Marine Drugs

332 KiB

Open AccessArticle

Cytotoxicity on Human Cancer Cells of Ophidiacerebrosides Isolated from the African Starfish Narcissia canariensis

by Fereshteh Farokhi, Gaetane Wielgosz-Collin, Monique Clement, Jean-Michel Kornprobst and Gilles Barnathan

Mar. Drugs 2010, 8(12), 2988-2998; https://doi.org/10.3390/md8122988 - 22 Dec 2010

Cited by 16 | Viewed by 9235

Abstract

The starfish Narcissia canariensis harvested from the coasts off Dakar, Senegal, was investigated for glycolipids (GL). This report deals with the isolation, characterization and biological activity of a fraction F13-3 separated from the GL mixture and selected according to its ability to inhibit [...] Read more.

The starfish Narcissia canariensis harvested from the coasts off Dakar, Senegal, was investigated for glycolipids (GL). This report deals with the isolation, characterization and biological activity of a fraction F13-3 separated from the GL mixture and selected according to its ability to inhibit KB cell proliferation after 72 hours of treatment. Firstly, a GL mixture F13 was obtained that accounted for 1.36% of starfish biomass (dry weight) and 0.36% of total lipids. The fraction F13-3 obtained from F13 contained three homologous GL identified as peracetylated derivatives on the basis of chemical and spectroscopic evidence. These contained a β-glucopyranoside as sugar head, a 9-methyl-branched 4,8,10-triunsaturated long-chain aminoalcohol as sphingoid base and amide-linked 2-hydroxy fatty acid chains. The majority (63%) had an amide-linked 2‑hydroxydocosanoic acid chain and was identified as the ophidiacerebroside-C, firstly isolated from the starfish Ophidiaster ophidiamus. The minor components of F13-3 differed by one more or one less methylene group, and corresponded to ophidiacerebroside-B and -D. We found that F13-3 displayed an interesting cytotoxic activity over 24 hours on various adherent human cancerous cell lines (multiple myeloma, colorectal adenocarcinoma and glioblastoma multiforme) with an IC₅₀ of around 20 μM. Full article

(This article belongs to the Special Issue Marine Lipids)

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131 KiB

Open AccessArticle

Biological Activity of Volatiles from Marine and Terrestrial Bacteria

by Stefan Schulz, Jeroen S. Dickschat, Brigitte Kunze, Irene Wagner-Dobler, Randi Diestel and Florenz Sasse

Mar. Drugs 2010, 8(12), 2976-2987; https://doi.org/10.3390/md8122976 - 22 Dec 2010

Cited by 55 | Viewed by 11451

Abstract

The antiproliferative activity of 52 volatile compounds released from bacteria was investigated in agar diffusion assays against medically important microorganisms and mouse fibroblasts. Furthermore, the activity of these compounds to interfere with the quorum-sensing-systems was tested with two different reporter strains. While some [...] Read more.

The antiproliferative activity of 52 volatile compounds released from bacteria was investigated in agar diffusion assays against medically important microorganisms and mouse fibroblasts. Furthermore, the activity of these compounds to interfere with the quorum-sensing-systems was tested with two different reporter strains. While some of the compounds specific to certain bacteria showed some activity in the antiproliferative assay, the compounds common to many bacteria were mostly inactive. In contrast, some of these compounds were active in the quorum-sensing-tests. γ-Lactones showed a broad reactivity, while pyrazines seem to have only low intrinsic activity. A general discussion on the ecological importance of these findings is given. Full article

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357 KiB

Open AccessArticle

Sterols from the Madagascar Sponge Fascaplysinopsis sp.

by Maurice Aknin, Emmanuelle Gros, Jean Vacelet, Yoel Kashman and Anne Gauvin-Bialecki

Mar. Drugs 2010, 8(12), 2961-2975; https://doi.org/10.3390/md8122961 - 17 Dec 2010

Cited by 13 | Viewed by 10450

Abstract

The sponge Fascaplysinopsis sp. (order Dictyoceratida, Family Thorectidae) from the west coast of Madagascar (Indian Ocean) is a particularly rich source of bioactive nitrogenous macrolides. The previous studies on this organism led to the suggestion that the latter should originate from associated microsymbionts. [...] Read more.

The sponge Fascaplysinopsis sp. (order Dictyoceratida, Family Thorectidae) from the west coast of Madagascar (Indian Ocean) is a particularly rich source of bioactive nitrogenous macrolides. The previous studies on this organism led to the suggestion that the latter should originate from associated microsymbionts. In order to evaluate the influence of microsymbionts on lipid content, 10 samples of Fascaplysinopsis sp. were investigated for their sterol composition. Contrary to the secondary metabolites, the sterol patterns established were qualitatively and quantitatively stable: 14 sterols with different unsaturated nuclei, D⁵, D⁷ and D^5,7, were identified; the last ones being the main sterols of the investigated sponges. The chemotaxonomic significance of these results for the order Dictyoceratida is also discussed in the context of the literature. The conjugated diene system in D^5,7 sterols is known to be unstable and easily photo-oxidized during storage and/or experiments to produce 5a,8a-epidioxy sterols. However, in this study, no 5a,8a-epidioxysterols (or only trace amounts) were observed. Thus, it was supposed that photo-oxidation was avoided thanks to the natural antioxidants detected in Fascaplysinopsis sp. by both the DPPH and b-caroten bleaching assays. Full article

