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Analysis of the Terpenoids from Syneilesis palmata Essential Oil and the Variation of the Sesquiterpene Compounds by Harvest Year

우산나물 정유의 테르펜 화합물 분석 및 수확 연도에 따른 Sesquiterpene 화합물 변화 조사

  • 최향숙 (경인여자대학교 식품영양과)
  • Received : 2013.05.10
  • Accepted : 2013.06.04
  • Published : 2013.06.30

Abstract

This study was investigated the chemical composition from Syneilesis palmata essential oil and the tendency of variation of the sesquiterpene compounds according to the harvesting time. The essential oils obtained by hydro distillation from the aerial parts of Syneilesis palmata were analyzed by GC and GC-MS. Ninety-eight compounds consisting of 9 aliphatic hydrocarbons, 17 sesquiterpene hydrocarbons, 11 aliphatic aldehydes, 1 terpene aldehyde, 8 aliphatic alcohols, 4 monoterpene alcohols, 16 sesquiterpene alcohols, 3 diterpene alcohols, 6 ketones, 11 esters, 8 oxides and epoxides, 3 acids and 1 miscellaneous one were identified from the oil. Spathulenol (22.33%) was the most abundant compound, followed by ${\beta}$- caryophyllene (6.23%), germacrene D (5.57%), longipinane (4.10%), and epiglobulol (3.65%). The volatile composition of Syneilesis palmata was characterized by higher contents of sesquiterpene compounds, especially sesquiterpene alcohols. The total content of 13 sesquiterpene compounds was decreased significantly from 2010 to 2012. ${\alpha}$-Caryophyllene, ${\beta}$-bisabolene, elemol, germacrene D, ${\beta}$-zingiberene, longipinane, and ${\beta}$-caryophyllene alcohol contents decreased, while ${\beta}$-bisabolol content increased during 3 years. The ecological responses to recent climate change may be influenced in the chemical components of natural plant terpenoids.

