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Cancer Inhibitors from Chinese Natural Medicines Cancer Inhibitors from Chinese Natural Medicines Jun-Ping Xu CRC Press Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2017 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group, an Informa business No claim to original U.S. Government works Printed on acid-free paper Version Date: 20160802 International Standard Book Number-13: 978-1-4987-8764-2 (Hardback) This book contains information obtained from authentic and highly regarded sources. Reasonable efforts have been made to publish reliable data and information, but the author and publisher cannot assume responsibility for the validity of all materials or the consequences of their use. The authors and publishers have attempted to trace the copyright holders of all material reproduced in this publication and apologize to copyright holders if permission to publish in this form has not been obtained. If any copyright material has not been acknowledged please write and let us know so we may rectify in any future reprint. Except as permitted under U.S. Copyright Law, no part of this book may be reprinted, reproduced, transmitted, or utilized in any form by any electronic, mechanical, or other means, now known or hereafter invented, including photocopying, microfilming, and recording, or in any information storage or retrieval system, without written permission from the publishers. For permission to photocopy or use material electronically from this work, please access www.copyright.com (http://www.copyright.com/) or contact the Copyright Clearance Center, Inc. (CCC), 222 Rosewood Drive, Danvers, MA 01923, 978-750-8400. CCC is a not-for-profit organization that provides licenses and registration for a variety of users. For organizations that have been granted a photocopy license by the CCC, a separate system of payment has been arranged. Trademark Notice: Product or corporate names may be trademarks or registered trademarks, and are used only for identification and explanation without intent to infringe. Library of Congress Cataloging‑in‑Publication Data Names: Xu, Jun-Ping. Title: Cancer inhibitors from Chinese natural medicines / Jun-Ping Xu. Description: Boca Raton, FL : CRC Press, 2017. | Includes bibliographical references and index. Identifiers: LCCN 2016032439 | ISBN 9781498787642 (hardcover : alk. paper) Subjects: LCSH: Cancer--Prevention. | Medicine, Chinese. | Herbs--Therapeutic use. Classification: LCC RC268 .X8 2017 | DDC 616.99/405--dc23 LC record available at https://lccn.loc.gov/2016032439 Visit the Taylor & Francis Web site at http://www.taylorandfrancis.com and the CRC Press Web site at http://www.crcpress.com This book is dedicated to Prof. P.R. Pettit, director of the Cancer Research Institute at Arizona State University, and to Prof. H. Itokawa, supervisor of my PhD program at Tokyo University of Pharmacy and Life Sciences, for their outstanding accomplishments in the discovery and development of novel anticancer agents from natural sources and herbs; to my wife, Wendy, and son, Alex, for their full understanding and strong support; to the memories of my parents, Mr. Bingheng Xu and Mrs. Tingying Li, for their deep love; and to my uncle-in-law, Dr. Mike Y.H. Wu, for his earnest encouragements. Contents Preface ...............................................................................................................................................................................................xlvii Author .................................................................................................................................................................................................xlix List of Herbs ...........................................................................................................................................................................................li 1. Anticancer Activities of Exogenous Pathogenic Factor-Eliminating Herbs .............................................................................1 1 Niu Bang Zi 牛蒡子...............................................................................................................................................................................................1 Great burdock seed...........................................................................................................................................................................1 Herb Origination .........................................................................................................................................................................1 Antitumor Activities and Constituents ........................................................................................................................................1 Arctiin ....................................................................................................................................................................................2 Arctigenin...............................................................................................................................................................................2 Lappaols .................................................................................................................................................................................2 Other Compounds ..................................................................................................................................................................3 Other Bioactivities .......................................................................................................................................................................3 References ........................................................................................................................................................................................3 2 Chai Hu 柴胡...........................................................................................................................................................................................................4 Chinese thorowax .............................................................................................................................................................................4 Herb Origination .........................................................................................................................................................................4 Antitumor Activity and Constituents ..........................................................................................................................................4 Saikosaponins ........................................................................................................................................................................4 Lignans and Flavones .............................................................................................................................................................5 Other Bioactivities .......................................................................................................................................................................5 References ........................................................................................................................................................................................5 3 Shi Hu Sui 石胡荽..................................................................................................................................................................................................7 Spreading sneezeweed .....................................................................................................................................................................7 Herb Origination .........................................................................................................................................................................7 Antitumor Activities ....................................................................................................................................................................7 Antitumor Constituents and Activities ........................................................................................................................................7 Sesquiterpene Lactones ..........................................................................................................................................................7 Polyphenols and Flavonoids ...................................................................................................................................................8 Triterpenes and Steroids .........................................................................................................................................................8 Other Bioactivities .......................................................................................................................................................................8 References ........................................................................................................................................................................................8 4 Sheng Ma 昇麻........................................................................................................................................................................................................9 Black cohosh ....................................................................................................................................................................................9 Herb Origination .........................................................................................................................................................................9 Antitumor Constituents and Activities ........................................................................................................................................9 Total Triterpenoid Glycosides ..............................................................................................................................................10 9,19-Cycloartane Triterpenes ...............................................................................................................................................10 9,19-Cycloartane Triterpenoid Glycosides ...........................................................................................................................10 Structure–Activity Relationships .........................................................................................................................................11 Sterol ....................................................................................................................................................................................11 Caffeic Acid Derivatives ......................................................................................................................................................11 Other Active Compounds .....................................................................................................................................................11 Other Bioactivities .....................................................................................................................................................................11 References ......................................................................................................................................................................................11 5 Ge 葛 ...........................................................................................................................................................................................13 Kudzu .............................................................................................................................................................................................13 Herb Origination .......................................................................................................................................................................13 Antitumor Constituents and Activity ........................................................................................................................................13 Isoflavonoids .........................................................................................................................................................................13 Spinasterol ............................................................................................................................................................................14 Nanoformulation .......................................................................................................................................................................14 vii viii Contents Other Bioactivities .....................................................................................................................................................................14 References ......................................................................................................................................................................................14 2. Anticancer Potentials of Antipyretic Herbs ...............................................................................................................................17 6 Chuan Xin Lian 穿心蓮.....................................................................................................................................................................................19 Green chirayta ................................................................................................................................................................................19 Herb Origination .......................................................................................................................................................................19 Antitumor Activities and Constituents ......................................................................................................................................19 Andrographolide and Analogs .............................................................................................................................................20 Flavanones ............................................................................................................................................................................22 Structure–Activity Relationship................................................................................................................................................22 Structural Modification .............................................................................................................................................................22 Other Bioactivities .....................................................................................................................................................................23 References ......................................................................................................................................................................................23 7 She Gan 射干........................................................................................................................................................................................................26 Blackberry lily or Leopard lily ......................................................................................................................................................26 Herb Origination .......................................................................................................................................................................26 Antitumor Activity ....................................................................................................................................................................26 Antitumor Constituents and Activity ........................................................................................................................................26 Triterpenoids ........................................................................................................................................................................26 Flavonoids ............................................................................................................................................................................26 Other Medical Uses ...................................................................................................................................................................27 References ......................................................................................................................................................................................27 8 Ya Dan Zi 鴉膽子................................................................................................................................................................................................28 Java brucea seed .............................................................................................................................................................................28 Herb Origination .......................................................................................................................................................................28 Antitumor Activities ..................................................................................................................................................................28 Seed Oil ................................................................................................................................................................................28 Aqueous Extracts .................................................................................................................................................................28 Antitumor Constituents and Activities ......................................................................................................................................29 Quassinoids ..........................................................................................................................................................................29 Quassinoid Glucosides .........................................................................................................................................................29 Other Types of Components.................................................................................................................................................29 Anticarcinogenic Constituents ..................................................................................................................................................29 Clinical Trials ............................................................................................................................................................................30 Other Bioactivities .....................................................................................................................................................................30 References ......................................................................................................................................................................................30 9 Lin Mao Jiu 鱗毛蕨............................................................................................................................................................................................32 Dryopteris ferns ..............................................................................................................................................................................32 Herb Origination .......................................................................................................................................................................32 Antitumor Activities and Constituents ......................................................................................................................................32 Phloroglucinol Derivatives ...................................................................................................................................................32 Sesquiterpenoids ..................................................................................................................................................................32 Coumarins and Lignans .......................................................................................................................................................33 Other Bioactivities .....................................................................................................................................................................33 References ......................................................................................................................................................................................33 10 Yu Xin Cao 魚腥草...........................................................................................................................................................................................34 Fishwort or Lizard Tail ..................................................................................................................................................................34 Herb Origination .......................................................................................................................................................................34 Antitumor Constituents and Activities ......................................................................................................................................34 Antitumor Activities ..................................................................................................................................................................34 Houttuynin ...........................................................................................................................................................................34 Flavonoids ............................................................................................................................................................................35 Alkaloids ..............................................................................................................................................................................35 