Essential Oil Composition of Ligulate and Tubular Flowers and Receptacle from Wild Chamomilla recutita (L.) Rausch. Grown in Italy

Essential Oil Composition of Ligulate and Tubular Flowers and Receptacle from Wild Chamomilla recutita (L.) Rausch. Grown in Italy

Tirillini, Bruno

Abstract

The compounds of the oil from tubular and ligulate florets and from the receptacle of Chamomilla recutita (L.) Rausch. were analyzed by GC and GC/MS. The major compounds were (E)-β-farnesene (14.4-17.1%), spathulenol (4.4-12.6%), α-bisabolone oxide A (9.2-11.2%), chamazulene (8.4-13.7%), α-bisabolol oxide A (4.9-11.6%) and cis-en-yn-bicycloether (2.7-13.4%).

Key Word Index

Chamomilla recutita, Asteraceae, essential oil composition, (E)-β-farnesene, spathulenol, α-bisabolone oxide A, chamazulene, α-bisabolol oxide A, cis-en-yn-bicycloether.

Introduction

Chamomilla recutita (L.) Rausch. (syn. Matricaria chamomilla L.) is a perennial plant belonging to the Asteraceae family. Chamomile is traditionally used as a medicinal plant for their antiphlogistic and spasmolytic properties. Non-volatile (flavonoids) and certain volatile compounds [e.g.(-)-α-bisabolol, chamazulene, dicycloethers] are important for the pharmacological properties of the chamomile (1). Many studies refer to the composition of the essential oil of C. recutita; material collected in Poland (2), Indo-Gangetic plain (3), Estonia (4), Cuba (5), Slovenia (6), Hungary (7), Greece (8), Bulgaria (9), Italy (10-11), Brazil (12), Turkey (13), and in the former Soviet Union (14) have been investigated previously. Studies of Das et al. (3), Pekic et al. (15), and Papazoglou et al.(8) distinguished between the oils from ligulate and tubular flowers; De Pasquale et al. (11) also took into account the oil from the receptacle.

The aim of this paper was to determine the composition of the essential oils from tubular and ligulate florets and from the receptacle of C. recutita growing wild in Italy.

Experimental

Plant material: Chamomilla recutita (L.) Rausch. was collected during their flowering period in June 2003. The plants were collected near Urbino (Italy). The variety was estimated according to the morphological description in Flora Europaea (16). Voucher specimens were deposited in the Institute of Botany, University of Urbino under acquisition No C.R.6/2003.

Oil isolation: Tubular and ligulate florets and receptacle were separated by air-dried flower head. Material was subjected to hydrodistillation using a Clevenger-type apparatus for 3 h. The oils were dried over anhydrous sodium sulfate and stored in sealed vials under refrigeration prior to analysis.

GC and GC/MS: The GC analyses were carried out using a Hewlett-Packard 5890 Series II dual FID instrument equipped with two capillary columns: HP-WAX and HP-5 (30 m x 0.25 mm, 0.25 µm film thickness), working with the following temperature program: 60°-220°C at a rate of 3°C/min; injector and detector temperatures, 250°C; carrier gas, helium (1 mL/min); split ratio, 1:20.

GC/MS analyses were carried out using a Hewlett-Packard 6890-5973 GC/MS system operating in the EI mode at 70 eV, using the above described capillary columns. The temperature program for HP Innowax was 60°-260°C at a rate of 3°C/min and for the HP-5 it was 60°-300°C at a rate of 3°C/min. Injector and transfer line temperatures 220°C and 280°C, respectively. Helium was used as the carrier gas, flow rate 1 mL/min. Split ratio, 1:10.

The identification of the compounds was performed, for both the columns, by comparison of their retention times with respect to n-paraffins (C6-C22) internal standards; the mass spectra and retention indices were comparated with those of commercial (NIST 98 and WILEY) and homemade library mass spectra built up from pure compounds and MS literature data (17-22). Area percent was obtained electronically from the GC-FID response without the use of an internal standard or correction factors.

Results and Discussion

The hydrodistillation of flower head parts gave blue oils with a yield of 0.95% (from the tubular florets), 0.70% (from the ligulate florets), and 0.75% (from the receptacle) on dry weight basis. The composition of the oils is given in Table I; the compounds were listed in order of their elution from a HP-5 column.

