Analysis of Helichrysum oligocephalum DC. essential oil

Document Type : Original paper


Department of Pharmacognosy and Isfahan Pharmaceutical Sciences Research Center, School of Pharmacy, Isfahan University of Medical Sciences, Hezar Jarib Avenue, Isfahan, Iran.


Background and objectives: Helichrysum oligocephalum DC. (Compositae)  is an endemic plant in Iran that has been recommended by Iranian traditional and folk medicine practitioners for gastrointestinal complaints. The plant is rich in essential oil and in the present investigation, the volatile composition of the species has been determined. Methods: The light yellow essential oil from the aerial parts of the plant was prepared according to the method which was recommended in British Pharmacopoeia by using hydrodistillation. The chemical composition of the oil was investigated by gas chromatography mass spectroscopy (GC/MS). Results: Thirty-seven compounds were identified; among them β-caryophyllene, α-humulene and epimanoyl oxide were dominant. Sesquiterpenoids were the most dominant compounds in the essential oil while monoterpenoides, fatty acids and diterpenoides were found to be less. These outcomes are a little bit different from what has been reported before. Conclusion: The differences between the results of the present study with previous works could be due to the diversity of variety, polymorphism, stage of plant growth and environmental factors.


[1]  Judd WS, Campbell CS, Kellogy EA, Stevens PF, Donoghue MJ. Plant systematics: a phylogenic approach. 2nd ed. Sunderland: Sinauer Association Inc, 2002.
[2]  Pankhurst R, Tlyam R. Plant and their names: A Concise Dictionary. Edinburgh: Oxford University Press, 1995.
[3]  Suntar I, Keles H, Yesilada E, Sarker SD. Exploration of the wound healing potential of Helichrysum graveolens (Bieb) Sweet: Isolation of apigenin as an active component. J Ethnopharmacol. 2013; 49: 103-110.
[4]  Mozaffarian V. Dictionary of Iranian plant names. Tehran: Farhang Moaser Publishers, 1996.
[5]  Ghahreman A. Iranian choromophites (Botanical systematic). Tehran: Iran University Press, 1994.
[6]  Lourens AC, Viljoen AM, van Heerden FR. South African Helichrysum species: A review of the traditional uses, biological activity and phytochemistry. J Ethnopharmacol. 2008; 119(3): 630-652.
[7]  Al-Rehaily AJ, Albishi OA, El-Olemy MM, Mossa JS. Flavonoids and terpenoids from Helichrysum forskahlii. Phytochemistry. 2008; 69(9): 1910-1914.
[8]   Süzgeç S, Meriçli AH, Houghton PJ, Çubukçu B.  Flavonoids of Helichrysum compactum and their antioxidant and antibacterial activity. Fitoterapia. 2005; 76(2): 269-272.
[9]  Lourens AC, Reddy D, Başer KH, Viljoen AM, Van Vuuren SF. In vitro biological activity and essential oil composition of four indigenous South African Helichrysum species. J Ethnopharmacol. 2004; 95 (2-3): 253-258.
[10]  Satta M, Tuberoso CIG, Angioni A, Pirisi FM, Cabras P. Analysis of the essential oil of Helichrysum italicum G. Don. ssp. microphyllum (Willd) Nym. J Essent Oil Res. 1999; 11(4): 711-715.
[11]  Antunes Viegas D, Palmeira-de-Oliveira A, Salgueiro L, Martinez-de-Oliveira J, Palmeira-de-Oliveira R. Helichrysum italicum: From traditional use to scientific data. J Ethnopharmacol. 2014; 151(1): 54-65.
[12]  Oji KA, Shafaghat A. Constituents and antimicrobial activity of the essential oil from leaf and stem of Helichrysum armenium. Nat Prod Commun. 2012; 7(5): 671-674.
[13]  Bougatsos C, Ngassapa O, Runyaro DK, Chinou IB. Chemical composition and in vitro antimicrobial activity of the essential oil of two Helichrysum species from Tanzania. Z Naturforsch C. 2004; 59(5-6): 368-372.
[14]  Bigovic D, Savikin K, Jankovic T, Menkovic N, Zdunic G, Stanokovic T, Djuric Z. Antiradical and cytotoxic activity of different Helichrysum plicatum flower extracts. Nat Prod Commun. 2011; 6(6): 819-822.
[15]  Legoalea PB, Mashimbyeb MJ, Van Rec T. Antiinflammatory and antioxidant flavonoides from Helichrysum kraussii and H. odoratissimum flower. Nat Prod Commun. 2013; 8(10): 1403-1404.
[16]  Bougatsos C, Meyer JJM, Magitatis P, Vagias C, Chinou JB. Composition and antimicrobial activity of essential oil of Helichrysum Kraussii and Helichrysum rugulosum Less from South Africa. Flavour Frag J. 2003; 18: 45-51.
