Artemisinin and plant secondary metabolism

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Jan 8, 2016 - Peizhen Zhang. Institute of Geology, China Earthquake Administration, China. Qifa Zhang. Huazhong Agricultural University, China.
Editorial Board Editor-in-Chief

Xiao-Ya Chen (Life & Medical Sciences)

Executive Editors

Yaoling Niu (Earth Sciences) Guilu Long (Physics & Astronomy) Yuliang Zhao (Chemistry) Lianzhou Wang (Materials Science) Tianshou Zhao (Engineering Sciences)

Institute of Plant Physiology and Ecology, Shanghai Institutes for Biological Sciences, CAS, China Durham University, UK Tsinghua University, China National Center for Nanoscience and Technology, China University of Queensland, Australia the Hong Kong University of Science and Technology, China

Associate Editors

Life &Medical Sciences

Suneng Fu Zhihong Hu Hai-Kun Liu Qingsong Liu Zhihua Liu Baorong Lu Sheng Luan Guangshuo Ou Lianghu Qu Yi Rao Fuchou Tang Jun Wang Rui Wang Dong Xie Xudong Xu Ruifu Yang Wei Yang Yonggang Yao Zengqiang Yuan Dabing Zhang Xia Zhang Jianru Zuo Xi-Nian Zuo

Tsinghua University, China Wuhan Institute of Virology, CAS, China German Cancer Research Center, Germany Hefei Institute of Physical Science, CAS, China Chinese Academy of Medical Sciences, China Fudan University, China University of California Berkeley, USA Tsinghua University, China Sun Yat-sen University, China Peking University, China Peking University, China BGI-Shenzh­en, China Lakehead University, Canada Shanghai Institutes for Biological Sciences, CAS, China Institute of Hydrobiology, CAS, China Beijing Institute of Microbiology and Epidemiology, China NIDDK, National Institutes of Health, USA Kunming Institute of Zoology, CAS, China Institute of Biophysics, CAS, China Shanghai Jiao Tong University, China University of Ottawa, Canada Institute of Genetics and Developmental Biology, CAS, China Institute of Psychology, CAS, China

Physics & Astronomy Xie Chen Zhigang Chen Fuguo Deng Hui Hu Chuanfeng Li Ming Li Lifan Wang Yayu Wang Xiaogang Wen Zhi-zhong Xing Jianping Yao Jun’ichi Yokoyama

Materials Science

Guozhong Cao Jian-Dong Ding Hua Kuang Zhao-Ping Lü Limin Qi Wencai Ren Jianlin Shi Dan Wang Xiaolin Wang Shu-Hong Yu Tianyou Zhai Di Zhang Tierui Zhang

California Institute of Technology, USA Nankai University, China & San Francisco State University, USA Beijing Normal University, China Swinburne University of Technology, Australia University of Science and Technology of China, China Institute of Semiconductors, CAS, China Texas A&M University, USA Tsinghua University, China Massachusetts Institute of Technology, USA Institute of High Energy Physics, CAS, China University of Ottawa, Canada The University of Tokyo, Japan

University of Washington, USA Fudan University, China Jiangnan University, China University of Science and Technology Beijing, China Peking University, China Institute of Metal Research, CAS, China Shanghai Institute of Ceramics, CAS, China Institute of Process Engineering, CAS, China University of Wollongong, Australia University of Science and Technology of China, China Huazhong University of Science and Technology, China Shanghai Jiao Tong University, China Technical Institute of Physics and Chemistry, CAS, China

Earth Sciences

Wolfgang Bach Paterno R. Castillo Qiang Fu Peng Gong Xiao-Long Huang Sanzhong Li Libo Liu Shuguang Song Fang-Zhen Teng Yang Wang Chun-Ming Wu Xunlai Yuan Lingsen Zeng Renhe Zhang Zhidan Zhao Yan Zheng Shiyuan Zhong Yongguan Zhu

