The Malaysian Journal of Analytical Sciences Vol 17 No 2 (2013): 255 – 261

 

 

 

STRUCTURE ELUCIDATION OF FLAVONOID COMPOUND FROM

THE LEAVES OF COLEUS ATROPURPUREUS BENTH USING

1D- AND 2D-NMR TECHNIQUES

 

(Elusidasi Struktur Sebatian Flavonoid Dari Daun Coleus Atropurpureus Benth Menggunakan Teknik 1D- Dan 2D-NMR)

 

Sovia Lenny¹*, Tonel Barus¹, Lamek Marpaung¹,  M.Pandapotan Nasution²

¹Department of Chemistry,

²Faculty of Pharmacy,

 University of Sumatera Utara, Medan, Republic of Indonesia

 

*Corresponding author: sovialeni@yahoo.com

 

 

Abstract

Isolation of flavonoid compound from ethylacetate extract of the leaves of Coleus atropurpureus Benth using column chromatography have been carried out. Structure elucidation of the isolated compounds was done by  one-and two-dimensional NMR (¹H, ¹³C, DEPT, COSY, HMQC and HMBC). Analysis of 1D-NMR spectra (¹H-NMR showed signals at δ 6-8 ppm for the aromatic region of the flavonoid aglycone  and ¹³C-NMR showed signals for three carbon atoms of the flavonoid ring C at δ 182.8 ppm (C-4), 103.9 ppm (C-3), 166.4 ppm (C-2) and DEPT showed the presence of  CH and CH₂ group). Analysis of 2D- NMR spectra (COSY showed  correlation of proton  at δ 7.86 and 6.92 ppm and HMBC showed correlation between proton at  δ  6.61 with 166.4 ppm and 6.92 with 123.3 ppm).

Keywords: Coleus atropurpureus Benth, column chromatography, flavonoid, structure elucidation, 1D- and 2D-NMR techniques

 

References

1.       Wink, M. (2003). Evolution of Secondary Metabolites from and Ecological and Molecular Phylogenetic Perspective, Phytochemistry (64), 3-19.

2.       Valant-Vetschera,K.M., Roitman,J.N. and Wollenweber,E. (2003). Chemodiversity of exudates flavonoids in some members of the Lamiaceae, Biochemical Systematics and Ecology (31), 1279-1289.

3.       Skaltsa. H., Karioti, A., Heilmann, J., and Sticher, O. (2003). Acylated Flavonoid and Phenylethanoid Glycosides from Marrubium velutinum, Phytochemistry (64), 655-660.

4.       Fossen, T. and Andersen, Q.M. (2006). Spectroscopic Techniques Applied to Flavonoids, In Markham, K.R. and  Andersen, Q.M., At Flavonoids : Chemistry, Biochemistry, and Applications, CRC Press.

5.       Sastrohamidjojo, H. (1994). Spektroskopi Resonansi Magnetik Inti (Nuclear Magnetic Resonance, NMR), Liberty Yogyakarta.

6.       Stobiecki, M. and Kachlicki, P. (2006).  Isolation and Identification of Flavonoids, In Grotewold, E., At The Science of Flavonoids, The Ohio State University Columbus, Ohio, USA.

7.       Rossomando, P.C. (2009). NMR, In Sampietro, D.A., Catalan, C.A.N., Vattuone, M.A, At Isolation, Identification and Characterization of Allelochemicals/Natural Products, Science Publishers, Enfield, USA.

8.       Markham, K.R., Chari, V.M., and Marby, T.J. (1982). Carbon-13 NMR Spectroscopy of Flavonoids, In Harborne, J.B. and Marby, T.J., At The Flavonoids : Advances in Research, Chapman and Hall, London.

9.       Silverstein, R.M., Bassler, G.C. and Morril, T.C. (1991) Spectrometric Identification of Organic Compounds, 5^th ed, John Wiley & Sons.

10.    Ternai, B and Markham, K.R. (1976). Carbon-13 NMR Studies of Flavonoids-I : Flavones and Flavonols, Tetrahedron Vol.   32, 565-569.