Marine Drugs

23 pages, 2787 KB

Open AccessArticle

Recruitment of Glycosyl Hydrolase Proteins in a Cone Snail Venomous Arsenal: Further Insights into Biomolecular Features of Conus Venoms

by Aude Violette^1,*, Adrijana Leonardi²

, David Piquemal³, Yves Terrat⁴, Daniel Biass¹, Sébastien Dutertre^1,†, Florian Noguier³, Frédéric Ducancel⁴, Reto Stöcklin¹, Igor Križaj²

and Philippe Favreau¹

^† These authors contributed equally to this work.

¹ Atheris Laboratories, Case postale 314, CH-1233 Bernex-Geneva, Switzerland

² Department of Molecular and Biomedical Sciences, Jožef Stefan Institute, Jamova 39, 1000 Ljubljana, Slovenia

³ Skuldtech, Cap Delta, 1682, rue de la Valsière, 34790 Grabels, France

⁴ CEA-Saclay, 91919 Gif sur Yvette Cedex, France

^† Institute for Molecular Bioscience, The University of Queensland, St Lucia QLD 4072, Australia.

Mar. Drugs 2012, 10(2), 258-280; https://doi.org/10.3390/md10020258 - 31 Jan 2012

Cited by 31 | Viewed by 10783

Abstract

Cone snail venoms are considered an untapped reservoir of extremely diverse peptides, named conopeptides, displaying a wide array of pharmacological activities. We report here for the first time, the presence of high molecular weight compounds that participate in the envenomation cocktail used by [...] Read more.

Cone snail venoms are considered an untapped reservoir of extremely diverse peptides, named conopeptides, displaying a wide array of pharmacological activities. We report here for the first time, the presence of high molecular weight compounds that participate in the envenomation cocktail used by these marine snails. Using a combination of proteomic and transcriptomic approaches, we identified glycosyl hydrolase proteins, of the hyaluronidase type (Hyal), from the dissected and injectable venoms (“injectable venom” stands for the venom variety obtained by milking of the snails. This is in contrast to the “dissected venom”, which was obtained from dissected snails by extraction of the venom glands) of a fish-hunting cone snail, Conus consors (Pionoconus clade). The major Hyal isoform, Conohyal-Cn1, is expressed as a mixture of numerous glycosylated proteins in the 50 kDa molecular mass range, as observed in 2D gel and mass spectrometry analyses. Further proteomic analysis and venom duct mRNA sequencing allowed full sequence determination. Additionally, unambiguous segment location of at least three glycosylation sites could be determined, with glycans corresponding to multiple hexose (Hex) and N-acetylhexosamine (HexNAc) moieties. With respect to other known Hyals, Conohyal-Cn1 clearly belongs to the hydrolase-type of Hyals, with strictly conserved consensus catalytic donor and positioning residues. Potent biological activity of the native Conohyals could be confirmed in degrading hyaluronic acid. A similar Hyal sequence was also found in the venom duct transcriptome of C. adamsonii (Textilia clade), implying a possible widespread recruitment of this enzyme family in fish-hunting cone snail venoms. These results provide the first detailed Hyal sequence characterized from a cone snail venom, and to a larger extent in the Mollusca phylum, thus extending our knowledge on this protein family and its evolutionary selection in marine snail venoms. Full article

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25 pages, 1168 KB

Open AccessReview

Tetrodotoxin (TTX) as a Therapeutic Agent for Pain

by Francisco Rafael Nieto^*

, Enrique José Cobos, Miguel Ángel Tejada, Cristina Sánchez-Fernández, Rafael González-Cano and Cruz Miguel Cendán^*

Department of Pharmacology and Institute of Neuroscience, Faculty of Medicine, University of Granada (Avenida de Madrid 11, 18012 Granada, Spain) and Biomedical Research Center, University of Granada, Parque Tecnológico de Ciencias de la Salud, 18100 Armilla, Granada, Spain

Mar. Drugs 2012, 10(2), 281-305; https://doi.org/10.3390/md10020281 - 31 Jan 2012

Cited by 125 | Viewed by 53161

Abstract

Tetrodotoxin (TTX) is a potent neurotoxin that blocks voltage-gated sodium channels (VGSCs). VGSCs play a critical role in neuronal function under both physiological and pathological conditions. TTX has been extensively used to functionally characterize VGSCs, which can be classified as TTX-sensitive or TTX-resistant [...] Read more.