Chemistry

Chunying Chen Angang Dong Xiaohong Fang Xuefeng Fu Chenzhong Li Xiaogang Liu Lehui Lu Guangsheng Luo Huan Meng Shuming Nie Qing Peng Weiping Su Weihong Tan Yong Tang Suyuan Xie Zhaoxiong Xie Jing-Juan Xu Aiqian Zhang

University of Bremen, Germany University of California, USA University of Washington, USA Center for Earth System Science, Tsinghua University, China Guangzhou Institute of Geochemistry, CAS, China Ocean University of China, China Institute of Geology and Geophysics, CAS, China Peking University, China University of Washington, USA Florida State University, USA University of Chinese Academy of Sciences, China Nanjing Institute of Geology and Palaeontology, CAS, China Institute of Geology, Chinese Academy of Geological Sciences, China Chinese Academy of Meteorological Sciences, China China University of Geosciences, China City University of New York at Queens College and Lamont-Doherty Earth Observatory of Columbia University, USA Michigan State University, USA Institute of Urban Environment, CAS, China National Center for Nanoscience and Technology, China Fudan University, China Institute of Chemistry, CAS, China Peking University, China Florida International University, USA National University of Singapore, Singapore Changchun Institute of Applied Chemistry, CAS, China Tsinghua University, China University of California, Los Angeles, USA Emory University and Georgia Institute of Technology, USA Tsinghua University, China Fujian Institute of Research on the Structure of Matter, CAS, China Hunan University, China Shanghai Institute of Organic Chemistry, CAS, China Xiamen University, China Xiamen University, China Nanjing University, China Research Center for Eco-Environmental Sciences, CAS, China

Engineering Sciences

Yitung Chen Zhenqian Chen Ned Djilali Zhiyong Fan Zhaoli Guo Yong Hao Qiang Liao Meng Ni Minhua Shao Xia Wang Chao Xu Chun Yang

University of Nevada Las Vegas, USA Southeast University, China University of Victoria, Canada The Hong Kong University of Science and Technology, China Huazhong University of Science and Technology, China Institute of Engineering Thermophysics, CAS, China Chongqing University, China The Hong Kong Polytechnic University, China Hong Kong University of Science and Technology, China Oakland University, USA North China Electric Power University, China Nanyang Technological University, Singapore

Kohei Miyazono Zhongcan Ouyang Degan Shu Erkang Wang Guangqian Wang Xiao-Fan Wang Peiheng Wu Jianbai Xia Qikun Xue Huanming Yang Aibing Yu Qifeng Yu Richard N. Zare Wanming Zhai Lihe Zhang Peizhen Zhang Qifa Zhang Yaping Zhang Ze Zhang Yongfei Zheng Daoben Zhu Jian-Kang Zhu Rixiang Zhu

the University of Tokyo, Japan Institute of Theoretical Physics, CAS, China Northwest University, China Changchun Institute of Applied Chemistry, CAS, China Tsinghua University, China Duke University Medical Center, USA Nanjing University, China Institute of Semiconductors, CAS, China Tsinghua University, China BGI-China, China Monash University, Australia National University of Defense Technology, China Stanford University, USA Southwest Jiaotong University, China Peking University, China Institute of Geology, China Earthquake Administration, China Huazhong Agricultural University, China Kunming Institute of Zoology, CAS, China Zhejiang University, China University of Science and Technology of China, China Institute of Chemistry, CAS, China Purdue University, USA Institute of Geology and Geophysics, CAS, China

Advisory Board Members Zhifang Chai Chi-Ming Che Saijuan Chen Xuemei Chen Hongyuan Chen Zhijian (James) Chen Shijie Cheng Han Ding Deli Gao Ruiping Gao Molin Ge Guangcan Guo Zhengtang Guo Fuchu He Wei Huang Nianzhi Jiao Jiayang Li Jinghai Li Lin Li Ke Lu Jianbin Luo Chad A. Mirkin

