ANGELICA SYLVESTRIS VAR. SYLVESTRIS L.: ESSENTIAL OILS AND ANTIOXIDANT ACTIVITY EVALUATION
Year 2020,
Volume: 21 Issue: 1, 39 - 48, 31.03.2020
Hale Gamze Ağalar
,
Fatih Göger
,
Betül Demirci
,
Prof.dr.hulusi Malyer
,
Neşe Kırımer
Abstract
In the present study, the volatile
compounds and antioxidant activities of A.
sylvestris var. sylvestris
belongs to the Apiaceae family were evaluated. The essential oils from roots,
leaves, flowers and fruits obtained by hydrodistillation were analyzed by Gas
Chromatography (GC) and Gas Chromatography-Mass Spectroscopy (GC-MS),
simultaneously. The volatile compounds were identified by using in-house and commercially libraries. The
possible antioxidant activities of each essential oil were determined at in vitro conditions and the results were
compared with positive controls.
References
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- [9] Sarker SD, Nahar L. Natural medicine: The genus Angelica. Curr Med Chem 2004; 11(11): 1479-1500.
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- [12] Seigler, DS. Coumarins. In: Plant Secondary Metabolism. Luwer Academic Publishers, Springer, Boston, MA, 1998. pp. 130-138.
- [13] Wang P, Su Z, Yuan W, Deng G, Li S. Phytochemical constituents and pharmacological activities of Eryngium L. (Apiaceae). Pharmaceut Crop 2012; 3: 99-120.
- [14] Zech JC. Flavonoid distribution of Mulinum (Apiaceae, Hydrocotyloideae, Mulineae). Brittonia 1999; 51(4): 415-421.
- [15] Shawky E, El Kheir, RM. Rapid discrimination of different Apiaceae species based on HPTLC fingerprints and targeted flavonoids determination using multivariate image analysis. Phytochem Anal 2017; 29: 452-462.
- [16] Drew DP, Krichau N, Reichwald K, Simonsen HT. Guaianolides in Apiaceae: perspectives on pharmacology and biosynthesis. Phytochem Rev 2009; 8: 581-599.
- [17] Andersen TB, Martinez-Swatson KA, Rasmussen SA, Boughton BA, Jorgensen K, Andersen-Ranberg J, Nyberg N, Christensen SB, Simonsen HT. Localization and in-vivo characterization of Thapsia garganica CYP76AE2 indicates a role in Thapsigargin biosynthesis. Plant Physiol 2017; 174: 56-72.
- [18] Iranshahi M, Rezaee R, Najafi MN, Haghbin A, Kasaian J. Cytotoxic activity of the genus Ferula (Apiaceae) and its bioactive constituents. Avicenna J Phytomed 2018; 8(4): 296-312.
- [19] Franz C, Novak J. Sources of Essential oils. In: Handbook of Essential oils: Science, Technology, and Applications (Eds KHC Başer & G Buchbauer), CRC Press, Boca Raton 2009. pp. 39-81.
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- [22] Sousa RMOF, Rosa JS, Oliveira L, Cunha A, Fernandes-Ferreira M. Activities of Apiaceae essential oils and volatile compounds on hatchability, development, reproduction and nutrition of Pseudaletia unipuncta (Lepidoptera: Noctuidae). Ind Crop Prod 2015; 63: 226-237.
- [23] Khoury M, El Beyrouthy M, Eparvier V, Ouaini N, Stien D. Chemical diversity and antimicrobial activity of the essential oils of four Apiaceae species growing wild in Lebanon. J Essent Oil Res 2018; 30(1): 25-31.
- [24] Lobiuc A, Zamfirache MM, Stratu A. Physiological aspects in two Angelica L. Taxa (Apiaceae). An Stiint Univ Al I Cuza Iasi Sect II a Biol veget 2012; 58(2): 81-87.
- [25] Baytop T. Türkiye’de Bitkilerle Tedavi, Geçmişte ve Bugün, 2. Baskı, İstanbul, Türkiye: Nobel Kitabevi, 1999. pp. 290-291.
