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Plant Orthoesters 1092 Chem. Rev. 2009, 109, 1092–1140 Plant Orthoesters Shang-Gao Liao, Hua-Dong Chen, and Jian-Min Yue* State Key Laboratory of Drug Research, Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai, 201203, P. R. China Received January 30, 2008 Contents 10. Acknowledgments 1136 11. References 1136 1. Introduction 1092 2. General View of Occurrence, Classification, and 1093 1. Introduction Activity 3. Daphnane Diterpenoid Orthoesters (DDOs) 1094 As the result of natural hosts’ “selection” for biologically 3.1. Structures, Classification, and Distribution 1094 active chemical modulators under certain conditions, natural products generated with diverse structural scaffolds have been 3.2. Structural Elucidation 1098 1-5 3.3. Biological Activities 1101 demonstrated to be a precious wealth in drug discovery. Natural molecules with certain functional subunits and 3.3.1. Anticancer Activity 1102 stereochemistry have shown their successful applications in 3.3.2. Activation of Transient Receptor Potential 1104 quite a number of drug discovery programs.6,7 The orthoester, Vanilloid 1 (TRPV1) a functional group that features three alkoxy groups attaching 3.3.3. Piscicidal, Insecticidal, Acaricidal, and 1106 Nematicidal Activity and Other Toxicities to a single carbon atom, has been widely discovered as a structural subunit in natural products of plant origin. This 3.3.4. Antifertility Activity 1107 functional group, when constructed upon a specific structural 3.3.5. Neurotrophic, Cholesterol-Lowering, and 1107 skeleton, allows the attachment of additional fragments and/ Antihyperglycemic Activity or rings to produce stereochemically more complex struc- 3.3.6. Irritant and Tumor-Promoting Activity 1107 tures. Some of the orthoester-containing compounds of plant 3.4. Synthesis 1108 origin have shown important biological activities and have 3.4.1. Strategies for Construction of the 1108 been widely used as pharmacological tools in the study of Daphnane Diterpene Skeleton biological processes or as drug leads or candidates. In 3.4.2. Strategies for Building the Orthoester 1113 particular, the daphnane diterpenoid orthoesters (DDOs) have Functionality and Acyl Groups onto the been demonstrated to be powerful anticancer agents (see Daphnane Diterpene Skeleton section 3.3.1 and the very recent communication8) and 4. Limonoid Orthoesters 1115 TRPV1 activators (see section 3.3.2). In a recent report, 4.1. Structures, Classification, and Distribution 1115 DDOs were found to be a new type of DNA topoisomerase 4.2. Strategies for Structural Elucidation 1118 I (topo I) inhibitors with potency comparable to or even better 4.3. Biological Activities 1120 than that of hydroxycamptothecin (hCPT),9 one of the most Downloaded by CKRN CNSLP MASTER on July 22, 2009 5. Steroid Orthoesters 1122 powerful DNA topo I inhibitors in clinical use. More 5.1. Structures, Classification, and Distribution 1122 recently, two DDOs were demonstrated to be a new class of 5.2. Structural Elucidation 1123 cholesterol-lowering agents with LDLR promoter activation Published on January 30, 2009 http://pubs.acs.org | doi: 10.1021/cr0782832 5.3. Biological Activities 1126 activity.10 Limonoid orthoesters and steroid orthoesters were 5.3.1. Biological Activities of Bufadienolide 1126 particularly fascinating for their remarkable antifeedant or Orthoesters insecticidal activities (see sections 4.3 and 5.3). Tremendous - 5.3.2. Biological Activities of Ergostane 1128 efforts aimed at the structure activity relationship (SAR) Orthoesters among the biologically active orthoester-containing natural 5.4. Synthesis 1128 compounds revealed that the orthoester group in these natural 5.4.1. Synthesis of Bufadieolide Orthoesters 1128 molecules may function as an essential pharmacophore or 5.4.2. Synthesis of Petuniasterone Orthoesters 1129 serve as a stereochemical constraining element to maintain the desired conformation for the biological activities. Struc- 6. Coumarinoid Orthoesters 1130 tural elucidation and construction of these orthoester- 6.1. Structures, Classification, and Distribution 1130 containing compounds with such a complex architecture have 6.2. Structural Elucidation 1131 often been the stumbling blocks of natural products chemistry 6.3. Biological Activity and Synthesis 1131 and synthetic chemistry, and they have also presented great 7. Miscellaneous 1132 challenges and opportunities to chemists in these fields. 