[17]  Baser KHC, Demirci B, Kirimer N. Compositions of essential oils of 4 Helichrysum species from Madagascar. J Essent Oil Res. 2002; 14: 53-55.
[18]  Formisano C, Mignola E, Rigano D, Senatore F, Arnold NA, Bruno M, Rosselli S. Constituents of leaves and flowers essential oils of Helichrysum pallassi (Spreng.) Ledeb Growing wild in Lebanon. J Med Food. 2009; 12(1): 203-207.
[19]  Zanetsie Kakam AM, Franke K, Ndom JM, Dongo E, Mpondo TN, Wessjohann LA. Secondary metabolites from Helichrysum foetidum and their chemotaxonomic significance. Biochem Syst Ecol. 2011; 39: 166-167.
[20]  Drewes SE, Mudau KE, van Vuuren SF, Viljoen AM. Antimicrobial monomeric and dimeric diterpenes from the leaves of Helichrysum tenax var tenax. Phytochemistry. 2006; 67(7): 716-722.
[21]  Mezzetti T, Orzalesi G, Rossi C, Bellavita V. A new triterpenoid lactone, alpha-amyrin and uvaol from Helichrysum italicum. Planta Med. 1970; 18(4): 326-331.
[22]  Jakupovic J, Zedro C, Grenz M, Tsichritzis F, Lehmann L, Hasheminejad SM, Bohlman F. Twenty-one acyclophlorglucinal and further constituents from South African Helichrysum species. Phytochemistry. 1989; 28: 119-131.
[23]  Bianchini A, Santoni F, Paolini J, Bernardini AF, Mouillot D, Costa J. Partitioning the relative contributions of inorganic plant composition and soil characteristics to the quality of  Helichrysum italicum subsp. italicum (Roth) G. Don fil. essential oil. Chem Biodivers. 2009; 6(7): 1014-1033.
[24]  Ghahreman A. Flora of Iran. Tehran: The Publication of Research Institute of Forests and Rangelands, 1992.
[25]  British Pharmacopoeia. London: HMSO Publication, 1988.
[26]  Adams RP. Identification of essential oil components by gas chromatography/mass spectroscopy. Illinois: Allured Publishing Corporation, 1995.
[27]  Swigar AA, Silverstein RM. Monoterpenes: infrared, mass, 1H-NMR, 13C-NMR spectra and kovats indices. Wisconsin: Aldrich Chemical Company, 1981.
[28]  Esmeili A. Biological activity and chemical composition of the stems and roots of Helichrysum oligocephalum DC. growing in Iran. Pak J Pharm Sci. 2013; 26(3): 599-604.
[29]  Sajjadi SE, Jafari A, Naderian M. Chemical composition of the essential oil of Helichrysum oligocephalum. Chem Nat Compd. 2009; 45(2): 269-271.
[30]  Roussis V, Tsoukatou M, Petrakis PV, Chinou I, Skoula M, Harborne JB. Volatile constituents of four Helichrysum species growing in Greece. Biochem Syst Ecol. 2000; 28(2):  163-175.
[31]  Cavalli JF, Ranarivelo L, Ratsimbason M, Bernardini AF, Casanova J. Constituents of the essential oil of six Helichrysum species from Madagascar. Flavour Frag J. 2001; 16(4): 253–256.
[32]  Rogerio AP, Andrade EL, Leite DFP, Figueiredo CP, Calixto JB. Preventive and therapeutic anti-inflammatory properties of the sesquiterpene α-humulene in experimental airways allergic inflammation. Brit J Pharmacol. 2009; 158: 1074–1087.
[33]  El Hadri A, Gomez Del Rio M, Sanz J, Coloma A, Idaomar M, Ozanas B. Cytotoxic activity of α-humulene and transcaryo-phyllene from Salvia officinalis in animal and human tumor cells. An R Acad Nac Farm. 2010; 76: 343-356.
[34]  Al Mansouri S, Ojha S, Al Maamari E, Al Ameri M, Nurulain SM, Bahi A. The cannabinoid receptor-2 agonist, β-caryophyllene, reduced voluntary alcohol intake and attenuated ethanol-induced place preference and sensitivity in mice. Pharmacol Biochem Be. 2014; 124: 260-268.
[35]  Paula-Freire LI, Andersen ML, Gama VS, Molska GR, Carlini EL. The oral administration of trans-caryophyllene attenuates acute and chronic pain in mice. Phytomedicine. 2014; 21(3): 356-362.
[36]  Bahi A, Al Mansouri S, Al Memari E, Al Ameri M, Nurulain SM, Ojha S. β-caryophyllene, a CB2 receptor agonist produces multiple behavioral changes relevant to anxiety and depression in mice. Physiol Behav. 2014; 135:119-124.
[37]  Chavan MJ, Wakte PS, Shinde DB. Analgesic and anti-inflammatory activity of caryophyllene oxide from Annona squamosa L. bark. Phytomedicine. 2010; 17(2):149-151.
[38]  Alcaraz MJ, Jimenez MJ, Valverde S, Sanz J, Rabanal RM, Villar A. Anti-inflammatory compounds from Sideritis javalambrensis n-hexane extract. J Nat Prod. 1989; 52(5): 1088-1091.
[39]  Minaiyan M, Ghassemi-Dehkordi N, Mahzouni P, Ahmadi N. Anti-inflammatory effect of Helichrysum oligocephalum DC. extract on acetic acid-induced acute colitis in rat. Adv Biomed Res. 2014; 3: 87.