Complex 2 (103 mg, 0.254 mmol) was dissolved in 10 mL THF and cooled to -30 "C. Benzylmagnesium chloride (1 M in ether, 481 mL, 0.481 mmol) was added, and the solution stirred at room temperature for 2 h. The solvents were removed in vacuo. Complex 4 was recovered by extraction of the residue with toluene. The volatile materials were removed to give 110 mg (88 %) of an orange solid. Analytically pure crystals of 4 can be obtained by vapor diffusion of pentane into a toluene solution of this solid at -30 'C. H NMR (C,D,): 6 = 7.27 (t, J = 7.7 Hz, 4 H, Ar), 7.12 (t. J =7.7 Hz, 4H, Ar). 6.90 (t. J = 7.2 Hz, 2H, Ar), 5.14 (dd, J =7.4 Hz. 2H.

Various branched isomers of 4-nonylphenol (NP) and, in addition, the other 4-alkylphenols (APs) were synthesized and their estrogenic activities were assessed using the yeast two-hybrid system. We investigated the relationships between the structure of the nonyl group of NP isomers and their estrogenic activities based on the following five factors: the length of the main alkyl chain, the degree of branching on the α-carbon, the degree of bulkiness, the position of the branch, and the cyclic structure in the nonyl group. An appropriate length of the main alkyl chain was essential for the estrogenic activity. A small effect of the branching on the α-carbon was observed. The importance of the bulkiness and position of the branch in the nonyl group was suggested from the results of the synthesized NP isomers possessing the high estrogenic activities. The bulkiness on the β-carbon was the most important factor for the high estrogenic activity. The investigation of the cyclic structure also indicated the significance of the bulkiness around the β-carbon. The bulkiness on the γ-carbon was also suggested to be an important factor. The metabolic effect of the synthesized APs on the estrogenic activity was also examined using a liver S9. The estrogenic activities of the selected APs were either reduced or lost. In addition, GC-MS analyses of the commercial NP and synthesized NP isomers revealed that the nine synthesized NP isomers were included in the commercial NP.

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With the increase in the proportion of older people in the population, the development of foods especially suitable for this segment of the population is eagerly expected. We produced a soft, sticky variety of natto that is easy for older people to masticate and to swallow, using a bacterial strain improved by mixed culture. By screening natto bacilli for their ability to make soft Itohiki-natto, we selected the strain Bacillus subtilis (natto) KFP 231, but the stickiness of the natto produced with this strain was very weak. Using a mixed culture of KFP 231 with Micrococcus luteus IAM+*/0, we obtained strain KFP 231++, which produced a soft, sticky natto. At approximately /., times that of KFP 231-natto, the relative viscosity of KFP 231++-natto was close to that of marketed natto. Similarly, the activity of the g-glutamyltranspeptidase of KFP 231 natto was approximately six times that of KFP 231++-natto. Analysis by capillary column gas chromatography detected the ten volatile substances that are responsible for the flavor of natto, showing that the flavor of KFP 231++-natto was similar to that of Japanese Itohiki-natto. Organoleptic tests were conducted on elderly subjects concerning the taste of the new soft, sticky natto at three o$cial centers for the elderly in Chiyodaku, Tokyo. The participants viewed the new soft, sticky natto as being slightly better than their generally held opinion of natto. Consequently, the newly developed soft, sticky natto proved to be a useful food for older people.