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A special issue of Marine Drugs (ISSN 1660-3397).

Deadline for manuscript submissions: closed (31 May 2018) | Viewed by 68437

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Special Issue Editors

Prof. Dr. Thomas E Adrian

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Guest Editor

Department of Physiology, United Arab Emirates University, Al Ain, Abu Dhabi, United Arab Emirates
Interests: identification of novel growth-related cancer therapeutic targets; cancer stem cells; lipoxygenase pathways in cancer; molecular mechanisms of cancer cachexia; drug combination studies

Prof. Dr. Francisco Sarabia

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Guest Editor

Department of Organic Chemistry, Faculty of Science, University of Málaga, 29071 Málaga, Spain
Interests: natural products; bioactive compounds; total synthesis; antitumor; antibiotics; cyclodepsipeptides; cyclopeptides
Special Issues, Collections and Topics in MDPI journals

Dr. Ivan Cheng-Sanchez

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Guest Editor

Department of Chemistry, University of Zurich, Zurich, Switzerland
Interests: total synthesis; natural products; medicinal chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

In recent years, there has been a steady increase in the publication of papers on the chemistry, biology, and potential clinical uses of marine glycosides. Indeed, more than half of the papers published in this field are less than a decade old. Glycosides have been isolated from species as diverse as algae, fungi, anthozoans, and echinoderms. Even fish of the genus Pardachirus produce glycosides that they use as shark repellents.

The major interest in these compounds as potential drugs stems from the broad spectrum of biological effects. They have been shown to have antimicrobial, antifungal, anti-inflammatory, immune modulatory immune modulatory and anticancer effects. The anticancer effects of marine glycosides include cell cycle suppression, induction of apoptosis, inhibition of migration, invasion and metastasis, as well as antiangiogenesis. Marine glycosides influence membrane permeability and at the molecular level, have been shown to influence membrane transport through effects on transport carriers and pumps, as well as effects on ligand-gated and voltage-gated channels. Various marine glycosides have been shown to activate sphingomyelinase and ceramide synthesis, to inhibit topoisomerase activity, receptor tyrosine kinase activity, multidrug resistance protein activity and to antagonize eicosanoid receptors.

This Special Issue will cover the entire scope of marine organism-derived glycosides that are of potential value as pharmaceutical agents or leads. These include, but are not limited to, tetracyclic triterpene glycosides; other triterpene glycosides; steroid glycosides; and glycosides of non-isoprenoid aglycones.

Prof. Dr. Thomas E Adrian
Prof. Dr. Francisco Sarabia
Dr. Ivan Cheng
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Marine Drugs is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2900 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

Marine glycosides
Triterpene glycosides
Steroid glycosides
Glycolipids
Glycosides of non-isoprenoid aglycones
Cancer
İnflammation
Antitumoral
Anti-microbial
Anti-fungal
İmmune modulation

Published Papers (12 papers)

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Research

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10 pages, 2354 KiB

Open AccessArticle

Angucycline Glycosides from an Intertidal Sediments Strain Streptomyces sp. and Their Cytotoxic Activity against Hepatoma Carcinoma Cells

by Aihong Peng, Xinying Qu, Fangyuan Liu, Xia Li, Erwei Li and Weidong Xie

Mar. Drugs 2018, 16(12), 470; https://doi.org/10.3390/md16120470 - 27 Nov 2018

Cited by 18 | Viewed by 3340

Abstract

Four angucycline glycosides including three new compounds landomycin N (1), galtamycin C (2) and vineomycin D (3), and a known homologue saquayamycin B (4), along with two alkaloids 1-acetyl-β-carboline (5) and indole-3-acetic acid (6), were isolated from the fermentation broth of an intertidal sediments-derived Streptomyces sp. Their structures were established by IR, HR-ESI-MS, 1D and 2D NMR techniques. Among the isolated angucyclines, saquayamycin B (4) displayed potent cytotoxic activity against hepatoma carcinoma cells HepG-2, SMMC-7721 and plc-prf-5, with IC₅₀ values 0.135, 0.033 and 0.244 μM respectively, superior to doxorubicin. Saquayamycin B (4) also induced apoptosis in SMMC-7721 cells as detected by its morphological characteristics in 4′,6-diamidino-2-phenylindole (DAPI) staining experiment. Full article