(This article belongs to the Special Issue Marine Lipids)

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330 KiB

Open AccessArticle

Antibacterial Compounds from Marine Vibrionaceae Isolated on a Global Expedition

by Matthias Wietz, Maria Mansson, Charlotte H. Gotfredsen, Thomas O. Larsen and Lone Gram

Mar. Drugs 2010, 8(12), 2946-2960; https://doi.org/10.3390/md8122946 - 13 Dec 2010

Cited by 88 | Viewed by 15269

Abstract

On a global research expedition, over 500 bacterial strains inhibitory towards pathogenic bacteria were isolated. Three hundred of the antibacterial strains were assigned to the Vibrionaceae family. The purpose of the present study was to investigate the phylogeny and bioactivity of five Vibrionaceae [...] Read more.

On a global research expedition, over 500 bacterial strains inhibitory towards pathogenic bacteria were isolated. Three hundred of the antibacterial strains were assigned to the Vibrionaceae family. The purpose of the present study was to investigate the phylogeny and bioactivity of five Vibrionaceae strains with pronounced antibacterial activity. These were identified as Vibrio coralliilyticus (two strains), V. neptunius (two strains), and Photobacterium halotolerans (one strain) on the basis of housekeeping gene sequences. The two related V. coralliilyticus and V. neptunius strains were isolated from distant oceanic regions. Chemotyping by LC-UV/MS underlined genetic relationships by showing highly similar metabolite profiles for each of the two V. coralliilyticus and V. neptunius strains, respectively, but a unique profile for P. halotolerans. Bioassay-guided fractionation identified two known antibiotics as being responsible for the antibacterial activity; andrimid (from V. coralliilyticus) and holomycin (from P. halotolerans). Despite the isolation of already known antibiotics, our findings show that marine Vibrionaceae are a resource of antibacterial compounds and may have potential for future natural product discovery. Full article

(This article belongs to the Special Issue Marine Antibiotics)

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233 KiB

Open AccessArticle

Cladielloides A and B: New Eunicellin-Type Diterpenoids from an Indonesian Octocoral Cladiella sp.

by Yung-Husan Chen, Chia-Ying Tai, Tsong-Long Hwang, Ching-Feng Weng, Jan-Jung Li, Lee-Shing Fang, Wei-Hsien Wang, Yang-Chang Wu and Ping-Jyun Sung

Mar. Drugs 2010, 8(12), 2936-2945; https://doi.org/10.3390/md8122936 - 06 Dec 2010

Cited by 38 | Viewed by 9620

Abstract

Two new eunicellin-type diterpenoids, cladielloides A (1) and B (2), which were found to possess a 2-hydroxybutyroxy group in their structures, were isolated from an Indonesian octocoral identified as Cladiella sp. The structures of eunicellins 1 and 2 were [...] Read more.

Two new eunicellin-type diterpenoids, cladielloides A (1) and B (2), which were found to possess a 2-hydroxybutyroxy group in their structures, were isolated from an Indonesian octocoral identified as Cladiella sp. The structures of eunicellins 1 and 2 were elucidated by spectroscopic methods. Cladielloide B (2) exhibited moderate cytotoxicity toward CCRF-CEM tumor cells and this compound displayed significant inhibitory effects on superoxide anion generation and elastase release by human neutrophils. Full article

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1926 KiB

Open AccessReview

Bioactive Dehydrotyrosyl and Dehydrodopyl Compounds of Marine Origin

by Manickam Sugumaran and William E. Robinson

Mar. Drugs 2010, 8(12), 2906-2935; https://doi.org/10.3390/md8122906 - 06 Dec 2010

Cited by 38 | Viewed by 9687

Abstract

The amino acid, tyrosine, and its hydroxylated product, 3,4-dihydroxyphenylalanine (dopa), plays an important role in the biogenesis of a number of potentially important bioactive molecules in marine organisms. Interestingly, several of these tyrosyl and dopa‑containing compounds possess dehydro groups in their side chains. [...] Read more.

