemonia viridis with an Anti-Angiogenic Activity.

    abstract::Sea anemones are a remarkable source of active principles due to a decentralized venom system. New blood vessel growth or angiogenesis is a very promising target against cancer, but the few available antiangiogenic compounds have limited efficacy. In this study, a protein fraction, purified from tentacles of Anemonia ...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md16040134

    authors: Loret EP,Luis J,Nuccio C,Villard C,Mansuelle P,Lebrun R,Villard PH

    更新日期:2018-04-19 00:00:00

  • Brevianamides and Mycophenolic Acid Derivatives from the Deep-Sea-Derived Fungus Penicillium brevicompactum DFFSCS025.

    abstract::Four new compounds (1-4), including two brevianamides and two mycochromenic acid derivatives along with six known compounds were isolated from the deep-sea-derived fungus Penicillium brevicompactum DFFSCS025. Their structures were elucidated by spectroscopic analysis. Moreover, the absolute configurations of 1 and 2 w...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md15020043

    authors: Xu X,Zhang X,Nong X,Wang J,Qi S

    更新日期:2017-02-17 00:00:00

  • Anti-Coagulant and Anti-Thrombotic Properties of Blacklip Abalone (Haliotis rubra): In Vitro and Animal Studies.

    abstract::Sulphated polysaccharides with anti-thrombotic and anti-coagulant activities have been found in various marine biota. In this study, a previously characterised anti-thrombotic and anti-coagulant extract from blacklip abalone was fractionated by anion exchange chromatography (AEC), pooled (on a sulphated polysaccharide...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md15080240

    authors: Suleria HAR,Masci PP,Zhao KN,Addepalli R,Chen W,Osborne SA,Gobe GC

    更新日期:2017-08-04 00:00:00

  • Prospecting Biotechnologically-Relevant Monooxygenases from Cold Sediment Metagenomes: An In Silico Approach.

    abstract::The goal of this work was to identify sequences encoding monooxygenase biocatalysts with novel features by in silico mining an assembled metagenomic dataset of polar and subpolar marine sediments. The targeted enzyme sequences were Baeyer-Villiger and bacterial cytochrome P450 monooxygenases (CYP153). These enzymes ha...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md15040114

    authors: Musumeci MA,Lozada M,Rial DV,Mac Cormack WP,Jansson JK,Sjöling S,Carroll J,Dionisi HM

    更新日期:2017-04-09 00:00:00

  • Effect of Low Molecular Weight Oligopeptides Isolated from Sea Cucumber on Diabetic Wound Healing in db/db Mice.

    abstract::Impaired wound healing is a major clinical problem in patients with diabetes and is the leading cause of lower limb amputation. This study is aimed to observe the effects of small molecule oligopeptides isolated from sea cucumber (SCCOPs) on the wound healing process in diabetic mice. Ninety db/db male mice were divid...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md16010016

    authors: Li D,Li L,Xu T,Wang T,Ren J,Liu X,Li Y

    更新日期:2018-01-08 00:00:00

  • Pretrichodermamides D-F from a Marine Algicolous Fungus Penicillium sp. KMM 4672.

    abstract::Three new epidithiodiketopiperazines pretrichodermamides D-F (1-3), together with the known N-methylpretrichodermamide B (4) and pretrichodermamide С (5), were isolated from the lipophilic extract of the marine algae-derived fungus Penicillium sp. KMM 4672. The structures of compounds 1-5 were determined based on spec...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md14070122

    authors: Yurchenko AN,Smetanina OF,Ivanets EV,Kalinovsky AI,Khudyakova YV,Kirichuk NN,Popov RS,Bokemeyer C,von Amsberg G,Chingizova EA,Afiyatullov SSh,Dyshlovoy SA

    更新日期:2016-06-27 00:00:00

  • Sinulolides A-H, new cyclopentenone and butenolide derivatives from soft coral Sinularia sp.

    abstract::Eight new compounds, sinulolides A-H (1-8), along with two known compounds, α-methoxy-2,3-dimethyl-butenolide (9) and sinularone D (10), were isolated from the soft coral Sinularia sp. The structures of these compounds were elucidated on the basis of extensive spectroscopic analysis. The absolute configurations were d...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md12105316

    authors: Yang B,Wei X,Huang J,Lin X,Liu J,Liao S,Wang J,Zhou X,Wang L,Liu Y

    更新日期:2014-10-23 00:00:00

  • Total Synthesis of Mycalisine B.

    abstract::The first total synthesis of the marine nucleoside Mycalisine B-a naturally occurring and structurally distinct 4,5-unsaturated 7-deazapurine nucleoside-has been accomplished in 10 linear steps with 27.5% overall yield from commercially available 1,2,3,5-tetra-O-acetyl-ribose and tetracyanoethylene. Key steps of the a...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md17040226

    authors: Ding H,Ruan Z,Kou P,Dong X,Bai J,Xiao Q

    更新日期:2019-04-14 00:00:00

  • Seaweed hydrocolloid production: an update on enzyme assisted extraction and modification technologies.