(This article belongs to the Special Issue Marine Glycosides)

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30 pages, 2725 KiB

Open AccessFeature PaperArticle

Distribution of Saponins in the Sea Cucumber Holothuria lessoni; the Body Wall Versus the Viscera, and Their Biological Activities

by Yadollah Bahrami, Wei Zhang and Christopher M. M. Franco

Mar. Drugs 2018, 16(11), 423; https://doi.org/10.3390/md16110423 - 01 Nov 2018

Cited by 35 | Viewed by 6077

Abstract

Sea cucumbers are an important ingredient of traditional folk medicine in many Asian countries, which are well-known for their medicinal, nutraceutical, and food values due to producing an impressive range of distinctive natural bioactive compounds. Triterpene glycosides are the most abundant and prime secondary metabolites reported in this species. They possess numerous biological activities ranging from anti-tumour, wound healing, hypolipidemia, pain relieving, the improvement of nonalcoholic fatty livers, anti-hyperuricemia, the induction of bone marrow hematopoiesis, anti-hypertension, and cosmetics and anti-ageing properties. This study was designed to purify and elucidate the structure of saponin contents of the body wall of sea cucumber Holothuria lessoni and to compare the distribution of saponins of the body wall with that of the viscera. The body wall was extracted with 70% ethanol, and purified by a liquid-liquid partition chromatography, followed by isobutanol extraction. A high-performance centrifugal partition chromatography (HPCPC) was conducted on the saponin-enriched mixture to obtain saponins with a high purity. The resultant purified saponins were analyzed using MALDI-MS/MS and ESI-MS/MS. The integrated and hyphenated MS and HPCPC analyses revealed the presence of 89 saponin congeners, including 35 new and 54 known saponins, in the body wall in which the majority of glycosides are of the holostane type. As a result, and in conjunction with existing literature, the structure of four novel acetylated saponins, namely lessoniosides H, I, J, and K were characterized. The identified triterpene glycosides showed potent antifungal activities against tested fungi, but had no antibacterial effects on the bacterium Staphylococcus aureus. The presence of a wide range of saponins with potential applications is promising for cosmeceutical, medicinal, and pharmaceutical products to improve human health. Full article

(This article belongs to the Special Issue Marine Glycosides)

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11 pages, 2489 KiB

Open AccessFeature PaperCommunication

Angucycline Glycosides from Mangrove-Derived Streptomyces diastaticus subsp. SCSIO GJ056

by Chun Gui, Yena Liu, Zhenbin Zhou, Shanwen Zhang, Yunfeng Hu, Yu-Cheng Gu, Hongbo Huang and Jianhua Ju

Mar. Drugs 2018, 16(6), 185; https://doi.org/10.3390/md16060185 - 28 May 2018

Cited by 11 | Viewed by 4277

Abstract

Nine new angucycline glycosides designated urdamycins N1–N9 (1–9), together with two known congener urdamycins A (10) and B (11), were obtained from a mangrove-derived Streptomyces diastaticus subsp. SCSIO GJ056. The structures of new compounds were elucidated on the basis of extensive spectroscopic data analysis. The absolute configurations of 6–9 were assigned by electronic circular dichroism calculation method. Urdamycins N7 (7) and N8 (8) represent the first naturally occurring (5R, 6R)-angucycline glycosides, which are diastereomers of urdamycins N6 (6) and N9 (9), respectively. Full article

(This article belongs to the Special Issue Marine Glycosides)

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10 pages, 679 KiB

Open AccessArticle

Cytotoxic Polyhydroxysteroidal Glycosides from Starfish Culcita novaeguineae

by Yunyang Lu, Hu Li, Minchang Wang, Yang Liu, Yingda Feng, Ke Liu and Haifeng Tang

Mar. Drugs 2018, 16(3), 92; https://doi.org/10.3390/md16030092 - 13 Mar 2018

Cited by 12 | Viewed by 4262

Abstract

Four new polyhydroxysteroidal glycosides—culcinosides A–D (1, 2, 4, and 7)—along with three known compounds—echinasteroside C (3), linckoside F (5), and linckoside L3 (6)—were isolated from the ethanol extract of starfish Culcita novaeguineae collected from the Xisha Islands of the South China Sea. The structures of new compounds were elucidated through extensive spectroscopic studies and chemical evidence, especially two-dimensional (2D) NMR techniques. The cytotoxicity of the new compounds against human glioblastoma cell lines U87, U251, and SHG44 were evaluated. Full article