Seventy-seven compounds were identified in the oil of the tubular florets, representing 99.1% of the oil. The oil was characterized by the four main constituents: (E)-β-farnesene (17.1%), spathulenol (11.3%), α-bisabolone oxide A (11.2%) and chamazulene (8.4%). The oxygenated sesquiterpenoid fraction had the highest contribution (42.0%). This fraction was dominated by spathulenol (11.3%) and α-bisabolone oxide A (11.2%). The sesquiterpene hydrocarbons represented 40.1% of the total oil, (E)-β-farnesene (17.1%) being the major compound. The oxygenated monoterpenes was relatively poor; it represented 8.3% of the total oil with artemisiaketone (2.1%) being the major constituent of this fraction. The ether fraction represented 2.8% of the total oil with cis-en-yn-bicycloether (2.7%) being the major compound; monoterpene hydrocarbons constituted only 0.4%.

Seventy-seven compounds were identified in the oil of the ligulate florets, representing 99.2% of the oil. The oil was characterized by the five main constituents: (E)-p-farnesene (14.4%), cis-en-yn-bicycloether (13.4%), chamazulene (10.5%), α-bisabolone oxide A ( 10.5%) and cc-bisabolol oxide-A (10.1%). The sesquiterpene hydrocarbons fraction had the highest contribution (40.7%). This fraction was dominated by (E)-β-farnesene ( 14.4%). The oxygenated sesquiterpenoid represented 28.3% of the total oil, α-bisabolone oxide-A (10.5%) and α-bisabolol oxide-A (10.1%) being the major compound. The ether fraction represented 13.7% of the total oil with cis-en-yn-bicycloether (13.4%) beingthe major compound. The oxygenated monoterpenes were relatively poor; it represented 5.7% of the total oil with artemisia ketone (1.3%) being the major constituent of this fraction. Monoterpene hydrocarbons constituted only 0.5%.

Seventy-two compounds were identified in the oil of the receptacle, representing99.2% of the oil. The oil was characterized by the four main constituents: (E)-β-farnesene (15.9%), chamazulene (13.7%), spathulenol (12.6%) and α-bisabolol oxide A (11.6%). The oxygenated sesquiterpenoid fraction had the highest contribution (44.9%). This fraction was dominated by spathulenol (12.6%). The sesquiterpene hydrocarbons represented 35.7% of the total oil, (E)-β-farnesene (15.9%) being the major compound. The oxygenated monoterpenes fraction was relatively poor; it represented 6.9% of the total oil with artemisia ketone (1.4%) being the major constituent of this fraction. The ether fraction represented 6.5% of the total oil with cis-en-yn-bicycloether(6.4%) beingthe major compound. Monoterpene hydrocarbons constituted only 0.4%.

Regarding the principal compounds found in previously analyzed specimens of C, recutita from Italy (11), some differences were noteworthy: the oil from the receptacle was characterized by bicycloether, farnesene, borneol and bisabolol oxide A; these compounds were more abundant than in the ligulate and tubular flowers; α-bisabolol, farnesol, and bisabolol oxide B were more abundant in the tubular flowers while thujone was more abundant in ligulate flowers. The oils from Indo-Gangetic plains (3) were characterizated by α-bisabolone oxide A, (20.4% and 8.9%), α-bisabolol (16.8% and 0.2%), and α-bisabolol oxide B (13.6% and 8.6%) in tubular flowers and ligulate flowers, respectively.

The oils from the former Yugoslavia (15) were characterized by α-bisabolol (34.2% and 21.3%), α-bisabolol oxide A (24.4% and 18.3%) and α-bisabolol oxide B (17.8% and 13.2%) in tubular flowers and ligulate flowers, respectively.

These studies on the oil composition from tubular and ligulate florets and from receptacle of C. recutita suggested that a receptacle could have its own secreting glandular system, and indeed some compounds [such as benzyl propanoate, (E)-2-decenal, and guaia-3,10(14)-dien-11-ol] were notpresent in oil from tubular and ligulate florets and the other compounds, also present in tubular and ligulate florets, have a different quantitative pattern.

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Bruno Tirillini*

Istituto di Botanica, Univ. di Urbino, Via Bramante 28, I-61029 Urbino, Italy

Rita Pagiotti and Luigi Menghini

Dipartimento di Biologia Vegetale, Univ. di Chieti-Perugia, Borgo XX Giugno, I-06100 Perugia, Italy

Giorgio Pintore

Dipartimento Fannaco-Chimico-Tossicologico, Univ. di Sassari, Via Muroni 23, I-07100 Sassari, Italy

* Address for correspondence

Received: October 2003

Revised: December 2003

Accepted: February 2004

Copyright Allured Publishing Corporation Jan/Feb 2006

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