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Extra info for A revision of Clavija - Opera Botanica 107 (Theophrastaceae)
It is readily isomerized into isohirtellin C in hot water at 95 °C via a Smiles rearrangement that enables the conversion of the p-GOG unit into a mGOG unit. This rearrangement is presumably facilitated by the release of steric effects originating from hydroxyl groups in the p-GOG linking unit. , 1993a). Application of this isomerization reaction was used to confirm the structure of tamarixinins B (a macrocyclic dimer) and C, both isolated from Tamarix pakistanica (Tamaricaceae). Indeed, their Smiles rearrangement led to analogs of established structures, tamarixinin B being thus converted into hirtellin C, and tamarixinin C into hirtellin A (Fig.
1 The GOG- and GOGOG-type units The GOG-type linking units are produced by C–O coupling between two galloyl groups (Fig. 5), as found in the p-GOG isodehydrodigalloyl group (p-O of a galloyl group C-linked to another galloyl group, mode a) and the m-GOG dehydrodigalloyl group (m-O of a galloyl group Clinked to another galloyl group, mode b). The GOGOG-type units are formed via an additional oxidative C–O coupling of a galloyl group with a GOG group. , The Concept of Tannins 19 1991c) are examples of dimers featuring the m-GO-m-GOG-type unit, also referred to as the hellinoyl group as shown below.
Thus, a search of such a correlation within subclasses of the Cronquist’s system of plant evolution for Dicotyledonae (Fig. , Rosidae, Dilleniidae, Hamamelidae, Caryophyllidae and Magnolidae (NB: ellagitannins are not found in Asteridae) unveiled the following aspects and several other features: The Concept of Tannins 33 i) Oxidized tannins of the types III and IV are frequently found in the Rosidae, while they are found only in a small number of plant species belonging to the Dileniidae and Hamamelidae.