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- [27] Vogl S, Picker P, Mihaly-Bison J, Fakhrudin N, Atanasov AG, Heiss EH, Wawrosch C, Reznicek G, Dirsch VM, Saukel J, Kopp B. Ethnopharmacological in vitro studies on Austria's folk medicine- an unexplored lore in vitro anti-inflammatory activities of 71 Austrian traditional herbal drugs. J Ethnopharmacol 2013; 149(3): 750-771.
- [28] Muckensturm B, Duplay D, Robert PC, Simonis MT, Kienlen J.-C. Substances antiappétantes pour insectes phytophages présentes dans Angelica silvestris et Heracleum sphondylium. Biochem Syst Ecol 1981; 9: 289-292.
- [29] Carbonnier J, Molho D. Furocoumarins in Archangelica officinalis and Angelica silvestris. Distribution of 5-beta-cyclolavandulyloxy-psoralen in the genus Angelica. Planta Medica 1982; 44: 162-165.
- [30] Lemmich J, Havelund S, Thastrup O. Dihydrofurocoumarin glucosides from Angelica archangelica and Angelica silvestris. Phytochem 1983; 22(2): 553-555.
- [31] Murphy EM, Nahar L, Byres M, Shoeb M, Siakalima M, Rahman MM, Gray AI, Sarker SD. Coumarins from the seeds of Angelica sylvestris (Apiaceae) and their distribution within the genus Angelica. Biochem Syst Ecol 2004; 32: 203-207.
- [32] Krzaczek T, Nowak R. Sterols in the roots and fruits from Angelica sylvestris L. Herba Polonica 2000; 46(4): 274-277.
- [33] Bernard C, Clair G. Essential oils of three Angelica L. species growing in the France. Part I. Root oils. J Essent Oil Res 1997; 9: 289-294.
- [34] Bernard C. Essential oils of three Angelica L. species growing in France. Part II: Fruit oils. J Essent Oil Res 2001; 13: 260-263.
- [35] Acimovic M, Varga A, Cvetkovic M, Stankovic J, Cabarkapa I. Chemical characterization and antibacterial activity of the essential oil of wild Angelica seeds. Botanica Serbica 2018; 42(2): 217-221.
- [36] Vinokurova EY, Shults EE, Bagryanskaya IY, Gatilov YV, Tolstikov GA. (+)-Globulol as a new sesquiterpene alcohol from Angelica sylvestris L. Russ Chem Bulletin 1999; 48: 600-603.
- [37] Bansode VJ. A review on pharmacological activities of Cinnamomum cassia Blume. Int J Green Pharm 2012; 6: 102-108.
- [38] Fu Z, Wang H, Hu X, Sun Z, Han C. The Pharmacological properties of Salvia essential oils. J Appl Pharmaceut Sci 2013; 3(07): 122-127.
- [39] Properzi A, Angelini P, Bertuzzi G, Venanzoni R. Some biological activities of essential oils. Med Aromat Plants 2013; 2(5): doi: 10.4172/2167-0412.1000136.
- [40] Ali B, Al-Wabel NA, Shams S, Ahamad A, Khan SA, Anwar F. Essential oils used in aromatherapy: A systemic review. Asian Pac J Trop Biomed 2015; 5(8): 601-611.
- [41] Elshafie HS, Camele I. An overview of the biological effects of some Mediterranean essential oils on human health. BioMed Res Int 2017; doi: 10.1155/2017/9268468.
- [42] Ribeiro-Santos R, Andrade M, Sanches-Silva A, de Melo NR. Essential oils for food application: natural substances with established biological activities. Food Bioproces Technol 2018; 11: 43-71.
- [43] Damasceno CSB, Higaki NTF, Dias JFG, Miguel MD, Miguel OG. Chemical composition and biological activities of essential oils, in the family Lauraceae: A systematic review of the literature. Plant Med 2019; 85(13): 1054-1072.
