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Characterization of diterpene crystals C20H28O4 by FT-Raman

and FT-IR spectroscopies and Density Functional Theory (DFT)


calculations
XXXIV ENFMC
1 .
Gusmão, G.O.M ; Silva, C.B. ; Freire, P.T.C. ; Santos, H.S. ; Rodrigues, A.S. ; Teixeira,
1 1 2 2
URCA

A.M.R. ; Sampaio, G.M.M. ; Bento, R.R.F.


3 3 4
1
Departamento de Física, Universidade Federal do Ceará; 2Coordenação do Curso de Química, Universidade Estadual Vale do Acaraú – UVA;
3
Departamentos de Física, Universidade Regional do Cariri – URCA; 4Departamento de Física, Universidade Federal do Mato Grosso -UFMT
*e-mail: amrteixeira@gmail.com
Assignment for vibrational modes of diterpene C20H28O4
Introdution
Diterpenes form the basis for biologically important compounds. The tetracyclic
diterpenoids, i.e., phyllocladanes and kauranes, have been recognized as biomarkers of
higher plants [1]. Importantly, derivatives of these compounds, known e.g., from present day
plants, exhibit interesting biological properties, including anti-viral, anti-microbial, anti-
parasitic, anti-fungal, insect anti-feedant, anti-HIV, anti-fertility, anti-inflammatory and anti-
cancer activities [2-5].
The present work reports a study of the characterization of diterpene crystals C20H28O4 by
performed through Fourier Transform infra red and Fourier Transform Raman
spectroscopies as well as Density Functional Theory (DFT) calculations.
The FT-IR and FT-Raman spectra of the crystal were recorded at room temperature in the
regions 400 cm-1 to 4000 cm-1 and 50 cm-1 to 4000 cm-1, respectively.
We did calculations of first principles using the Gaussian 98 programme package [6] with
the intention of to classify and to analyze the vibrations molecular produced by the
technique of FT-Raman and FT-IR spectroscopy.

Experimental and Computational details

 FT-Raman spectrum was taken using a Bruker RFS100/S FTR system and a D418-T
detector, with the sample excited by means of the 1064 nm line of a Nd:YAG laser. Infra red
spectrum was obtained by using an Equinox/55 (Bruker) Fourier Transformed Infra red
(FTIR) spectrometer.
 The normal modes of vibrations were obtained using Density Functional Theory
(DFT) with B3LYP functional and 6-31 G(d,p) basis set.
 Frequency calculations are valid only at stationary points on the potential energy surface.
We want a minimum generally, because the equilibrium structure for the lowest energy
conformation of ours molecule is a minimum.Thus, frequency calculations must be
performed on optimized structures.
Selected representations of atomic vibrations of C20H28O4
DITERPENOIDS

ωcalc=112 cm-1
ωcalc=1490 cm -1 ωcalc=1814 cm-1

Retinal (vitamin A) Kaurane-type diterpene


Conclusions
New Kaurane-type diterpene We conclude that Croton argyrophylloides Mull. Arg.. belongs to a fairly large group of
kaurenoic acid (C20H30O2) (C20H28O4) Brazilian Euphorbiaceae species which produce kaurane-type diterpene.
The IR spectrum showed absorption bands suggesting the presence of hydroxyl at 3415
cm-1 and carbonyl groups at 1713 cm-1 and 1725 cm-1.
A new kaurene-type diterpene from the stems of Croton argyrophylloides Mull. Arg..
Vibrations type-rocking are characteristic mainly in range 660 cm−1 < ωcalc < 1244 cm−1.
In the range 1326 cm−1 < ωcalc < 1442 cm−1 are observed vibrations type-wagging.
A new kaurane-type diterpene of molecular structure C20H28O4 was assigned as rel
 Vibrations type-scissoring of CH2 and CH3 are characteristic mainly in range 1436 cm−1 <
(1S,4aS,7S,8aS) -7-(1-vinyl)-tetradecahydro-1,4a dimethylphenanthrene-7,8a-
carbolactone-1-carboxylic acid [7]. ωcalc < 1536 cm−1.
For organic crystals the region about 3000 cm-1, contains the bands originated from
stretching of C-H, CH2, CH3, and N-H vibrations.
The calculated results were observed to reproduce the experiments with good
agreement. This agreement allowed us to assign the normal modes present in the FT-IR
and FT-Raman spectra of the dipertene crystal C20H28O4, characterizing, in this way, a
potential drug to be exploited by pharmaceutical industry.
References
[1] Simoneit, B.R.T.A review of current applications of mass spectrometry for
biomarker/molecular tracer elucidations. Mass Spectrometry Reviews 24, (2005) 719–
765
[2] Ghisalberti, E.L. The biological activity of naturally occurring kaurane diterpenes.
Fitoterapia LXVIII, (1997) 303–325.
[3] Kondoh, M., et al. Kaurene diterpene induces apoptosis in human leukemia cells partly
FT-Raman and FT-IR Spectra of crystal C20H28O4 through a Caspase-8-dependent pathway. Journal of Pharmacology and Experimental
Therapeutics 311, (2004) 115–122
[4] Boeck, P., et al. A simple synthesis of kaurenoic esters and other derivatives and
evaluation of their antifungal activity. Journal of the Brazilian Chemical Society 16
( 2005)1360–1366.
[5] Peria, F. M., et al. Journal of Clinical Oncology, 2010 ASCO Annual Meeting
Proceedings (Post-Meeting Edition).Vol 28, No 15 suppl (May 20 Supplement), 2010:
e13641.
[6] Frisch M. J., et al. Gaussian 98 (Revision A.11.2), Gaussian, Inc., Pittsburgh PA, 2001
[7]Santos, S. S., et al. J. Nat. Prod. 72 (2009) 1884.

Acknowledgments

UFC UFMT UVA

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