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Soil and Plant Relationships of Inositol Phosphate Stereoisomers; the Identification of D-Chiro- and Muco-Inositol Phosphates in a Desert Soil and Plant System¹

ABSTRACT

Inositol phosphate stereoisomers were isolated from a forest soil and its surface organic horizon of undecomposed ponderosa pine (Pinus ponderosa) needles, and also from a desert soil and its surface plant matter of undecomposed velvet mesquite (Prosopis juliflora var. velutina) leaves. Qualitative and preparative paper chromatography, mass spectrometry, infrared (IR) and nuclear magnetic resonance (NMR) spectroscopy were the principal methods used to identify the stereochemistry of the inositol moieties. Nuclear magnetic resonance spectroscopy proved to be the most useful means of differentiating among the soil and plant inositol phosphates. Myo- and "DL"-chiroinositol phosphates (optical rotation unknown) were found in the pine needles of P. ponderosa and its underlying soil. Myo-, D-chiro-, and muco-inositol phosphates were found in the leaves of P. juliflora var. velutina; however, only myo- and D-chiroinositol phosphates were identified in the underlying desert soil. The presence of D-chiro-inositol phosphate but absence of muco-inositol phosphate in the desert soil poses questions concerning the fate of the latter in the soil. Epimerization reactions involving a cyclic ketone intermediate are considered, which could occur between the muco- and D-chiro-inositol moieties and also between the myo- and D-chiro inositol moieties, in which the isomers in both cases differ in the stereochemistry of only one carbon atom.

¹ Contribution from the Department of Agricultural Chemistry and Soils, Univ. of Arizona, Tucson. Presented before Div. S-3, Soil Science Soc. of Amer. meetings, Aug. 27, 1970, Tucson, Ariz. Arizona Agr. Exp. Sta. Technical Paper no. 1699.

² Research Associate, and Professor and Head of Department, respectively. The senior author is presently Herbicide Residue Chemist at Amchem Products, Inc., Ambler, Penna. 19002.

Received for publication September 3, 1970. Accepted for publication March 10, 1971.