- [44] Zhong Y, Hu P, Huang X, Yang M, Ren G, Du Q, Luo J, Zhang K, Li J, Wu H, Guo Y, Liu S. Sedative and hypnotic effects of compound Anshen essential oil inhalation for imsonia. BMC Complemt Altern Med 2019; 19: doi:10.1186/s12906-019-2732-0.
- [45] Sarker SD, Eynon E, Fok K, Kumarasamy Y, Murphy EM, Nahar L, Shaeen EM, Shaw NM, Siakalima M. Screening the extracts of the seeds of Achillea millefolium, Angelica sylvestris and Phleum pretense for antibacterial, antioxidant activities and general toxicity. Oriental Pharm Experiment Med 2003; 3(3): 157-162.
- [46] Kittisrisopit S, Parnthong S, Itharat A. Antiinflammatory and antimicrobial activities of Thai plant extracts for hemorrhoid treatment. Thai J Pharmacol 2010; 32(1): 119-121.
- [47] Canlı K, Yetgin A, Akata I, Altuner EM. In vitro antimicrobial activity of Angelica sylvestris roots. Int J Biol Sci 2016; 1(1): 1-7.
- [48] Stankovic N, Mihajilov-Krstev T, Zlatkovic B, Stankov-Jovanovic V, Mitic V, Jovic J, Comic L, Kocic B, Bernstein N. Antibacterial and antioxidant activity of traditional medicinal plants from the Balkan Peninsula. Wageningen J Life Sci 2016; 78: 21-28.
- [49] Demirci B, Yusufoglu HS, Tabanca N, Temel HE, Bernier UR, Agramonte NM, Alqasoumi SI, Al-Rehaily AJ, Başer KHC, Demirci F. Rhanterium epapposum Oliv. Essential oil: Chemical composition and antimicrobial, insect-repellent and anticholinesterase activities. Saudi Pharmaceut J 2017; 25: 703-708.
- [50] Duymuş HG, Göger F, Başer KHC. In vitro antioxidant properties and anthocyanin compositions of elderberry extracts. Food Chem 2014; 155: 112-119.
- [51] Adams RP. Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry. Carol Stream, IL: Allured Publ. Corp, 2007.
- [52] Hochmuth DH. MassFinder-4, Hamburg, Germany: Hochmuth Scientific Consulting, 2008.
- [53] McLafferty FW, Stauffer DB. The Wiley/NBS Registry of Mass Spectral Data, New York: J. Wiley and Sons, 1989.
- [54] Nivinskienë O, Butkienë R, Mockutë D. Chemical composition of seed (fruit) essential oils of Angelica archangelica L. growing wild in Lithuania. CHEMIJA 2005; 16(3-4): 51-54.
- [55] Bernard C, Clair G. Essential oils of Three Angelica L. species growing in France. Part I. Root oils. J Essent Oil Res 1997; 9: 289-294.
- [56] Orhan IE, Tosun F, Skalicka-Woźniak K. Cholinesterase and tyrosinase inhibitory, and antioxidant potential of randomly selected Umbelliferous plant species and the chromatographic profile of Heracleum platytaenium Boiss. and Angelica sylvestris L. var. sylvestris. J Serbian Chem Soc 2016; 81(4): 357-368.
Year 2020,
Volume: 21 Issue: 1, 39 - 48, 31.03.2020
Hale Gamze Ağalar
,
Fatih Göger
,
Betül Demirci
,
Prof.dr.hulusi Malyer
,
Neşe Kırımer
References
- [1] Davis PH. Flora of Turkey and The East Aegean Islands. Edinburgh, England: Edinburgh University Press, 4, 1972. pp. 265-267.
- [2] Crowden RK, Harborne JB, Heywood VH. Chemoystematics of the Umbelliferae-A general survey. Phytochem 1969; 8: 1963-1984.
- [3] Davis PH, Mill RR, Tan K. Flora of Turkey and the East Aegean Islands. Vol. 10. Edinburgh, England: Edinburgh University Press, 1988. pp. 265-267.
- [4] Pimenov MG, Leonov MV. The genera of the Umbelliferae, Whitstable Litho, Whitstable, Kent, Great Britain, 1993.