(This article belongs to the Special Issue Marine Glycosides)

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2129 KiB

Open AccessArticle

Three New Cytotoxic Steroidal Glycosides Isolated from Conus pulicarius Collected in Kosrae, Micronesia

by Yeon-Ju Lee, Saem Han, Su Hyun Kim, Hyi-Seung Lee, Hee Jae Shin, Jong Seok Lee and Jihoon Lee

Mar. Drugs 2017, 15(12), 379; https://doi.org/10.3390/md15120379 - 04 Dec 2017

Cited by 7 | Viewed by 3830

Abstract

Three new sulfated steroidal glycosides (3–5), along with known cholesterol derivatives (1,2), were isolated from the visceral extract of the cone snail Conus pulicarius. The structure of each new compound was elucidated by nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry. The three new compounds exhibited significant in vitro cytotoxicity (GI₅₀ values down to 0.49 μM) against the K562 human leukemia cell line. Full article

(This article belongs to the Special Issue Marine Glycosides)

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3365 KiB

Open AccessArticle

Metabolite Profiling of Triterpene Glycosides of the Far Eastern Sea Cucumber Eupentacta fraudatrix and Their Distribution in Various Body Components Using LC-ESI QTOF-MS

by Roman S. Popov, Natalia V. Ivanchina, Alexandra S. Silchenko, Sergey A. Avilov, Vladimir I. Kalinin, Igor Yu. Dolmatov, Valentin A. Stonik and Pavel S. Dmitrenok

Mar. Drugs 2017, 15(10), 302; https://doi.org/10.3390/md15100302 - 02 Oct 2017

Cited by 18 | Viewed by 4388

Abstract

The Far Eastern sea cucumber Eupentacta fraudatrix is an inhabitant of shallow waters of the south part of the Sea of Japan. This animal is an interesting and rich source of triterpene glycosides with unique chemical structures and various biological activities. The objective of this study was to investigate composition and distribution in various body components of triterpene glycosides of the sea cucumber E. fraudatrix. We applied LC-ESI MS (liquid chromatography–electrospray mass spectrometry) of whole body extract and extracts of various body components for metabolic profiling and structure elucidation of triterpene glycosides from the E. fraudatrix. Totally, 54 compounds, including 26 sulfated, 18 non-sulfated and 10 disulfated glycosides were detected and described. Triterpene glycosides from the body walls, gonads, aquapharyngeal bulbs, guts and respiratory trees were extracted separately and the distributions of the detected compounds in various body components were analyzed. Series of new glycosides with unusual structural features were described in E. fraudatrix, which allow clarifying the biosynthesis of these compounds. Comparison of the triterpene glycosides contents from the five different body components revealed that the profiles of triterpene glycosides were qualitatively similar, and only some quantitative variabilities for minor compounds were observed. Full article

(This article belongs to the Special Issue Marine Glycosides)

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1689 KiB

Open AccessFeature PaperArticle

Nine New Triterpene Glycosides, Magnumosides A₁–A₄, B₁, B₂, C₁, C₂ and C₄, from the Vietnamese Sea Cucumber Neothyonidium (=Massinium) magnum: Structures and Activities against Tumor Cells Independently and in Synergy with Radioactive Irradiation

by Alexandra S. Silchenko, Anatoly I. Kalinovsky, Sergey A. Avilov, Vladimir I. Kalinin, Pelageya V. Andrijaschenko, Pavel S. Dmitrenok, Ekaterina A. Chingizova, Svetlana P. Ermakova, Olesya S. Malyarenko and Tatyana N. Dautova

Mar. Drugs 2017, 15(8), 256; https://doi.org/10.3390/md15080256 - 16 Aug 2017

Cited by 26 | Viewed by 4562

Abstract

Nine new sulfated triterpene glycosides, magnumosides A₁ (1), A₂ (2), A₃ (3), A₄ (4), B₁ (5), B₂ (6), C₁ (7), C₂ [...] Read more.

