Handbook of Anticancer Drugs from Marine Origin

Handbook of Anticancer Drugs

from Marine Origin

Se-Kwon Kim

Editor

Handbook of Anticancer

Drugs from Marine Origin

1 3

ISBN 978-3-319-07144-2 ISBN 978-3-319-07145-9 (eBook)

DOI 10.1007/978-3-319-07145-9

Springer Cham Heidelberg New York Dordrecht London

Library of Congress Control Number: 2014957505

© Springer International Publishing Switzerland 2015

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Editor

Se-Kwon Kim

Specialized Graduate School Science &

Technology Convergence

Department of Marine-Bio Convergence

Science

Marine Bioprocess Research Center

Pukyong National University

Yongdong Campus, 365, Sinseon-ro

Nam-gu, Busan 608-739

Republic of Korea

v

Preface—Anticancer Drugs from Marine Origin

Over the years, the invention of new compounds are isolated by using advanced

technology has expanded significantly. There are number of compounds developed

from marine environment for the treatment of various diseases. Increasing evidence

suggested that anticancer drug discovery leads from the marine environment. This

book combines the knowledge about the compounds isolated from marine environ￾ment and their product development. This handbook is divided into five parts.

Chapter 1 provides general introduction and sponges, seaweed, microbes, tuni￾cates and other miscellaneous compounds derived from marine organisms.

Part I—Sponges (Chaps. 2–6), described the sponge derived drugs represent one

of the most promising sources of research for finding new anticancer drugs. These

chapters discusses about the anticancer and angiogenesis inhibitors isolated from

marine sponges and mechanism of action and preclinical and clinical studies.

Part II—About the marine algae derived compounds on cancer targets

(Chaps. 6–11)—explained the compounds isolated from algae species, amelioration

and anti tumor effect of a tertiary sulfonium compound, dimethylsulfoniopropio￾nate, carotenoids, polysaccharides etc and the possible mechanisms of action are

described. Also the health benefits of seaweeds biological roles and potential ben￾efits for female cancers to be discussed in this part.

Part III—Provides (Chaps. 12–17) the details about marine microbial derived

compounds for cancer therapeutics. The antitumor compounds isolated from marine

microbes such as fungi, bacteria and actinobacteria are discussed.

Part IV—Discusses (Chap. 18) with marine tunicate derived compounds for can￾cer therapeutics.

Part V—The final part of the book covers others marine organisms derived com￾pounds and mechanism of actions. In this part sources of the marine compounds,

pyridoacridine alkaloids, triterpene glycosides, meroterpenoids for cancer targets

such as microtubules, apoptosis, angiogenesis and also discovery and computer￾aided drug design studies of the anticancer marine triterpene sipholanes as novel

P-gp and Brk modulators to be discussed in these chapters.

This book provides details about compounds isolation, chemistry, and applica￾tion in detail. Hence, anticancer drugs from marine origin are important for aca￾demic research, pharmaceutical, nutraceutical and biomedical industries. I would

vi Preface—Anticancer Drugs from Marine Origin

like to acknowledge Springer publisher, for their encouragement and suggestions to

get this wonderful compilation related marine drugs for cancer treatment. I would

also like to extend my sincere gratitude to all the contributors for providing help,

support, and advice to accomplish this task.

Busan, South Korea Prof. Se-Kwon Kim

vii

Contents

1 Introduction to Anticancer Drugs from Marine Origin ....................... 1

Se-Kwon Kim and Senthilkumar Kalimuthu

2 Triterpenoids as Anticancer Drugs from Marine Sponges ................... 15

Yong-Xin Li and Se-Kwon Kim

3 Marine Sponge Derived Antiangiogenic Compounds ........................... 29

Ana R. Quesada, Beatriz Martínez-Poveda, Salvador

Rodríguez-Nieto and Miguel Ángel Medina

4 Marine Sponge Derived Eribulin in Preclinical and Clinical

Studies for Cancer .................................................................................... 59

Umang Swami, Umang Shah and Sanjay Goel

5 Antitumour Effect of Cyclodepsipeptides from Marine Sponges ........ 101

Rosa Lemmens-Gruber

6 Cytotoxic Cyclic Peptides from the Marine Sponges ............................ 113

Toshiyuki Wakimoto, Karen Co Tan, Hiroki Tajima and Ikuro Abe

7 Fucoidan, A Sulfated Polysaccharides from Brown Algae as

Therapeutic Target for Cancer ............................................................... 145