Tetrodotoxin (TTX) is a potent neurotoxin that blocks voltage-gated sodium channels (VGSCs). VGSCs play a critical role in neuronal function under both physiological and pathological conditions. TTX has been extensively used to functionally characterize VGSCs, which can be classified as TTX-sensitive or TTX-resistant channels according to their sensitivity to this toxin. Alterations in the expression and/or function of some specific TTX-sensitive VGSCs have been implicated in a number of chronic pain conditions. The administration of TTX at doses below those that interfere with the generation and conduction of action potentials in normal (non-injured) nerves has been used in humans and experimental animals under different pain conditions. These data indicate a role for TTX as a potential therapeutic agent for pain. This review focuses on the preclinical and clinical evidence supporting a potential analgesic role for TTX. In addition, the contribution of specific TTX-sensitive VGSCs to pain is reviewed. Full article

(This article belongs to the Special Issue Tetrodotoxin 2011)

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13 pages, 874 KB

Open AccessArticle

New Cytotoxic Cembranolides from the Soft Coral Lobophytum michaelae

by Shang-Kwei Wang¹ and Chang-Yih Duh^2,3,*

¹ Department of Microbiology, Kaohsiung Medical University, Kaohsiung 807, Taiwan

² Department of Marine Biotechnology and Resources, National Sun Yat-Sen University, Kaohsiung 804, Taiwan

³ Asia-Pacific Ocean Research Center, National Sun Yat-Sen University, Kaohsiung 804, Taiwan

Mar. Drugs 2012, 10(2), 306-318; https://doi.org/10.3390/md10020306 - 31 Jan 2012

Cited by 36 | Viewed by 7380

Abstract

Six new cembranolides, michaolides L–Q (1–6), and a known cembranolide, lobomichaolide (7) were isolated from the CH₂Cl₂ extract of the soft coral Lobophytum michaelae. Their structures were established by extensive spectral analysis. The [...] Read more.

Six new cembranolides, michaolides L–Q (1–6), and a known cembranolide, lobomichaolide (7) were isolated from the CH₂Cl₂ extract of the soft coral Lobophytum michaelae. Their structures were established by extensive spectral analysis. The anti-HCMV (human cytomegalovirus) activity of 1–7 and their cytotoxicity against selected cell lines were evaluated. Full article

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10 pages, 263 KB

Open AccessArticle

Five New Amicoumacins Isolated from a Marine-Derived Bacterium Bacillus subtilis

by Yongxin Li¹, Ying Xu¹, Lingli Liu¹, Zhuang Han¹, Pok Yui Lai¹, Xiangrong Guo², Xixiang Zhang², Wenhan Lin³

and Pei-Yuan Qian^1,*

¹ KAUST Global Collaborative Research, Division of Life Science, Hong Kong University of Science and Technology, Clear Water Bay, Hong Kong, China

² Advanced Nano-fabrication, Imaging & Characterization Core lab, King Abdullah University of Science and Technology, Thuwal 23955-6900, Saudi Arabia

³ State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, China

Mar. Drugs 2012, 10(2), 319-328; https://doi.org/10.3390/md10020319 - 3 Feb 2012

Cited by 62 | Viewed by 11081

Abstract

Four novel amicoumacins, namely lipoamicoumacins A–D (1–4), and one new bacilosarcin analog (5) were isolated from culture broth of a marine-derived bacterium Bacillus subtilis, together with six known amicoumacins. Their structures were elucidated on the basis [...] Read more.