The amino acid, tyrosine, and its hydroxylated product, 3,4-dihydroxyphenylalanine (dopa), plays an important role in the biogenesis of a number of potentially important bioactive molecules in marine organisms. Interestingly, several of these tyrosyl and dopa‑containing compounds possess dehydro groups in their side chains. Examples span the range from simple dehydrotyrosine and dehydrodopamines to complex metabolic products, including peptides and polycyclic alkaloids. Based on structural information, these compounds can be subdivided into five categories: (a) Simple dehydrotyrosine and dehydrotyramine containing molecules; (b) simple dehydrodopa derivatives; (c) peptidyl dehydrotyrosine and dehydrodopa derivatives; (d) multiple dehydrodopa containing compounds; and (e) polycyclic condensed dehydrodopa derivatives. These molecules possess a wide range of biological activities that include (but are not limited to) antitumor activity, antibiotic activity, cytotoxicity, antioxidant activity, multidrug resistance reversal, cell division inhibition, immunomodulatory activity, HIV-integrase inhibition, anti-viral, and anti-feeding (or feeding deterrent) activity. This review summarizes the structure, distribution, possible biosynthetic origin, and biological activity, of the five categories of dehydrotyrosine and dehydrodopa containing compounds. Full article

(This article belongs to the Special Issue Marine Natural Products - Advances in Separation, Characterisation and Chemical Profiling Methodologies)

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421 KiB

Open AccessArticle

Screening and cDNA Cloning of Kv1 Potassium Channel Toxins in Sea Anemones

by Yoshikazu Yamaguchi, Yuichi Hasegawa, Tomohiro Honma, Yuji Nagashima and Kazuo Shiomi

Mar. Drugs 2010, 8(12), 2893-2905; https://doi.org/10.3390/md8122893 - 02 Dec 2010

Cited by 22 | Viewed by 7728

Abstract

When 21 species of sea anemones were screened for Kv1 potassium channel toxins by competitive inhibition of the binding of ¹²⁵I-α-dendrotoxin to rat synaptosomal membranes, 11 species (two species of Actiniidae, one species of Hormathiidae, five species of Stichodactylidae and three species [...] Read more.

When 21 species of sea anemones were screened for Kv1 potassium channel toxins by competitive inhibition of the binding of ¹²⁵I-α-dendrotoxin to rat synaptosomal membranes, 11 species (two species of Actiniidae, one species of Hormathiidae, five species of Stichodactylidae and three species of Thalassianthidae) were found to be positive. Furthermore, full-length cDNAs encoding type 1 potassium channel toxins from three species of Stichodactylidae and three species of Thalassianthidae were cloned by a combination of RT-PCR, 3′RACE and 5′RACE. The precursors of these six toxins are commonly composed of signal peptide, propart and mature peptide portions. As for the mature peptide (35 amino acid residues), the six toxins share more than 90% sequence identities with one another and with κ_1.3-SHTX-She1a (Shk) from Stichodactyla helianthus but only 34–63% identities with the other type 1 potassium channel toxins. Full article

(This article belongs to the Special Issue Ion Channel Inhibiting Marine Toxins)

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253 KiB

Open AccessReview

Potential Anti-HIV Agents from Marine Resources: An Overview

by Thanh-Sang Vo and Se-Kwon Kim

Mar. Drugs 2010, 8(12), 2871-2892; https://doi.org/10.3390/md8122871 - 29 Nov 2010

Cited by 145 | Viewed by 15014

Abstract

Human immunodeficiency virus (HIV) infection causes acquired immune deficiency syndrome (AIDS) and is a global public health issue. Anti-HIV therapy involving chemical drugs has improved the life quality of HIV/AIDS patients. However, emergence of HIV drug resistance, side effects and the necessity for [...] Read more.

Human immunodeficiency virus (HIV) infection causes acquired immune deficiency syndrome (AIDS) and is a global public health issue. Anti-HIV therapy involving chemical drugs has improved the life quality of HIV/AIDS patients. However, emergence of HIV drug resistance, side effects and the necessity for long-term anti-HIV treatment are the main reasons for failure of anti-HIV therapy. Therefore, it is essential to isolate novel anti-HIV therapeutics from natural resources. Recently, a great deal of interest has been expressed regarding marine-derived anti-HIV agents such as phlorotannins, sulfated chitooligosaccharides, sulfated polysaccharides, lectins and bioactive peptides. This contribution presents an overview of anti-HIV therapeutics derived from marine resources and their potential application in HIV therapy. Full article

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369 KiB

Open AccessReview

Cytotoxic Terpene Quinones from Marine Sponges

by Marina Gordaliza

Mar. Drugs 2010, 8(12), 2849-2870; https://doi.org/10.3390/md8122849 - 24 Nov 2010

Cited by 104 | Viewed by 13470

Abstract

The 1,4-benzoquinone moiety is a common structural feature in a large number of compounds that have received considerable attention owing to their broad spectrum of biological activities. The cytotoxic and antiproliferative properties of many natural sesquiterpene quinones and hydroquinones from sponges of the [...] Read more.

The 1,4-benzoquinone moiety is a common structural feature in a large number of compounds that have received considerable attention owing to their broad spectrum of biological activities. The cytotoxic and antiproliferative properties of many natural sesquiterpene quinones and hydroquinones from sponges of the order Dictyoceratida, such as avarol, avarone, illimaquinone, nakijiquinone and bolinaquinone, offer promising opportunities for the development of new antitumor agents. The present review summarizes the structure and cytotoxicity of natural terpenequinones/hydroquinones and their bioactive analogues and derivatives. Full article

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Mar. Drugs, Volume 8, Issue 12 (December 2010) – 9 articles , Pages 2849-2998

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