Senthilkumar Kalimuthu and Se-Kwon Kim

8 Seaweeds-Derived Bioactive Materials for the Prevention

and Treatment of Female’s Cancer ........................................................ 165

Ratih Pangestuti and Se-Kwon Kim

9 Antitumor and Antimetastatic Effects of Marine

Algal Polyphenols ..................................................................................... 177

Fatih Karadeniz and Se-Kwon Kim

viii Contents

10 Seaweed Carotenoids for Cancer Therapeutics .................................. 185

Meganathan Boominathan and Ayyavu Mahesh

11 Amelioration Effect of a Tertiary Sulfonium Compound,

Dimethylsulfoniopropionate, in Green Sea Algae on Ehrlich

Ascitic-tumor, Solid Tumor and Related Diseases ............................... 205

Kenji Nakajima

12 The Current Status of Novel Anticancer Drugs from

Marine Actinobacteria ........................................................................... 239

Panchanathan Manivasagan and Se-Kwon Kim

13 Natural Products with Anticancer Activity from Marine Fungi ....... 253

Valliappan Karuppiah, Fengli Zhang and Zhiyong Li

14 Toluquinol, A Marine Fungus Metabolite, Inhibits Some of

the Hallmarks of Cancer ....................................................................... 269

Melissa García-Caballero, Miguel Ángel Medina and Ana R. Quesada

15 Anticancer Diketopiperazines from the Marine Fungus .................... 301

Zhan-Lin Li and Hui-Ming Hua

16 Meroterpenoids from Marine Microorganisms: Potential

Scaffolds for New Chemotherapy Leads .............................................. 323

Nelson G. M. Gomes, Suradet Buttachon and Anake Kijjoa

17 Antitumor Compounds from Actinomycetes in Deep-sea

Water of Toyama Bay ............................................................................. 367

Yasuhiro Igarashi

18 Tunicates: A Vertebrate Ancestral Source of Antitumor

Compounds ............................................................................................. 383

Edwin L. Cooper and Ralph Albert

19 Trabectedin (ET-743) from Marine Tunicate for Cancer Treatment 397

Harika Atmaca and Emir Bozkurt

20 Anti-Cancer Effects of Chitin and Chitosan Derivatives ................... 413

Mustafa Zafer Karagozlu and Se-Kwon Kim

21 Meroterpenes from Marine Invertebrates: Chemistry and

Application in Cancer ............................................................................ 423

David M. Pereira, Patrícia Valentão and Paula B. Andrade

Contents ix

22 Marine Sponge Sesterpenoids as Potent Apoptosis-Inducing

Factors in Human Carcinoma Cell Lines ............................................ 439

Giuseppina Tommonaro, Salvatore De Rosa, Rosa Carnuccio,

Maria Chiara Maiuri and Daniela De Stefano

23 Advances of Microtubule-Targeting Small Molecular

Anticancer Agents from Marine Origin ............................................... 481

Xiaobo Wang, Lun Yu, Zhiguo Liu, Pengfei Xu, Huilong Tan,

Tao Wu and Wenbin Zeng

24 Cytotoxic Triterpene Glycosides from Sea Cucumbers ...................... 515

Valeria P. Careaga and Marta S. Maier

25 Targeting Cellular Proapoptotic Agents from Marine Sources ......... 529

Ming Liu, Xiukun Lin and Lanhong Zheng

26 Discovery and Computer-Aided Drug Design Studies of the

Anticancer Marine Triterpene Sipholanes as Novel P-gp

and Brk Modulators .............................................................................. 547

Ahmed I. Foudah, Asmaa A. Sallam and Khalid A. El Sayed

27 Molecular Targets of Anticancer Agents from Filamentous

Marine Cyanobacteria ........................................................................... 571

Lik Tong Tan and Deepak Kumar Gupta

28 P-gp Inhibitory Activity from Marine Sponges, Tunicates

and Algae................................................................................................. 593

Xiao-cong Huang, Priyank Kumar, Nagaraju Anreddy,

Xue Xiao, Dong-Hua Yang and Zhe-Sheng Chen

29 Marine Cyanobacteria Compounds with Anticancer

Properties: Implication of Apoptosis .................................................... 621

