Eupomatia laurina

6-Diazafluoranthene (78) has been synthesized and shown to be identical with eupolauridine, which had been isolated previously from this species. Two other alkaloids, eupolauramine and hydroxyeupolauramine, were shown not to be related to (78) or synthetic 3,4-diazafluoranthene (79). 

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Aporphine alkaloids have been identified in Eupomatia laurina, which also gave a positive test in this study. 

The biogenetic relevance of spirodienone intermediate A is supported by the isolation of other spirodienones from Eupomatia laurina, namely the eupodienones [85], which were found to rearrange under acid conditions to give dibenzocyclooctadiene-type lignans [86]. 

The 1,6-diazafluoranthene eupolauridine (69) is also found in Cananga odorata Hook f. et Thompson (Annonaceae).73 Eupomatia laurina R. Br., which was the... 

Stephania japonica Liriodendron tulipifera Triclisia patens Liriodendron tulipifera Eupomatia laurina Cananga odorata Talauma mexicana ... 

An investigation of the alkaloidal content of the Australian Eupomatia laurina R. Br. (Eupomatiaceae), yielded a number of alkaloids, among which are the oxoaporphine liriodenine and the 7-hydroxynoraporphine norushinsunine. A new minor alkaloid from this source is eupolauridine (48) whose structure was proven conclusively by total synthesis (Scheme 6). ... 

Analogous rearrangements were reported for similar systems such as proaporphines , the alkaloids of Croton sparsiflorusMorong and cannabinoids . The dienone-phenol and dienol-benzene rearrangements were studied in the eupodienone-1 series (a constituent of Eupomatia laurina R. Br.). These compounds 311 were transformed under a variety of acidic conditions into dibenzocyclooctene derivatives (equation 149). 

Another monogeneric family of great antiquity, the Eupomatiaceae, was also investigated in the University of Sydney, and the first species studied, Eupomatia laurina. 

In 1978, Taylor et al. isolated a yellow crystalline substance, EL-base-5, from the bark of Eupomatia laurina (Eupomatiaceae) R. Br. collected in North Queensland 183). A more thorough investigation of this material in 1991 revealed that it consisted of two closely related compounds, eupomatidine-2 (431) and eupomatidine-3 (432). Their structure elucidations were reported, along with that of the newly isolated alkaloid eupomati-dine-1 (430), from the aerial parts of E. bennettii collected in the Mt. Lindsay Forest, New South Wales (iS4). 

An important example is the formal synthesis of eupolauramine, an alkaloid from the bark of the African plant Eupomatia laurina. This approach involves addition of the carbanion of allyl phenyl sulfone to l-methoxy-4-nitronaphthalene followed by cOTiversion of the o adduct formed into the conesponding nitrosoarene. Further intramolecular condensation affords phenylsulfonyl-substituted azaphenanthrene (Scheme 83) [82]. The sulfone obtained was transformed into tricyclic azaaromatic acid, from which in turn the final alkaloid can be obtained following the known procedure [206],... 

Picker, K., E. Ritchie, and W. C. Taylor Constituents of Eupomatia Species. III. New Eupomatenoid Lignans from the Leaves and Wood of Eupomatia laurina. Austral. J. Chem. 26, nil (1973). 

Magnoli Annon Eupomati Eupomatia laurina EupEuplau... 

Thy lor WC 1981 The constituents of Eupomatia laurina. Proc Fourth Asian Symp Med Plants Spices. Mahidol Univ, Bangkok, Thailand, p. 150-160... 

From the stem bark of C. odorata was isolated an alkaloid named canangine (XIV.30). Its identity with eupolauridine (XIV.30), a new naphthyridine alkaloid recently isolated from Eupomatia lamina, was later consolidated. Occurrence of eupolauridine in both E. laurina and C. odorata may be of taxonomic significance, since several authors have included Eupomatia in Annonaceae before considering it as a sole genus of the family Eupomatiaceae. 

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