Metabolites of 7-O-methyl-luteone from Botrytis cinerea.

Abstract

An antifungal isoflavone 7-0-methyl-luteone [5, 2', 4'-trihydroxy-7-methoxy-6-(3, 3-dimethylallyl) isoflavone, 2] was metabolized in cultures of Botrytis cinerea. The substrate was transformed into dihydropyrano-isoflavone [(+)-3] and 2, 3-dihydrodihydroxyprenyl-isoflavone [(-) (2S)-5] as major metabolites. A small quantity of dihydrofurano-isoflavone (4) was also yielded. However the initial intention to detecting a possible metabolic intermediate, 7-O-methyl-luteone epoxide, from 2 to 3-5 was unsuccessful.

Structures of Two New Flavonoids and Effects of Licorice Phenolics on Vancomycin-Resistant Enterococcus Species

“…The licorice phenolics (Figures 1 and 2) were isolated from the ethyl acetate extract in the following way: the extract was subjected to countercurrent distribution with CHCl 3 -CH 3 OH-H 2 O, and the less polar fractions were respectively chromatographed on silica gel, ODS-gel, and MCI-gel CHP-20P, to give licoricidin (1) [16], allolicoisoflavone B (2) [17], 3'-(γ,γ-dimethylallyl)-kievitone (3) [18], 7-O-methylluteone (4) [19], kaempferol 3-O-methyl ether (5) [20], and kaempferol (6) [21], and fractions containing phenolics. Those fractions were purified by preparative TLC on silica gel or by preparative HPLC to give isolicoflavonol (7) [22], isoglycycoumarin (8) [23], licoarylcoumarin (9) [24], formononetin (10) [25], and 6"-O-acetylliquiritin (11) [26].…”

“…Those fractions were purified by preparative TLC on silica gel or by preparative HPLC to give isolicoflavonol (7) [22], isoglycycoumarin (8) [23], licoarylcoumarin (9) [24], formononetin (10) [25], and 6"-O-acetylliquiritin (11) [26]. On the other hand, the remaining part of the ethyl acetate fraction was directly subjected to column chromatography on ODS-gel, and fractions from the column were further purified by column chromatography on MCI-gel CHP-20P, and by preparative HPLC or preparative TLC, to give liquiritin (12) [27], p-hydroxybenzoic acid (13), semilicoisoflavone B (14) [28], glycyrol (15) [29], glycyrin (16) [29], gancaonin I (17) [30], isoglycyrol (18) [31], liquiritigenin (19) [27], gancaonin G (20) [36], glicoricone (25) [37], glycycoumarin (26) [38], licocoumarone (27) [29], licoricone (28) [39], glyasperin D (29) [40], isoangustone A (30) [41], and two additional compounds temporarily named compounds A (31), and B (32). Since several phenolics from licorice display potent antibacterial effects against methicillin-resistant Staphylococcus aureus (MRSA), and also show suppressing effects on the oxacillin resistance of MRSA, as we have reported previously [11], we have also investigated the effect of these licorice phenolics on VRE.…”

Structures of New Phenolics Isolated from Licorice, and the Effectiveness of Licorice Phenolics on Vancomycin-Resistant Enterococci

“…A part of the EtOAc extract obtained from powdered licorice was subjected to column chromatography on ODS-gel and eluted with increasing concentrations of MeOH in H 2 O and then with increasing concentrations of CHCl 3 in MeOH. The eluate with 50% CHCl 3 in MeOH was subjected to column chromatography on MCI-gel CHP-20P with increasing concentrations of MeOH in H 2 O. Fractions from the column were purified by preparative HPLC, to give 16 licorice phenolics, including licoricidin ( 2 ) [18], 7- O -methylluteone ( 3 ) [19], glyasperin J trimethyl ether ( 4 ) [20], 3'-(γ,γ-dimethylallyl)-kievitone ( 5 ) [21], isoangustone A ( 6 ) [22], glyasperin J ( 7 ) [20], compound A ( 8 ), licoriphenone ( 9 ) [23], demethylhomopterocarpan ( 10 ) [24], glycyrrhisofavone ( 11 ) [25], licopyranocoumarin ( 12 ) [26], glyasperin C ( 13 ) [27], compound B ( 14 ), glycyrrhiza-isofavone B ( 15 ) [28], glycybenzofuran ( 16 ) [29], and 8-(γ,γ-dimethylallyl)-wighteone ( 17 ) [30] from the respective fractions. The structures of 2 – 7 , 9 – 13 , and 15 – 17 (Figure 1) were identified by comparisons of spectral data with values reported in the literature [18,19,20,21,22,23,24,25,26,27,28,29,30], whereas the two arylbenzofurans, temporarily named compounds A ( 8 ) and B ( 14 ) (Figure 1), are new, and their structure elucidations are described below.…”

Prenylated Isoflavonoids: Botanical Distribution, Structures, Biological Activities and Biotechnological Studies. An Update (1995 – 2006)

“…Also the biotransormation studies of the prenyl side chain of isoflavonoids are not rich of examples, after the outstanding results of the investigation prior to 1995, including the conversion of 7-O-methylluteone (158) into the corresponding dihydropyrano derivative (159) in cell cultures of Botrytis cinerea [219].…”