A new benzofuran from the seeds of Styrax officinalis L.

Abstract

The glycosidic fraction isolated from the seeds of Styrax officinalis L. yielded on acid hydrolysis egonol and a new benzofuran derivative which was formulated as 2-(3.4-dimethoxyphenyl) -5-(3-hydroxypropyl)-7-methoxybenzofuran. EGONOL was isolated by Okadal as an unsaponifiable constituent of the semen-oil of Styrax japonicum Sieb et Zucc; and Kawai et aL2 elucidated its structure and formulated it as 5-(3-hydroxypropyl)-7-methoxy-2-(3,4methylenedioxyphenyl) benzofuran (I).The glycosidic fraction of the seeds of Styrax oficinalis L. yielded after acid hydrolysis and chromatography egonol (I) and two other minor constituents. We describe here the structure elucidation of one of the crystalline minor constituents, for which we propose the formula 2-(3,4-dimethoxyphenyl)-5-(3-hydroxypropyl)-7-methoxybenzofuran (11).The empirical formula C,,H,,05 indicated for compound (11) by analysis was supported by mass spectro-

The Styracaceae

“…Since then, the elucidation of the chemical structure of this saponin has been the subject of a number of investigations (Asahina;Momoya, 1914a, b, Sone, 1934, 1936, Tobinaga, 1958. However, in spite of these intensive studies, no structure could be proposed for this saponin until the years 1967and 1969(Nakano et al, 1967, 1969. The earlier workers (Asahina;Momoya, 1914a, b;Sone, 1934Sone, , 1936Tobinaga, 1958) reported that the acid hydrolysis of jegosaponin yielded 2 equivalents each of glucuronic acid and glucose (Matsunami, 1927) as well as a sapogenin which, on digestion with alkali, was hydrolyzed to tiglic acid and jegosapogenol (46) (Nakano et al, 1967).…”

“…The compounds styraxlignolide B-F (14-18), taraxerol (19), syringin (20) Pastorova et al, 1997;Djerassi et al, 1955;Schroeder, 1968;Reinitzer, 1914Reinitzer, , 1921 Yoshikawa et al, 2000;Nakano et al, 1967aNakano et al, , b, 1969Kitagawa et al, 1974aKitagawa et al, , b, 1975Kitagawa et al, , 1980Sugiyama et al, 1967a, b Segal et al, 1964;Zehavi et al, 1986;Yayla et al, 2002;Anil, 1979 seeds 7-9, 54-59, 66, 67, 72, 124-130 Anil, 2003a, b;Anil, 1980;Segal et al, 1967;Ulubelen et al, 1976 S. paralleloneurum resin Reynolds, 1982;Schroeder, 1968;Reinitzer, 1914Reinitzer, , 1921Huang, 1999;Wang et al, 2006a,b to the control. Therefore the effect of compounds on the expression of type I procollagen, and the MMP-1 proteins (matrix metalloproteinases) in cultured human dermal fi broblasts was examined, and 23 increased the type I procollagen protein expression level by 518.9 18.0%, and decreased the MMP-1 protein expression level signifi cantly by an average of 62.1 8.3 % at 10 M, compared with the vehicle-treated controls cells.…”

Influence of <i>Styrax camporum</i> and of Chemical Markers (Egonol and Homoegonol) on DNA Damage Induced by Mutagens with Different Mechanisms of Action

“…8) EG is an aryl-benzofuran containing a hydroxyl group attached to C3″, which was first isolated from S. japonicum seed oil, 13) while HE is a veratryl analog originally isolated from S. officinalis. 14) Furthermore, EG and HE attracted attention of synthetic organic chemists due their activity against tumor cell lines. [10][11][12][13][14][15] Previous studies from our research group showed the absence of genotoxic activity of the hydroalcoholic extract of S. camporum stems (SCHE) in different tissues examined in Swiss mice; however, the extract reduced genomic and chromosome damage induced by the mutagens methyl methanesulfonate (MMS) and doxorubicin.…”

“…14) Furthermore, EG and HE attracted attention of synthetic organic chemists due their activity against tumor cell lines. [10][11][12][13][14][15] Previous studies from our research group showed the absence of genotoxic activity of the hydroalcoholic extract of S. camporum stems (SCHE) in different tissues examined in Swiss mice; however, the extract reduced genomic and chromosome damage induced by the mutagens methyl methanesulfonate (MMS) and doxorubicin. 7) These data demonstrated promising chemopreventive activity of SCHE.…”

Benzofuran Compositions of Unsaponifiables of Styrax japonica Sieb. Et Zucc

“…Egonol has also been isolated from other Styrax species (S, formosanus , S. obassia and S, americana) and its spectroscopic data were reported2'. From the glycosidic fraction obtained from the seeds of S, of f icinalis, Segal et al 3' isolated egonol and veratryl analogue, which has been indexed as homoegonol (4 )4'. Egonol and demethoxyegonol (1 ) were obtained from the unsaponif iable constituent of the seed oil of Styrax obassia Sieb.…”