Four novel amicoumacins, namely lipoamicoumacins A–D (1–4), and one new bacilosarcin analog (5) were isolated from culture broth of a marine-derived bacterium Bacillus subtilis, together with six known amicoumacins. Their structures were elucidated on the basis of extensive spectroscopic (2D NNR, IR, CD and MS) analysis and in comparison with data in literature. Full article

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11 pages, 1033 KB

Open AccessArticle

Toxicity of Cultured Bullseye Puffer Fish Sphoeroides annulatus

by Erick J. Nuñez-Vazquez^1,2,*, Armando Garcia-Ortega^3,4, Angel I. Campa-Cordova¹, Isabel Abdo De la Parra⁴, Lilia Ibarra-Martinez¹, Alejandra Heredia-Tapia² and Jose L. Ochoa^1,†

¹ Centro de Investigaciones Biologicas del Noroeste (CIBNOR), Apdo. Postal 128, La Paz, B.C.S. 23000, Mexico

² Investigacion para la Conservacion y el Desarrollo (INCODE), Andador 2, 245. Col. Banobras. La Paz, B.C.S. 23080, Mexico

³ College of Agriculture, Forestry and Natural Resource Management, Pacific Aquaculture & Coastal Resources Center, University of Hawaii at Hilo, 200 W. Kawili St., Hilo, HI 96720, USA

⁴ Centro de Investigacion en Alimentacion y Desarrollo (CIAD), Unidad Mazatlan. Apdo. Postal 711, C.P. 82010. Mazatlan, Sinaloa 82010, Mexico

^† Deceased in November 2007.

Mar. Drugs 2012, 10(2), 329-339; https://doi.org/10.3390/md10020329 - 3 Feb 2012

Cited by 11 | Viewed by 13558

Abstract

The toxin content in various life cycle stages of tank-cultivated bullseye puffer (Sphoeroides annulatus) were analyzed by mouse bioassay and ESI-MS spectrometry analysis. The presence of toxin content was determined in extracts of sperm, eggs, embryo, larvae, post-larvae, juvenile, pre-adult, and [...] Read more.

The toxin content in various life cycle stages of tank-cultivated bullseye puffer (Sphoeroides annulatus) were analyzed by mouse bioassay and ESI-MS spectrometry analysis. The presence of toxin content was determined in extracts of sperm, eggs, embryo, larvae, post-larvae, juvenile, pre-adult, and adult fish, as well as in food items used during the cultivation of the species. Our findings show that only the muscle of juveniles, the viscera of pre-adults, and muscle, liver, and gonad of adult specimens were slightly toxic ( < 1 mouse unit). Thus, cultivated S. annulatus, as occurs with other cultivated puffer fish species, does not represent a food safety risk to consumers. This is the first report of toxin analysis covering the complete life stages of a puffer fish under controlled conditions. Full article

(This article belongs to the Special Issue Tetrodotoxin 2011)

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9 pages, 281 KB

Open AccessArticle

Four Eremophilane Sesquiterpenes from the Mangrove Endophytic Fungus Xylaria sp. BL321

by Yongxiang Song^1,2, Jiajian Wang¹, Hongbo Huang^1,2, Lin Ma¹, Jun Wang^3,4, Yucheng Gu⁵

, Lan Liu^1,3,*

and Yongcheng Lin^1,3,*

¹ School of Chemistry and Chemical Engineering, Sun Yat-Sen University, 135 Xingang West Road, Guangzhou 510275, China

² CAS Key Laboratory of Marine Bio-resources Sustainable Utilization, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Rd., Guangzhou 510301, China

³ Guangdong Province Key Laboratory of Functional Molecules in Oceanic Microorganism (Sun Yat-Sen University), Bureau of Education of Guangdong, Guangzhou, 510275, China

⁴ School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou 510080, China

⁵ Syngenta Jealott’s Hill International Research Centre, Bracknell, Berkshire, RG42 6EY, UK

Mar. Drugs 2012, 10(2), 340-348; https://doi.org/10.3390/md10020340 - 6 Feb 2012

Cited by 42 | Viewed by 8675

Abstract

Three new eremophilane sesquiterpenes (1–3) were isolated from the mangrove endophytic fungus Xylaria sp. BL321 together with 07H239-A (4), a known analogue of the new compounds. The structures of these compounds were elucidated by analysis of their [...] Read more.

