Chemical studies of essential oils of Juniperus oxycedrus ssp. badia

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Abstract

Leaf and (unripe and ripe) berry essential oils of Juniperus oxycedrus ssp. badia (H. Gay) Debeaux grown wild in Spain have been analysed by capillary GC and GC-MS in combination with retention indices. A seasonal investigation of both leaf and berry oils was also performed. Among the approximately 80 constituents investigated (representing 90–98% of the oils) 60–68 were identified (80–97% of the oil composition). The leaf oils were mainly composed of α-pinene (40–57%) and manoyl oxide (5–10%). The (unripe) berry oils were dominated by α-pinene (65%) with moderate amounts of myrcene, limonene, germacrene D or γ-muurolene. Several differences in yields and chemical composition from a qualitative and quantitative point of view were detected when comparing all the oil samples analysed. In addition, two oil samples were examined, but found inactive, against the replication of HIV-1(IIIB) and HIV-2(ROD) in cell culture, whereas the samples were toxic for the cells at a 50% cytotoxic concentration of 106 and 123 μg/ml, respectively.

Introduction

Juniperus oxycedrus L. (Cupressaceae) is one of the ten species which comprise the section Juniperus (=Oxycedrus) of the genus Juniperus throughout the world (Adams, 1998). This shrub or tree has a typical Mediterranean distribution (Amaral Franco, 1964) and three subspecies have been recognized in the Iberian Peninsula: ssp. oxycedrus, ssp. macrocarpa (Sibth. & Sm.) Ball and ssp. badia (H. Gay) Debeaux, the first one being the most abundant (Amaral Franco, 1986).

The main use of J. oxycedrus is to prepare the so-called oil of cade (also known in pharmacy as juniper tar) by destructive distillation of the branches and wood of the plant. This empyreumatic oil has been widely employed in human and veterinary dermatology to treat chronic eczema and other skin diseases (Bouhlal et al., 1988) and rectified cade oil is used as a fragrance component in soaps, detergents, creams, lotions and perfumes (Leung and Foster, 1996). Decoctions of the plant are also used in traditional medicine in the mountainous area of the Sierra de la Pandera (Jaén, Spain) as a mouth analgesic and for stomach disorders (Fernández et al., 1996).

In regard to pharmacology or biological activities, cade oil has been reported to have keratolytic and antipruritic properties, and antimicrobial activities in vitro (Leung and Foster, 1996). Methanol and dichloromethane extracts of leaves and stems of J. oxycedrus ssp. oxycedrus (from Spain) have been found to reduce the blood pressure of normotensive rats (Bello et al., 1997), to inhibit the response to histamine, serotonin and acetylcholine (Moreno et al., 1997), and to exhibit significant anti-inflammatory activity (Moreno et al., 1998). Several extracts of leaves, resins, barks and fruits of J. oxycedrus ssp. oxycedrus (from Turkey) were found to inhibit the growth of several bacteria, but did not show antifungal effects (Digrak et al., 1999). However, the essential oil of the heartwood of the same subspecies (from Italy) did show activity against gram-positive bacteria and most of the screened blastomycetes (Bonsignore et al., 1990). Besides, essential oils from leaves and berries of J. oxycedrus ssp. oxycedrus and J. oxycedrus ssp. macrocarpa (from Greece) exhibited activity against several microorganisms (Stassi et al., 1996).

From a chemical viewpoint J. oxycedrus ssp. have been the subject of considerable work on both non-volatile (Barrero et al., 1987) and volatile compounds (Adams, 1998, Barrero et al., 1993). However, little is known about the rest of the subspecies with the exception of a recent study on chemotaxonomy based on analysis of the terpenoids from leaf oils obtained from Greek and Spanish trees (Adams et al., 1999). This work has cleared up the sometimes controversial recognition of badia subspecies, as these trees have been frequently catalogued as large specimens of J. oxycedrus ssp. oxycedrus.

The almost absence of phytochemical studies of this taxon and the previous use of the plant makes it of interest to look for seasonal differences of the metabolite profiles. In addition, the existence of antiviral agents based on pinenes (Imai et al., 1996) prompted us to evaluate the inhibitory activity of this pinene-rich essential oil against the cytopathic effects of HIV-1-(IIIB) and HIV-2-(ROD) in cell culture.

Section snippets

Plant material

The leaf and berry samples of J. oxycedrus ssp. badia were collected in January, May and September 1998 from a female tree growing wild on the Sierra de la Pandera in the province of Jaén (Spain) at an altitude of 850 m. The leaf samples consisted in several branchlets collected from each ordinal direction of the tree. The berry samples were formed by green unripe fruits (B-1, B-2, B-3a) and red-brown mature fruits (B-3b) (Table 1). Voucher specimens were deposited at the JAEN herbarium

Results and discussion

The yield of the leaf essential oil obtained from a single female tree of J. oxycedrus ssp. badia (H. Gay) Debeaux was lower (0.27%) than the one of berries’ essential oil (1.14%). The chemical composition of both essential oils prepared from plant material collected in winter is summarized in Table 1, where the constituents are listed in order of their elution from a SE-54 type-phase capillary column and their identification has been carried out by means of GC and GC-MS analyses in combination

Acknowledgments

We wish to thank Dr Carlos Fernández and Dr Robert P. Adams for the identification of the plant material and the Junta de Andalucı́a (Spain) for financial support. This work was partially supported by the Flemish Fonds voor Wetenschappelijk Onderzoek (FWO Grant G.0104.98) and the Belgian Geconcerteerde Onderzoeksacties (GOA 00/12). We also thank ISEP/FORTIS for financial support, and Kristien Erven for excellent technical assistance with the anti-HIV assays.

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