Recent progress on the lupine alkaloids in leguminous plants growing mainly in Japan

The existence of the lupine alkaloids in leguminous plants mainly growing i n Japan has been thoroughly ascertained, and 106 kinds of lupine alkaloids, including 51 kinds of novel lupine-type alkaloids, have been isolated and characterized from 28 species belonging to the 9 genera of leguminous plant s (Table 1). Among them (e.g. Fig. 1-2), a number of unusual types of alkal oids (e.g. Fig. 2) may be regarded as possible metabolites of the lupine al kaloids that coexist in the same plant, such as (+)-kuraramine-type, (-)-ma manine-type (Fig. 3); (-)-tsukushinamine-type (Fig. 5) and (+)-hupeol-type (Fig. 7) alkaloids, or as products of alternative biosynthetic pathway, suc h as tashiromine-type and (-)-camoensidine-type alkaloids in the Maackia sp ecies. The biosynthetic pathways (Fig. 8) by enzymes (Fig. 9) and some of b iological activities (e.g. Table 2) of the lupine alkaloids have also been presented. The leguminous plants that accumulate the common lupine alkaloid s may be divided into three main groups: plants which produce the matrine, the cytisine/sparteine, and the lupinine-type alkaloids. In addition, the M aackia species and a few other species produce rare bases. Some of more det ailed chemical properties of the lupine alkaloids that have been isolated a nd studied in our laboratory, including a newly proposed biosynthetic pathw ay, biotechnological studies, a summary of biological activities, and a dis cussion of chemotaxonomic aspects of the leguminous plants which accumulate lupine alkaloids, have been reviewed by authors in English papers shown in References 1, 55, 65, and also reviewed by one of the authors (I.M.) in a Japanese papers shown in Ref. 66, in which many aspects of the active resea rch history on (+)-matrine and its relatively alkaloids since 1892 in Japan are described.