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BIOLOGICALLY ACTIVE NATURAL PRODUCTS: AGROCHEMICALS - CHAPTER 8

Phytotoxin, coronatine (1), được phân lập từ phytopathogenic vi khuẩn Pseudomonas syringae pv. atropurpurea gây bệnh đốm sô-cô-la trên lá ryegrass.1 Ý Sau khi xác định cấu trúc của 1, nó đã được tìm thấy rằng một số pathovars của Pseudomonas syringae và Xanthomonas campestris pv. phormiicola sản xuất 1 như là một hợp chất phytotoxic. | 8__ Coronatine Chemistry and Biological Activities Akitami Ichihara and Hiroaki Toshima CONTENTS 8.1 Introduction 8.2 Structures of Coronatine and Analogs 8.3 Biosynthesis of Coronatine 8.4 Syntheses of Coronatine and Biosynthetic Analogs of Jasmonic Acid 8.4.1 Asymmetric Total Synthesis of Coronatine 8.4.2 Synthesis of Analogs of Jasmonic Acid and its Biosynthetic Intermediates 8.5 Biological Activities of Coronatine 8.5.1 Allocoronamic Acid as Inhibitors of Ethylene Biosynthesis 8.5.2 Similar Biological Activities of Coronatine to Those of Jasmonic Acid 8.6 Perspective References 8.1 Introduction The phytotoxin coronatine 1 was isolated from the phytopathogenic bacterium Pseudomonas syringae pv. atropurpurea which causes chocolate spot disease on the leaves of Italian ryegrass.1 After structural determination of 1 it was found that several pathovars of Pseudomonas syringae and Xanthomonas campestris pv. phormiicola produce 1 as a phytotoxic compound. Closely related analogues of 1 were isolated from Pseudomonas syringae pv. gly-cinea pv. tomato and Xanthomonas campestris pv. phormiicola. Recently there has been much interest in 1 since various biological activities similar to those of jasmonic acid were shown in assays for tuber-inducing activity etc. Furthermore the potent activities of 1 are 100 to 10 000 times higher than those of jasmonic acid. Therefore 1 is the most valuable probe in the area of plant physiological studies relating to jasmonic acid. In order to supply a sufficient amount of 1 an efficient synthetic method is urgently needed since the productivity of 1 by P. syringae pathovars is rather fluctuated depending on the culture conditions and or mutation. The total synthesis of optically active coronatine 1 was accomplished and made it possible to supply a practical amount of -1. Analogues of 1 and jasmonic acid and the compounds related to biosynthetic intermediates and amino acid conjugates of jasmonic acid