Abstract

MARTINEZ, Miguel et al. DETERMINATION OF AN ACTIVE PRINCIPLE OF POLYGONUM PUNCTATUM ELUOT; FULL NMR SPECTRA OF STIGMAST-5-EN-3P-OL (500/125 MHz). Rev. Bol. Quim [online]. 2017, vol.34, n.1, pp.14-27. ISSN 0250-5460.

ABSTRACT The aim of this report is to provide full NMR spectra (^:H 500 MHz, ¹³C 125.8 MHz) of stigmast-5-en-3/?-ol (1), whose other common ñames are: /f-sitosterol, /f-sitosterin, 22,23-dihydrostigmasterol, and IUPAC ñame: 17-(5-ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,ll,12,14,15,16,17-dodecahydro-l-cyclopenta[a]phenanthren-3-ol., and IUPAC ñame: The spectra set includes HMBC, HSQC and COSY studies. ROESY or NOESY studies were excluded. Compound 1 is found to be the major component of the alcoholic extract of roots of Polygonum punctatum (Polygonaceae), a macrophyte native species of Paraguay with varied therapeutic applications like anti-inflammatory among others. Compound 1 was extracted by maceration in EtOH 96° and it was isolated by using chromatographic techniques. A bibliographic research allowed to establish a correlation between traditional medicine information of anti-inflammatory property of P. punctatum and the isolated compound 1 for which a series of reports about its pharmacological properties permitted to affirm that 1, being the major secondary metabolite in the alcoholic extract of roots, is one of the active principies of the plant, namely the anti-inflammatory principie. The spectroscopic work and the structural elucidation permitted the identification of compound 1 as /f-sitosterol. The bibliographic research allowed to label /f-sitosterol (1) as a new compound in the species P. punctatum for which only polygodial, a potent antifungal sesquiterpene, was previously described. With the present reporting of compound 1 in P. punctatum, the total number of secondary metabolites and active principies thus far described in the species reaches the cipher of two (according to the newest bibliographic review on the chemical content of the Polygonum genus, 2014).

Keywords : Stigmast-5-en-3-ol; Sitosterol; Polygonum punctatum Elliott; Polygonaceae; Roots; Anti-inflammatory; NMR spectra; 500 MHz.

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