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Isotopically-labeled natural products I. Biosynthesis and isolation of 1-menthol-14C

✍ Scribed by F. L. Gager Jr.; M. T. Core; R. T. Bass; R. W. Jenkins Jr.

Publisher
John Wiley and Sons
Year
1969
Tongue
French
Weight
368 KB
Volume
5
Category
Article
ISSN
0022-2135

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✦ Synopsis

The biosynthesis by and the isolation of l-menthol-14C from

Mentha arvensis grown in W O z are described. Crystals (18 mg; 3.2 mCilg) were obtained after column chromatographic purijication of the steam distillate of the leaves. Purity of greater than 99.5 % was established by gas-liquid radiochromatography.

INTRODUCTION.

Menthol is used by the pharmaceutical, toiletry, and tobacco industries. However, labeled menthol has not become available commercially.

Radioactive mint oils have been produced by several groups (** 2* 3, in biogenesis studies. Time-course experiments with 14C0, plus the incorporation of specific precursors have supported the biogenic scheme proposed by Reitsema (4). Only Mitsuhashi and co-workers ( 5 ) isolated labeled menthol and, by chemical degradations, showed the incorporation of carboxyl-labeled acetate.

Two groups have produced radioactive material for tracer studies, but details have not been published. In one report, Stepka and Larson (6), described elaborate facilities and listed natural products isolated, but only mentioned growing mint. In the second report, Newell, Latimer, and Haefele (') described the use of biosynthesized randomly-labeled menthol-14C in cigarette smoke experiments.

Our specific interest in tobacco products, in which menthol is a frequent additive, created a need for high specific activity labeled menthol. We therefore grew Mentha arvensis in 14C02 and isolated the I-mentholJ4C. The facility coupled with appropriate isolation procedures, should be useful for the production of a broad spectrum of labeled natural products.

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