Maria do Rosário Martins and Margarida Costa

30 Cytotoxic Cembrane Diterpenoids ....................................................... 649

Bin Yang, Juan Liu, Junfeng Wang, Shengrong Liao and Yonghong Liu

31 Anti-cancer Effects of Triterpene Glycosides, Frondoside A

and Cucumarioside A2

-2 Isolated from Sea Cucumbers .................... 673

Chang Gun Kim and Jong-Young Kwak

32 Pederin, Psymberin and the Structurally Related

Mycalamides: Synthetic Aspects and Biological Activities ................. 683

Zbigniew J. Witczak, Ajay Bommareddy and Adam L. VanWert

x Contents

33 Antitumor Effects of Sea Hare-Derived Compounds in Cancer ........ 701

Masaki Kita and Hideo Kigoshi

34 Marine Sponge Derived Actinomycetes and Their

Anticancer Compounds ......................................................................... 741

Kannan Sivakumar, Panchanathan Manivasagan and Se-Kwon Kim

35 Cytotoxic Terpene-Purines and Terpene-Quinones from the Sea ..... 757

Marina Gordaliza

36 Pyridoacridine Alkaloids from Marine Origin: Sources and

Anticancer Activity ................................................................................ 771

Anake Kijjoa

Index ................................................................................................................ 803

