Homoisoflavonoids and xanthones from the tubers of wild and in vitro regenerated Ledebouria graminifolia and cytotoxic activities of some of the homoisoflavonoids

COX-2 inhibitory activity of homoisoflavanones and xanthones from the bulbs of the Southern African Ledebouria socialis and Ledebouria ovatifolia (Hyacinthaceae: Hyacinthoideae)

“…Ledebouria ovatifolia (Pohl et al, 2001), scillascillin (Kawasaki et al, 1973), 1,6-dihydroxy-3-methoxy-8-methyl-9H-xanthen-9-one (McMaster et al, 1960;Mutanyatta et al, 2003), (R)-4',5,7-trihydroxy-3'-methoxyspiro{2H-1-benzopyran-3(4H)-9-bicyclo[4.2.0]octa [1,3,5]triene}-4-one (Adinolfi et al, 1985), (R)-3',5,7-trihydroxy-4'-methoxyspiro{2H-1-benzopyran-3(4H)-9-bicyclo[4.2.0]octa [1,3,5]triene}-4-one (Adinolfi et al, 1987), (R)-5,7-dihydroxy-3-(4'-methoxybenzyl)chroman-4-one (Heller et al, 1976), eucomol (Bohler and Tamm, 1967), and (R)-7-hydroxy-3-(4'-hydroxybenzyl)-5-methoxychroman-4-one (Finckh and Tamm, 1970) which had been isolated previously from the Hyacinthaceae, and coniferaldehyde (Seikel et al, 1971) and chondrillasterol (Bergmann and Feeney, 1948) which had not been isolated previously from this family. The ethyl acetate extract yielded one novel homoisoflavanone, ovatifolionone (5), and the known compounds, drimiopsin C (Mulholland et al, 2004), norlichexanthone (Aghoramurthy and Seshadri, 1953;Mutanyatta et al, 2003), 22-acetoxy-15-deoxoeucosterol (Amschler et al, 1997;Pohl et al, 2001), (R)-(3-(3',4'-dihydroxybenzyl)-5,7-dihydroxychroman-4-one (Adinolfi et al, 1987, 4'-demethyl-5-O-methyl-dihydroeucomin (Finckh andTamm, 1970), (R)-3-(3',4'-dihydroxybenzyl)-7-hydroxy-5-methoxychroman-4-one (Adinolfi et al, 1987), and (E)-3-(3',4'-dihydroxybenzylidene)-7-hydroxy-5-methoxychroman-4-one (Masterova et al, 1991) which have all been isolated from the Hyacinthaceae previously and p-anisic aldehyde (Gottlieb et al, 1970) and 4-hydroxyphenylethanol (Gharbo et al, 1970) which have not been reported from this family.…”

“…The ethyl acetate extract yielded one novel homoisoflavanone, ovatifolionone (5), and the known compounds, drimiopsin C (Mulholland et al, 2004), norlichexanthone (Aghoramurthy and Seshadri, 1953;Mutanyatta et al, 2003), 22-acetoxy-15-deoxoeucosterol (Amschler et al, 1997;Pohl et al, 2001), (R)-(3-(3',4'-dihydroxybenzyl)-5,7-dihydroxychroman-4-one (Adinolfi et al, 1987, 4'-demethyl-5-O-methyl-dihydroeucomin (Finckh andTamm, 1970), (R)-3-(3',4'-dihydroxybenzyl)-7-hydroxy-5-methoxychroman-4-one (Adinolfi et al, 1987), and (E)-3-(3',4'-dihydroxybenzylidene)-7-hydroxy-5-methoxychroman-4-one (Masterova et al, 1991) which have all been isolated from the Hyacinthaceae previously and p-anisic aldehyde (Gottlieb et al, 1970) and 4-hydroxyphenylethanol (Gharbo et al, 1970) which have not been reported from this family. The methanol extract also yielded polybotrin (Zou et al, 2007).…”

“…The phytochemistry of several members of Ledebouria have been investigated previously (Pohl et al, 2000(Pohl et al, , 2001Mutanyatta et al, 2003), including both species reported in the current account. The widespread Ledebouria ovatifolia (Bak.)…”

A New Homostilbene and Two New Homoisoflavones from the Bulbs of Scilla scilloides

“…3-(4-hydroxybenzylidene)-5,7-dihydroxychroman-4-one (8), 9) 3-(3,4-dihydroxybenzylidene)-5,7-dihydroxy-6-methoxychroman-4-one (9), 10) scillascillin (10), 11) 2-hydroxy-scillascillin (11), 12) 1,6-dihydroxy-3-methoxy-8-methylxanthone (12), 13) pinoresinol (13), 14) 3-dehydro-15-deoxoeucosterol (14), 4) 15-deoxoeucosterol (15), 4) and 30-hydroxy-15-deoxoeucosterol (16), 4) respectively, based on their physical and spectral data, although 1 H-and 13 C-NMR spectral data in dimethylsulfoxide (DMSO)-d 6 of 5, 7, 8, 11, and 12, and 13 C-NMR data in DMSO-d 6 of 10 have not been reported in the literature (Fig. 1).…”

“…2. Accordingly, 1 was characterized as 3,5,4Ј-trihydroxy-4-methyl-trans-stilbene, which was recently synthesized and named 4-methylresveratrol, 15) H-NMR data of the reported 4-methylresveratrol were similar to those of 1, but its 13 C-NMR data were different from those of 1.…”