Keywords

References

  1. Alvarez-Castellamos PP, Bishop CD, Pascual-Villalobos MJ. 2000. Antifungal activity of the essential oils of flowerheads of garland chrysanthemum (Chrysanthemum coronarium). Phytochemistry 57:99-102
  2. Amiel E, Ofir R, Dudai N, Soloway E, Rabinsky T, Rachmilevitch S. 2012. $\beta$-Caryophyllene, a compound isolated from the biblical balm of gilead (Commiphora gileadensis), is a selective apoptosis inducer for tumor cell lines. Evidence-Based Complementary and Alternative Medicine 2012:1-8
  3. Arctander S. 1969. Perfume and Flavor Chemicals. Published by Author. NJ, USA
  4. Ben-Yehoshua S, Rodov V, Fang DQ, Kim JJ. 1995. Preformed antifungal compounds of citrus fruit: effect of postharvest treatments with heat and growth regilators. J Agric Food Chem 43:1062-1066 https://doi.org/10.1021/jf00052a040
  5. Bulow N, Konig WA. 2000. The role of germacrene D as a precursor in sesquiterpene biosynthesis: investigations of acid catalyzed, photochemically and thermally induced rearrangements. Phytochemistry 55:141-168 https://doi.org/10.1016/S0031-9422(00)00266-1
  6. Choi HS. 2005. Characteristic odor component of kumquat (Fortunella japonica Swingle) peel oil. J Agric Food Chem 53:1642-1647 https://doi.org/10.1021/jf040324x
  7. Ghannadi A, Rabbani M, Ghaemmaghami L, Malekian N. 2012. Phytochemical screening and essential oil analysis of one of the Persian sedges; Cyperus rotundus L. Int J Pharm Sci Res 3:424-427
  8. Gomez Ne, Witte L. 2001. A simple method to extract essential oils from tissue samples by using microwave radiation. J Chem Ecol 27:2351-2359 https://doi.org/10.1023/A:1012295307740
  9. Heath HB. 1986. Flavor Chemistry and Technology. pp. 2-157. Macmillan Publishers Ltd. London, England
  10. Jang HW, Lee HJ, Lee KG. 2005. Analysis and antioxidant activity of volatile extracts from plants commonly used in Korean foods. Korea J Food Sci Technol 37:723-729
  11. Kim TJ. 2009. Wilds Flowers and Resources Plants in Korea. p. 59. Seoul National University Publisher. Seoul, Korea
  12. Kwon CS, Kwon YS, Kim YS, Kwom GS. 2004. Inhibitory activities of edible and medicinal herbs against human thrombin. J Life Sci 14:509-513 https://doi.org/10.5352/JLS.2004.14.3.509
  13. Lee E, 2011. Effects of Ixeris dentata ext. on lowering lipid and anti-oxidation. Korean J Plant Res 24:55-60 https://doi.org/10.7732/kjpr.2011.24.1.055
  14. Lee KH, Choi SU, Lee KR. 2005. Sesquiterpenes from Syneilesis palata and their cytotoxicity against human cancer cell lines in vitro. Arch Pharm Res 28:280-284 https://doi.org/10.1007/BF02977792
  15. Lee KI, Rhee LS, Park KY. 1999. Anticancer activity of phytol and eicosatrienoic acid identified from perilla leaves. J Korean Soc Food Sci Nutr 28:1107-1112
  16. Lee KS, Kim GH, Kim HH, Kim ES, Park HM, Oh MJ. 2008. Quality characteristics of tea thermally processed from Ixeris dentata root. Korean J Food Preserv 15:524-531
  17. Lee YS, Ahn DS, Joo EY, Kim NW. 2009a. Antioxidant activities of Syneilesis palata extracts. J Korean Soc Food Sci Nutr 38:1471-1477 https://doi.org/10.3746/jkfn.2009.38.11.1471
  18. Lee YS, Seo SJ, Kim NW. 2009b. Analysis of general components of Syneilesis palata Maxim. Korean J Food Preserv 16:412-418
  19. Mendes S, Nunes DS, Marques MB, Tardivo RC, Fillho VC, Simionatto EL, Wisniewski A. 2008. Essential oil of Baccharis semiserrata, a source of spathulenol. Ci Agr Eng 14:241-245
  20. Park MH, Kim MJ, Cho WI, Chang PS, Lee JH. 2009. Effects of treatments on the distribution of volatiles in Artemisia princeps Pampan. Korea J Food Sci Technol 41:587-591
  21. Phoenix J, Edwards RH, Jackson MJ. 1989. Inhibition of $Ca^{2+}$-induced cytosolic enzyme efflux from skeletal muscle by vitamin E and related compounds. Biochem J 257:207-213 https://doi.org/10.1042/bj2570207
  22. Raja RR, Ramalakshmi S, Muthuchekuan K. 2011. GC-MS analysis of bioactive components from ethanolic leaf extract of Canthium dicoccum (Gaertn.) Teijsm & Binn. J Chem Pharm Res 3:792-798
  23. Sakai K, Nagao T, Okabe T. 1999. Triterpenoid saponins from the ground part of Aster ageratoides var. ovatus. Phytochemistry 51:309-318 https://doi.org/10.1016/S0031-9422(98)00766-3
  24. Setzer W. 2008. Germacrene D cycization: An ab initioinvestigation. Int J Mol Sci 9:89-97 https://doi.org/10.3390/ijms9010089
  25. Shunying Z, Yang Y, Huaidong Y, Yue Y, Guolin. 2005. Chemical composition and antimicrobial activity of the essential oils of Chrysanthemum indicum. J Ethnopharm 96:151-158 https://doi.org/10.1016/j.jep.2004.08.031
  26. Toshihiro A, Yumiko K, Kazuo K, Takaaki T, Ken Y, Koichi A, Yasuhiro S, Tamotsu N, Astertarone A. 1998. A triterpenoid ketone isolated from the roots of Aster tataricus L. Chemical Bulletin 46:1824-1826 https://doi.org/10.1248/cpb.46.1824
  27. Ziaei A, Ramezani M, Wright L, Paetz C, Schneider B, Amirghofran Z. 2011. Identification of spathulenol in Salvia mirzayanii and the immunomodulatory effects. Phytotherapy Res 25:557-562 https://doi.org/10.1002/ptr.3289

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