Daphniphyllum humile

Morita, H. Yoshida, N. Kobayashi, J. (1999) Daphnezomines C-E, new alkaloids with an AT-oxide moiety from Daphniphyllum humile. Tetrahedron, 55, 12549-56. 

Two new alkaloids from Daphniphyllum gracile Gage have been reported.2 Plants of the related species Daphniphyllum humile Maxim have been implicated in cattle poisonings in Hokkaido, Japan.3... 

The Alkaloids of Daphniphyllum humile Deoxy-yuzurimine and Isodaphnilact-one-B.-Yamamura and Terada55 have isolated two new alkaloids from the leaves of D. humile M. Deoxy-yuzurimine (150), C27H37NO6, m.pt. 132 °C, was found to be identical with the previously reported product56 of the reduction of yuzurimine... 

Alkaloids of Daphniphyllum humile Deoxy-yuzurimine and Isodaphnilactone-B 243... 

Many grazing cattle have long been known to die from eating poisonous plants such as bracken fern and others. In 1978, a disease with jaundice, colic, and photophobia as the main symptoms broke out among cattle in Hokkaido, the northern island of Japan. It was demonstrated by Sonoda et al. to be plant poisoning caused by Daphniphyllum humile Maxim. (Ezo-Yuzuriha) (6), from which some new alkaloids were isolated in addition to several known ones. Pharmacological properties are also described briefly in Section III. 

Of 10 structurally known alkaloids belonging to the yuzurimine group, deox-yyuzurimine [36 mp 132-124°C C27H37O6N m/z 471 (M )] (Fig. 5) was isolated as a minor component from the species Daphniphyllum humile (7). The spectral data of 26 were completely identical to those of the reduction product obtained from yuzurimine (5) on zinc reduction in acetic acid (90-95°C, 2 hr). 

T. Kubota, T. Suzuki, K. I. Ishiuchi, T. Kuhara, J. I. Kobayashi, Daphnezomines T-V, alkaloids from Daphniphyllum humile, Chem. Pharm. Bull. 57 (2009) 504-507. 

The limited reports of work on the Daphniphyllum alkaloids include the description of the isolation of two new compounds from D. humile. 

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]. 

During the course of our studies for biogenetic intermediates of the daphniphyllum alkaloids, a project was initiated on the alkaloids of D. humile. A series of new daphniphyllum alkaloids, daphnezomines A-S (37-55), which were isolated from the leaves, stems, and fruits of D. humile, are of considerable interest from a biogenetic point of view. All these structures are listed in Figure 18.6. 

Four new alkaloids, daphnezomines P-S (S2-SS) have been isolated from the fruits of D. humile and daphnezomines P (52) and Q (S3) were the first daphniphyllum alkaloids with an iridoid glycoside moiety [78]. 

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. ... 

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