Marine Drugs

22 pages, 369 KB

Open AccessReview

Cytotoxic Terpene Quinones from Marine Sponges

by Marina Gordaliza

Department of Pharmaceutical Chemistry, Pharmacy Faculty, Salamanca University, Campus Miguel de Unamuno, 37007 Salamanca, Spain

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

Cited by 112 | Viewed by 15060

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

▼ Show Figures

Graphical abstract

22 pages, 253 KB

Open AccessReview

Potential Anti-HIV Agents from Marine Resources: An Overview

by Thanh-Sang Vo¹ and Se-Kwon Kim^1,2,*

¹ Marine Biochemistry Laboratory, Department of Chemistry, Pukyong National University, Busan 608-737, Korea

² Marine Bioprocess Research Center, Pukyong National University, Busan 608-737, Korea

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

Cited by 156 | Viewed by 16924

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

▼ Show Figures

13 pages, 421 KB

Open AccessArticle

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

by Yoshikazu Yamaguchi¹, Yuichi Hasegawa¹, Tomohiro Honma^1,2, Yuji Nagashima¹ and Kazuo Shiomi^1,*

¹ Department of Food Science and Technology, Tokyo University of Marine Science and Technology, Konan-4, Minato-ku, Tokyo 108-8477, Japan

² Department of Food Nutrition, Tokai University Junior College, Miyamae-cho, Aoi-ku, Shizuoka 420-8511, Japan

Mar. Drugs 2010, 8(12), 2893-2905; https://doi.org/10.3390/md8122893 - 2 Dec 2010

Cited by 24 | Viewed by 8428

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)

▼ Show Figures

Graphical abstract

30 pages, 1926 KB

Open AccessReview

Bioactive Dehydrotyrosyl and Dehydrodopyl Compounds of Marine Origin

by Manickam Sugumaran^1,* and William E. Robinson²

¹ Department of Biology, University of Massachusetts Boston, Boston, MA 02125, USA

² Environmental, Earth and Ocean Sciences Department, University of Massachusetts Boston, Boston, MA 02125, USA

Mar. Drugs 2010, 8(12), 2906-2935; https://doi.org/10.3390/md8122906 - 6 Dec 2010

Cited by 42 | Viewed by 10621

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)

▼ Show Figures

10 pages, 233 KB

Open AccessArticle

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

by Yung-Husan Chen¹, Chia-Ying Tai^1,2, Tsong-Long Hwang³

, Ching-Feng Weng⁴, Jan-Jung Li¹, Lee-Shing Fang⁵, Wei-Hsien Wang^1,6,7, Yang-Chang Wu^8,9,* and Ping-Jyun Sung^1,2,4,6,7,*

¹ National Museum of Marine Biology & Aquarium, Pingtung 944, Taiwan

² Graduate Institute of Marine Biotechnology, National Dong Hwa University, Pingtung 944, Taiwan

³ Graduate Institute of Natural Products, Chang Gung University, Taoyuan 333, Taiwan

⁴ Department of Life Science and Institute of Biotechnology, National Dong Hwa University, Hualien 974, Taiwan

⁵ Department of Sport, Health, and Leisure, Cheng Shiu University, Kaohsiung 833, Taiwan

⁶ Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan

⁷ Asia-Pacific Ocean Research Center, National Sun Yat-sen University, Kaohsiung 804, Taiwan

⁸ Graduate Institute of Integrated Medicine, College of Chinese Medicine, China Medical University, Taichung 404, Taiwan

⁹ Natural Medicinal Products Research Center, China Medical University Hospital, Taichung 404, Taiwan

Mar. Drugs 2010, 8(12), 2936-2945; https://doi.org/10.3390/md8122936 - 6 Dec 2010

Cited by 39 | Viewed by 10444

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

▼ Show Figures

15 pages, 330 KB

Open AccessArticle

Antibacterial Compounds from Marine Vibrionaceae Isolated on a Global Expedition

by Matthias Wietz^1,†, Maria Mansson^2,†, Charlotte H. Gotfredsen³, Thomas O. Larsen² and Lone Gram^1,*

¹ National Food Institute, Technical University of Denmark, 2800 Kgs. Lyngby, Denmark

² Centre for Microbial Biotechnology, Department of Systems Biology, Technical University of Denmark, 2800 Kgs. Lyngby, Denmark

³ Department of Chemistry, Technical University of Denmark, 2800 Kgs. Lyngby, Denmark

^† These authors contributed equally to this work.

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

Cited by 96 | Viewed by 16578

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)

▼ Show Figures

Graphical abstract

15 pages, 357 KB

Open AccessArticle

Sterols from the Madagascar Sponge Fascaplysinopsis sp.

by Maurice Aknin¹, Emmanuelle Gros¹, Jean Vacelet², Yoel Kashman³ and Anne Gauvin-Bialecki^1,*

¹ Laboratoire de Chimie des Substances Naturelles et des Sciences des Aliments, Faculté des Sciences et Technologies, Université de la Réunion, 15 Avenue René Cassin, BP 7151, 97715 St Denis Messag Cedex 9, La Réunion, France

² Centre d’Océanologie de Marseille, Aix-Marseille Université, CNRS UMR 6540 DIMAR, Station Marine d’Endoume, rue Batterie des Lions, 13007 Marseille, France

³ School of Chemistry Tel Aviv University, Sackler Faculty of Medicine, Tel Aviv University, Ramat Aviv 69978, Israel

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

Cited by 13 | Viewed by 11248

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)

▼ Show Figures

12 pages, 131 KB

Open AccessArticle

Biological Activity of Volatiles from Marine and Terrestrial Bacteria

by Stefan Schulz^1,*, Jeroen S. Dickschat¹, Brigitte Kunze², Irene Wagner-Dobler², Randi Diestel³ and Florenz Sasse³

¹ Institute of Organic Chemistry, University of Braunschweig—Institute of Technology, Hagenring 30, 38106 Braunschweig, Germany

² Research Group Microbial Communication, Helmholtz Center for Infection Research, Inhoffenstrasse 7, 38124 Braunschweig, Germany

³ Department of Chemical Biology, Helmholtz Center for Infection Research, Inhoffenstrasse 7, 38124 Braunschweig, Germany

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

Cited by 58 | Viewed by 12486

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

▼ Show Figures

Graphical abstract

Journal Menu

Journal Browser

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

Further Information

Guidelines

MDPI Initiatives

Follow MDPI