Three new eremophilane sesquiterpenes (1–3) were isolated from the mangrove endophytic fungus Xylaria sp. BL321 together with 07H239-A (4), a known analogue of the new compounds. The structures of these compounds were elucidated by analysis of their MS, 1D and 2D NMR spectroscopic data. Compound 4 showed activation activity on α-glucosidase at 0.15 μM (146%), and then, 4 gradually produced inhibitory activity on α-glucosidase with increasing concentration, and the IC₅₀ value is 6.54 μM. Full article

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9 pages, 237 KB

Open AccessArticle

Two New Tryptamine Derivatives, Leptoclinidamide and (-)-Leptoclinidamine B, from an Indonesian Ascidian Leptoclinides dubius

by Hiroyuki Yamazaki¹, Defny S. Wewengkang^1,2, Teruaki Nishikawa³, Henki Rotinsulu¹, Remy E. P. Mangindaan² and Michio Namikoshi^1,*

¹ Department of Natural Product Chemistry, Tohoku Pharmaceutical University, Komatsushima, Aoba-ku, Sendai 981-8558, Japan

² Faculty of Fisheries and Marine Science, Sam Ratulangi University, Kampus Bahu, Manado 95115, Indonesia

³ Laboratory of Taxonomy, Department of Biology, Faculty of Science, Toho University, Miyama, Funabashi 274-8510, Japan

Mar. Drugs 2012, 10(2), 349-357; https://doi.org/10.3390/md10020349 - 10 Feb 2012

Cited by 12 | Viewed by 8287

Abstract

Two new tryptamine-derived alkaloids, named as leptoclinidamide (1) and (-)-leptoclinidamine B (2), were isolated from an Indonesian ascidian Leptoclinides dubius together with C²-α-D-mannosylpyranosyl-L-tryptophan (3). The structure of 1 was assigned on the basis of spectroscopic [...] Read more.

Two new tryptamine-derived alkaloids, named as leptoclinidamide (1) and (-)-leptoclinidamine B (2), were isolated from an Indonesian ascidian Leptoclinides dubius together with C²-α-D-mannosylpyranosyl-L-tryptophan (3). The structure of 1 was assigned on the basis of spectroscopic data for 1 and its N-acetyl derivative (4). Compound 1 was an amide of tryptamine with two β-alanine units. Although the planar structure of 2 is identical to that of the known compound (+)-leptoclinidamine B (5), compound 2 was determined to be the enantiomer of 5 based on amino acid analysis using HPLC methods. Compounds 1 to 4 were evaluated for cytotoxicity against two human cancer cell lines, HCT-15 (colon) and Jurkat (T-cell lymphoma) cells, but none of the compounds showed activity. Full article

(This article belongs to the Special Issue Alkaloid Analogs)

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45 pages, 632 KB

Open AccessReview

Synthetic Strategies to Terpene Quinones/Hydroquinones

by Marina Gordaliza

Farmacy Faculty and Institute of Science and Technology Studies, Campus Miguel de Unamuno, Salamanca University, 37007 Salamanca, Spain

Mar. Drugs 2012, 10(2), 358-402; https://doi.org/10.3390/md10020358 - 14 Feb 2012

Cited by 34 | Viewed by 13432

Abstract

The cytotoxic and antiproliferative properties of many natural sesquiterpene-quinones and -hydroquinones from sponges offer promising opportunities for the development of new drugs. A review dealing with different strategies for obtaining bioactive terpenyl quinones/hydroquinones is presented. The different synthetic approches for the preparation of [...] Read more.

The cytotoxic and antiproliferative properties of many natural sesquiterpene-quinones and -hydroquinones from sponges offer promising opportunities for the development of new drugs. A review dealing with different strategies for obtaining bioactive terpenyl quinones/hydroquinones is presented. The different synthetic approches for the preparation of the most relevant quinones/hydroquinones are described. Full article

(This article belongs to the Special Issue Synthesis around Marine Natural Products)

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14 pages, 683 KB

Open AccessArticle

Antioxidant Activity of Hawaiian Marine Algae

by Dovi Kelman¹, Ellen Kromkowski Posner², Karla J. McDermid², Nicole K. Tabandera¹, Patrick R. Wright^1,3 and Anthony D. Wright^1,*

¹ Department of Pharmaceutical Sciences, College of Pharmacy, University of Hawaii at Hilo, 34 Rainbow Drive, Hilo, HI 96720, USA