Other Bioactivities .....................................................................................................................................................................35 References ......................................................................................................................................................................................35 11 Jin Yin Hua 金銀花..........................................................................................................................................................................................36 Honeysuckle flower ........................................................................................................................................................................36 Herb Origination .......................................................................................................................................................................36 Contents ix Antitumor Activities and Constituents ......................................................................................................................................36 Volatile Components ............................................................................................................................................................36 Polyphenolic Components ....................................................................................................................................................36 Flavonoids ............................................................................................................................................................................36 Biflavonoids ..........................................................................................................................................................................37 Lignan ..................................................................................................................................................................................37 Polysaccharides ....................................................................................................................................................................37 Other Bioactivities .....................................................................................................................................................................37 References ......................................................................................................................................................................................37 12 Bei Dou Gen 北豆根.........................................................................................................................................................................................38 Asian moonseed .............................................................................................................................................................................38 Herb Origination .......................................................................................................................................................................38 Antitumor Constituents and Activities ......................................................................................................................................38 Alkaloids ..............................................................................................................................................................................38 Polysaccharides ....................................................................................................................................................................38 Other Bioactivities .....................................................................................................................................................................38 References ......................................................................................................................................................................................38 13 She She Cao 蛇舌草..........................................................................................................................................................................................40 Spreading hedyotis .........................................................................................................................................................................40 Herb Origination .......................................................................................................................................................................40 Antitumor Activities ..................................................................................................................................................................40 Antitumor Constituents and Activities ......................................................................................................................................40 Iridoids and Pheophytins .....................................................................................................................................................40 Anthraquinones ....................................................................................................................................................................41 Flavonoids ............................................................................................................................................................................41 Triterpenoids ........................................................................................................................................................................41 Sterol ....................................................................................................................................................................................41 Polysaccharides ....................................................................................................................................................................41 Other Bioactivities .....................................................................................................................................................................42 References ......................................................................................................................................................................................42 14 Chong Lou 重樓.................................................................................................................................................................................................43 Rhizoma Paridis .............................................................................................................................................................................43 Herb Origination .......................................................................................................................................................................43 Antitumor Activities and Constituents ......................................................................................................................................43 Steroidal Saponins ...............................................................................................................................................................43 Structure and Activity Relationship .....................................................................................................................................45 Other Types of Active Components .....................................................................................................................................45 Other Bioactivities .....................................................................................................................................................................45 References ......................................................................................................................................................................................45 15 Mu Tou Hui 墓頭回..........................................................................................................................................................................................48 Herb Origination .......................................................................................................................................................................48 Antitumor Activities ..................................................................................................................................................................48 Antitumor Constituents and Activities ......................................................................................................................................48 Iridoids .................................................................................................................................................................................48 Triterpenes ...........................................................................................................................................................................49 Total Glycosides ...................................................................................................................................................................49 Lignans .................................................................................................................................................................................49 Polysaccharides ....................................................................................................................................................................49 Clinical Trial .............................................................................................................................................................................50 Other Medical Uses ...................................................................................................................................................................50 References ......................................................................................................................................................................................50 16 Bai Jiang Cao 敗酱草.........................................................................................................................................................................................51 Herb Origination .......................................................................................................................................................................51 Antitumor Activity ....................................................................................................................................................................51 Extract from P. scabiosaefolia .............................................................................................................................................51 Extract from P. villosa .........................................................................................................................................................51 