IJUP08 - Universidade do Porto

5-(Hydroxymethyl)-2-furfural, a natural compound isolated from
Strophioblachia fimbricalyx Boerl. (Euphorbiaceae)
K.C. Marques 1 , A.E. Oliveira 1 , A.P. Almeida 1,2 , H. Cidade 1,2 , A. Kijjoa 3,4 and
M.S.J. Nascimento 2,5
1 Department of Organic Chemistry, Faculty of Pharmacy, University of Porto, Portugal.
2 Research Centre of Organic Chemistry, Phytochemistry and Pharmacology of the University of
Porto (CEQOFFUP), Faculty of Pharmacy, University of Porto, Portugal.
3 Department of Chemistry, Institute of Biomedical Sciences Abel Salazar (ICBAS), University of
Porto, Portugal.
4 Centre of Marine and Environmental Research (CIIMAR), University of Porto, Portugal.
5 Department of Microbiology, Faculty of Pharmacy, University of Porto, Portugal.
Strophioblachia fimbricalyx Boerl. (Euphorbiaceae) is a small shrub up to 1.5 m high
native in northeast Thailand. Megastigmanes and flavone glycosides were isolated from the
aerial parts of this species [1]. As a part of continuing search for novel bioactive
substances, we are investigating the chemical composition of roots of S. fimbricalyx Boerl.,
that were collected on Prachuab Kirikan Province (Thailand). The extract purification led
to the isolation of 5-(hydroxymethyl)-2-furfural (Fig. 1), a known substance with
antitumoral activity [2]. The structure determination was based on spectroscopic data ( 1 H
NMR, 13 C NMR, HSQC and HMBC) and was according with the literature [3]. To the best
of our knowledge this is the first report of 5-(hydroxymethyl)-2-furfural in this species.
References:
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Fig. 1 – Structure of 5-(hydroxymethyl)-2-furfural
[1] Kaewkrud, W., Otsuka, H., Ruchirawat, S. and Kanchanapoom, T. (2008), Megastigmane and
Flavone Glycosides from Strophioblachia fimbricalyx Boerl., Journal of Natural Medicines, 62 (1),
124-125.
[2] Michail, K., Matzi, V., Maier, A., Herwig, R., Greilberger, J., Juan, H., Kunert, O. and
Wintersteiger, R. (2007), Hydroxymethylfurfural: An Enemy or a Friendly Xenobiotic? A
Bioanalytical Approach, Analytical and Bioanalytical Chemistry, 387 (8), 2801-2814.
[3] Mizushina, Y., Yagita, E., Kuramochi, K., Kuriyama, I., Shimazaki, N., Koiwai, O., Uchiyama,
Y., Yomezawa, Y., Sugawara, F., Kobayashi, S., Sakaguchi, K. and Yoshida, H. (2006), 5-
(Hydroxymethyl)-2-furfural: A Selective Inhibitor of DNA Polymerase λ and Terminal
Deoxynucleotidyltransferase, Archives of Biochemistry and Biophysics, 446 (1), 69-76.
Acknowledgements: FCT (I&D, nº226/94), FEDER, POCI, U. Porto, and Caixa Geral de Depósitos
for financial support.
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