Tiliacora racemosa

Berberis actinacantha (Berberidaceae) daib 45, 2160 85 Berberis boliviano (Berberidaceae) jnp 52,81 89 Bongardia chrysogonum (Berberidaceae) jnp 52,818 89 Pdyalthia acuminata (Annonaceae) jnp 45,471 82 Roemeria refracta (Papaveraceae) hca 75,260 92 Tiliacora racemosa (Menispermaceae) cc 226 78... 

The stereochemistry of tiliacorine and that of its diastereomer tiliacorinine were determined by feeding the enantiomers of specifically radioactively labeled V-methylcoclaurine to Tiliacora racemosa and degrading the resulting alkaloids (Section VII,A) (41,42). Accordingly, tiliacorine has structure 65, and tiliacorinine is represented by 40. 

A new base with a diphenyl linkage and two diphenyl ether links is tiliamosine, from Tiliacora racemosa, which has the structure (51 R1 = H, R2 = Me) the N-acetyl-nor-compound (51 R1 = COMe, R2 = H) has also been isolated and characterized.62... 

Tiliacorine (CXXXII) and tiliarine (CXXXIII) were isolated from the roots of Tiliacora racemosa Colebr. (95, 96). 

Work on the alkaloids of Tiliacora racemosa has been summarized. The position of the free phenolic hydroxy function in one of these, tiliacorine (185 R = H), has been settled by conversion of O-acetyltiliacorine (185 R = Ac) into the p-hydroxybenzaldehyde derivative (186) (Scheme 20). it follows that nor-tiliacorinines A and B also have a free phenolic hydroxy-group at the 12 -position. ... 

Tiliacora racemosa Colebr. (Menispennaceae)[also called Tiliacora acuminata (Lam.) Miers (Menispermaceae)][381,382]... 

There are three alkaloids in this group, each of which bears a C(5) methoxy group, and is phenolic at C(12 ). The stereochemistry of the chiral centers at N(2) and N(2 ) is unknown. Tiliamosine (120) has been isolated from both Pachygone ovata (Menispermaceae) and Tiliacora racemosa (Menispermaceae), while pachygonamine (249) and N-methylpachygonamine (243) have only been isolated from the former plant. 

The only alkaloid of this type is tiliaresine (429), a base that only occurs in Tiliacora racemosa (Menispermaceae). The most unusual feature of this alkaloid is the lack of oxygenation at C(6), which is extremely uncommon for a bisbenzylisoquinoline alkaloid. 

The diastereoisomeric bases tiliacorine and tiliacorinine (61) have been found to incorporate radioactivity from tyrosine, norcoclaurine (58), coclaurine (59), and N-methylcoclaurine (60) in Tiliacora racemosa the fully methylated isoquinoline, as to be expected, was not utilized for biosynthesis. Degradation of... 

Saxena NK, Bhakuni DS 1980 Quaternary alkaloids of Tiliacora racemosa Colebr. J Indian Chem Soc 57 773-774... 

Galeffi C, La Bua R, Messana I, Zapata Alcazar R, Marini-Bett61o GB (1978) The Alkaloids of Sciadotenia toxifera Krukoff and A.C. Smith. Gazz Chim Ital 108 97-100 Guha KP, Das PC, Mukherjee B, Mukherjee R, Juneau GP, Bhacca NS (1976) Structure of tili-amosine a new diphenyl bisbenzylisoquinoline alkaloid from Tiliacora racemosa. Tetrahedron Lett 4241—4244... 

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