New dimeric and monomeric chromanones,gonytolides D–G,isolated from the fungus Gonytrichum sp.

In the course of the screening of innate immune regulators from natural resources, we isolated new dimeric and monomeric chromanones, gonytolides D–G (4–7), from Gonytrichum sp. along with a known innate immune promoter, gonytolide A (1). The structures of these compounds were determined by spectral analysis, chemical conversion, and biogenetic consideration. The compounds 4–7 were evaluated on the innate immune response, indicating that the 8,8′-linked bischromanone rings were crucial for innate immune-promoting activity.     

Studies on the constituents of Scutellaria species (XXII). Constituents of the roots of Scutellaria amabilis HARA

From the roots of Scutellaria amabilis HARA, eleven new flavonoids, 5,7,2'-trihydroxy-8-methoxyflavone 7-O-beta-D-glucopyranoside, 5,7,2'-trihydroxy-8-methoxyflavone 2'-O-beta-D-glucopyranoside, 5,7-dihydroxy-8,2'-dimethoxyflavone 7-O-beta-D-glucopyranoside, 5,7,2'-trihydroxyflavone 2'-O-beta-D-glucopyranoside, 5,7,2',5'-tetrahydroxyflavone 7-O-beta-D-glucuronopyranoside, (2S)-5,7,2',5'-tetrahydroxyflavanone, (2S)-5,7,2',5'-tetrahydroxyflavanone 7-O-beta-D-glucopyranoside, (2S)-5,7,2',5'-tetrahydroxyflavanone 7-O-beta-D-glucuronopyranoside, (2S)-7,2'-dihydroxy-5-methoxyflavanone 7-O-beta-D-glucuronopyranoside, (I-2S)-I-5,II-5,I-7,II-7,I-2',II-2',II-5'-heptahydroxy-[I-6,II-6']-flavanonylflavone and (I-2S)-I-5,II-5,I-7,II-7,I-2',II-2',I-5',II-5'-octahydroxy-[I-6,II-6']-flavanonylflavone, were isolated, together with ten known flavonoids, wogonin (5,7-dihydroxy-8-methoxyflavone), 5,7-dihydroxy-8,2'-dimethoxyflavone, (2S)-5,7,2'-trihydroxyflavanone, scutevulin (5,7,2'-trihydroxy-8-methoxyflavone), 5,7,4'-trihydroxy-8-methoxyflavone, alpinetin ((2S)-7-hydroxy-5-methoxyflavanone), 5,7,2'-trihydroxyflavone, 5,7,2',5'-tetrahydroxyflavone, (2S)-7,2'-dihydroxy-5-methoxyflavanone and 5,7-dihydroxy-8,2'-dimethoxyflavone 7-O-beta-D-glucuronopyranoside. The structures were determined on the basis of chemical and spectral data.     

Synthesis of poly(lactide‐ran‐MOHEL) and its biodegradation with proteinase K

Homopoly(L ‐lactide) and homopoly(D,L ‐lactide) were almost inert for biodegradation with tricine buffer or normal enzymes such as bromelain, pronase, and cholesterol esterase but biodegradable with proteinase K. Significantly enhanced biodegradation was observed when an optically active (R)‐ or (S)‐3‐methyl‐4‐oxa‐6‐hexanolide (MOHEL) unit was introduced into poly(L ‐lactide) [poly(L ‐LA)] or poly(D,L ‐lactide) [poly(D,L ‐LA)] sequences. Poly[L ‐LA‐ran‐(R)‐MOHEL] in molar ratios of 86/14 to 43/57 showed good biodegradability that was independent of crystallinity. The biodegradation of polymers with proteinase K increased in the following order: poly[D,L ‐LA‐ran‐(R)‐MOHEL] > poly[L ‐LA‐ran‐(R)‐MOHEL] > poly[D,L ‐LA‐ran‐(S)‐MOHEL] > poly[L ‐LA‐ran‐(S)‐MOHEL] > poly(R)‐MOHEL > poly(D,L ‐LA). The number‐average molecular weight, molecular weight distribution, glass‐transition temperature, and melting temperature did not change before and after the biodegradation of poly[L ‐LA‐ran‐(R)‐MOHEL], indicating that the degradation occurred from the polymer surface. © 2001 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 39: 1374–1381, 2001     

Preparation of SnO2 Monolithic Gel by Sol-Gel Method

The effects of aging of a wet gel at room temperature and a use of a drying control chemical additive (DCCA) were investigated on the prevention of cracking of the gel during drying. N,N-Dimethylformamide (DMF) having low surface tension was used as a DCCA in this study. Before drying, the aged wet gel was immersed in DMF for several days to replace the pore liquid in the wet gel with DMF.The longer the aging and DMF immersing times became, a fewer cracks generated during drying. Especially, the immersion in DMF for over 8 days made it possible to obtain the SnO₂ gel monolith without cracking from the wet gel aged for short time (1 day). However, the wet gel aged for long time without immersing in DMF could not be dried without cracking. Therefore, the replacement of the pore liquid in the wet gel with DMF having low surface tension is thought to be more effective on avoiding a crack generation than aging. From a pore size distribution measurement by N₂ gas adsorption, it was found that the pore size and the breadth of the pore size distribution of the dried gel became larger and narrower respectively with increasing DMF immersing time. DMF is thought to be capable of forming strong hydrogen bonding to hydroxyl groups remaining on the surface of the wet gel and providing a shielding cage around the reactants (Sn–OH), thus further condensation reaction is probably suppressed. Consequently, a large pore distribution is developed in the gel, which reduces the magnitude of capillary stress induced during drying.