- [5] Güner A, Özhatay N, Ekim T, Başer KHC. Flora of Turkey and The East Aegean Islands. Vol. 11, Edinburgh, England: Edinburgh University Press, 2000. p. 141.
- [6] Erik S, Tarıkahya B. Türkiye Florası üzerine. Kebikeç 2004; 17: 139-163.
- [7] Özhatay N, Akalın E, Özhatay E, Ünlü S. Rare and endemic taxa of Apiaceae in Turkey and their conservation significance. İstanbul Ecz Fak Mec 2009; 40(1): 1-15.
- [8] Şenol SG, Eroğlu V, Pelit NB, Bozyel D. Ekimia ozcan-secmenii (Apiaceae), a new very species from Southwest Anatolia, Turkey. Turk J Bot 2018; 42: 510-517.
- [9] Sarker SD, Nahar L. Natural medicine: The genus Angelica. Curr Med Chem 2004; 11(11): 1479-1500.
- [10] Doğan A, Bulut G, Tuzlacı E, Şenkardeş İ. A review of edible plants on the Turkish Apiaceae species. J Fac Pharm Istanbul 2014; 44(2): 251-262.
- [11] Güner E. Revision of Seseli L. (Umbelliferae) genus in Turkey. PhD, Gazi University, Ankara, Turkey, 2006.
- [12] Seigler, DS. Coumarins. In: Plant Secondary Metabolism. Luwer Academic Publishers, Springer, Boston, MA, 1998. pp. 130-138.
- [13] Wang P, Su Z, Yuan W, Deng G, Li S. Phytochemical constituents and pharmacological activities of Eryngium L. (Apiaceae). Pharmaceut Crop 2012; 3: 99-120.
- [14] Zech JC. Flavonoid distribution of Mulinum (Apiaceae, Hydrocotyloideae, Mulineae). Brittonia 1999; 51(4): 415-421.
- [15] Shawky E, El Kheir, RM. Rapid discrimination of different Apiaceae species based on HPTLC fingerprints and targeted flavonoids determination using multivariate image analysis. Phytochem Anal 2017; 29: 452-462.
- [16] Drew DP, Krichau N, Reichwald K, Simonsen HT. Guaianolides in Apiaceae: perspectives on pharmacology and biosynthesis. Phytochem Rev 2009; 8: 581-599.
- [17] Andersen TB, Martinez-Swatson KA, Rasmussen SA, Boughton BA, Jorgensen K, Andersen-Ranberg J, Nyberg N, Christensen SB, Simonsen HT. Localization and in-vivo characterization of Thapsia garganica CYP76AE2 indicates a role in Thapsigargin biosynthesis. Plant Physiol 2017; 174: 56-72.
- [18] Iranshahi M, Rezaee R, Najafi MN, Haghbin A, Kasaian J. Cytotoxic activity of the genus Ferula (Apiaceae) and its bioactive constituents. Avicenna J Phytomed 2018; 8(4): 296-312.
- [19] Franz C, Novak J. Sources of Essential oils. In: Handbook of Essential oils: Science, Technology, and Applications (Eds KHC Başer & G Buchbauer), CRC Press, Boca Raton 2009. pp. 39-81.
- [20] Chizzola R. Essential oil composition of wild growing from Europe and the Mediterranean. Nat Prod Commun 2010; 5(9): 1477-1492.
- [21] Baser KHC, Kırımer N. Essential oils of Anatolian Apiaceae-A profile. Nat Vol Essent Oil 2014; 1(1): 1-50.
- [22] Sousa RMOF, Rosa JS, Oliveira L, Cunha A, Fernandes-Ferreira M. Activities of Apiaceae essential oils and volatile compounds on hatchability, development, reproduction and nutrition of Pseudaletia unipuncta (Lepidoptera: Noctuidae). Ind Crop Prod 2015; 63: 226-237.
