Highland Agriculture Research Center, National Institute of Crop Science, Rural Development Administration1
R&D Performance Evaluation & Management Division, Research Policy Bureau, Rural Development Administration, 2
Division of Horticulture and Landscape Architecture, Pai Chai University3
Department of Plant Science, Seoul National University4
This study was conducted to compare the volatile flavor compounds found in the leaves of 15 taxa of Korean native Chrysanthemum species. The volatile flavor compounds from the taxa were collected using a simultaneous steam distillation and extraction technique and were analyzed using gas chromatography/mass selective detector (GC/MSD). A total of 45 volatile flavor compounds were identified with six functional groups: 14 alcohols, 4 ketones, 19 hydrocarbons, 5 esters, 2 acids, and 1 aldehyde. The main functional group in 15 taxa of Chrysanthemum species was alcohols, accounting for 28.7% of volatile flavor compounds, followed by ketones (21.2%) and hydrocarbons (13.2%). Camphor, which is known for its antimicrobial properties, was the most abundant volatile compound (30%) in C. zawadskii ssp. latilobum and var. leiophyllum. In particular, C. indicum subspecies and C. boreale contained -thujone, which has outstanding anti-bacterial, anti-cancer, anti-inflammatory, anti-ulcer, and anti-diabetic efficacies. C. indicum var. albescens could be used in perfumes, since it showed 21 times more camphene than C. indicum. In addition, C. indicum var. acuta contained a fairly high content of 1,8-cineole, which has an inhibitory effect on mutagenesis. C. lineare contained only pentadecanoic acid compounds, whereas other taxa hexadecanoic acids. Overall, the Korean native Chrysanthemum species had considerable variation in volatile flavor compounds in their leaves. This study provides a good indication of specific potential use for various applications.
1. Ahn, J.C., M.Y. Kim, O.T. Kim, K.S. Kim, S.H. Kim, S.H. Kim, and B. Hwang. 2002. Selection of the high yield capacity of Hwangchil lacquer and identification of aromatic components in essential oil of Dendropana × morbifera Lev. Kor. J. Med. Crop Sci. 10:126-131.
2. Arctander, S. 1969. Perfume and flavor chemicals (aroma chemicals). Allured Pub. Corp., Montclair, NJ, USA.
3. Bae, H.J., H.Y. Lee, and J.E. Paik. 2009. Physicochemical properties of sugar-snap cookies prepared with Chrysanthemum indicum Linne powder. Kor. J. Food Nutr. 22:570-576.
4. Bae, S.M. and S.C. Lee. 2008. Effect of hot-air drying temperature on volatile compounds in Chrysanthemum boreale M. flowers. Kor. J. Food Technol. 40:466-469.
5. Byun, Y.H., Y. Shim, S. Lim, S.H. Choi, N.H. Park, S.R. Moon, I.H. Koo, K.U. Lee, M.Y. Lee, H.J. Hong, H.S. Chung, Y.H. Lee, and S.W. Shin. 2006. Development of natural drugs against antibiotics-resistant bacteria from Artemisia and Chrysanthemum species in Korea and study on its active mechanism (1). Duksung Bull. Pharm. Sci. 17:13-21.
6. Cha, J.D., T.Y. Kim, W.H. Woo, K.Y. Chung, Y.O. You, K.J. Kim, and B.S. Kil. 2000. Effect of Chrysanthemum boreale essential oil to several microorganisms. Bull. Life Sci. Biotechnol. 7:1-17.
7. Chang, K.M. and G.H. Kim. 2008. Comparative analysis of volatile flavor compounds from Zanthoxylum piperitum A.P. DC. J. Food Sci. Nutr. 13:33-39.
8. Chang, K.M. and G.H. Kim. 2009. Comparative chemical composition of domestic and imported Chrysanthemum indicum L. flower oils. Food Sci. Biotechnol. 18:1288-1292.
9. Choe, S.H., S.I. Im, E.Y. Jang, and Y.S. Jo. 2004. Volatile compounds of flower and seed of safflower. Kor. J. Food Sci. Technol. 36:196-201.