    abstract::Agar, alginate, and carrageenans are high-value seaweed hydrocolloids, which are used as gelation and thickening agents in different food, pharmaceutical, and biotechnological applications. The annual global production of these hydrocolloids has recently reached 100,000 tons with a gross market value just above US$ 1....

    journal_title:Marine drugs

    pub_type: 杂志文章,评审

    doi:10.3390/md13063340

    authors: Rhein-Knudsen N,Ale MT,Meyer AS

    更新日期:2015-05-27 00:00:00

  • Capgermacrenes A and B, Bioactive Secondary Metabolites from a Bornean Soft Coral, Capnella sp.

    abstract::Two new bicyclogermacrenes, capgermacrenes A (1) and B (2), were isolated with two known compounds, palustrol (3) and litseagermacrane (4), from a population of Bornean soft coral Capnella sp. The structures of these metabolites were elucidated based on spectroscopic data. Compound 1 was found to inhibit the accumulat...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md13053103

    authors: Phan CS,Ng SY,Kim EA,Jeon YJ,Palaniveloo K,Vairappan CS

    更新日期:2015-05-19 00:00:00

  • Structure of fucoidan from brown seaweed Turbinaria ornata as studied by electrospray ionization mass spectrometry (ESIMS) and small angle X-ray scattering (SAXS) techniques.

    abstract::The purpose of this study is to elucidate both the chemical and conformational structure of an unfractionated fucoidan extracted from brown seaweed Turbinaria ornata collected at Nha-trang bay, Vietnam. Electrospray ionization mass spectrometry (ESI-MS) was used for determining the chemical structure and small angle X...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md11072431

    authors: Thanh TT,Tran VT,Yuguchi Y,Bui LM,Nguyen TT

    更新日期:2013-07-12 00:00:00

  • Briarane diterpenoids isolated from gorgonian corals between 2011 and 2013.

    abstract::The structures, names, bioactivities and references of 138 briarane-type diterpenoids, including 87 new compounds, are summarized in this review. All the briarane-type compounds mentioned in this review article were obtained from gorgonian corals including the genus Briareum, Dichotella, Junceella and Verrucella. Some...

    journal_title:Marine drugs

    pub_type: 杂志文章,评审

    doi:10.3390/md12042164

    authors: Sheu JH,Chen YH,Chen YH,Su YD,Chang YC,Su JH,Weng CF,Lee CH,Fang LS,Wang WH,Wen ZH,Wu YC,Sung PJ

    更新日期:2014-04-10 00:00:00

  • Preparation of calibration standards of N1-H paralytic shellfish toxin analogues by large-scale culture of cyanobacterium Anabaena circinalis (TA04).

    abstract::Mouse bioassay is the official testing method to quantify paralytic shellfish toxins (PSTs) in bivalves. A number of alternative analytical methods have been reported. Some methods have been evaluated by a single laboratory validation. Among the different types of methods, chemical analyses are capable of identifying ...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md9030466

    authors: Watanabe R,Suzuki T,Oshima Y

    更新日期:2011-03-22 00:00:00

  • Discovery of new eunicellin-based diterpenoids from a Formosan soft coral Cladiella sp.

    abstract::A new eunicellin diterpenoid, cladieunicellin I (1), and a new natural eunicellin, litophynin I diacetate (2), were isolated from a Formosan soft coral identified as Cladiella sp. The structures of eunicellins 1 and 2 were elucidated by spectroscopic methods and by comparison of the spectral data with those of related...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md11114585

    authors: Chen TH,Lu MC,Chang YC,Su YD,Chen YH,Lin NC,Fang LS,Wu YC,Sung PJ

    更新日期:2013-11-14 00:00:00

  • From Marine Venoms to Drugs: Efficiently Supported by a Combination of Transcriptomics and Proteomics.

    abstract::The potential of marine natural products to become new drugs is vast; however, research is still in its infancy. The chemical and biological diversity of marine toxins is immeasurable and as such an extraordinary resource for the discovery of new drugs. With the rapid development of next-generation sequencing (NGS) an...

    journal_title:Marine drugs

    pub_type: 杂志文章,评审

    doi:10.3390/md15040103

    authors: Xie B,Huang Y,Baumann K,Fry BG,Shi Q

    更新日期:2017-03-30 00:00:00

  • Correction: Zhang, G.; Cheng, G.; Jia, P.; Jiao, S.; Feng, C.; Hu, T.; Liu, H.; Du, Y. The Positive Correlation of the Enhanced Immune Response to PCV2 Subunit Vaccine by Conjugation of Chitosan Oligosaccharide with the Deacetylation Degree. Marine Drugs

    abstract::The authors wish to correct Figure 1 in this paper [1] to be as follows:[...]. ...