- [23] Khoury M, El Beyrouthy M, Eparvier V, Ouaini N, Stien D. Chemical diversity and antimicrobial activity of the essential oils of four Apiaceae species growing wild in Lebanon. J Essent Oil Res 2018; 30(1): 25-31.
- [24] Lobiuc A, Zamfirache MM, Stratu A. Physiological aspects in two Angelica L. Taxa (Apiaceae). An Stiint Univ Al I Cuza Iasi Sect II a Biol veget 2012; 58(2): 81-87.
- [25] Baytop T. Türkiye’de Bitkilerle Tedavi, Geçmişte ve Bugün, 2. Baskı, İstanbul, Türkiye: Nobel Kitabevi, 1999. pp. 290-291.
- [26] Özek T, Özek G, Başer KHC, Duran A, Sagiroglu M. Composition of the essential oils of Angelica sylvestris L. var. sylvestris isolated from the fruits by different isolation techniques. J Essent Oil Res 2008; 20(5): 408-411.
- [27] Vogl S, Picker P, Mihaly-Bison J, Fakhrudin N, Atanasov AG, Heiss EH, Wawrosch C, Reznicek G, Dirsch VM, Saukel J, Kopp B. Ethnopharmacological in vitro studies on Austria's folk medicine- an unexplored lore in vitro anti-inflammatory activities of 71 Austrian traditional herbal drugs. J Ethnopharmacol 2013; 149(3): 750-771.
- [28] Muckensturm B, Duplay D, Robert PC, Simonis MT, Kienlen J.-C. Substances antiappétantes pour insectes phytophages présentes dans Angelica silvestris et Heracleum sphondylium. Biochem Syst Ecol 1981; 9: 289-292.
- [29] Carbonnier J, Molho D. Furocoumarins in Archangelica officinalis and Angelica silvestris. Distribution of 5-beta-cyclolavandulyloxy-psoralen in the genus Angelica. Planta Medica 1982; 44: 162-165.
- [30] Lemmich J, Havelund S, Thastrup O. Dihydrofurocoumarin glucosides from Angelica archangelica and Angelica silvestris. Phytochem 1983; 22(2): 553-555.
- [31] Murphy EM, Nahar L, Byres M, Shoeb M, Siakalima M, Rahman MM, Gray AI, Sarker SD. Coumarins from the seeds of Angelica sylvestris (Apiaceae) and their distribution within the genus Angelica. Biochem Syst Ecol 2004; 32: 203-207.
- [32] Krzaczek T, Nowak R. Sterols in the roots and fruits from Angelica sylvestris L. Herba Polonica 2000; 46(4): 274-277.
- [33] Bernard C, Clair G. Essential oils of three Angelica L. species growing in the France. Part I. Root oils. J Essent Oil Res 1997; 9: 289-294.
- [34] Bernard C. Essential oils of three Angelica L. species growing in France. Part II: Fruit oils. J Essent Oil Res 2001; 13: 260-263.
- [35] Acimovic M, Varga A, Cvetkovic M, Stankovic J, Cabarkapa I. Chemical characterization and antibacterial activity of the essential oil of wild Angelica seeds. Botanica Serbica 2018; 42(2): 217-221.
- [36] Vinokurova EY, Shults EE, Bagryanskaya IY, Gatilov YV, Tolstikov GA. (+)-Globulol as a new sesquiterpene alcohol from Angelica sylvestris L. Russ Chem Bulletin 1999; 48: 600-603.
- [37] Bansode VJ. A review on pharmacological activities of Cinnamomum cassia Blume. Int J Green Pharm 2012; 6: 102-108.
- [38] Fu Z, Wang H, Hu X, Sun Z, Han C. The Pharmacological properties of Salvia essential oils. J Appl Pharmaceut Sci 2013; 3(07): 122-127.
- [39] Properzi A, Angelini P, Bertuzzi G, Venanzoni R. Some biological activities of essential oils. Med Aromat Plants 2013; 2(5): doi: 10.4172/2167-0412.1000136.