10. Choi, S.H., S.I. Im, and J.E. Bae. 2006. Analysis of aroma components flower tea of German chamomile and Chrysanthemum boreale Makino. Kor. J. Food Cookery Sci. 22:768-773.
11. Choi, Y.J. 1992. Korean ethonobotany. Academy Book, Seoul, Korea p. 53-58.
12. Ham, H.S., S.Y. Lee, D.W. Lee, J.H. Seong, H.S. Kim, D.S. Kim, and Y.G. Lee. 2012. Isolation and identification of antioxidant compounds of various solvents extracted from Eriobotrya japonica leaves. J. Life Sci. 22:1166-1172.
13. Hong, C.U. 2002. Essential oil composition of Chrysanthemum boreale and Chrysanthemum indicum. J. Kor. Soc. Agr. Chem. Biotechnol. 45:108-113.
14. Huang, Y.F., Y.M. Zhang, L. Tao, and H.Q. Wu. 2001. Chemical components of essential oil from flowers of Chrysanthemi indicum in Guangzhou. J. Instr. Anal. 20:40-41.
15. Indo, M. 1996. Synthetic perfume and materials-chemistry and products information. The Chemical Daily Co., Ltd., Tokyo, Japan.
16. Inoue, Y., T. Hada, A. Shiraishi, K. Hirose, H. Hamashina, and S. Kobayashi. 2005. Biphasic effects of geranylgeraniol, teprenone, and phytol on the growth of Staphylococcus aureus. Antimicrob. Agents Chemother. 49:1770-1774.
17. Jang, D.S., K.H. Park, J.R. Lee, T.J. Ha, Y.B. Park, S.H. Nam, and M.S. Yang. 1999. Antibacterial activities of sesquiterpene lactones isolated from Hemisteptia lyrata, Chrysanthemum zawadskii, and Chrysanthemum boreale. J. Kor. Soc. Agr. Chem. Biotechnol. 42:176-179.
18. Jang, M.R., J.E. Seo, J.H. Lee, M.S. Chung, and G.H. Kim. 2010. Antibacterial action against food-borne pathogens by the volatile flavor of essential oil from Chrysanthemum morifolium flower. Kor. J. Food Nutr. 23:154-161.
19. Jiang, H., F. Li, and S. Zeng. 2005. Capillary GC determination of β-elemene, camphor, and borneol in Chrysanthemum morifolium Ramat. Yaowu Fenzi Zazhi 25:508-511.
20. Jung, E.K. 2009. Chemical composition and antimicrobial activity of the essential oil of Chrysanthemum indicum against oral bacteria. J. Bacteriol. Virol. 39:61-69.
21. Kim, H.G., Y.E. Kim, J.R. Do, Y.C. Lee, and B.Y. Lee. 1995. Antioxidative activity and physiological activity of some Korean medicinal plants. Kor. J. Food Sci. Technol. 27:80-85.
22. Kim, J.H. 1997. Variation of concentration of terpenes in Chrysanthemum boreale. Kor. J. Ecol. 20:397-403.
23. Kim, J.O., Y.S. Kim, J.H. Lee, M.N. Kim, S.H. Rhee, S.H. Moon, and K.Y. Park. 1992. Antimutagenic effect of the major volatile compounds identified from mugwort (Artemisia asictica Nakai) leaves. J. Kor. Soc. Food Nutr. 21:308-313.
24. Kim, S.J., J.H. Nam, Y.I. Jin, S.Y. Hong, Y.H. Yoon, J.C. Jeong, and K.S. Kim. 2011. Classification of the genus Chrysanthemum in Korea by flower morphological characteristics. Kor. J. Hort. Sci. Technol. 29(Suppl. II):149. (Abstr.)
25. Kim, S.K., S.C. Lee, D.K. Kang, S.H. Chung, and S.D. Lee. 1998. Essential oil content and composition of aromatic constituents in some medicinal plant. Kor. J. Plant Res. 11:279-282.
26. Kim, Y.S., J.H. Lee, M.N. Kim, W.G. Lee, and J.O. Kim. 1994. Volatile flavor compounds from raw mugwort leaves and parched mugwort tea. J. Kor. Soc. Food Nutr. 23:261-267.
