Suberitamides A-C, Aryl Alkaloids from a Pseudosuberites sp. Marine Sponge that Inhibit Cbl-b Ubiquitin Ligase Activity.

Abstract:

:Three new aryl alkaloids named suberitamides A-C (1-3), were isolated from an extract of the marine sponge Pseudosuberites sp. collected along the coast of North Carolina. Their planar structures were established by extensive nuclear magnetic resonance (NMR) and mass spectrometry (MS) analysis. To assign the challenging relative configuration of the saturated five-membered ring in suberitamide A (1), a simple and efficient NMR protocol was applied that is based on the analysis of 2- and 3-bond 1H-13C spin-spin coupling constants using a PIP (pure in-phase) HSQMBC (heteronuclear single quantum multiple bond correlation) IPAP (in-phase and anti-phase) experiment. Suberitamides A (1) and B (2) inhibited Cbl-b, an E3 ubiquitin ligase that is an important modulator of immune cell function, with IC50 values of approximately 11 μM.

journal_name

Mar Drugs

journal_title

Marine drugs

authors

Kim CK,Wang D,Wilson BAP,Saurí J,Voeller D,Lipkowitz S,O'Keefe BR,Gustafson KR

doi

10.3390/md18110536

subject

Has Abstract

pub_date

2020-10-28 00:00:00

issue

11

issn

1660-3397

pii

md18110536

journal_volume

18

pub_type

杂志文章
  • Polysaccharide from Codium fragile Induces Anti-Cancer Immunity by Activating Natural Killer Cells.

    abstract::Natural polysaccharides exhibit beneficial immune modulatory effects, including immune stimulatory and anti-cancer activities. In this study, we examined the effect of Codium fragile polysaccharide (CFP) on natural killer (NK) cell activation, and its effect on tumor-bearing mice. Intravenous CFP treatment of C57BL/6 ...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md18120626

    authors: Park HB,Hwang J,Zhang W,Go S,Kim J,Choi I,You S,Jin JO

    更新日期:2020-12-08 00:00:00

  • The Mediterranean red alga Asparagopsis: a source of compounds against Leishmania.

    abstract::Crude extracts and column fractions from the red algae Asparagopsis taxiformis and A. armata from the Strait of Messina (Italy) were screened for the production of antimicrobial compounds. Extracts from both species revealed remarkable antiprotozoal activity against Leishmania, revealing such algae as a great source o...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md7030361

    authors: Genovese G,Tedone L,Hamann MT,Morabito M

    更新日期:2009-08-11 00:00:00

  • Ubiquitin-Proteasome Modulating Dolabellanes and Secosteroids from Soft Coral Clavularia flava.

    abstract::We performed a high-content screening (HCS) assay aiming to discover bioactive molecules with proteasome inhibitory activity. By structural elucidation, we identified six compounds purified from soft coral Clavularia flava, which potentiates proteasome inhibition. Chemical structure elucidation revealed they are dolab...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md18010039

    authors: Chiu CY,Ling XH,Wang SK,Duh CY

    更新日期:2020-01-03 00:00:00

  • Bioactive peptides and depsipeptides with anticancer potential: sources from marine animals.

    abstract::Biologically active compounds with different modes of action, such as, antiproliferative, antioxidant, antimicrotubule, have been isolated from marine sources, specifically algae and cyanobacteria. Recently research has been focused on peptides from marine animal sources, since they have been found as secondary metabo...

    journal_title:Marine drugs

    pub_type: 杂志文章,评审

    doi:10.3390/md10050963

    authors: Suarez-Jimenez GM,Burgos-Hernandez A,Ezquerra-Brauer JM

    更新日期:2012-05-01 00:00:00

  • Glycol Chitosan-Docosahexaenoic Acid Liposomes for Drug Delivery: Synergistic Effect of Doxorubicin-Rapamycin in Drug-Resistant Breast Cancer.

    abstract::Marine ecosystems are the most prevalent ecosystems on the planet, providing a diversity of living organisms and resources. The development of nanotechnology may provide solutions for utilizing these thousands of potential compounds as marine pharmaceuticals. Here, we designed a liposomal glycol chitosan formulation t...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md17100581

    authors: Kim MW,Niidome T,Lee R

    更新日期:2019-10-12 00:00:00

  • Shrimp lipids: a source of cancer chemopreventive compounds.