² Department of Marine Science, University of Hawaii at Hilo, 200 West Kawili Street, Hilo, HI 96720, USA

³ Summer Scholar visiting from University of Freiburg, Freiburg 79085, Germany

Mar. Drugs 2012, 10(2), 403-416; https://doi.org/10.3390/md10020403 - 15 Feb 2012

Cited by 206 | Viewed by 18070

Abstract

Marine algae are known to contain a wide variety of bioactive compounds, many of which have commercial applications in pharmaceutical, medical, cosmetic, nutraceutical, food and agricultural industries. Natural antioxidants, found in many algae, are important bioactive compounds that play an important role against [...] Read more.

Marine algae are known to contain a wide variety of bioactive compounds, many of which have commercial applications in pharmaceutical, medical, cosmetic, nutraceutical, food and agricultural industries. Natural antioxidants, found in many algae, are important bioactive compounds that play an important role against various diseases and ageing processes through protection of cells from oxidative damage. In this respect, relatively little is known about the bioactivity of Hawaiian algae that could be a potential natural source of such antioxidants. The total antioxidant activity of organic extracts of 37 algal samples, comprising of 30 species of Hawaiian algae from 27 different genera was determined. The activity was determined by employing the FRAP (Ferric Reducing Antioxidant Power) assays. Of the algae tested, the extract of Turbinaria ornata was found to be the most active. Bioassay-guided fractionation of this extract led to the isolation of a variety of different carotenoids as the active principles. The major bioactive antioxidant compound was identified as the carotenoid fucoxanthin. These results show, for the first time, that numerous Hawaiian algae exhibit significant antioxidant activity, a property that could lead to their application in one of many useful healthcare or related products as well as in chemoprevention of a variety of diseases including cancer. Full article

(This article belongs to the Special Issue Marine Carotenoids and Oxidative Stress)

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10 pages, 160 KB

Open AccessCommunication

Antihypertensive Effect of Long-Term Oral Administration of Jellyfish (Rhopilema esculentum) Collagen Peptides on Renovascular Hypertension

by Yongliang Zhuang^*, Liping Sun, Yufeng Zhang

and Gaoxiang Liu

Research Center of Food Engineering, College of Chemistry and Engineering, Kunming University of Science and Technology, Kunming, Yunnan 650600, China

Mar. Drugs 2012, 10(2), 417-426; https://doi.org/10.3390/md10020417 - 15 Feb 2012

Cited by 75 | Viewed by 9202

Abstract

Antihypertensive effect of long-term oral administration of jellyfish (Rhopilema esculentum) collagen peptides (JCP) on renovascular hypertension rats (RVHs) was evaluated. The systolic blood pressure and diastolic blood pressure of the RVHs were significantly reduced with administration of JCP (p p [...] Read more.

Antihypertensive effect of long-term oral administration of jellyfish (Rhopilema esculentum) collagen peptides (JCP) on renovascular hypertension rats (RVHs) was evaluated. The systolic blood pressure and diastolic blood pressure of the RVHs were significantly reduced with administration of JCP (p < 0.05), compared with model control group. However, the arterial blood pressure of normal rats showed no significant changes during long-term oral treatment with high dose JCP (p > 0.05). Furthermore, effect of JCP on angiotensin II (Ang II) concentration of plasma had no significance (p > 0.05), but JCP significantly inhibited the Ang II concentration in RVHs’ kidney (p < 0.05). The kidney should be the target site of JCP. Full article

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12 pages, 933 KB

Open AccessArticle

Terpenoids from the Octocorals Menella sp. (Plexauridae) and Lobophytum crassum (Alcyonacea)

by Cheng-Hung Lee^1,2,3, Chia-Ying Kao^4,5, Shih-Yao Kao^4,5, Chih-Han Chang¹, Jui-Hsin Su^4,5,6, Tsong-Long Hwang⁷

, Yueh-Hsiung Kuo⁸

, Zhi-Hong Wen^6,*

and Ping-Jyun Sung^4,5,6,*

¹ Department of Biomedical Engineering, National Cheng Kung University, Tainan 701, Taiwan

