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Theoretical and experimental study of aparisthman: A natural product with anti‐ulcer activity
Author(s) -
Brasil D. S. B.,
Moreira R. Y. O.,
Müller A. H.,
Alves C. N.
Publication year - 2006
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.21031
Subject(s) - chemistry , furan , protonation , computational chemistry , basis set , natural product , stereochemistry , density functional theory , organic chemistry , ion
Abstract Aparisthman is a furan diterpenoid with a clerodane skeleton isolated from Aparisthmium cordatum (Juss.) Bail. (Euphorbiaceae). This natural product presents significant anti‐ulcer activity to the level of cimetidine (Tagamet®), a compound used for the treatment of ulcers provoked by stress. The structure of X‐ray diffraction of the aparisthman was compared with theoretical calculations and the results showed that the theory is in accordance with the experimental data. The infrared (IR) and nuclear magnetic resonance (NMR) spectra also were obtained and compared with theoretical calculations. The B3LYP theory level, with the 6‐31G( d,p ) basis set, leads the value to the IR absorption close to the value experimentally observed. NMR theoretical obtained with HF/6‐311+G(2 d,p ) shows little deviation of experimental results. Calculations of molecular electrostatic potential and stabilization energies suggest that the protonation of aparisthman will be able to occur on carbonyl oxygen atom (O4). © 2006 Wiley Periodicals, Inc. Int J Quantum Chem, 2006