    abstract::Shrimp is one of the most popular seafoods worldwide, and its lipids have been studied for biological activity in both, muscle and exoskeleton. Free fatty acids, triglycerides, carotenoids, and other lipids integrate this fraction, and some of these compounds have been reported with cancer chemopreventive activities. ...

    journal_title:Marine drugs

    pub_type: 杂志文章,评审

    doi:10.3390/md11103926

    authors: López-Saiz CM,Suárez-Jiménez GM,Plascencia-Jatomea M,Burgos-Hernández A

    更新日期:2013-10-16 00:00:00

  • Clinical trial: marine lipid suppositories as laxatives.

    abstract:UNLABELLED:Cod-liver oil and other marine products containing polyunsaturated fatty acids have anti-inflammatory, anti-bacterial and anti-viral effects and may be useful in the treatment of various inflammatory and infectious diseases. We developed suppositories and ointment with 30% free fatty acid (FFA) extract from ...

    journal_title:Marine drugs

    pub_type: 临床试验,杂志文章,随机对照试验

    doi:10.3390/md10092047

    authors: Ormarsson OT,Geirsson T,Bjornsson ES,Jonsson T,Moller P,Loftsson T,Stefansson E

    更新日期:2012-09-01 00:00:00

  • Marinopyrrole derivatives with sulfide spacers as selective disruptors of Mcl-1 binding to pro-apoptotic protein Bim.

    abstract::A series of novel marinopyrroles with sulfide and sulphone spacers were designed and synthesized. Their activity to disrupt the binding of the pro-apoptotic protein, Bim, to the pro-survival proteins, Mcl-1 and Bcl-xL, was evaluated using ELISA assays. Fluorescence-quenching (FQ) assays confirmed the direct binding of...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md12084311

    authors: Cheng C,Liu Y,Balasis ME,Garner TP,Li J,Simmons NL,Berndt N,Song H,Pan L,Qin Y,Nicolaou KC,Gavathiotis E,Sebti SM,Li R

    更新日期:2014-07-29 00:00:00

  • Xeniaphyllane-Derived Terpenoids from Soft Coral Sinularia nanolobata.

    abstract::A novel tetranorditerpenoid, sinubatin A (1) (having an unprecedented carbon skeleton), a new norditerpenoid, sinubatin B (2) (a 4,5-epoxycaryophyllene possessing an unusual methylfuran moiety side chain), and a known diterpenoid, gibberosin J (3) were isolated from soft coral Sinulariananolobata. The structures of th...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md16020040

    authors: Hsu FY,Wang SK,Duh CY

    更新日期:2018-01-24 00:00:00

  • Molecular docking studies of marine diterpenes as inhibitors of wild-type and mutants HIV-1 reverse transcriptase.

    abstract::AIDS is a pandemic responsible for more than 35 million deaths. The emergence of resistant mutations due to drug use is the biggest cause of treatment failure. Marine organisms are sources of different molecules, some of which offer promising HIV-1 reverse transcriptase (RT) inhibitory activity, such as the diterpenes...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md11114127

    authors: Miceli LA,Teixeira VL,Castro HC,Rodrigues CR,Mello JF,Albuquerque MG,Cabral LM,de Brito MA,de Souza AM

    更新日期:2013-10-29 00:00:00

  • Aplisulfamines, new sulfoxide-containing metabolites from an aplidium tunicate: absolute stereochemistry at chiral sulfur and carbon atoms assigned through an original combination of spectroscopic and computational methods.

    abstract::Two new sulfoxide-containing metabolites, aplisulfamines A and B, have been isolated from an Aplidium sp. collected in the Bay of Naples. Their planar structure and geometry of a double bond were readily determined by using standard methods, mainly NMR spectroscopy. An original approach was used to assign the absolute...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md10010051

    authors: Aiello A,Fattorusso E,Imperatore C,Luciano P,Menna M,Vitalone R

    更新日期:2012-01-01 00:00:00

  • Posidonia oceanica (L.) Delile Ethanolic Extract Modulates Cell Activities with Skin Health Applications.