Institute of High Energy Physics, CAS, China the University of Hong Kong, China Shanghai Jiao Tong University School of Medicine, China University of California, Riverside, USA Nanjing University, China Howard Hughes Medical Institute, UT Southwestern Medical Center at Dallas, USA Huazhong University of Science and Technology, China Huazhong University of Science and Technology, China China University of Petroleum-Beijing, China National Natural Science Foundation of China, China Nankai University, China University of Science and Technology of China, China Institute of Geology and Geophysics, CAS, China Academy of Military Medical Sciences, China Nanjing Tech University, China Xiamen University, China Institute of Genetics and Developmental Biology, CAS, China Institute of Process Engineering, CAS, China Shanghai Institutes for Biological Sciences, CAS, China Institute of Metal Research, CAS, China Tsinghua University, China Northwest University, USA

Senior Consulting Editor Dangsheng Li

Shanghai Institutes for Biological Sciences, CAS, China

CONTENTS COVER

Artemisia annua, a traditional Chinese medicinal plant, is well-known for producing a valuable compound, artemisinin, in its glandular secretary trichomes (GSTs). Artemisinin is a sesquiterpene lactone endoperoxide which is widely used in treatment with malaria disease. The artemisinin-based combination therapies (ACTs) are recommended by WHO as the first line drug for the treatment of cerebral malaria caused by strains of Plasmodium falciparum. It has saved millions of lives from malaria. The Chinese pharmacologist Youyou Tu received the 2011 Lasker Award in clinical medicine and the 2015 Nobel Prize in Physiology or Medicine for her contribution to the discovery of artemisinin from the natural plants. The biosynthetic pathway of artemisinin is almost completely elucidated, but the regulation mechanism remains largely unknown. In recent years, a set of transcription factors have been reported to participate in regulating the biosynthesis and accumulation of artemisinin and several of them were used in the genetic modification of A. annua plants to obtain a higher artemisinin content. The recent investigations on these transcription factors were summarized by Kexuan Tang’s research group from Shanghai Jiao Tong University, who have been dedicated to the study of regulatory mechanisms underlying artemisinin biosynthesis and the strategies to improve the artemisinin content in A. annua plants. The cover figure shows a transgenic A. annua plant with high artemisinin content by over-expressing AabZIP1, a transcription factor that regulates the expression levels of artemisinin biosynthetic pathway genes ADS and CYP71AV1 (see the review by Qian Shen et al. on page 18).

Volume 61 Number 1 January 2016

SPECIAL TOPIC: Advances in Artemisinin Study EDITORIAL 1

Artemisinin and plant secondary metabolism Xiao-Ya Chen • Zhihong Xu

REVIEWS 3



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Recent advances in biosynthesis of bioactive compounds in traditional Chinese medicinal plants Lei Yang • Changqing Yang • Chenyi Li • Qing Zhao • Ling Liu • Xin Fang • Xiao-Ya Chen Transcriptional regulation of artemisinin biosynthesis in Artemisia annua L. Qian Shen • Tingxiang Yan • Xueqing Fu • Kexuan Tang

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Artemisia annua glandular secretory trichomes: the biofactory of antimalarial agent artemisinin Ling Xiao • Hexin Tan • Lei Zhang Development of artemisinin drugs in the treatment of autoimmune diseases Yanwei Wu • Wei Tang • Jianping Zuo

COMMENTARY 42

Artemisia annua, artemisinin, and the Nobel Prize: beauty of natural products and educational significance De-Yu Xie

www.scichina.com | www.springer.com/scp

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www.scibull.com NEWS & VIEWS 45

Nanotechnology in the programmed cell therapy: nowhere to escape of cancer Jinxia Li • Yuliang Zhao

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Neutrino oscillation: discovery and perspectives Jun Cao • Miao He

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PROGRESS 52

Chemistry

Uniform design ray in the assessment of combined toxicities of multi-component mixtures Shu-Shen Liu • Qian-Fen Xiao • Jin Zhang • Mo Yu

REVIEW 59

Physics & Astronomy

Transformation optics applied to van der Waals interactions Rongkuo Zhao • Yu Luo • J. B. Pendry

