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Essential Oil of Nigella Damascena L.
(Ranunculaceae) Seeds
ARTICLE in JOURNAL OF ESSENTIAL OIL RESEARCH · JANUARY 2003
Impact Factor: 0.79 · DOI: 10.1080/10412905.2003.9712267

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Ammar Bader

Guido Flamini

Umm Al-Qura University

Università di Pisa

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25 µm) and a Varian Saturn 2000 ion trap mass detector. Essent. Experimental Plant material: N.. Oil isolation: The natural and commercial seeds (respectively 50 g and 100 g) were powdered and then submitted to hydrodistillation in a Clevenger-type apparatus for 3 h. seeds. via Bonanno 33. essential oil composition. (5) purified and identified the sesquiterpene hydrocarbons β-elemene and α-selinene. similar to those of N.3%) and nine monoterpenes in trace amounts. The alkaloids were damascenine and methyl 2-amino3-methoxy benzoate.. the latter being detected for the first time in this species. Italy Abstract The chemical composition of the essential oil of Nigella damascena L. are black and minute and.* Pier Luigi Cioni and Ivano Morelli Dipartimento di Chimica Bioorganica e Biofarmacia. The literature reports the diuretic effect of N. Identification of the constituents was based on comparison of the retention times with those of authentic samples and on computer matching against commercial (Nist 98 and ADAMS) and home-made library mass spectra built up from pure substances and components of known oils and MS literature data (6-9). Twenty-eight compounds were identified in wild seeds by GC/MS: 10 sesquiterpene hydrocarbons (93. The commercial seeds were purchased from Ingegnoli. Introduction Nigella damascena L.2 µl (10% hexane solution). is an herbaceous annual plant growing in grasslands. Twenty-six compounds were identified in commercial seeds by GC/MS: 15 sesquiterpene hydrocarbons (90.3%) and three monoterpenes in trace amounts. Moreover. germacrene A. coating thickness 0. β-elemene. (Ranunculaceae) Seeds Gelsomina Fico. GC/MS: GC/EIMS analyses were performed with a Varian CP-3800 gas chromatograph equipped with a DB-5 capillary column (30 m x 0. Ranunculaceae. damascena seeds stimulated our interest in studying their oil. J. Tillequin et al.00/0—© 2003 Allured Publishing Corp. operating in the same conditions described for GC/EIMS analyses. respectively. 56-57 (January/February 2003) Essential Oil of Nigella damascena L. two alkaloids (0. Oil Res. Università di Pisa. carrier gas helium at 1 µL/min. From the hexane extract of the grounded seeds. they are used in gastronomy in Asian cultures. The seeds of this plant. Guido Flamini. often in trace amounts.8%). two alkaloids (3. damascena seeds (2). 56/Journal of Essential Oil Research Accepted: February 2001 Vol. collected from fruiting plants in their natural habitat. in Arnaccio (Pisa. sativa L.4%). The main constituents of wild plants were germacrene A and βReceived: November 2000 *Address for correspondence Revised: January 2001 1041-2905/03/0056-0057$6. A voucher specimen was deposited in the Dipartimento di Chimica Bioorganica e Biofarmacia. The characteristic odor and taste of N. Analytical conditions: injector and transfer line temperatures 220°C and 240°C.et al. 56126 Pisa. Key Words Index Nigella damascena. A previous paper about the composition of seed oil described only the presence of the alkaloid damascenine and suggested the presence of sesquiterpenes (4). University of Pisa. and the popular medicine suggests the decoction to regularize and give rise to menstruation (3). while monoterpenes were scarcely represented. was examined in comparison with commercial seeds. damascena seeds were collected in the first week of August 1999.25 mm. because of their characteristic strawberry flavor. oven temperature programmed from 60°-240°C at 3°C/min. Milano (Italy). Ammar Bader. Italy) at 20 m above the sea level. Flamini 15. 15. January/February 2003 . in temperate zones in Europe (1). and here we report the oil composition of natural and commercial seeds. alkaloids. all the molecular weights of the identified substances were confirmed by GC/CIMS using MeOH as CI reagent gas. split ratio 1:30. Results and Discussion The results presented in Table I show that both the samples contained mainly sesquiterpenes. injection of 0.