- [40] Ali B, Al-Wabel NA, Shams S, Ahamad A, Khan SA, Anwar F. Essential oils used in aromatherapy: A systemic review. Asian Pac J Trop Biomed 2015; 5(8): 601-611.
- [41] Elshafie HS, Camele I. An overview of the biological effects of some Mediterranean essential oils on human health. BioMed Res Int 2017; doi: 10.1155/2017/9268468.
- [42] Ribeiro-Santos R, Andrade M, Sanches-Silva A, de Melo NR. Essential oils for food application: natural substances with established biological activities. Food Bioproces Technol 2018; 11: 43-71.
- [43] Damasceno CSB, Higaki NTF, Dias JFG, Miguel MD, Miguel OG. Chemical composition and biological activities of essential oils, in the family Lauraceae: A systematic review of the literature. Plant Med 2019; 85(13): 1054-1072.
- [44] Zhong Y, Hu P, Huang X, Yang M, Ren G, Du Q, Luo J, Zhang K, Li J, Wu H, Guo Y, Liu S. Sedative and hypnotic effects of compound Anshen essential oil inhalation for imsonia. BMC Complemt Altern Med 2019; 19: doi:10.1186/s12906-019-2732-0.
- [45] Sarker SD, Eynon E, Fok K, Kumarasamy Y, Murphy EM, Nahar L, Shaeen EM, Shaw NM, Siakalima M. Screening the extracts of the seeds of Achillea millefolium, Angelica sylvestris and Phleum pretense for antibacterial, antioxidant activities and general toxicity. Oriental Pharm Experiment Med 2003; 3(3): 157-162.
- [46] Kittisrisopit S, Parnthong S, Itharat A. Antiinflammatory and antimicrobial activities of Thai plant extracts for hemorrhoid treatment. Thai J Pharmacol 2010; 32(1): 119-121.
- [47] Canlı K, Yetgin A, Akata I, Altuner EM. In vitro antimicrobial activity of Angelica sylvestris roots. Int J Biol Sci 2016; 1(1): 1-7.
- [48] Stankovic N, Mihajilov-Krstev T, Zlatkovic B, Stankov-Jovanovic V, Mitic V, Jovic J, Comic L, Kocic B, Bernstein N. Antibacterial and antioxidant activity of traditional medicinal plants from the Balkan Peninsula. Wageningen J Life Sci 2016; 78: 21-28.
- [49] Demirci B, Yusufoglu HS, Tabanca N, Temel HE, Bernier UR, Agramonte NM, Alqasoumi SI, Al-Rehaily AJ, Başer KHC, Demirci F. Rhanterium epapposum Oliv. Essential oil: Chemical composition and antimicrobial, insect-repellent and anticholinesterase activities. Saudi Pharmaceut J 2017; 25: 703-708.
- [50] Duymuş HG, Göger F, Başer KHC. In vitro antioxidant properties and anthocyanin compositions of elderberry extracts. Food Chem 2014; 155: 112-119.
- [51] Adams RP. Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry. Carol Stream, IL: Allured Publ. Corp, 2007.
- [52] Hochmuth DH. MassFinder-4, Hamburg, Germany: Hochmuth Scientific Consulting, 2008.
- [53] McLafferty FW, Stauffer DB. The Wiley/NBS Registry of Mass Spectral Data, New York: J. Wiley and Sons, 1989.
- [54] Nivinskienë O, Butkienë R, Mockutë D. Chemical composition of seed (fruit) essential oils of Angelica archangelica L. growing wild in Lithuania. CHEMIJA 2005; 16(3-4): 51-54.
- [55] Bernard C, Clair G. Essential oils of Three Angelica L. species growing in France. Part I. Root oils. J Essent Oil Res 1997; 9: 289-294.
- [56] Orhan IE, Tosun F, Skalicka-Woźniak K. Cholinesterase and tyrosinase inhibitory, and antioxidant potential of randomly selected Umbelliferous plant species and the chromatographic profile of Heracleum platytaenium Boiss. and Angelica sylvestris L. var. sylvestris. J Serbian Chem Soc 2016; 81(4): 357-368.