Chemical composition of the essential oil of Stachys byzanthin C. Koch. from Iran

Journal of Essential Oil Research: JEOR, Mar/Apr 2003 by Khanavi, Mahnaz, Hadjiakhoondi, Abbas, Shafiee, Abbas, Masoudi, Shiva, Rustaiyan, Abdolhosein

Abstract

The chemical composition of the oil obtained by hydrodistillation of the aerial parts of Stachys byzanthina C. Koch. was investigated by GC and GC/MS analysis. Twenty-four components representing 88.5% of the total oil were identified, of which sesquiterpenes-a-copaene (16.5%), spathulenol 16.1%), (beta)-caryophyllene (14.3%) and (beta)-- cubebene (12.6%)-were the major components.

Key Word Index

Stachys byzanthina, Lamiaceae, essential oil composition, (alpha)-copaene, spatulenol, (beta)-cubebene.

Plant Name

Stachys byzanthina C. Koch. (Lamiaceae) (1).

S. byzanthina was collected during the flowering period from Khalkhal, province of Azarbayjan-Sharghi, Iran in June 1999. A voucher specimen was deposited in the Herbarium of the Department of Pharmacognosy, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran (No. 6513).

Plant Part

Air-dried flowering aerial parts were subjected to hydrodistillation for 3 h using a Clevenger-type apparatus. After decanting and drying the oil on anhydrous sodium sulfate, the corresponding oil was isolated in a yield of 0.3%

Previous Work

The genus Stachys has been the subject of only a few studies that addressed either oils or extracts (2-7). The chemical composition of the oil of S. byzanthina has not yet been described, therefore we decided to examine this oil.

Present Work

The oil of the aerial part of S. byzanthina was analyzed by GC using an FID Packard 439 fitted with a 25 in x 0.25 mm, CP Sil 5CB column, film thickness 0.39 (mu)m, temperature programmed as follows: 60 deg-220 deg C at 5 deg C/min with N^sub 2^ as carrier gas (0.8 mL/min); injector and detector temperatures were 270 deg C.

GC/MS was carried out on a Varian 3700, with a CP Sil 5CB column 25 m x 0.25 mm, film thickness 0.39 (mu)m, combined with a Varian MAT 44S (70 eV), with temperature programmed as above with He as the carrier gas.

Component identifications were made by comparison of their mass spectra and retention indices (RI) with those of authentic samples (8,9). The identified constituents can be seen in Table 1.

Twenty-four components were detected in the oil of S. byzanthina, representing 88.5% of the total oil. The oil was characterized by large amounts of sesquiterpenes (81%), mostly hydrocarbons (54.9%), with alpha-copaene (16.5%), spathulenol (16.1%), beta-caryophyllene (14.3%) and beta-cubebene (12.6%) being the major constituents found. The monoterpene fraction was relatively small, representing only 1.7% of the total oil.

In addition, six aliphatic hydrocarbons (5.8%) were detected in the oil. Previous investigations on the oil of members of the Stachys genus showed varying compositions (10-13). For example, an oil of S. glutinosa from France was found to contain terpinen-4-ol (13.1%) (10). 1-Octen-3-ol (18.7%) and linalool (11.0%) were reported in the oil of S. athorecalyx (11). The oil of S. candida consisted of manoyl oxide (12.07%), caryophyllene oxide (11.5%) and beta-caryophyllene (9.58%) (12). Finally, the oil of S. obliqua contained germacrene D (25.4%) and thymol (16.4%) (13).

References

1. K.H. Rechinger, Stachys, In: Flora Iranica, Labiatae No. 150. Edits., K.H. Rechinger and LC. Hedge, Akademische Druck Veragsanstalt, Graz, Austria. p. 361 (1982).

2. B.M. Lawrence, J.W. Hogg, S.J. Terhune, J.K. Morton and L.S. Gill, Terpenoid composition of some Canadian Labiatae. Phytochemistry, 11, 2636-2638 (1972).

3. K. Takeda, J.B. Harborne and R. Self, Identification ol malonated anthocyanins in the Liliaceae and Labiatae. Phytochemistry, 25,2191-2192 (1986).

4. M.A. EI-Ansari, D. Barron, M.F. Abdalla, N.A.M. Saleh and J.L. Le Quere, Flavonoid constituents of Stachys aegyptiaca. Phytochemistry, 30,1169-1173 (1991).

5. F. Piozzi, G. Savona and J.R. Hanson, Kaurenoid diterpenes from Stachys lanata. Phytochemistry, 19, 1237-1238 (1980).

6. M. Adinolfi, G. Barone, R. Lanzetta, G. Laonigro, L. Mangoni and M. Parrilli, Diterpenes from Stachys recta. J. Nat. Prod., 47,541-543 (1984). 7. C. Fazio, S. Passannanti, M.P. Patemostro and F. Piozzi, Neo-clerodane

diterpenoids from Stachys rosea. Phytochemistry, 31,3147-3149 (1992). S. R.P. Adams, Identification of essential oil components by Gas chromatography/Mass spectroscopy. Allured Publ. Corp., Carol Stream, IL, USA (1995).

9. N.W. Davies, Gas Chromatographic retention indices of monoterpenes and sesquiterpenes on methyl silicone and Carbowax 20M Phases. J. Chromatogr., 503,1-24 (1990).

10. J.P. Mariotti, J. Costa, A. Bianchini, A.F. Bernardini and J. Casanova, Composition and variability of the essential oil of Stachys glutinosa L. from Corsica (France). Flav. Fragr. J., 12, 205-209 (1997).

11. M.E. Duru, A. Cakir, M. Harmander, S. Isumi and T. Hirata, The volatile constituents of Stachys athorecalyx C. Koch. from Turkey. Flav. Fragr. J., 14, 12-14 (1999).

12. H.D. Skaltsa, D.M. Lazari, LB. Chinou and A.E. LOW% Composition and antibacterial activity of the essential oils of Stachys candida and Stachys chrysantha from southern Greece. Planta Med., 65, 255-256 (1999).

 

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