Alkaloids from Daphniphyllum gracile

Alkaloids from Daphniphytlum gracile.— Five new alkaloids were isolated by preparative t.l.c. from the leaves of Daphniphyllum gracile Gage, which grows in the Trust Territory of New Guinea/  

Daphnigracine (137), C24H37NO4, a viscous liquid, and daphnigraciline (138), C23H35NO4, m.p. 76—78 °C, were found to differ only by the alkyl group at C-16. On treatment of daphnigraciline methiodide with acetic acid in methanol, yuzurine methiodide (139) was obtained. The n.m.r. spectra of (137) and (138) indicated 

On treatment of (137), (138), and (141) with acetic anhydride-acetic acid, the dehydration products (143), (144), and (145), respectively, were obtained. The structural assignments of these compounds were confirmed by the C n.m.r. spectral data. 

Yamamura, J. A. Lamberton, H. Irikawa, Y. Okumura, and Y. Hirata, Chem. Letters, 1975, 923. S. Yamamura, K. Sasaki, M. Toda, and Y. Hirata, Tetrahedron Letters, 1974, 2023. 

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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 chemistry of the Daphniphyllum alkaloids has been reviewed. Terpenoid alkaloids are also reviewed in the Specialist Periodical Report The Alkaloids . Two new alkaloids, deoxyyuzurimine (13) and isodaphnilactone B (14), have been isolated from the leaves of Daphniphyllum gracile ... 

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