Apiose and mono-O-methyl sugars as minor constituents of the leaves of deciduous trees and various other species

1. Leaves of a number of species were hydrolysed with aqueous sulphuric acid and the resulting mixtures of sugars were fractionated by chromatography on activated charcoal. Paper chromatography of the fractions showed the presence in all the hydrolysates of minor constituents with R(F) values similar to or greater than those of the common hexoses and pentoses. 2. Two of these were identified as 2-O-methylxylose and 2-O-methylfucose. Estimates of the amounts present in whole leaves, and in fractions prepared from them, showed that they were associated with the hemicelluloses. 3. A third constituent was identified, by the formation of its di-isopropylidene derivative, as apiose. It also was associated chiefly with the hemicellulose fraction; none could be found in aqueous extracts from leaves of Tilia vulgaris, nor in aqueous extracts of Zostera marina, in which apiose is a major constituent of the water-insoluble polysaccharide. 4. A further constituent, after further purification by preparative paper chromatography, was tentatively identified, by gas-liquid chromatography of derivatives, as 3-O-methylgalactose, and was probably accompanied by small amounts of 4-O-methylgalactose. 5. These observations confirm the widespread occurrence of 2-O-methylxylose, 2-O-methylfucose and apiose, but 3-O-methylgalactose was hitherto known only in slippery-elm mucilage, and 4-O-methylgalactose in soil polysaccharides. Some experiments on the digestion of leaf hemicellulose fractions by snail crop-juice suggested that the mono-O-methyl sugars might confer resistance to enzymic degradation.