    journal_title:Marine drugs

    pub_type: 杂志文章,已发布勘误

    doi:10.3390/md15090292

    authors: Zhang G,Cheng G,Jia P,Jiao S,Feng C,Hu T,Liu H,Du Y

    更新日期:2017-09-20 00:00:00

  • The Marine-Derived Fungus Clonostachys rosea, Source of a Rare Conjugated 4-Me-6E,8E-hexadecadienoic Acid Reducing Viability of MCF-7 Breast Cancer Cells and Gene Expression of Lipogenic Enzymes.

    abstract::A marine-derived strain of Clonostachys rosea isolated from sediments of the river Loire estuary (France) was investigated for its high lipid production. The fungal strain was grown on six different culture media to explore lipid production changes. An original branched conjugated fatty acid, mainly present in triglyc...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md13084934

    authors: Dias AC,Ruiz N,Couzinet-Mossion A,Bertrand S,Duflos M,Pouchus YF,Barnathan G,Nazih H,Wielgosz-Collin G

    更新日期:2015-08-06 00:00:00

  • Drimane Sesquiterpene-Conjugated Amino Acids from a Marine Isolate of the Fungus Talaromyces minioluteus (Penicillium Minioluteum).

    abstract::Four new sesquiterpene lactones (3, 4, 6 and 7) and three known compounds, purpuride (1), berkedrimane B (2) and purpuride B (5), were isolated from the marine fungus, Talaromyces minioluteus (Penicillium minioluteum). New compounds were drimane sesquiterpenes conjugated with N-acetyl-l-valine, and their structures we...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md13063567

    authors: Ngokpol S,Suwakulsiri W,Sureram S,Lirdprapamongkol K,Aree T,Wiyakrutta S,Mahidol C,Ruchirawat S,Kittakoop P

    更新日期:2015-06-05 00:00:00

  • Investigation of the Possible Pharmacologically Active Forms of the Nicotinic Acetylcholine Receptor Agonist Anabaseine.

    abstract::Three major forms of the nicotinic agonist toxin anabaseine (cyclic iminium, cyclic imine and the monocationic open-chain ammonium-ketone) co-exist in almost equal concentrations at physiological pH. We asked the question: Which of these forms is pharmacologically active? First, we investigated the pH dependence of an...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md17110614

    authors: Andrud K,Xing H,Gabrielsen B,Bloom L,Mahnir V,Lee S,Green BT,Lindstrom J,Kem W

    更新日期:2019-10-29 00:00:00

  • Phytoene Accumulation in the Novel Microalga Chlorococcum sp. Using the Pigment Synthesis Inhibitor Fluridone.

    abstract::Carotenoids are lipophilic pigments found in plants and algae, as well as some bacteria, archaea, and fungi that serve two functions-(1) as light harvesting molecules-primary carotenoids, and (2) as antioxidants, acting against reactive oxygen species⁻secondary carotenoids. Because of their strong antioxidant properti...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md17030187

    authors: Laje K,Seger M,Dungan B,Cooke P,Polle J,Holguin FO

    更新日期:2019-03-22 00:00:00

  • Carrageenans as a new source of drugs with metal binding properties.

    abstract::Carrageenans are abundant and safe non-starch polysaccharides exerting their biological effects in living organisms. Apart from their known pro-inflammation properties and some pharmacological activity, carrageenans can also strongly bind and hold metal ions. This property can be used for creation of the new drugs for...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md8041106

    authors: Khotimchenko YS,Khozhaenko EV,Khotimchenko MY,Kolenchenko EA,Kovalev VV

    更新日期:2010-04-01 00:00:00

  • Costatone C-A New Halogenated Monoterpene from the New Zealand Red Alga Plocamium angustum.

    abstract::Red algae of the genus Plocamium have been a rich source of halogenated monoterpenes. Herein, a new cyclic monoterpene, costatone C (7), was isolated from the extract of P. angustum collected in New Zealand, along with the previously reported (1E,5Z)-1,6-dichloro-2-methylhepta-1,5-dien-3-ol (8). Elucidation of the pla...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md17070418

    authors: Bracegirdle J,Sohail Z,Fairhurst MJ,Gerth ML,Zuccarello GC,Ali Hashmi M,Keyzers RA

    更新日期:2019-07-19 00:00:00

  • Effects of long chain fatty acid synthesis and associated gene expression in microalga Tetraselmis sp.

    abstract::With the depletion of global fish stocks, caused by high demand and effective fishing techniques, alternative sources for long chain omega-3 fatty acids are required for human nutrition and aquaculture feeds. Recent research has focused on land-based cultivation of microalgae, the primary producers of omega-3 fatty ac...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md12063381

    authors: Adarme-Vega TC,Thomas-Hall SR,Lim DK,Schenk PM

    更新日期:2014-06-04 00:00:00