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Chemical Constituents of Heliotropium hirsitutissimum Grauer (Heliotrope) (Sigil otu, Bambil) (Sonnenwende) and Ecotype
Corresponding Author(s) : Hatice Demiray
Asian Journal of Chemistry,
Vol. 25 No. 7 (2013): Vol 25 Issue 7
Abstract
The aim of this study is to examine the chemical constituents of Heliotropium hirsitutissimum GRAUER naturally spreaded in Denizli and its ecotype spreaded a hotter region in Izmir (Bornova-campus) and to identify them by GC-MS. After the extraction of fresh leaves, one alkaloid and a mixture of phenols, essential oils: 2,3- butanediol, 2-3- dimethyl- (CAS) pinacol (other name: tetramethylethylene glycol), phenol, 4-(3-hydroxy-1-propenyl-2-methyl-(CAS) coniferyl alcohol (other name 4-hydroxy-3-methoxycinnamyl alcohol), 1H-pyrrolizine-7-methanol-2,3,5,7,a-tetrahydro-1-hydroxy-(IS-Cis)- (CAS)=heliotridine, Xycaine$ Aceteamide, 2-(diethylamino)-N-(2,6-dimethylphenyl) and 2,6,10,14,18,22-tetracosahexaene (other name: squalene) were identified in the species spreaded naturally in Denizli. Izmir ecotype gave a mixture of essential oils and phenol 1-hexadecanol; tetracosane acid, butyl 2-methylpropyl ester, phenol: phenol, 4,4¢-(1-methylethylidene)bis-(CAS) 2,2-bis(p-hydroxyphenyl)propane, ethanol, 2-2¢-(1-2-ethanediol bis(oxy))bis-(CAS)triethylene glycol, octadecanoic acid (other name stearic acid), 2-hydroxy-1-(hydroxymethyl) ethyl ester (CAS) and 2-Monostearin. The main components of the two ecotypes was 1,2-benzene dicarboxylic acid and hexadecanol. The presence of triethylene glycol was found to be as the significant structural difference of Izmir ecotype. These results indicated that the composition of heliotrops highly dependent on the climate conditions.
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- L. Villarroel, R. Torres, A. Urzu’a, M. Reina, R. Cabrera and A. Gonza´lez-Coloma, J. Nat. Prod., 64, 1123 (2001).
- P.H. Davis, Flora of Turkey and East Aegean Islands, Univ. of Edinburg, Vol. 3 (1982).
- K.P. Tiwari and M. Masood, Proc. Nat. Acad. Science (India) A, 47, 72 (1977).
- S. Mohanraj, P. Kuanthhaivel, P. Subramanian and W. Herz, Phytochemistry, 20, 1991 (1981).
- A.M. Rizk, F.M. Hammonda and N.M. Hassan, Qatar Univ. Sci. J., 11, 113 (1991).
- D.H. Abu, S.E. Adam and G. Tartour, Br. Veterinary J., 138, 463 (1982).
- J.H. Creeper, A.A. Mitchell, T.F. Jubb and S.M. Colegate, Aust. Veterin. J., 77, 401 (1999).
- L.B. Bull, C.C.J. Culvenor and A.T. Dick, The Pyrrolizidine Alkaloids, North-Holland Publishing Company, Amsterdam (1968).
- H. Wiedenfeld and J. Edgar, Phytochem. Rev., 10, 137 (2011).
- Anonymous, Tubives (2012), Turkish Plants Data Service Online at: http://turkherb.ibu.edu.tr.
- B. Dell and A.J. McComb, Adv. Bot. Res., 6, 277 (1978).
- R.G. Kelsey, G.W. Reynolds and E. Rodriges, In eds.: E. Rodriguez, P. Healy and L Metha, In Biology and Chemistry of Plant Trichomes, Planum Press: New York; Ch. 8, pp. 187-241 (1984).
- N.D. Johnson, Biochem. Syst. Ecol., 11, 211 (1983).
- L. Villarroel, R. Tórres, A. Urzua, B. Modak, J. Henriquez and I. Salgado, Rev. Latinoamer. Quím., 25, 109 (1997).