    abstract::Seagrasses are high plants sharing adaptive metabolic features with both terrestrial plants and marine algae, resulting in a phytocomplex possibly endowed with interesting biological properties. The aim of this study is to evaluate the in vitro activities on skin cells of an ethanolic extract obtained from the leaves ...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md16010021

    authors: Cornara L,Pastorino G,Borghesi B,Salis A,Clericuzio M,Marchetti C,Damonte G,Burlando B

    更新日期:2018-01-10 00:00:00

  • Recently confirmed apoptosis-inducing lead compounds isolated from marine sponge of potential relevance in cancer treatment.

    abstract::Despite intense efforts to develop non-cytotoxic anticancer treatments, effective agents are still not available. Therefore, novel apoptosis-inducing drug leads that may be developed into effective targeted cancer therapies are of interest to the cancer research community. Targeted cancer therapies affect specific abe...

    journal_title:Marine drugs

    pub_type: 杂志文章,评审

    doi:10.3390/md9091580

    authors: Essack M,Bajic VB,Archer JA

    更新日期:2011-01-01 00:00:00

  • Polyhydroxylated steroids from the South China Sea soft coral Sarcophyton sp. and their cytotoxic and antiviral activities.

    abstract::Chemical investigation on the soft coral Sarcophyton sp. collected from the South China Sea yielded three new polyhydroxylated steroids, compounds (1-3), together with seven known ones (4-10). Their structures were established by extensive spectroscopic methods and comparison of their data with those of the related kn...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md11124788

    authors: Gong KK,Tang XL,Zhang G,Cheng CL,Zhang XW,Li PL,Li GQ

    更新日期:2013-12-02 00:00:00

  • 5-Hydroxycyclopenicillone, a New β-Amyloid Fibrillization Inhibitor from a Sponge-Derived Fungus Trichoderma sp. HPQJ-34.

    abstract::Abstract: A new cyclopentenone, 5-hydroxycyclopeni cillone (1), was isolated together with three known compounds, ar-turmerone (2), citreoisocoumarin (3), and 6-O-methyl-citreoisocoumarin (4), from a culture of the sponge-derived fungus Trichoderma sp. HPQJ-34. The structures of 1-4 were characterized using comprehens...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md15080260

    authors: Fang F,Zhao J,Ding L,Huang C,Naman CB,He S,Wu B,Zhu P,Luo Q,Gerwick WH,Yan X,Wang Q,Zhang Z,Cui W

    更新日期:2017-08-19 00:00:00

  • Cyanobacterial Metabolite Calothrixins: Recent Advances in Synthesis and Biological Evaluation.

    abstract::The marine environment is host to unparalleled biological and chemical diversity, making it an attractive resource for the discovery of new therapeutics for a plethora of diseases. Compounds that are extracted from cyanobacteria are of special interest due to their unique structural scaffolds and capacity to produce p...

    journal_title:Marine drugs

    pub_type: 杂志文章,评审

    doi:10.3390/md14010017

    authors: Xu S,Nijampatnam B,Dutta S,Velu SE

    更新日期:2016-01-12 00:00:00

  • Influence of Chitosan Swelling Behaviour on Controlled Release of Tenofovir from Mucoadhesive Vaginal Systems for Prevention of Sexual Transmission of HIV.

    abstract::The main challenges facing efforts to prevent the transmission of human immunodeficiency virus (HIV) are the lack of access to sexual education services and sexual violence against young women and girls. Vaginal formulations for the prevention of sexually transmitted infections are currently gaining importance in drug...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md15020050

    authors: Notario-Pérez F,Martín-Illana A,Cazorla-Luna R,Ruiz-Caro R,Bedoya LM,Tamayo A,Rubio J,Veiga MD

    更新日期:2017-02-21 00:00:00

  • Biotransfer of β-N-methylamino-L-alanine (BMAA) in a eutrophicated freshwater lake.