8. Conclusions 1134 Several reviews that covered some of the naturally 9. Abbreviations 1135 occurring plant orthoesters are available, but none has provided a full-aspect and in-depth view on this array of * To whom correspondence should be addressed. Telephone: 86-21- natural products. Earlier reviews related to the occurrence 50806718. Fax: 86-21-50806718. E-mail: [email protected]. and biological activity of daphnane diterpenoids were 10.1021/cr0782832 CCC: $71.50 2009 American Chemical Society Published on Web 01/30/2009 Plant Orthoesters Chemical Reviews, 2009, Vol. 109, No. 3 1093 Shang-Gao Liao was born in Guizhou, China, in 1972. He received his Jian-Min Yue is a Professor of Medicinal Chemistry at State Key Laboratory B.S. degree in Chemistry from Beijing Normal University in 1995. In the of Drug Research, Institute of Materia Medica, Shanghai Institutes for same year he joined the Guiyang Medical College as an instructor. In Biological Sciences, Chinese Academy of Sciences. He received his B.Sc. 2002, he moved to the research group of Professor Jian-Min Yue as a degree in Chemistry in 1984 from Lanzhou University, where he completed Ph.D. student at the Shanghai Institute of Materia Medica, Chinese his Ph.D. degree in Natural Products Chemistry in 1990 under the guidance Academy of Sciences, and graduated with his Ph.D. degree in 2007. He of the late Professor Yao-Zu Chen. He was a postdoctoral fellow then returned to a lectureship in Medicinal Natural Products Chemistry at (1991-1993) in the Department of Phytochemistry, Kunming Institute of Guiyang Medical College, where he remains up to now. His research Botany, Chinese Academy of Sciences, with Professor Han-Dong Sun. interests include the structure and function of various secondary He was a postdoctoral fellow (1993-1994) in the School of Chemistry, metabolites and their biological significance in the Traditional Chinese University of Bristol, with Professor Geoffrey Eglinton in Geoorganic Medicine system. Chemistry. Then he returned to Kunming Institute of Botany and worked as an Associate Professor (1994-1996). He joined the staff of the Joint Laboratory of Unilever Research and Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, as a Senior Research Scientist (1996-1999) on Natural Products Chemistry. He was then moved to Shanghai Institute of Materia Medica, where he remains up to now. During his research career, he has published over 140 scientific papers, book chapters, and patents. He currently served as an editorial member for Journal of Integrative Plant Biology, Journal of Chinese Pharmaceutical Sciences, and Natural Products Research & Development (in Chinese). His group is actively involved in the isolation, structure determination, and synthetic optimization of Natural Products, and is currently focused on natural products with activity against infectious diseases, cancer, and neurodegenerative disorders. steroids, and of coumarin origin have been discussed in detail. In the cases where sufficient information is available, the structure activity relationship (SAR) or the mode-of- action of the biologically active plant orthoesters has been Downloaded by CKRN CNSLP MASTER on July 22, 2009 Hua-Dong Chen was born in Hebei Province, China, in 1981. He received discussed. Strategies for the structural elucidation of these his B.S. degree in Chemistry from Nankai University in 2004. In the same orthoesters, especially of those with complex architectures, year he joined the research group of Professor Jian-Min Yue as a Ph.D. have been presented. The approaches to the orthoester subunit Published on January 30, 2009 http://pubs.acs.org | doi: 10.1021/cr0782832 student at the Shanghai Institute of Materia Medica, Chinese Academy of Sciences, where he is carrying out research on isolation and structural and synthetic efforts toward some of the biologically elucidation of biologically active natural products. important plant orthoesters have also been summarized. reported in 197811 and 1988,12 where only a limited number 2. General View of Occurrence, Classification, of DDOs were covered. Two minireviews were provided and Activity recently by De Kimpe’s group,13,14 focused on the occurrence and major biological and pharmacological discoveries of ca. An overview of published materials on plant orthoesters 80 naturally occurring DDOs as well as the stereochemical showed that the presence of these orthoesters was limited to requirements and the approaches to construct their orthoester only a few families, and they were present mainly in the unit. In 2002,15 Mulholland and co-workers reviewed the compound classes of daphnane diterpenoids, phragmalin structures of about 30 limonoid orthoesters from the Meli- limonoids, bufadienolide and ergostanoid steroids, and cou- aceae family in Southern and Eastern Africa and Madagascar. marin derivatives. In 198916 and 1991,17 Elliger reviewed his group’s excellent From a biological point of view, the most important plant work on the insect
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