Nine new sulfated triterpene glycosides, magnumosides A₁ (1), A₂ (2), A₃ (3), A₄ (4), B₁ (5), B₂ (6), C₁ (7), C₂ (8) and C₄ (9) as well as a known colochiroside B₂ (10) have been isolated from the tropical Indo-West Pacific sea cucumber Neothynidium (=Massinium) magnum (Phyllophoridae, Dendrochirotida) collected in the Vietnamese shallow waters. The structures of new glycosides were elucidated by 2D NMR spectroscopy and mass-spectrometry. All the isolated new glycosides were characterized by the non-holostane type lanostane aglycones having 18(16)-lactone and 7(8)-double bond and differed from each other by the side chains and carbohydrate moieties structures. Magnumoside A₁ (1) has unprecedented 20(24)-epoxy-group in the aglycone side chain. Magnumosides of the group A (1–4) contained disaccharide monosulfated carbohydrate moieties, of the group B (5, 6)—tetrasaccharide monosulfated carbohydrate moieties and, finally, of the group C (7–9)—tetrasaccharide disulfated carbohydrate moieties. The cytotoxic activities of the compounds 1–9 against mouse spleen lymphocytes, the ascites form of mouse Ehrlich carcinoma cells, human colorectal carcinoma DLD-1 cells as well as their hemolytic effects have been studied. Interestingly, the erythrocytes were more sensitive to the glycosides action than spleenocytes and cancer cells tested. The compounds 3 and 7 significantly inhibited the colony formation and decreased the size of colonies of DLD-1 cancer cells at non-cytotoxic concentrations. Moreover, the synergism of effects of radioactive irradiation and compounds 3 and 7–9 at subtoxic doses on proliferation of DLD-1 cells was demonstrated. Full article

(This article belongs to the Special Issue Marine Glycosides)

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756 KiB

Open AccessArticle

Poecillastrosides, Steroidal Saponins from the Mediterranean Deep-Sea Sponge Poecillastra compressa (Bowerbank, 1866)

by Kevin Calabro, Elaheh Lotfi Kalahroodi, Daniel Rodrigues, Caridad Díaz, Mercedes de la Cruz, Bastien Cautain, Rémi Laville, Fernando Reyes, Thierry Pérez, Bassam Soussi and Olivier P. Thomas

Mar. Drugs 2017, 15(7), 199; https://doi.org/10.3390/md15070199 - 26 Jun 2017

Cited by 16 | Viewed by 4715

Abstract

The first chemical investigation of the Mediterranean deep-sea sponge Poecillastra compressa (Bowerbank, 1866) led to the identification of seven new steroidal saponins named poecillastrosides A–G (1–7). All saponins feature an oxidized methyl at C-18 into a primary alcohol or a carboxylic acid. While poecillastrosides A–D (1–4) all contain an exo double bond at C-24 of the side-chain and two osidic residues connected at O-2′, poecillastrosides E–G (5–7) are characterized by a cyclopropane on the side-chain and a connection at O-3′ between both sugar units. The chemical structures were elucidated through extensive spectroscopic analysis (High-Resolution Mass Spectrometry (HRESIMS), 1D and 2D NMR) and the absolute configurations of the sugar residues were assigned after acidic hydrolysis and cysteine derivatization followed by LC-HRMS analyses. Poecillastrosides D and E, bearing a carboxylic acid at C-18, were shown to exhibit antifungal activity against Aspergillus fumigatus. Full article

(This article belongs to the Special Issue Marine Glycosides)

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Review

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52 pages, 11231 KiB

Open AccessFeature PaperReview

Chemistry and Biology of Bioactive Glycolipids of Marine Origin

by Iván Cheng-Sánchez and Francisco Sarabia

Mar. Drugs 2018, 16(9), 294; https://doi.org/10.3390/md16090294 - 22 Aug 2018

Cited by 16 | Viewed by 6926

Abstract

Glycolipids represent a broad class of natural products structurally featured by a glycosidic fragment linked to a lipidic molecule. Despite the large structural variety of these glycoconjugates, they can be classified into three main groups, i.e., glycosphingolipids, glycoglycerolipids, and atypical glycolipids. In the particular case of glycolipids derived from marine sources, an impressive variety in their structural features and biological properties is observed, thus making them prime targets for chemical synthesis. In the present review, we explore the chemistry and biology of this class of compounds. Full article