- R. Torres, L. Villarroel, A. Urzuá, F. Delle Monache, G. Delle Monache and E. Gacs-Baitz, Phytochemistry, 36, 249 (1994).
- K. Tan, A. Çelik, Y. Gemici, M. Gemici and H. Yildirim, Adv. Sci. Lett., 1, 132 (2008).
- T. Machan, J. Korth, S. Liawruangrath and S.G. Pyne, Flavour Fragr. J., 21, 265 (2006).
- A.R. Chamberlin and J.Y.L. Chung, Am. Chem. Soc., 105, 11 (1983).
- C.K. Atal, Prog. Chem. Org. Nat. Prod., 41, 115 (1978).
- A.F.M. Rizk, Naturally Occurring Pyrrolizidine Alkaloids, CRC Press, Boca Raton (1991).
- H. Baxter, J.B. Harborne and G.P. Moss, Phytochemical Dictionary. A Handbook of Bioactive Compounds from Plants, Taylor and Francis ISBN: 0-203-48375-8, edn. 2 (2009).
- J.L. Catalfamo, M.W. Frohlich, W.B. Martin Jr. and H. Brecta, Phytochemistry, 21, 2677 (1982).
- H. Birecka and J.L. Catalfamo, Phytochemistry, 21, 2645 (1982).
- Atta-ur-Rahman, Studies in Natural Products Chemistry, V 31. Elsevier B.V., The Netherlands (2005).
- M. Susan and J. Peñuelas, Trends Plant Sci., 10, 9 (2005).
- E.L. Singsaas and T.D. Sharkey, Plant Cell Environ., 23, 751 (2000).
- J. Kesselmeier and M. Staudt, J. Atmos. Chem., 33, 23 (1999).
- Y. Liu, H. Kreppel, J. Liu, S. Choudhuri and C.D. Klaassen, J. Pharmacol. Exp. Ther., 266, 400 (1993).
- J. Liu, Y. Liu, Q. Mao and C.D. Klaassen, Fundam. Appl. Toxicol., 22, 34 (1994).
- Z.A. Shaikh, T.T. Vu and K. Zaman, Toxicol. Appl. Pharmacol., 154, 256 (1999).
- S.B. Mahato, S.K. Sarkar and G. Poddar, Phytochemistry, 27, 3037 (1988).
- O.J. Catchpole, J.C. von Kamp and J.B. Grey, Ind. Eng. Chem. Res., 36, 4318 (1997).
- A. Pietsch and P. Jaeger, Eur. J. Lipid Sci. Technol., 109, 1077 (2007).
- E.A. Emken, Am. J. Clin. Nutri., 60, 1023S (1994).
- J.E. Hunter, J. Zhang, K. Etherton and M. Penny, Am. J. Clin. Nutr., 91, 46 (2010).
- M. Hamayun, S.A. Khan, Z.K. Shinwari, A.L. Khan, N. Ahmad and J.L. In, Pak. J. Bot., 42, 977 (2010).
- A. Balasubramani and G. Balasubramani, J. Biotechnol. Mol. Biol. Rev., 6, 31 (2011).
References
L. Villarroel, R. Torres, A. Urzu’a, M. Reina, R. Cabrera and A. Gonza´lez-Coloma, J. Nat. Prod., 64, 1123 (2001).
P.H. Davis, Flora of Turkey and East Aegean Islands, Univ. of Edinburg, Vol. 3 (1982).
K.P. Tiwari and M. Masood, Proc. Nat. Acad. Science (India) A, 47, 72 (1977).
S. Mohanraj, P. Kuanthhaivel, P. Subramanian and W. Herz, Phytochemistry, 20, 1991 (1981).
A.M. Rizk, F.M. Hammonda and N.M. Hassan, Qatar Univ. Sci. J., 11, 113 (1991).
D.H. Abu, S.E. Adam and G. Tartour, Br. Veterinary J., 138, 463 (1982).
J.H. Creeper, A.A. Mitchell, T.F. Jubb and S.M. Colegate, Aust. Veterin. J., 77, 401 (1999).