Antitumor Constituents and Activities ......................................................................................................................................51 Triterpenoid Saponins ..........................................................................................................................................................51 Flavonoids ............................................................................................................................................................................52 x Contents Lignan ..................................................................................................................................................................................52 Other Medical Uses ...................................................................................................................................................................52 References ......................................................................................................................................................................................52 17 Ma Chi Xian 馬齒莧.........................................................................................................................................................................................54 Common Purslane or Verdolaga ....................................................................................................................................................54 Herb Origination .......................................................................................................................................................................54 Antitumor Activities and Constituents ......................................................................................................................................54 Alkaloids ..............................................................................................................................................................................54 Flavonoids ............................................................................................................................................................................54 Triterpenoids ........................................................................................................................................................................55 Cerebroside...........................................................................................................................................................................55 Betacyanins ..........................................................................................................................................................................55 Glycolipids ...........................................................................................................................................................................55 Polysaccharides ....................................................................................................................................................................55 Other Bioactivities .....................................................................................................................................................................55 References ......................................................................................................................................................................................55 18 Bai Tou Weng 白頭翁.......................................................................................................................................................................................57 Chinese pulsatilla anemone ...........................................................................................................................................................57 Herb Origination .......................................................................................................................................................................57 Antitumor Activities ..................................................................................................................................................................57 Antitumor Constituents and Activities ......................................................................................................................................57 Triterpene Acids ...................................................................................................................................................................57 Saponins ...............................................................................................................................................................................58 Lignans .................................................................................................................................................................................58 Polysaccharides ....................................................................................................................................................................58 Glycoprotein .........................................................................................................................................................................58 Formulations .............................................................................................................................................................................59 Other Bioactivities .....................................................................................................................................................................59 References ......................................................................................................................................................................................59 19 Ban Zhi Lian 半枝蓮........................................................................................................................................................................................60 Barbat skullcap ...............................................................................................................................................................................60 Herb Origination .......................................................................................................................................................................60 Antitumor Activities ..................................................................................................................................................................60 BZL101 .................................................................................................................................................................................60 Clinical Trials of BZL101 ....................................................................................................................................................61 Antitumor Constituents and Activities ......................................................................................................................................61 Flavonoids ............................................................................................................................................................................61 Diterpenoids .........................................................................................................................................................................61 Diterpenoid Alkaloids ..........................................................................................................................................................62 Pheophorbide-a ....................................................................................................................................................................62 Phenylbutenones ...................................................................................................................................................................62 Polysaccharides ....................................................................................................................................................................62 Other Bioactivities .....................................................................................................................................................................62 References ......................................................................................................................................................................................62 20 Tu Fu Ling 土茯苓............................................................................................................................................................................................65 Sarsaparilla .....................................................................................................................................................................................65 Herb Origination .......................................................................................................................................................................65 Antitumor Activities and Constituents ......................................................................................................................................65 Glycoprotein .........................................................................................................................................................................65 Proteins.................................................................................................................................................................................65 Other Bioactivities .....................................................................................................................................................................65 References ......................................................................................................................................................................................65 21 Shan Dou Gen 山豆根......................................................................................................................................................................................67 Vietnamese sophora root ................................................................................................................................................................67 Herb Origination .......................................................................................................................................................................67 Antitumor Activity and Constituents ........................................................................................................................................67 Alkaloids ..............................................................................................................................................................................67 Flavonoids ............................................................................................................................................................................67

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