Elsevier

Phytochemistry

Volume 10, Issue 12, December 1971, Pages 3161-3166
Phytochemistry

The structures of salicortin and tremulacin,☆☆

https://doi.org/10.1016/S0031-9422(00)97369-2Get rights and content

Abstract

The structure of the labile glucoside, salicortin, an important component of the bark and leaves of all Populus and Salix species, was proved to be the ω-(1-hydroxy-6-oxo-2-cyclohexene-1-carboxylic acid ester) of salicin by means of hydrogenolysis, acid and alkaline hydrolysis, and IR, NMR and mass spectra. In similar manner, the structure of tremulacin, an important glucoside component of several Populus species barks and leaves, was demonstrated to be the 2-O-benzoyl ester of salicortin.

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  • Phenolic glucosides from bark of Populus alba × glandulosa (Salicaceae)

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    Phenolic glucosides, including salicin and its derivatives with a benzyl glucopyran skeleton, are characteristic markers of the genus Populus (Thieme, 1967). Phenolic glucosides isolated from previous phytochemical studies on Populus species include salireposide (Pearl and Darling, 1968a,b, 1971a; Van Hoof et al., 1989; Kim et al., 2006; Zhang et al., 2006b), populoside (Pearl and Darling, 1969; Erickson et al., 1970; Zhang et al., 2006b), and salicortin (Pearl and Darling, 1969, 1971a,b) as salicin derivatives. In the present study we report, for the first time, five phenolic glucosides from Populus alba × glandulosa: sakuranin (1), neosakuranin (2), salireposide (3), suwonpopuloside (4), and newly identified grandidentin A (5).

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Part XXVIII in the series “Studies on the Barks of the Family Salicaceae” and Part XV in the series “Studies on the Leaves of the Family Salicaceae”.

☆☆

A preliminary communication of these results appeared in Tetrahedron Letters44, 3827 (1970).

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