(This article belongs to the Special Issue Marine Glycosides)

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28 pages, 5644 KiB

Open AccessFeature PaperReview

Marine Carbohydrate-Based Compounds with Medicinal Properties

by Ariana A. Vasconcelos and Vitor H. Pomin

Mar. Drugs 2018, 16(7), 233; https://doi.org/10.3390/md16070233 - 09 Jul 2018

Cited by 40 | Viewed by 9815

Abstract

The oceans harbor a great diversity of organisms, and have been recognized as an important source of new compounds with nutritional and therapeutic potential. Among these compounds, carbohydrate-based compounds are of particular interest because they exhibit numerous biological functions associated with their chemical diversity. This gives rise to new substances for the development of bioactive products. Many are the known applications of substances with glycosidic domains obtained from marine species. This review covers the structural properties and the current findings on the antioxidant, anti-inflammatory, anticoagulant, antitumor and antimicrobial activities of medium and high molecular-weight carbohydrates or glycosylated compounds extracted from various marine organisms. Full article

(This article belongs to the Special Issue Marine Glycosides)

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16 pages, 434 KiB

Open AccessReview

The Anti-Cancer Effects of Frondoside A

by Thomas E. Adrian and Peter Collin

Mar. Drugs 2018, 16(2), 64; https://doi.org/10.3390/md16020064 - 19 Feb 2018

Cited by 24 | Viewed by 6534

Abstract

Frondoside A is a triterpenoid glycoside from the Atlantic Sea Cucumber, Cucumaria frondosa. Frondoside A has a broad spectrum of anti-cancer effects, including induction of cellular apoptosis, inhibition of cancer cell growth, migration, invasion, formation of metastases, and angiogenesis. In cell lines and animal models studied to date, the anti-cancer effects of the compound are seen in all solid cancers, lymphomas, and leukemias studied to date. These effects appear to be due to potent inhibition of p21-activated kinase 1 (PAK1), which is up-regulated in many cancers. In mouse models, frondoside A has synergistic effects with conventional chemotherapeutic agents, such as gemcitabine, paclitaxel, and cisplatin. Frondoside A administration is well-tolerated. No side effects have been reported and the compound has no significant effects on body weight, blood cells, or on hepatic and renal function tests after long-term administration. Frondoside A may be valuable in the treatment of malignancies, either as a single agent or in combination with other therapeutic modalities. Full article

(This article belongs to the Special Issue Marine Glycosides)

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5377 KiB

Open AccessReview

Sea Cucumber Glycosides: Chemical Structures, Producing Species and Important Biological Properties

by Muhammad Abdul Mojid Mondol, Hee Jae Shin, M. Aminur Rahman and Mohamad Tofazzal Islam

Mar. Drugs 2017, 15(10), 317; https://doi.org/10.3390/md15100317 - 17 Oct 2017

Cited by 58 | Viewed by 8623

Abstract

Sea cucumbers belonging to echinoderm are traditionally used as tonic food in China and other Asian countries. They produce abundant biologically active triterpene glycosides. More than 300 triterpene glycosides have been isolated and characterized from various species of sea cucumbers, which are classified as holostane and nonholostane depending on the presence or absence of a specific structural unit γ(18,20)-lactone in the aglycone. Triterpene glycosides contain a carbohydrate chain up to six monosaccharide units mainly consisting of d-xylose, 3-O-methy-d-xylose, d-glucose, 3-O-methyl-d-glucose, and d-quinovose. Cytotoxicity is the common biological property of triterpene glycosides isolated from sea cucumbers. Besides cytotoxicity, triterpene glycosides also exhibit antifungal, antiviral and hemolytic activities. This review updates and summarizes our understanding on diverse chemical structures of triterpene glycosides from various species of sea cucumbers and their important biological activities. Mechanisms of action and structural–activity relationships (SARs) of sea cucumber glycosides are also discussed briefly. Full article

(This article belongs to the Special Issue Marine Glycosides)

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