5%).8 0.1 - 0.3 0. D.6% and 49. Jennings and T. Wiley & Sons. and (Z)-9-octadecen-1-ol (2.8-cineole.6 0. Flora Europea.1 1. camphor and pulegone. It is known (10) that methinionine methylate mostly the nitrogen atom than the oxygen or the carboxylic group of anthranilic acid..4%).1%). β-pinene.W.1%) 9. Stenhagen. N.1 3. 145146. Berlin (1980). Paris. Walters and D.4%.H.M. E. Paris. (1964). limonene.4 0. γ-terpinene. Other important compounds were viridiflorene (9.W. New York (1976). 141-150 (1993). Composition of the essential oils of Nigella damascena seeds Compound α-pinene β-pinene myrcene 2-pentylfuran p-cymene limonene 1. 6. Burges.8-cineole γ-terpinene camphor pulegone α-copaene β-bourbonene β-elemene β-caryophyllene β-gurjunene β-cadinene γ-gurjunene germacrene D β-selinene valencene α-selinene viridiflorene germacrene A 7-epi-α-selinene methyl 2-amino-3methoxyl benzoate damascenine spathulenol (Z)-9-octadecen-1-ol yield% Wild plants Commercial plants 941 984 992 993 1030 1035 1039 1064 1154 1243 1377 1384 1390 1420 1430 1462 1476 1481 1489 1493 1495 1496 1506 1520 ta t t 0. 7-epi-αselinene (3. respectively). The monoterpenes were α-pinene and limonene.1 0. Commercial seeds contained a higher concentration of damascenine (3. D.6 3. Int. Monoterpenes in trace amounts were α-pinene.5%).1%). Rivista Italiana E. Tillequin. Recherche de principes odorants des graines de Nigelle de Damas. A further seven sesquiterpenes were detected. S. V. 30. Bekemeier.27 0. In: Secondary Plant Products.P. 4. Davies. Abrahamsson and F.4 1. 168. Gröger.A. Academic Press. 61. M. Unger.G. 8. Journal of Essential Oil Research/57 .13 RI at = trace (<0.S. 59-61 (1976). Valentine. Charlwood.5 23.3 52. Chromatogr. References 1. F. Tutin.1 0..7% and 38. Qualitative Analysis of Flavor and Fragrance Volatiles by Glass Capillary Chromatography. p 209.V.P. T. N. G.5 1549 1569 1578 1805 0. Y.0 49. 503. 64.4 0. Carbures sesquiterpeniques des graines de Nigella damascena. H. Analysis of Essential Oils by Gas Chromatography and Mass Spectrometry.1 2. 15.4 0. J.7 0.4 9. 1. J. Vol. Arch. Heywood. Clair and J. 3.6 0.1 0. January/February 2003 Table I. Both the oils contained the alkaloids damascenine and methyl 2-amino-3-methoxy benzoate. Shmollack. Planta Med. 10. but in this case the latter was the main component (23.6 0. Gas Chromatographic retention indexes of monoterpenes and sesquiterpenes on methyl silicone and Carbowax 20M phases. Wiley & Sons. Edits.2%) than those from wild plants (0. J.A. p. myrcene.1 t t t t 0. 1-24 (1990). W. Webb. but in very low amounts (less than 1%). New York (1974). Lecompte and M. E. Antipyretische. New York (1980). 5. Registry of Mass spectral data. Alkaloids derived from tryptophan and anthranilic acid. antioedematose und analgetische wirkung von damascenin im vergleich mit acetylsalicylsaure und phenylbutazon. The commercial seed oil also contained germacrene A and β-elemene as main constituents. 2. p-cymene. Bell and B.Nigella damascena elemene (52. Springer-Verlag.6 0. M. S. 199-211 (1967). Leuschner and W.A. The compound methyl 2amino-3-methoxy benzoate has been never previously identified in this species. Massada.1 t t t 0. 225-227 (1979). Shibamoto. Le piante di uso officinale nella Barbagia di Seui (Sardegna Centrale) Fitoterapia.O. respectively) followed by βcaryophyllene (1... G. Fresu. McLafferty. Ballero and I.2 0. Cambridge University Press: Cambridge.6%.2 0. 7.1 0. Pharmacodyn. C.1 38. Consequently the latter alkaloid should be a metabolic product of damascenine.4 0.H.