² Department of Nutrition, HungKuang University, Taichung 433, Taiwan

³ Department of Orthopedics, Taichung Veterans General Hospital, Taichung 407, Taiwan

⁴ Graduate Institute of Marine Biotechnology and Department of Life Science and Institute of Biotechnology, National Dong Hwa University, Pingtung 944, Taiwan

⁵ National Museum of Marine Biology and Aquarium, Pingtung 944, Taiwan

⁶ Department of Marine Biotechnology and Resources and Division of Marine Biotechnology, Asia-Pacific Ocean Research Center, National Sun Yat-sen University, Kaohsiung 804, Taiwan

⁷ Graduate Institute of Natural Products, Chang Gung University, Taoyuan 333, Taiwan

⁸ School of Chinese Pharmaceutical Sciences and Chinese Medicine Resources and Tsuzuki Institute for Traditional Medicine, College of Pharmacy, China Medical University, Taichung 404, Taiwan

Mar. Drugs 2012, 10(2), 427-438; https://doi.org/10.3390/md10020427 - 15 Feb 2012

Cited by 30 | Viewed by 8174

Abstract

A new germacrane-type sesquiterpenoid, menelloide E (1), and a new cembrane-type diterpenoid, lobocrassin F (2), were isolated from the octocorals Menella sp. and Lobophytum crassum, respectively. The structures of terpenoids 1 and 2 were determined by spectroscopic and [...] Read more.

A new germacrane-type sesquiterpenoid, menelloide E (1), and a new cembrane-type diterpenoid, lobocrassin F (2), were isolated from the octocorals Menella sp. and Lobophytum crassum, respectively. The structures of terpenoids 1 and 2 were determined by spectroscopic and chemical methods and compound 2 was found to display a significant inhibitory effect on the release of elastase by human neutrophils. Full article

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12 pages, 591 KB

Open AccessArticle

Steroids from the Soft Coral Sinularia crassa

by Chih-Hua Chao^1,2, Kuei-Ju Chou³, Chiung-Yao Huang³, Zhi-Hong Wen^3,4

, Chi-Hsin Hsu^3,4, Yang-Chang Wu⁵, Chang-Feng Dai⁶ and Jyh-Horng Sheu^3,4,*

¹ Chinese Medicinal Research and Development Center, China Medical University Hospital, Taichung 40402, Taiwan

² China Medical University, Taichung, 40402, Taiwan

³ Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 80424, Taiwan

⁴ Asian Pacific Ocean Research Center, National Sun Yat-sen University, Kaohsiung 80424, Taiwan

⁵ Graduate Institute of Integrated Medicine, College of Chinese Medicine, China Medical University, Taichung 40402, Taiwan

⁶ Institute of Oceanography, National Taiwan University, Taipei, 10617, Taiwan

Mar. Drugs 2012, 10(2), 439-450; https://doi.org/10.3390/md10020439 - 16 Feb 2012

Cited by 41 | Viewed by 8029

Abstract

One new sterol, crassarosterol A (1), and four new steroidal glycosides, crassarosterosides A–D (2–5) were isolated from the Formosan soft coral Sinularia crassa. The absolute configuration of 1 was determined using the Mosher’s method. The absolute [...] Read more.

One new sterol, crassarosterol A (1), and four new steroidal glycosides, crassarosterosides A–D (2–5) were isolated from the Formosan soft coral Sinularia crassa. The absolute configuration of 1 was determined using the Mosher’s method. The absolute configurations for the sugar moieties of 2–5 were determined by HPLC analysis on the o-tolylthiocarbamates derived from the liberated sugar after acid hydrolysis. Compounds 2 and 4 could significantly inhibit the expression of pro-inflammatory iNOS protein at 10 µM. In contrast, 1–3 were found to stimulate the expression of COX-2 protein at this concentration. Steroids 1 and 4 also showed cytotoxicity toward the selected human liver cancer cells. Full article

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14 pages, 407 KB

Open AccessArticle

Novel Marine Phenazines as Potential Cancer Chemopreventive and Anti-Inflammatory Agents

by Tamara P. Kondratyuk¹, Eun-Jung Park¹, Rui Yu², Richard B. Van Breemen², Ratnakar N. Asolkar³, Brian T. Murphy^2,3, William Fenical³ and John M. Pezzuto^1,*