ARTICLES 68

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Materials Science

One-step synthesis of cobalt, nitrogen-codoped carbon as nonprecious bifunctional electrocatalyst for oxygen reduction and evolution reactions Sijie Guo • Yanmei Yang • Naiyun Liu • Shi Qiao • Hui Huang • Yang Liu • Zhenhui Kang

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Engineering Sciences

Reconstruction of solid oxide fuel cell electrode microstructure and analysis of its effective conductivity Keqing Zheng • Meng Ni Performance improvement of solution-processed CdS/CdTe solar cells with a thin compact TiO2 buffer layer Aashir Waleed • Qianpeng Zhang • Mohammad Mahdi Tavakoli • Siu-Fung Leung • Leilei Gu • Jin He • Xiaoliang Mo • Zhiyong Fan

Earth Sciences

Oxygen isotopic variations in modern cetacean teeth and bones: implications for ecological, paleoecological, and paleoclimatic studies Burcu Ciner • Yang Wang • William Parker Instructions for Authors

www.scichina.com | www.springer.com/scp

Sci. Bull. (2016) 61(1):1–2 DOI 10.1007/s11434-015-0987-5

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Editorial

Artemisinin and plant secondary metabolism Xiao-Ya Chen • Zhihong Xu

Published online: 8 January 2016 Ó Science China Press and Springer-Verlag Berlin Heidelberg 2016

In March of 1977, a team of pharmacologists and chemists published a one-page article in Chinese Science Bulletin [1], which reports that the antimalarial component present in the traditional Chinese herb Artemisia annua L. (sweet wormwood) is a sesquiterpene endoperoxide lactone, and they named it artemisinin. Mrs. Youyou Tu, a woman scientist, is one of the authors who formed the famous ‘‘coordinating research group for the structure of artemisinin.’’ This novel compound is effective against not only chloroquine-resistant but also multidrug-resistant strains of the malarial parasite, Plasmodium falciparum, and it kills P. falciparum of all asexual stages by radicals released from break of the endoperoxide motif, although the exact molecular mode of the action still remains unclear. In 2004, World Health Organization suggested the artemisininbased combination therapies as the most effective strategy for malaria treatment. The drug and its derivatives have saved millions of lives from malaria, and Prof. Youyou Tu received the Nobel Prize in Physiology or Medicine in 2015. The discovery of artemisinin benefited from multidisciplinary knowledge. First of all, A. annua was selected owing to its malaria-treating records in Traditional Chinese SPECIAL TOPIC: Advances in Artemisinin Study X.-Y. Chen (&) State Key Laboratory of Plant Molecular Genetics, CAS Center for Excellence in Molecular Plant Sciences, Institute of Plant Physiology and Ecology, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai 200032, China e-mail: [email protected] Z. Xu College of Life Sciences, Peking University, Beijing 100871, China

Medicine (TCM) literatures. Prof. Youyou Tu recalled that she was inspired by a manual-like description in Principal Prescriptions for Emergency compiled by Hong Ge in 340 AD, which hinted her to use ethyl ether to extract the herb of A. annua, and it proved to be the key step to the finding of artemisinin. However, the artemisinin story is also an excellent example of modern pharmaceutical approach: the isolation of active components, the clinical trial, the structure elucidation and the structure–activity relations. The success of artemisinin application greatly promoted the development of several fields. Its complex structure encouraged organic chemists to synthesize the compound, but the low overall yield makes these syntheses unattractive [2]. Engineering the artemisinin biosynthesis pathway into yeast for semisynthetic production has greatly promoted the development of synthetic biology [3]. These achievements represent only a few well-known examples of research following the discovery of artemisinin. To help our readers obtain a quick snap of the knowledge about recent advances in artemisinin investigations, we present in this issue five articles on this special topic, including four reviews and one commentary, which cover biosynthesis of bioactive compounds in plants, transcriptional regulation of artemisinin biosynthesis in A. annua, tissue-specific biosynthesis and accumulation of artemisinin, development of artemisinin in the treatment of autoimmune diseases and the educational significance of the Nobel Prize awarded to Prof. Tu. Historically, plant secondary metabolites, such as morphine, quinine and aspirin, have played an important role in human’s battles against diseases. The finding of artemisinin demonstrated that traditional medicines are still a rich and promising resource for discovery and development of new drugs. Unfortunately, these valuable compounds are mostly present in small quantities and as a mix in plant tissues, and