    abstract::β-N-Methylamino-L-alanine (BMAA), a neurotoxic non-protein amino acid, plays a significant role as an environmental risk factor in neurodegenerative diseases, such as amyotrophic lateral sclerosis. BMAA producers occur globally, colonizing almost all habitats and represent species from distinct phytoplanktonic groups,...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md13031185

    authors: Lage S,Annadotter H,Rasmussen U,Rydberg S

    更新日期:2015-03-02 00:00:00

  • New Mammalian Target of Rapamycin (mTOR) Modulators Derived from Natural Product Databases and Marine Extracts by Using Molecular Docking Techniques.

    abstract::Mammalian target of rapamycin (mTOR) is a PI3K-related serine/threonine protein kinase that functions as a master regulator of cellular growth and metabolism, in response to nutrient and hormonal stimuli. mTOR functions in two distinct complexes-mTORC1 is sensitive to rapamycin, while, mTORC2 is insensitive to this dr...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md16100385

    authors: Ruiz-Torres V,Losada-Echeberría M,Herranz-López M,Barrajón-Catalán E,Galiano V,Micol V,Encinar JA

    更新日期:2018-10-15 00:00:00

  • Inhibitory activity of marine sponge-derived natural products against parasitic protozoa.

    abstract::In this study, thirteen sponge-derived terpenoids, including five linear furanoterpenes: furospinulosin-1 (1), furospinulosin-2 (2), furospongin-1 (3), furospongin-4 (4), and demethylfurospongin-4 (5); four linear meroterpenes: 2-(hexaprenylmethyl)-2-methylchromenol (6), 4-hydroxy-3-octaprenylbenzoic acid (7), 4-hydro...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md8010047

    authors: Orhan I,Sener B,Kaiser M,Brun R,Tasdemir D

    更新日期:2010-01-15 00:00:00

  • Bromoperoxidase Producing Bacillus spp. Isolated from the Hypobranchial Glands of a Muricid Mollusc Are Capable of Tyrian Purple Precursor Biogenesis.

    abstract::The secondary metabolite Tyrian purple, also known as shellfish purple and royal purple, is a dye with historical importance for humans. The biosynthetic origin of Tyrian purple in Muricidae molluscs is not currently known. A possible role for symbiotic bacteria in the production of tyrindoxyl sulphate, the precursor ...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md17050264

    authors: Ngangbam AK,Mouatt P,Smith J,Waters DLE,Benkendorff K

    更新日期:2019-05-03 00:00:00

  • Effect of Marine-Derived Ice-Binding Proteins on the Cryopreservation of Marine Microalgae.

    abstract::Ice-binding protein (IBPs) protect cells from cryo-injury during cryopreservation by inhibiting ice recrystallization (IR), which is a main cause of cell death. In the present study, we employed two IBPs, one, designated LeIBP from Arctic yeast, and the other, designated FfIBP from Antarctic sea ice bacterium, in the ...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md15120372

    authors: Kim HJ,Koo BW,Kim D,Seo YS,Nam YK

    更新日期:2017-12-01 00:00:00

  • Emerging concepts promising new horizons for marine biodiscovery and synthetic biology.

    abstract::The vast oceans of the world, which comprise a huge variety of unique ecosystems, are emerging as a rich and relatively untapped source of novel bioactive compounds with invaluable biotechnological and pharmaceutical potential. Evidence accumulated over the last decade has revealed that the diversity of marine microor...

    journal_title:Marine drugs

    pub_type: 杂志文章,评审

    doi:10.3390/md13052924

    authors: Reen FJ,Gutiérrez-Barranquero JA,Dobson AD,Adams C,O'Gara F

    更新日期:2015-05-13 00:00:00

  • Hydrothermal Processing of Laminaria ochroleuca for the Production of Crude Extracts Used to Formulate Polymeric Nanoparticles.

    abstract::A green extraction process using only water was proposed for the simultaneous extraction of alginate and bioactive compounds from Laminaria ochroleuca. Operation was carried out during non-isothermal heating up to maximal temperatures over the range of 70 °C to 100 °C. Once separated, the alginate and the crude extrac...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md18070336

    authors: Flórez-Fernández N,Álvarez-Viñas M,Guerreiro F,Torres MD,Grenha A,Domínguez H