¹ College of Pharmacy, University of Hawaii at Hilo, 34 Rainbow Drive, Hilo, HI 96720, USA

² Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, USA

³ Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California-San Diego, La Jolla, CA 92093, USA

Mar. Drugs 2012, 10(2), 451-464; https://doi.org/10.3390/md10020451 - 16 Feb 2012

Cited by 119 | Viewed by 10381

Abstract

Two new (1 and 2) and one known phenazine derivative (lavanducyanin, 3) were isolated and identified from the fermentation broth of a marine-derived Streptomyces sp. (strain CNS284). In mammalian cell culture studies, compounds 1, 2 and 3 inhibited TNF-α-induced [...] Read more.

Two new (1 and 2) and one known phenazine derivative (lavanducyanin, 3) were isolated and identified from the fermentation broth of a marine-derived Streptomyces sp. (strain CNS284). In mammalian cell culture studies, compounds 1, 2 and 3 inhibited TNF-α-induced NFκB activity (IC₅₀ values of 4.1, 24.2, and 16.3 μM, respectively) and LPS-induced nitric oxide production (IC₅₀ values of >48.6, 15.1, and 8.0 μM, respectively). PGE₂ production was blocked with greater efficacy (IC₅₀ values of 7.5, 0.89, and 0.63 μM, respectively), possibly due to inhibition of cyclooxygenases in addition to the expression of COX-2. Treatment of cultured HL-60 cells led to dose-dependent accumulation in the subG1 compartment of the cell cycle, as a result of apoptosis. These data provide greater insight on the biological potential of phenazine derivatives, and some guidance on how various substituents may alter potential anti-inflammatory and anti-cancer effects. Full article

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12 pages, 1240 KB

Open AccessArticle

Anti-Melanogenic Property of Geoditin A in Murine B16 Melanoma Cells

by Florence W. K. Cheung¹, Jia Guo¹, Yick-Hin Ling¹, Chun-Tao Che² and Wing-Keung Liu^1,*

¹ School of Biomedical Sciences, Faculty of Medicine, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China

² Department of Medical Chemistry & Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood Street, Chicago, IL 60612, USA

Mar. Drugs 2012, 10(2), 465-476; https://doi.org/10.3390/md10020465 - 16 Feb 2012

Cited by 20 | Viewed by 9169

Abstract

Geoditin A, an isomalabaricane triterpene isolated from marine sponge Geodia japonica, has been demonstrated to induce apoptosis in leukemia HL60 cells and human colon HT29 cancer cells through an oxidative stress, a process also interfering with normal melanogenesis in pigment cells. Treatment [...] Read more.

Geoditin A, an isomalabaricane triterpene isolated from marine sponge Geodia japonica, has been demonstrated to induce apoptosis in leukemia HL60 cells and human colon HT29 cancer cells through an oxidative stress, a process also interfering with normal melanogenesis in pigment cells. Treatment of murine melanoma B16 cells with geoditin A decreased expression of melanogenic proteins and cell melanogenesis which was aggravated with adenylate cyclase inhibitor SQ22536, indicating melanogenic inhibition was mediated through a cAMP-dependent signaling pathway. Immunofluorescence microscopy and glycosylation studies revealed abnormal glycosylation patterns of melanogenic proteins (tyrosinase and tyrosinase-related protein 1), and a co-localization of tyrosinase with calnexin (CNX) and lysosome-associated membrane protein 1 (LAMP-1), implicating a post-translational modification in the ER and a degradation of tyrosinase in the lysosome. Taken together, potent anti-melanogenic property and the relatively low cytotoxicity of geoditin A have demonstrated its therapeutic potential as a skin lightening agent. Full article

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20 pages, 1069 KB

Open AccessArticle

Ovatoxin-a and Palytoxin Accumulation in Seafood in Relation to Ostreopsis cf. ovata Blooms on the French Mediterranean Coast

by Zouher Amzil^1,*

, Manoella Sibat¹

, Nicolas Chomerat², Hubert Grossel³, Francoise Marco-Miralles³, Rodolphe Lemee^4,5, Elisabeth Nezan² and Veronique Sechet¹