27. Ko, K.S. and E.S. Jeon. 2003. Ferns, fern-allis and seed bearing plants of Korea. Iljinsa, Seoul, Korea.
28. Kondjoyan, N. and J.L. Berdague 1996. A compilation of relative retention indices for the analysis of aromatic compounds. Laboratoire Flaveur, Clemont-Ferrand, Paris, France.
29. Kubo, I., H. Muroi, and M. Himejima. 1992. Antimicrobial activity of green tea flavor compounds and their combination effects. J. Agr. Food Chem. 40:245-248.
30. Lee, J.H., E.H. Kim, and J.H. Lee. 2008. Effect of Chrysanthemum zawadskii var. latilobum on the release of inflammatory mediators from LPS-stimulated mouse macrophages. J. Orient. Neuropsych. 19:209-221.
31. Lee, K.C, J.Y. Sa, M.H. Wang, and S.S. Han. 2012. Comparison of volatile aroma compounds between Synurus deltoids and Aster scaber leaves. J. Medi. Crop. Sci. 20:54-62.
32. Lee, S.H. and J.S. Lee. 2007. Production and characteristics of antidandruff compound from Chrysanthemum zawadskii. Kor. J. Microbiol. Biotechnol. 35:220-225.
33. Lee, Y.N. 2006. New flora of Korea II. Kyohaksa, Seoul, Korea.
34. Maggi, F, F. Papa, G. Cristalli, G. Sagratini, and S. Vittori. 2010. Characterization of the mushroom-like flavour of Melittis melissophyllum L. subsp. melissophyllum by headspace solid- phase micro extraction (HS-SPME) coupled with gas chro-mato-graphy (GC-FID) and gas chromatography-mass spectrometry (GC-MS). Food Chem. 123:983-992.
35. Matsuda, H., T. Morikawa, I. Toguchida, S. Harima, and M. Yoshikawa. 2002. Absolute stereo structures of two new flavanone glycosides and a phenylbutanoid glycoside from the flowers of Chrysanthemum indicum L.: Their inhibitory activities for rat lens aldose reductase medicinal flowers. VI. Chem. Pharm. Bull. 50:972-975.
36. Nam, S.H. and M.S. Yang. 1995. Antibacterial activities of extracts from Chrysanthemum boreale M. J. Agr. Food Chem. 38:269-272.
37. Nam, S.H., S.D. Choi, J.S. Choi, D.S. Jang, S.U. Choi, and M.S. Yang. 1997. Effects of sesquiterpene lactones isolated from Chrysanthemum boreale M. against sarcoma 180 implanted in ICR mice. J. Kor. Soc. Food Sci. Nutr. 26:144-147.
38. Park, G.S., M.Y. Choi, and J.G. Im. 2000. Comparative degree of gelatinization and retrogradation on Gamkugsulgie with added of Gamkug. J. East Asian Diet. Life 10:514-521.
39. Park, G.S. and Y.J. Shin. 1998. Mechanical characteristics and preferences of Gamkugsulgie-dduk by different addition of Chrysanthemum indicum L. J. East Asian Diet. Life 8:289-296.
40. Pattnaik, S., V.R. Subramanyam, M. Bapaji, and C.R. Kole. 1997. Antibacterial and antifungal activity of aromatic constituents of essential oils. Microbios 89:39-46.
41. Pirbalouti, A.G., M. Hashemi, and F.T. Ghahfarokhic. 2013. Essential oil and chemical compositions of wild and cultivated Thymus daenensis Celak and Thymus vulgaris L. Ind. Crops Prod. 48:43-48.
42. Ravindran, P.N., K.N. Babu, and M. Shylaja. 2004. Cinnamon and Cassia: The genus Cinnamonmum. Medicinal and Aromatic Plants-Industrial Profiles. CRC Press. New York, USA.
43. Rivero-Cruz, B., I. Rivero-Cruz, J.M. Rodriguez, C.M. Cerda- Garcia-Rojas, and R. Mata. 2006. Qualitative and quantitative analysis of the active compounds of the essential oil from Brickellia veronicaefolia by nuclear magnetic resonance spectroscopy. J. Nat. Prod. 69:1172-1176.