L.B. Bull, C.C.J. Culvenor and A.T. Dick, The Pyrrolizidine Alkaloids, North-Holland Publishing Company, Amsterdam (1968).
H. Wiedenfeld and J. Edgar, Phytochem. Rev., 10, 137 (2011).
Anonymous, Tubives (2012), Turkish Plants Data Service Online at: http://turkherb.ibu.edu.tr.
B. Dell and A.J. McComb, Adv. Bot. Res., 6, 277 (1978).
R.G. Kelsey, G.W. Reynolds and E. Rodriges, In eds.: E. Rodriguez, P. Healy and L Metha, In Biology and Chemistry of Plant Trichomes, Planum Press: New York; Ch. 8, pp. 187-241 (1984).
N.D. Johnson, Biochem. Syst. Ecol., 11, 211 (1983).
L. Villarroel, R. Tórres, A. Urzua, B. Modak, J. Henriquez and I. Salgado, Rev. Latinoamer. Quím., 25, 109 (1997).
R. Torres, L. Villarroel, A. Urzuá, F. Delle Monache, G. Delle Monache and E. Gacs-Baitz, Phytochemistry, 36, 249 (1994).
K. Tan, A. Çelik, Y. Gemici, M. Gemici and H. Yildirim, Adv. Sci. Lett., 1, 132 (2008).
T. Machan, J. Korth, S. Liawruangrath and S.G. Pyne, Flavour Fragr. J., 21, 265 (2006).
A.R. Chamberlin and J.Y.L. Chung, Am. Chem. Soc., 105, 11 (1983).
C.K. Atal, Prog. Chem. Org. Nat. Prod., 41, 115 (1978).
A.F.M. Rizk, Naturally Occurring Pyrrolizidine Alkaloids, CRC Press, Boca Raton (1991).
H. Baxter, J.B. Harborne and G.P. Moss, Phytochemical Dictionary. A Handbook of Bioactive Compounds from Plants, Taylor and Francis ISBN: 0-203-48375-8, edn. 2 (2009).
J.L. Catalfamo, M.W. Frohlich, W.B. Martin Jr. and H. Brecta, Phytochemistry, 21, 2677 (1982).
H. Birecka and J.L. Catalfamo, Phytochemistry, 21, 2645 (1982).
Atta-ur-Rahman, Studies in Natural Products Chemistry, V 31. Elsevier B.V., The Netherlands (2005).
M. Susan and J. Peñuelas, Trends Plant Sci., 10, 9 (2005).
E.L. Singsaas and T.D. Sharkey, Plant Cell Environ., 23, 751 (2000).
J. Kesselmeier and M. Staudt, J. Atmos. Chem., 33, 23 (1999).
Y. Liu, H. Kreppel, J. Liu, S. Choudhuri and C.D. Klaassen, J. Pharmacol. Exp. Ther., 266, 400 (1993).
J. Liu, Y. Liu, Q. Mao and C.D. Klaassen, Fundam. Appl. Toxicol., 22, 34 (1994).
Z.A. Shaikh, T.T. Vu and K. Zaman, Toxicol. Appl. Pharmacol., 154, 256 (1999).
S.B. Mahato, S.K. Sarkar and G. Poddar, Phytochemistry, 27, 3037 (1988).
O.J. Catchpole, J.C. von Kamp and J.B. Grey, Ind. Eng. Chem. Res., 36, 4318 (1997).
A. Pietsch and P. Jaeger, Eur. J. Lipid Sci. Technol., 109, 1077 (2007).
E.A. Emken, Am. J. Clin. Nutri., 60, 1023S (1994).
J.E. Hunter, J. Zhang, K. Etherton and M. Penny, Am. J. Clin. Nutr., 91, 46 (2010).
M. Hamayun, S.A. Khan, Z.K. Shinwari, A.L. Khan, N. Ahmad and J.L. In, Pak. J. Bot., 42, 977 (2010).
A. Balasubramani and G. Balasubramani, J. Biotechnol. Mol. Biol. Rev., 6, 31 (2011).