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Marine Glycosides marine drugs Marine Glycosides Edited by Thomas E Adrian, Francisco Sarabia and Ivan Cheng-Sanchez Printed Edition of the Special Issue Published in Marine Drugs www.mdpi.com/journal/marinedrugs Marine Glycosides Marine Glycosides Special Issue Editors Thomas E Adrian Francisco Sarabia Ivan Cheng-Sanchez MDPI • Basel • Beijing • Wuhan • Barcelona • Belgrade Special Issue Editors Thomas E Adrian Francisco Sarabia Mohammed Bin Rashid University of Medicine and Health Sciences University of Malaga Dubai, UAE Spain Ivan Cheng-Sanchez University of Malaga Spain Editorial Office MDPI St. Alban-Anlage 66 4052 Basel, Switzerland This is a reprint of articles from the Special Issue published online in the open access journal Marine Drugs (ISSN 1660-3397) from 2017 to 2018 (available at: https://www.mdpi.com/journal/ marinedrugs/special issues/marine glycosides) For citation purposes, cite each article independently as indicated on the article page online and as indicated below: LastName, A.A.; LastName, B.B.; LastName, C.C. Article Title. Journal Name Year, Article Number, Page Range. ISBN 978-3-03897-902-9 (Pbk) ISBN 978-3-03897-903-6 (PDF) c 2019 by the authors. Articles in this book are Open Access and distributed under the Creative Commons Attribution (CC BY) license, which allows users to download, copy and build upon published articles, as long as the author and publisher are properly credited, which ensures maximum dissemination and a wider impact of our publications. The book as a whole is distributed by MDPI under the terms and conditions of the Creative Commons license CC BY-NC-ND. Contents About the Special Issue Editors ..................................... vii Preface to ”Marine Glycosides” ..................................... ix Kevin Calabro, Elaheh Lotfi Kalahroodi, Daniel Rodrigues, Caridad D´ıaz, Mercedes de la Cruz, Bastien Cautain, R´emi Laville, Fernando Reyes, Thierry P´erez, Bassam Soussi and Olivier P. Thomas Poecillastrosides, Steroidal Saponins from the Mediterranean Deep-Sea Sponge Poecillastra compressa (Bowerbank, 1866) Reprinted from: Mar. Drugs 2017, 15, 199, doi:10.3390/md15070199 ................. 1 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 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 Reprinted from: Mar. Drugs 2017, 15, 256, doi:10.3390/md15080256 ................. 13 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 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 Reprinted from: Mar. Drugs 2017, 15, 302, doi:10.3390/md15100302 ................. 35 Muhammad Abdul Mojid Mondol, Hee Jae Shin, M. Aminur Rahman and Mohamad Tofazzal Islam Sea Cucumber Glycosides: Chemical Structures, Producing Species and Important Biological Properties Reprinted from: Mar. Drugs 2017, 15, 317, doi:10.3390/md15100317 ................. 52 Yeon-Ju Lee, Saem Han, Su Hyun Kim, Hyi-Seung Lee, Hee Jae Shin, Jong Seok Lee and Jihoon Lee Three New Cytotoxic Steroidal Glycosides Isolated from Conus pulicarius Collected in Kosrae, Micronesia Reprinted from: Mar. Drugs 2017, 15, 379, doi:10.3390/md15120379 ................. 87 Thomas E. Adrian and Peter Collin The Anti-Cancer Effects of Frondoside A Reprinted from: Mar. Drugs 2018, 16, 64, doi:10.3390/md16020064 .................. 95 Yunyang Lu, Hu Li, Minchang Wang, Yang Liu, Yingda Feng, Ke Liu and Haifeng Tang Cytotoxic Polyhydroxysteroidal Glycosides from Starfish Culcita novaeguineae Reprinted from: Mar. Drugs 2018, 16, 92, doi:10.3390/md16030092 ..................111 Chun Gui, Yena Liu, Zhenbin Zhou, Shanwen Zhang, Yunfeng Hu, Yu-Cheng Gu, Hongbo Huang and Jianhua Ju Angucycline Glycosides from Mangrove-Derived Streptomyces diastaticus subsp. SCSIO GJ056 Reprinted from: Mar. Drugs 2018, 16, 185, doi:10.3390/md16060185 .................121 v Ariana A. Vasconcelos and Vitor H. Pomin Marine Carbohydrate-Based Compounds with Medicinal Properties Reprinted from: Mar. Drugs 2018, 16, 233, doi:10.3390/md16070233 .................132 Iv´an Cheng-S´anchez and Francisco Sarabia Chemistry and Biology of Bioactive Glycolipids of Marine Origin Reprinted from: Mar. Drugs 2018, 16, 294, doi:10.3390/md16090294 .................160 Yadollah Bahrami, Wei Zhang and Christopher M. M. Franco Distribution of Saponins in the Sea Cucumber Holothuria lessoni; the Body Wall Versus the Viscera, and Their Biological Activities Reprinted from: Mar. Drugs 2018, 16, 423, doi:10.3390/md16110423 .................212 Aihong Peng, Xinying Qu, Fangyuan Liu, Xia Li, Erwei Li