Daphniphyllum teijsmanni

Quite recently, three new alkaloids were isolated as minor components from the fruits of the plant Daphniphyllum teijsmanni Zollinger and their structures also determined on the basis of their physical and chemical data (43). In addition, the structure of yuzurine,9 one of the alkaloids of undetermined structure (see Section II, F), was also elucidated by means of an X-ray crystallographic analysis of its methiodide (44). 

Four new alkaloids have been isolated from the fruits of Daphniphyllum teijsmanni Zollinger.These bases are minor components and co-occur with daphnilactone-B (5), which is the major alkaloid. ... 

Further reports on the chemistry of daphniphylline (1), methyl homodaphniphyl-late (90), and daphnilactone-B, isolated from Daphniphyllum teijsmanni Zollinger, D. macropodum Miquel, and D. humile Maxim, have appeared. ... 

Four alkaloids belong to a group of secodaphniphylline-type ones represented by secodaphniphylline (2), which is considered to be the central biosynthesis precursor to the triterpenoid alkaloids that constitute the daphniphyllum alkaloids. Of them, daphniteijsmanine (18) (Fig. 3) has been newly isolated from the species Daphniphyllum teijsmanni, and its structure also been elucidated as follows (9). 

Daphilactone-B (4) is a major component of several alkaloids isolated from the fruits of three kinds of plants growing in Japan (7). Further examination of the alkaloidal components in the fruits of the species Daphniphyllum teijsmanni Zollinger (70) led to the isolation of a zwitterionic alkaloid (32) (Fig. 4), which was recently proved to be only one major component of the water-soluble fraction of the methanol extract (76). This alkaloid [32 mp 247-248°C C22H33O3N miz 359 (M+)] produces the following spectral data (Nujol)... 

Daphnilactone B (24) was isolated as one of the major alkaloids from the fruits of three Daphniphyllum species in Japan, D. macropodum, D. teijsmanni, and D. humile, and the structure was deduced by extensive spectral analysis, as well as by chemical evidence, and finally assigned by X-ray crystallographic analysis [34,35,37]. Isodaphnilactone B (25) was isolated from the leaves of D. humile and the structure was analyzed by spectroscopic methods [30]. A zwitterionic alkaloid 26, the hydration product of daphnilactone B, was isolated from the fruits of D. teijsmanni, and the structure determined on the basis of its spectral and chemical properties [38]. 

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