Daphniphyllum macropodum

Daphniphyllidine has been cited as the alkaloid D isolated from the bark and leaves of the plant Daphniphyllum macropodum Miquel [see Toda et al. (14)]. 

Daphniphyllum macropodum contains a great variety of related alkaloids whose structures are quite complex and novel (Section II). It is structurally evident that these alkaloids with an isopropyl or a potential isopropyl group are regarded as a terpene alkaloid. Bio-genetieally, these Daphniphyllum alkaloids, particularly C22 alkaloids, have been proposed to be derived from four molecules of mevalonic acid (MVA) and one acetate unit (15, 39). However, the recent tracer experiments showed that these alkaloids could be biosynthesized from six MVA molecules through a squalene-like intermediate. Accordingly, they should be included in a group of triterpene alkaloid. 

Asperuloside (= Asperulin Daphniphyllum macropodum PI3K (2) [laxative]... 

The full paper on the alkaloids of Daphniphyllum macropodum and D. gracile has been published. ... 

Yuzurine.—From the bark and leaves of Daphniphyllum macropodum Miquel, a new alkaloid, yuzurine, C24H37NO4, has been isolated as a colourless viscous liquid.This base was previously identified as the Alkaloid-A2. °... 

Structural and synthetic studies of the diterpene alkaloids of the Aconitum, Delphinium, and Garrya species continue to provide more insight into the chemistry of these complex bases. In recent years Japanese workers have isolated a series of isoprenoid alkaloids from plants of Daphniphyllum macropodum Miquel. Structural work on four new alkaloids representing three new structural types has been reported during this year. 

Daphniphyllum Alkaloids.—Secodaphniphylline and Methyl Homosecodaphni-phyllate. These alkaloids have been isolated from Daphniphyllum macropodum Miquel. Secodaphniphylline, C30H47NO3, m.p. 130 °C, has been chemically correlated with methyl homosecodaphniphyllate, C23H37NO2, m.p. 103 °C, via (52) as outlined in Scheme... 

A heavy-atom X-ray crystal-structure analysis of methyl IV-bromoacetyl-homosecodaphniphyllate (53) established the structures of secodaphniphylline and methyl homosecodaphniphyllate as (54) and (55), respectively. " The absolute configuration of this derivative was determined by anomalous dispersion procedures. These alkaloids are members of another new group of alkaloids isolated from Daphniphyllum macropodum. 

Daphnilactone-B. The fruits of Daphniphyllum macropodum Miquel yield as a major alkaloidal component daphnilactone-B, C22H31NO2, m.p. 92—94°C. Spectral data indicated the presence of a secondary methyl group, a vinyl proton, and a lactone ring. The structure of this compound was established as (60) by an... 

Decoctions of the bark and leaves of Daphniphyllum macropodum have long been used as a remedy for vermicide and asthma. This species is known to contain a number of alkaloids, general pharmacological tests of which have been cited briefly in the previous review (i). 

A group of structurally complicated triterpene alkaloids from bark and leaves of the Japanese Yuzuriha tree (Daphniphyllum macropodum) and other D. spe-... 

N. Sakabe, H. Irikawa, H. Sakurai, Y. Hirata, Isolation of 3 new alkaloids from Daphniphyllum macropodum Miquel, Tetrahedron Lett. 1 (1966) 963-964. 

From Daphniphyllum macropodum, a group of alkaloids (164) with complicated structures has been isolated (131). This plant is large evergreen tree growing in the central to southwestern parts of Japan. Taxonomically this genus is classified in Euphorbiaceae but there is an argument that this genus should be treated as an independent family, Daphniphyllaceae. 

C32H46CINO7, Chasmanine 14-a-benzoate hydrochloride, 43B, 764 C32HsoBrN05, Daphniphylline hydrobromide, 31B, 257 C32H52INO3, Alkaloid II methiodide (from daphniphyllum macropodum), 31B, 258... 

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