xi

Contributors

Ikuro Abe Lab of Natural Products Chemistry, Graduate School of Pharmaceutical

Sciences, The University of Tokyo, Tokyo, Japan

Ralph Albert Laboratory of Comparative Neuroimmunology, Department

of Neurobiology, David Geffen School Of Medicine at UCLA, University of

California, Los Angeles, CA, USA

Paula B. Andrade REQUIMTE/Laboratório de Farmacognosia, Departamento de

Química, Faculdade de Farmácia, Universidade do Porto, Porto, Portugal

Nagaraju Anreddy Department of Pharmaceutical Sciences, College of Pharmacy

and Health Sciences, St. John’s University, New York, NY, USA

Harika Atmaca Faculty of Science and Letters, Department of Biology, Section of

Molecular Biology, Celal Bayar University, Muradiye, Manisa, Turkey

Ajay Bommareddy Department of Pharmaceutical Sciences, Nesbitt School of

Pharmacy, Wilkes University, Wilkes-Barre, PA, USA

Meganathan Boominathan School of Biological Sciences, Madurai Kamaraj

University, Madurai, Tamil Nadu, India

Emir Bozkurt Faculty of Science and Letters, Department of Biology, Section of

Molecular Biology, Celal Bayar University, Muradiye, Manisa, Turkey

Suradet Buttachon ICBAS—Instituto de Ciências Biomédicas Abel Salazar

and Centro Interdisciplinar de Investigação Marinha e Ambiental (CIIMAR),

Universidade do Porto, Porto, Portugal

Valeria P. Careaga Facultad de Ciencias Exactas y Naturales, UMYMFOR—

Departamento de Química Orgánica, Universidad de Buenos Aires, Pabellón 2,

Ciudad Universitaria, Buenos Aires, Argentina

Rosa Carnuccio Dipartimento di Farmacia, Facoltà di Scienze Biotecnologiche,

Università degli Studi di Napoli Federico II, Napoli, Italy

Zhe-Sheng Chen Department of Pharmaceutical Sciences, College of Pharmacy

and Health Sciences, St. John’s University, New York, NY, USA

xii Contributors

Edwin L. Cooper Laboratory of Comparative Neuroimmunology, Department

of Neurobiology, David Geffen School Of Medicine at UCLA, University of

California, Los Angeles, CA, USA

Margarida Costa Interdisciplinary Centre of Marine and Environmental

Research—CIIMAR/CIMAR, Porto University, Porto, Portugal

Khalid A. El Sayed Department of Basic Pharmaceutical Sciences, School of

Pharmacy, University of Louisiana at Monroe, Monroe, LA, USA

Ahmed I. Foudah Department of Basic Pharmaceutical Sciences, School of

Pharmacy, University of Louisiana at Monroe, Monroe, LA, USA

Melissa García-Caballero Department of Molecular Biology and Biochemistry,

Faculty of Sciences, Unidad 741 de “CIBER de Enfermedades Raras”, University

of Málaga, Málaga, Spain

Sanjay Goel Albert Einstein College of Medicine, Department of Medical

Oncology, Montefiore Medical Center, Bronx, NY, USA

Nelson G. M. Gomes ICBAS—Instituto de Ciências Biomédicas Abel Salazar

and Centro Interdisciplinar de Investigação Marinha e Ambiental (CIIMAR),

Universidade do Porto, Porto, Portugal

Marina Gordaliza Pharmacy Faculty, Institute of Science and Technology Studies,

IBSAL, Campus Miguel de Unamuno, Salamanca University, Salamanca, Spain

Deepak Kumar Gupta National Institute of Education, Nanyang Technological

University, Nanyang, Singapore

Hui-Ming Hua School of Traditional Chinese Materia Medica, Shenyang

Pharmaceutical University, Shenyang, China

Xiao-cong Huang Division of Chemistry and Structural BiologyInstitute for

Molecular Bioscience, The University of Queensland, Brisbane, QLD, Australia

Yasuhiro Igarashi Department of Biotechnology, Biotechnology Research Center,

Toyama Prefectural University, Imizu, Toyama, Japan

Senthilkumar Kalimuthu Specialized Graduate School Science and Technology

Convergence, Department of Marine Bio Convergence Science, Marine Bioprocess

Research Center, Pukyong National University, Busan, Republic of Korea

Fatih Karadeniz Marine Bioprocess Research Center, Pukyong National

University, Busan, Republic of Korea

Mustafa Zafer Karagozlu Marine Bioprocess Research Center, Pukyong National

University, Busan, Republic of Korea

Valliappan Karuppiah Marine Biotechnology Laboratory, State Key Laboratory

of Microbial Metabolism and School of Life Sciences and Biotechnology, Shanghai

Jiao Tong University, Shanghai, P.R. China

Contributors xiii

Hideo Kigoshi Graduate School of Pure and Applied Sciences, University of

Tsukuba, Tsukuba, Japan

Anake Kijjoa ICBAS—Instituto de Ciências Biomédicas Abel Salazar and Centro

Interdisciplinar de Investigação Marinha e Ambiental (CIIMAR), Universidade do

Porto, Porto, Portugal

ICBAS-Instituto de Ciências Biomédicas de Abel Salazar and Centro Interdisciplinar

