Daphnandra repandula

The orange-yellow alkaloid daphnine (113) was isolated from Daphnandra repandula (66). The structure was proven by NOEDS studies (see Section VI,A,2,b) of its dihydro diacetate in CD3C02D. These measurements showed the connectivity relationships of 2 -Me-3 -H-4 -H-5 -H-6 -OMe and 5-H-6-OMe, which served to eliminate other isomeric structures, notably a 7-6 ether-linked dimer (67). The structure of daphnine was confirmed by an X-ray analysis of the dihydroiodide. It was postulated that daphnine, the only bisbenzyliso-quinoline alkaloid with a 7-7 ether linkage, arises by rearrangement of (-)-nortenuipine (114) or its enantiomer, which also occur in Daphnandra species (66). 

Daphnandra dielsii Perk. (Monimiaceae)[27] Daphnandra Johnsonii Schodde (Monimiaceae)[336] Daphnandra repandula F. Muell. (Monimiaceae)[27] Isopyrum ihalictroides L. (Ranunculaceae)t323]... 

Spiral Whorls or spiral (Daphnandra repandula) mostly di- or tetramerous whorls, some trimerous or complex whorls Two whorls of 3-4 (-6) or one whorl of 4-8 Spiral (Monimioideae and Hortonia) or dimerous or complex whorls (Mollinedioideae) Mostly trimerous whorls... 

DAPHNANDRA spp. Bancroft recorded the presence of alkaloids in several Daphnandra species, notably D. repandula and D. micrantha. The latter was examined by Pyman and shown to contain three alkaloids, daphnandrine, micranthine and daphnoline. 

There is only one racemic alkaloid in the type X alkaloid group. Repandinine ((+/-)-tenuipine](90) has been isolated from four Daphnandra species, including D. dielsii, D. johnsonii, D. repandula, and D. tenuipes. 

Daphnine (191), the highly conjugated N(2) zwitterionic alkaloid from Daphnandra dielsii and D. repandula (Monimiaceae), is the sole representative of this type of alkaloid. Daphnine is of very restricted distribution to the genus Daphnandra. 

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