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chemical synthesis is often tedious due to their complex structure and multiple chiral centers, which hinder their utilization in medicine or industry. Understanding biosynthetic pathways of these bioactive compounds is the prerequisite to producing them through biological engineering. In this special topic, Xiao-Ya Chen and colleagues [4] provide us a comprehensive overview of recent progresses in elucidation of biosynthesis of secondary (or specialized) metabolites, including phenylpropanoids, terpenoids and alkaloids, in plants, mostly of the TCM background. Synthetic biology approaches for artemisinin production have not yielded artemisinin itself directly in any of the non-plant vectors, which may be due to lack of special cellular environment in yeast or other microorganisms but essential for artemisinin formation in A. annua. Thus, engineering the artemisinin pathway in A. annua plant could be a promising solution. One of the features of plant secondary metabolism pathways is their spatial and temporal pattern, being restricted to or enriched in specific tissues or organs, in which transcription factors play a decisive role. These regulatory genes could be targets for increasing artemisinin production in plant. One review article by Kexuan Tang and colleagues summarizes current knowledge of transcriptional regulation of artemisinin biosynthesis in A. annua; indeed, over-expressing transcription factor genes, such as the AP2-type AaORA, substantially elevated the artemisinin yield [5]. Lei Zhang and colleagues discuss recent investigations in glandular secretory trichomes of A. annua, where artemisinin and related sesquiterpenoids are synthesized and stored, and it provides a new target for engineering secondary metabolism [6]. Old drug may have new applications. Although most well known for its antimalarial effect, artemisinin and its derivatives also show promising antitumor, anti-inflammatory, antifungal and antiviral activities. In this regard, Jianping Zuo and colleagues briefly introduce the research

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Sci. Bull. (2016) 61(1):1–2

progress of artemisinin drugs in the treatment of autoimmune diseases [7]. Finally, De-Yu Xie gives his comments on the Nobel Prize awarded to artemisinin and Prof. Tu [8]. Examples like artemisinin are rare, while the numbers of natural products synthesized by plants are huge. On the other hand, herbs are common in markets and considered to have medicinal or functional benefits to humans with or without a knowledge of their (active) components. We hope that this special topic will give readers valuable information on artemisinin investigations and beyond, attract more scientists to the areas of plant secondary metabolism, medicinal plant and healthy food, and encourage more research efforts to mine treasures from TCMs, in particular from plants, to better our lives. As the organizing editors, we thank all authors for their contribution.

References 1. Coordinating Research Group for the structure of artemisinin (1977) A new type of sesquiterpene lactone—artemisinin. Chin Sci Bull 22:142 (in Chinese) 2. Schmid G, Hofheinz W (1983) Total synthesis of qinghaosu. J Am Chem Soc 105:624–625 3. Paddon CJ, Westfall PJ, Pitera DJ et al (2013) High-level semisynthetic production of the potent antimalarial artemisinin. Nature 496:528–532 4. Yang L, Yang C, Li C et al (2015) Recent advances in biosynthesis of bioactive compounds in traditional Chinese medicinal plants. Sci Bull 61:3–17 5. Shen Q, Yan T, Fu X et al (2015) Transcriptional regulation of artemisinin biosynthesis in Artemisia annua L. Sci Bull 61:18–25 6. Xiao L, Tan H, Zhang L (2015) Artemisia annua glandular secretory trichomes: the biofactory of antimalarial agent artemisinin. Sci Bull 61:26–36 7. Wu Y, Tang W, Zuo J (2015) Development of artemisinin drugs in the treatment of autoimmune diseases. Sci Bull 61:37–41 8. Xie DY (2015) Artemisia annua, artemisinin, and the Nobel Prize: beauty of natural products and educational significance. Sci Bull 61:42–44

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