44. Schultz, T.H., R.A. Flath, T.R. Mon, S.B. Eggling, and R. Teranishi. 1977. Isolation of volatile compounds from a model system. J. Agr. Food Chem. 25:446-449.
45. Shin, K.H., S.S. Kang, E.A. Seo, and S.W. Shin. 1995. Isolation of aldose reductase inhibitiors from the flowers of Chrysanthemum boreale. Arch. Pharm. Res. 18:65-68.
46. Shin, Y.J., J.R. Jeon, and G.S. Park. 2004. Physiochemical properties of Gamgug (Chrysanthemum indicum L.). J. Kor. Soc. Food Sci. Nutr. 33:146-151.
47. Shu, C., J. Cai, L. Huang, X. Zhu, and Z. Xu. 2011. Biocatalytic production of ethyl butyrate from butyric acid with immobilized Candida rugosa lipase on cotton cloth. J. Mol. Cat. B: Enzymatic 72:139-144.
48. Shunying, Z., Y. Yang, Y. Huaidong, Y. Yue, and Z. Guolin. 2005. Chemical composition and antimicrobial activity of the essential oils of Chrysanthemum indicum. J. Ethnopharmacol. 96:151-158.
49. Sung, J.Y., W.A. Joe, Y.H. Kim, S.J. Cheon, M.J. Jang, H.J. Choi, J.S. Lee, E.Y. Choi, H.S. Lee, D.I. Kim, J.O. Kim, B.J. An, and J.T. Lee. 2007. Study on the anti-oxidant activity of extracts from the Chrysanthemum indicum L. J. Appl. Orient. Med. 7:1-5.
50. Tzakou, O., D. Pitarokili, I.B. Chinou, and C. Harvala. 2001. Composition and antimicrobial activity of the essential oil of Salvia ringens. Planta Med. 67:81-83.
51. Viljoen, A., S. van Vuuren, E. Ernst, M. Klepser, B. Demirci, H. Baser, and B.E. van Wyk. 2003. Osmitopsis asteriscoides (Asteraceae)-the antimicrobial and essential oil composition of a Cape-Dutch remedy. J. Ethnopharmacol. 88:137-143.
52. Wang, Y.J. and X.W. Yang. 2006. GC-MS analysis of essential oil of the flower of the Chrysanthemum morifolium by the different processing methods. Zhongguo Zhong Yao Za Zhia 31:456-459.
53. Wang, Y.J., Q.S. Guo, X.W. Yang, W.B. Xu, and H.Y. Tao. 2008. Characterization of chemical components of essential oil from flowers of Chrysanthemum morifolium produced in Anhui province. China J. Chinese Materia Medica 33:2207-2211.
54. Woo, K.S., J.S. Yu., I.G. Hwang, Y.R. Lee, C.H. Lee, H.S. Yoon., J.S. Lee, and H.S. Jeong. 2008. Antioxidative activity of volatile compounds in flower of Chrysanthemum indicum, C. morifolium, and C. zawadskii. J. Kor. Soc. Food Sci. Nutr. 37:805-809.
55. Yeon, B.R., H.M. Cho, M.S. Yun, J.W. Jhoo, J.W. Jung, Y.H. Park, and S.M. Kim. 2012. Comparison of fragrance and chemical composition of essential oils in ‘Gom-chewi’ (Ligularia fischeri) and ‘Handaeri gom-chewi’ (Ligularia fischeri var. spicifoprmis). J. Kor. Soc. Food Sci. Nutr. 41:1758-1763.
56. Yoon, O.H. and J.S. Cho. 2007. Optimization of extraction conditions for hot water extracts from Chrysanthemum indicum L. by response surface methodology. Kor. J. Food Cookery Sci. 23:1-8.
57. Yu, J.M., Y.H. Park, and S.M. Kim. 2008. Floral volatile composition of daisy fleabean (Erigeron annuus L. Pers.). Kor. J. Weed Sci. 28:274-278.