    更新日期:2020-06-27 00:00:00

  • Synthesis and Antiplasmodial Evaluation of Analogues Based on the Tricyclic Core of Thiaplakortones A-D.

    abstract::Six regioisomers associated with the tricyclic core of thiaplakortones A-D have been synthesized. Reaction of 1H-indole-4,7-dione and 1-tosyl-1H-indole-4,7-dione with 2-aminoethanesulfinic acid afforded a regioisomeric series, which was subsequently deprotected and oxidized to yield the tricyclic core scaffolds presen...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md13095784

    authors: Schwartz BD,Coster MJ,Skinner-Adams TS,Andrews KT,White JM,Davis RA

    更新日期:2015-09-15 00:00:00

  • Astaxanthin Inhibits Proliferation and Induces Apoptosis of Human Hepatocellular Carcinoma Cells via Inhibition of Nf-Κb P65 and Wnt/Β-Catenin in Vitro.

    abstract::Hepatocellular carcinoma (HCC) is a malignant tumor that can cause systemic invasion; however, the exact etiology and molecular mechanism are unknown. Astaxanthin (ASX), a powerful antioxidant, has efficient anti-oxidant, anti-inflammatory, and other activities, and has great research prospects in cancer therapy. We s...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md13106064

    authors: Li J,Dai W,Xia Y,Chen K,Li S,Liu T,Zhang R,Wang J,Lu W,Zhou Y,Yin Q,Abudumijiti H,Chen R,Zheng Y,Wang F,Lu J,Zhou Y,Guo C

    更新日期:2015-09-24 00:00:00

  • Spiromastixones Inhibit Foam Cell Formation via Regulation of Cholesterol Efflux and Uptake in RAW264.7 Macrophages.

    abstract::Bioassay-guided evaluation shows that a deep sea-derived fungus, Spiromastix sp. MCCC 3A00308, possesses lipid-lowering activity. Chromatographic separation of a culture broth resulted in the isolation of 15 known depsidone-based analogues, labeled spiromastixones A-O (1-15). Each of these compounds was tested for its...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md13106352

    authors: Wu C,Chen R,Liu M,Liu D,Li X,Wang S,Niu S,Guo P,Lin W

    更新日期:2015-10-14 00:00:00

  • Rumphellaoic acid A, a novel sesquiterpenoid from the formosan gorgonian coral Rumphella antipathies.

    abstract::A novel sesquiterpenoid, rumphellaoic acid A (1), was isolated from the gorgonian coral Rumphella antipathies, and was found to possess a carbon skeleton that was obtained for the first time from a natural sources. The structure of 1 was elucidated by spectroscopic methods and this compound and was found to exert a mo...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md12125856

    authors: Chung HM,Wang WH,Hwang TL,Fang LS,Wen ZH,Chen JJ,Wu YC,Sung PJ

    更新日期:2014-12-04 00:00:00

  • Unraveling the Detoxification Mechanism of 2,4-Dichlorophenol by Marine-Derived Mesophotic Symbiotic Fungi Isolated from Marine Invertebrates.

    abstract::Chlorophenols (CPs) are environmental pollutants that are produced through various anthropogenic activities and introduced in the environment. Living organisms, including humans, are exposed to these toxic xenobiotics and suffer from adverse health effects. More specifically, 2,4-dichlorophenol (2,4-DCP) is released i...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md17100564

    authors: Nikolaivits E,Agrafiotis A,Termentzi A,Machera K,Le Goff G,Álvarez P,Chavanich S,Benayahu Y,Ouazzani J,Fokialakis N,Topakas E

    更新日期:2019-09-30 00:00:00

  • Extraction, Identification, Modification, and Antibacterial Activity of Histone from Immature Testis of Atlantic salmon.

    abstract::In the present study, histone from immature testis of Atlantic salmon was extracted and identified, and its antibacterial activity after enzymolysis was investigated. Histone extracted from Atlantic salmon (Salmo salar) testis using the acid extraction method was successfully identified by LC-MS/MS, and revealed signi...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md18030133

    authors: Fu B,Lin H,Ramesh Pavase T,Mi N,Sui J

    更新日期:2020-02-26 00:00:00