Volatile Constituents of Ridolfia segetum (L.) Moris Gathered in Central Spain: Castilla la Mancha Province

Journal of Essential Oil Research: JEOR, Mar/Apr 2005 by Palá-Paúl, Jesús, Velasco-Negueruela, Arturo, Pérez-Alonso, Ma José, Vallejo, María Concepción García

Abstract

The oils isolated from the aerial parts of Ridolfia segetum (L.) Moris (Apiaceae) gathered in Castilla la Mancha (Spain) were analyzed by capillary GC and GC/MS. The oil from the flowers was dominated by a-phellandrene (32.0-33.8%), terpinolene (18.0-21.4%) and (Z)-β-ocimene (12.4-14.5%), while the main components of the fruit oils were found to be dillapiole (5.1-39.6%), β-pinene (10.3-20.9%), α-pinene (3.0-16.1%), α-phellandrene (13.7-15.3%) and (Z)-β-ocimene (8.1-12.8%). The oil from the stems was characterized by a high content of p-cymene (15.1-79.5%), (Z)-β-ocimene(0.9-38.5%) and α-phellandrene (1.1-14.4%), whereas the oil from the leaves was shown to contain p-cymene (8.8-83.6%), (Z)-β-ocimene (t-32.6%), myrcene (t-12.5%) and β-pinene (2.1-12.1%) as major constituents.

Key Word Index

Ridolfia segetum, Apiaceae, essential oil composition, α-pinene, β-pinene, myrcene, α-phellandrene, p-cymene, (Z)-β-ocimene, terpinolene, dillapiole.

Introduction

Ridolfiasegetum(L.) Moris belongstothe Apiaceae family and grows wild throughout Europe. In Spain it inhabits the southern part, especially in Andaluciaprovince, but it also appears in Castilla la Mancha and Extremadura provinces of central Spain (1).

A survey of the literature reveals that the oil composition of R. segetum has been previously studied. The oil from the flowers of R. segetum collected in The Holy Land and the Sinai (2) was found to contain α-phellandrene (44.1-48.9%), piperitenone oxide (8.3-18.0%) and terpinolene (11.8-16.3%), whereas that from its leaves had as main constituents α-phellandrene (29.8-37.1%), piperitenone oxide (8.2-14.2%) and p-cymene (8.4-15.2%). In earlier studies, the oil of the fruits of R. segetum from Morocco (3,4) was found to be rich in α-phellandrene (55.0%) and myristicin (33.0%).

As a part of our work on Apiaceae family, we have also studied the oils of this species before (5). The oils of R. segetum gathered in Andalucia province showed that the oil from the steins was characterized by α-phellandrene (39.4-62.0%), p-cymene (10.4-22.7%), (Z)-β-ocimene (10.2-11.7%) and terpinolene (7.0-15.6%) whereas the oil from the leaves contained α-phellandrene (61.8%-69.5%), (Z)-β-ocimene (10.7-12.0%) and terpinolene (6.0-10.7%) as major constituents. The oil from the flowers was also dominated by α-phellandrene (44.5-54.7%), (Z)-β-ocimene (8.5-10.6%) and terpinolene (20.1-27.6%), while the fruit oils were characterized by β-pinene (1.5-11.9%), α-phellandrene (5.2-56.9%), p-cymene (4.2-25.2%), β-phellandrene (0.9-15.6%), terpinolene (4.3-12.5%) and dillapiole (0.1-45.7%).

In the present work, we report on the chemical composition of the oils of R. segetum gathered in Castilla la Mancha province and we compare their composition with that of the oils isolated from this species gathered by us in Andalucia province also in Spain (5).

Experimental

Plant material: Fresh leaves, stems, flowers and fruits of R. segetum were collected from the species growing on two localities (Table I) from Castilla la Mancha province in Spain. Voucher specimens were deposited at the Herbarium of the Faculty of Biology, Complutense University, Madrid, Spain.

Analysis: Plant material was hydrodistilled in an all glass apparatus according to the method recommended in the Spanish Pharmacopoeia (6). The oils were dried over anhydrous sodium sulfate and stored at 4°C in the dark. The yields based on dry weight of samples are shown in Table I.

GC: This was carried out on a Varian 3300 gas chromatograph fitted with a fused methyl silicone DB-1 column (50 m x 0.25 mm, 0.25 µm film thickness). Temperature was programmed from 95°-240°C at 4°C/min. Injection was performed at 250°C in the split mode. A flow of 1.5 mL/min carrier gas (N^sub 2^). Detection was performed by FID. Injection volume for all samples was 0.1 µL.

GC/MS analyses: These were carried out in a Hewlet Packard 5890 gas chromatograph fitted with a fused Silica SE-30 capillary column (25 m x 0.22 mm, 0.25 µm film thickness), coupled to an HP5971A mass selective detector. Column temperature was programmed from 70°-220°C at 4°C/min, and helium was used as carrier gas. Mass spectra were recorded in the scan mode at 70 eV.

Qualitative analyses: Most constituents were tentatively identified by GC by comparison of their retention indices with those of authentic standards available in the author's laboratory or with retention indices in close agreement with references (7-11). Further identification was achieved by GC/MS. Other constituents were either synthesised or identified in oils of known composition. The fragmentation patterns of mass spectra were compared with those stored in the spectrometer data base using the NBS54K.L and Wiley.L built in libraries and with those published in the literature (7-12).

Results and Discussion

The yields of the samples studied in the present work and their localities are shown in Table I. The stems were the part of the plant with a lower amount of oil (0.2-0.4 v/w) although the rest of the parts of the plant yielded more than 1 mL per sample (1.2-2.3 v/w). The samples from the Andalucia province (5) showed higher yields than the samples studied in the present work.