¹ IFREMER, Phycotoxins Laboratory, BP 21105, F-44311 Nantes Cedex 3, France

² IFREMER, LER-FBN, Marine Biological Station, BP 40537, F-29185 Concarneau Cedex, France

³ IFREMER, LER-PAC, La Seyne sur Mer, F-83507, Toulon, France

⁴ Oceanography Laboratory of Villefranche, Pierre et Marie Curie University, BP 28, F-06234, Villefranche-sur-Mer cedex, France

⁵ CNRS, Marine Microbilal Ecology and Biogeochemistry, Pierre et Marie Curie-Paris 6 University, BP 28, F-06234, Villefranche-sur-Mer, France

Mar. Drugs 2012, 10(2), 477-496; https://doi.org/10.3390/md10020477 - 17 Feb 2012

Cited by 137 | Viewed by 12673

Abstract

Dinoflagellates of the genus Ostreopsis are known to cause (often fatal) food poisoning in tropical coastal areas following the accumulation of palytoxin (PLTX) and/or its analogues (PLTX group) in crabs, sea urchins or fish. Ostreopsis spp. occurrence is presently increasing in the [...] Read more.

Dinoflagellates of the genus Ostreopsis are known to cause (often fatal) food poisoning in tropical coastal areas following the accumulation of palytoxin (PLTX) and/or its analogues (PLTX group) in crabs, sea urchins or fish. Ostreopsis spp. occurrence is presently increasing in the northern to north western Mediterranean Sea (Italy, Spain, Greece and France), probably in response to climate change. In France, Ostreopsis. cf. ovata has been associated with toxic events during summer 2006, at Morgiret, off the coast of Marseille, and a specific monitoring has been designed and implemented since 2007. Results from 2008 and 2009 showed that there is a real danger of human poisoning, as these demonstrated bioaccumulation of the PLTX group (PLTX and ovatoxin-a) in both filter-feeding bivalve molluscs (mussels) and herbivorous echinoderms (sea urchins). The total content accumulated in urchins reached 450 µg PLTX eq/kg total flesh (summer 2008). In mussels, the maximum was 230 µg eq PLTX/kg (summer 2009) compared with a maximum of 360 µg found in sea urchins during the same period at the same site. This publication brings together scientific knowledge obtained about the summer development of Ostreopsis spp. in France during 2007, 2008 and 2009. Full article

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12 pages, 369 KB

Open AccessArticle

A Sterol and Spiroditerpenoids from a Penicillium sp. Isolated from a Deep Sea Sediment Sample

by Yan Li¹, Dezan Ye², Zongze Shao², Chengbin Cui^1,* and Yongsheng Che^1,*

¹ Beijing Institute of Pharmacology & Toxicology, Beijing 100850, China

² Key Laboratory of Marine Biogenetic Resources, The Third Institute of Oceanography, The State Oceanic Administration, Xiamen 361005, China

Mar. Drugs 2012, 10(2), 497-508; https://doi.org/10.3390/md10020497 - 20 Feb 2012

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Abstract

A new polyoxygenated sterol, sterolic acid (1), three new breviane spiroditerpenoids, breviones I–K (2–4), and the known breviones (5–8), were isolated from the crude extract of a Penicillium sp. obtained from a deep [...] Read more.

A new polyoxygenated sterol, sterolic acid (1), three new breviane spiroditerpenoids, breviones I–K (2–4), and the known breviones (5–8), were isolated from the crude extract of a Penicillium sp. obtained from a deep sea sediment sample that was collected at a depth of 5115 m. The structures of 1–4 were elucidated primarily by NMR experiments, and 1 was further confirmed by X-ray crystallography. The absolute configurations of 2 and 3 were deduced by comparison of their CD spectra with those of the model compounds. Compounds 2 and 5 showed significant cytotoxicity against MCF-7 cells, which is comparable to the positive control cisplatin. Full article

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Mar. Drugs, Volume 10, Issue 2 (February 2012) – 17 articles , Pages 258-520

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