de Investigação Marinha e Ambiental (CIIMAR), Universidade do Porto, Porto,

Portugal

Chang Gun Kim Immune-network Pioneer Research Center & Department of

Biochemistry, School of Medicine, Dong-A University, Busan, Korea

Se-Kwon Kim Specialized Graduate School Science and Technology Convergence,

Department of Marine Bio Convergence Science, Marine Bioprocess Research

Center, Pukyong National University, Busan, Republic of Korea

Masaki Kita Graduate School of Pure and Applied Sciences, University of

Tsukuba, Tsukuba, Japan

Priyank Kumar Department of Pharmaceutical Sciences, College of Pharmacy

and Health Sciences, St. John’s University, New York, NY, USA

Jong-Young Kwak Immune-network Pioneer Research Center & Department of

Biochemistry, School of Medicine, Dong-A University, Busan, Korea

Rosa Lemmens-Gruber Department of Pharmacology and Toxicology, University

of Vienna, Vienna, Austria

Yong-Xin Li Marine Bioprocess Research Center, Pukyong National University,

Busan, South Korea

Zhan-Lin Li School of Traditional Chinese Materia Medica, Shenyang

Pharmaceutical University, Shenyang, China

Zhiyong Li Marine Biotechnology Laboratory, State Key Laboratory of Microbial

Metabolism and School of Life Sciences and Biotechnology, Shanghai Jiao Tong

University, Shanghai, P.R. China

Shengrong Liao CAS Key Laboratory of Tropical Marine Bio-resourcesand

Ecology, South China Sea Institute of Oceanology, Chinese Academy of Sciences,

Guangzhou, China

Xiukun Lin Department of Pharmacology, Capital Medical University, Beijing,

Youanmen, China

Juan Liu CAS Key Laboratory of Tropical Marine Bio-resourcesand Ecology,

South China Sea Institute of Oceanology, Chinese Academy of Sciences,

Guangzhou, China

Ming Liu Key Laboratory of Marine Drugs, Ministry of Education of China,

School of Medicine and Pharmacy, Ocean University of China, Qingdao, China

xiv

Yonghong Liu CAS Key Laboratory of Tropical Marine Bio-resourcesand

Ecology, South China Sea Institute of Oceanology, Chinese Academy of Sciences,

Guangzhou, China

Zhiguo Liu School of Pharmaceutical Sciences, Central South University,

Changsha, P. R. China

Ayyavu Mahesh School of Biological Sciences, Madurai Kamaraj University,

Madurai, Tamil Nadu, India

Marta S. Maier Facultad de Ciencias Exactas y Naturales, UMYMFOR—

Departamento de Química Orgánica, Universidad de Buenos Aires, Pabellón 2,

Ciudad Universitaria, Buenos Aires, Argentina

Maria Chiara Maiuri INSERM U848, Institut Gustave Roussy, Villejuif, France

Panchanathan Manivasagan Specialized Graduate School Science & Technology

Convergence, Department of Marine-Bio Convergence Science, Marine Bioprocess

Research Center, Pukyong National University, Busan, Republic of Korea

Beatriz Martínez-Poveda Department of Molecular Biology and Biochemistry,

Faculty of Sciences, University of Málaga, Málaga, Spain

Miguel Ángel Medina Department of Molecular Biology and Biochemistry,

Faculty of Sciences, University of Málaga, Málaga, Spain

Unidad 741 de CIBER “de Enfermedades Raras”, Málaga, Spain

Miguel Ángel Medina Department of Molecular Biology and Biochemistry,

Faculty of Sciences, Unidad 741 de “CIBER de Enfermedades Raras”, University

of Málaga, Málaga, Spain

Kenji Nakajima Department of Nutrition, Faculty of Nutrition, Graduate School

of Koshien University, Takarazuka, Hyogo, Japan

Kawanishi, Hyogo, Japan

Ratih Pangestuti Research Center for Oceanography, The Indonesian Institute of

Sciences, Jakarta, Republic of Indonesia

David M. Pereira REQUIMTE/Laboratório de Farmacognosia, Departamento de

Química, Faculdade de Farmácia, Universidade do Porto, Porto, Portugal

Ana R. Quesada Department of Molecular Biology and Biochemistry, Faculty of

Sciences, University of Málaga, Málaga, Spain

Unidad 741 de CIBER “de Enfermedades Raras”, Málaga, Spain

Department of Molecular Biology and Biochemistry, Faculty of Sciences, Unidad

741 de “CIBER de Enfermedades Raras”, University of Málaga, Málaga, Spain

Salvador Rodríguez-Nieto Genes and Cancer Group, Cancer Epigenetics and

Biology Program (PEBC-IDIBELL), Barcelona, Spain

Contributors

xv

Salvatore De Rosa National Research Council of Italy, Institute of Biomolecular

Chemistry, Pozzuoli, NA, Italy

Maria do Rosário Martins Health and Environmental Research Center, Superior

School of Allied Health Sciences of Porto, Polytechnic Institute of Porto, Vila Nova

de Gaia, Portugal

Interdisciplinary Centre of Marine and Environmental Research—CIIMAR/

CIMAR, Porto University, Porto, Portugal

Asmaa A. Sallam Department of Basic Pharmaceutical Sciences, School of

Pharmacy, University of Louisiana at Monroe, Monroe, LA, USA

Umang Shah Albert Einstein College of Medicine, Department of Medical

Oncology, Montefiore Medical Center, Bronx, NY, USA

Kannan Sivakumar Faculty of Marine Sciences, Centre of Advanced Study in

Marine Biology, Annamalai University, Parangipettai, Tamil Nadu, India

Daniela De Stefano Dipartimento di Farmacia, Facoltà di Scienze Biotecnologiche,

Università degli Studi di Napoli Federico II, Napoli, Italy

Umang Swami St. Barnabas Hospital, Bronx, NY, USA

Hiroki Tajima Lab of Natural Products Chemistry, Graduate School of

Pharmaceutical Sciences, The University of Tokyo, Tokyo, Japan

Huilong Tan School of Pharmaceutical Sciences, Central South University,

Changsha, P. R. China

Karen Co Tan Lab of Natural Products Chemistry, Graduate School of

Pharmaceutical Sciences, The University of Tokyo, Tokyo, Japan

Lik Tong Tan National Institute of Education, Nanyang Technological University,

Nanyang, Singapore

Giuseppina Tommonaro National Research Council of Italy, Institute of

Biomolecular Chemistry, Pozzuoli, NA, Italy

Patrícia Valentão REQUIMTE/Laboratório de Farmacognosia, Departamento de

Química, Faculdade de Farmácia, Universidade do Porto, Porto, Portugal

Toshiyuki Wakimoto Lab of Natural Products Chemistry, Graduate School of

Pharmaceutical Sciences, The University of Tokyo, Tokyo, Japan

Junfeng Wang CAS Key Laboratory of Tropical Marine Bio-resourcesand

Ecology, South China Sea Institute of Oceanology, Chinese Academy of Sciences,

Guangzhou, China

Xiaobo Wang School of Pharmaceutical Sciences, Central South University,

Changsha, P. R. China

Adam L. Van Wert Department of Pharmaceutical Sciences, Nesbitt School of

Pharmacy, Wilkes University, Wilkes-Barre, PA, USA

Contributors