Perillic Acid Research Articles

Bioconversion of (+)‐Limonene by Pseudomonas gladioli

ABSTRACT Pseudomonas gladioli was isolated by an enrichment culture technique using limonene as the sole source of carbon. Fermentations were conducted for 4–10 days in shake flasks at 25°C using a pH 6.5 mineral salts medium and 1.0% (+)‐limonene. Major conversion products were identified as (+)‐α‐terpineol and (+)‐perillic acid. Quantitative analysis of α‐terpineol and perillic acid during the fermentation revealed that α‐terpineol was resistant to further degradation by the bacterium, while perillic acid was readily degraded.

Metabolism of alpha-terpineol by Pseudomonas incognita.

Details of the metabolism of alpha-terpineol by Pseudomonas incognita are presented. Degradation of alpha-terpineol by this organism resulted in the formation of a number of acidic and neutral metabolites. Among the acidic metabolites, beta-isopropyl pimelic acid, 1-hydroxy-4-isopropenyl-cyclohexane-1-carboxylic acid, 8-hydroxycumic acid, oleuropeic acid, cumic acid, and p-isopropenyl benzoic acid have been identified. Neutral metabolites identified were limonene, p-cymene-8-ol, 2-hydroxycineole, and uroterpenol. Cell-free extracts prepared from alpha-terpineol adapted cells were shown to convert alpha-terpineol, p-cymene-8-ol, and limonene to oleuropeic acid, 8-hydroxycumic acid, and perillic acid, respectively, in the presence of NADH. The same cell-free extract contained NAD+ -specific dehydrogenase(s) which converted oleuropyl alcohol, p-cymene-7,8-diol, and perillyl alcohol to their corresponding 7-carboxy acids. On the basis of various metabolites isolated from the culture medium, together with the supporting evidence obtained from enzymatic and growth studies, it appears that P. incognita degrades alpha-terpineol by at least three different routes. While one of the pathways seems to operate via oleuropeic acid, a second may be initiated through the aromatization of alpha-terpineol. The third pathway may involve the formation of limonene from alpha-terpineol and its further metabolism.

Microbial transformation of ?-pinene

A bacterium capable of utilizing α-pinene as a sole carbon and energy source was isolated from soil. This strain, named strain S201-1, which was identified as Pseudomonas maltophilia on the basis of its taxonomical properties, accumulated limonene, borneol, camphor, perillic acid, and 2-(4-methyl-3-cyclohexenylidene) propionic acid from α-pinene in the culture broth. It was demonstrated that α-pinene, β-pinene, borneol, camphor, and a number of p-menthane derivatives were oxidized by this strain. Relations between the protonation of α-pinene and the formation of the products by the microbe are discussed.

Propyl gallate: A clandestine sensitizer?: Kahn, G., Phanuphak, P. & Claman, H. N. (1974). Propyl gallate-contact sensitization and orally-induced tolerance. Archs Derm.109, 506.

A simple and sensitive isocratic high-performance liquid chromatographic (HPLC) method with UV detection for the quantitation of perillic acid, a major circulating metabolite of perillyl alcohol and d-limonene, in plasma is described. Sample preparation involved protein precipitation and subsequent transfer and dilution with 10 mM NaHCO3. The mobile phase consisted of acetonitrile (36%) and 0.05 M ammonium acetate buffer pH 5.0 (64%). Separations were achieved on a C18 column and the effluent monitored for UV absorption at the analytes' respective UVmax. Separation was excellent with no interference from endogenous plasma constituents. This method was found suitable for quantifying drug concentrations in the range of 0.25 to 200.0 μg/ml using a 0.05-ml plasma sample, and was used to study the plasma pharmacokinetics of perillic acid in mice.

Studies on the Metabolism ofd-Limonene (p-Mentha-1,8-diene): II. The Metabolic Fate ofd-Limonene in Rabbits

Abstract1. The metabolic fate of d-limonene (p-mentha-1,8-diene) was investigated in the rabbit.2. Following oral administration of [14C]d-limonene to three male rabbits, about 72% and 7% of the dose was excreted in urine and faeces during 72 h, respectively.3. Metabolites isolated from the urine after administration of d-limonene were p-mentha-1,8-dien-10-ol, p-menth-1-ene-8,9-diol, perillic acid, perillic acid 8,9-diol, p-mentha-1,8-dien-10-yl-β-D-glucopyranosiduronic acid and 8-hydroxy-p-menth-1-en-9-yl-β-D-glucopyranosiduronic acid.

Structure of Thujic Acid ('Dehydroperillic Acid')

'DEHYDROPERILLIC acid’ (C10H12O2) is an optically inactive acid which has been isolated from the heartwood of western red cedar (Thuja plicata). It possesses only a low fungicidal activity. Anderson and Sherrard1 attributed to this acid the structure I, which is closely related to that of perillic acid, mainly on account of its easy conversion to cuminic acid (II) with dilute hydrochloric acid.