and Weidong Xie Angucycline Glycosides from an Intertidal Sediments Strain Streptomyces sp. and Their Cytotoxic Activity against Hepatoma Carcinoma Cells Reprinted from: Mar. Drugs 2018, 16, 470, doi:10.3390/md16120470 .................242 vi About the Special Issue Editors Thomas E Adrian, Professor of Physiology, trained at the Royal Postgraduate Medical School (Imperial College School of Medicine) in London where he received his Ph.D. and M.R.C.Path. He moved to Yale University as director of the GI Surgical Research Laboratory, then to Creighton University in Omaha, Nebraska as Professor and head of the Physiology Division and Research Director in the Cancer Center, and then to Northwestern University School of Medicine in Chicago, where he was the Edward Elcock Professor and Director of Gastrointestinal Cancer Research. In 2006, he moved to Al Ain as Professor and Chairman of the Department of Physiology, College of Medicine at United Arab Emirates University. In 2018, he moved to the new College of Medicine at MBRU in Dubai. Professor Adrian has published more than 400 scholarly articles in peer-reviewed journals (Citations > 25,000; h-index = 80) and more than 80 reviews and book chapters. Francisco Sarabia, Full Professor in Organic Chemistry, received his PhD degree from the University of Malaga´ (Spain) in 1994 under the supervision of Prof. Lopez-Herrera.´ After postdoctoral research with Prof. K. C. Nicolaou at the Scripps Research Institute in La Jolla (1995–1997), he returned to the University of Malaga´ in 1998 as an Assistant Professor, where he was promoted to Full Professor in 2011. Prof. Sarabia was employed as a Visiting Professor at the Technological Institute of Zurich¨ (ETH) in 1998 with Prof. A. Vasella, The Scripps Research Institute in 2001 with Prof. Nicolaou, and Scripps Florida in 2013 with Prof. W. R. Roush. His research interests include the total synthesis of natural products, the development of new synthetic methodologies, and the medicinal chemistry and discovery of new bioactive compounds of marine origin. He has been the Chairman of the Department of Organic Chemistry since 2014 and is responsible for the NMR facilities of the University of Malaga.´ Ivan Cheng-Sanchez, Research Associate, was born in Malaga´ (Spain) in 1992. He received his B.Sc. in Chemistry in 2014 and his M.Sc. in Chemistry in 2015 from the University of Malaga´ after conducting research in the laboratories of Prof. F. Sarabia. In November 2015 he started his Ph.D. studies under the guidance of Prof. F. Sarabia at the same university. In 2017 he joined the laboratories of Prof. C. Nevado at the University of Zurich for three months, where he was involved in the synthesis of novel ATAD2 bromodomain inhibitors for cancer treatment. His research interests include the total synthesis of natural products, the design and synthesis of new bioactive agents inspired by natural products, and medicinal chemistry. vii Preface to ”Marine Glycosides” This Special Issue of Marine Drugs highlights the chemistry, biology, and medicinal applications of recently discovered marine glycosides. Featuring a wide structural diversity and challenging molecular frameworks, these natural products exhibit a broad range of biological activities, which have propelled them as potential and promising leads in Medicinal Chemistry, prompting a great interest in scientific and medical circles. The papers included in this Special Issue have been written by authors who are leading experts in the field, and cover the isolation, structural elucidation, and/or biological evaluation of new glycosides of marine origin, including novel angucycline-, polyhydroxysteroidal-, steroidal saponin-, and sulfated triterpene-type glycosides, among others. The distribution of saponins and triterpene glycosides in sea cucumbers is also discussed. In addition, this Special Issue is supplemented by four reviews focused on the anticancer effects of Frondoside A, sea cucumber glycosides, marine carbohydrate-based compounds with medicinal properties, and the chemistry and biology of bioactive glycolipids of marine origin. Thomas E Adrian, Francisco Sarabia, Ivan Cheng-Sanchez Special Issue Editors ix marine drugs Article Poecillastrosides, Steroidal Saponins from the Mediterranean Deep-Sea Sponge Poecillastra compressa (Bowerbank, 1866) Kevin Calabro 1,2, Elaheh Lotfi Kalahroodi 3, Daniel Rodrigues 3,4, Caridad Díaz 5, Mercedes de la Cruz 5, Bastien Cautain 5,Rémi Laville 2, Fernando Reyes
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