Aromatic annelation with .ALPHA.-phenylsulfinyl-.GAMMA.-butyrolactones. A novel route to 4-(2-hydroxyalkyl)-1,3-benzenediols.

Inhibition of tyrosinase activity and melanine pigmentation by 2-hydroxytyrosol

“…In our screening for tyrosinase inhibitors of microbial origin using mushroom tyrosinase, 2-HT was isolated and identified from the fungal culture broth. Although 2-HT was originally reported as a synthetic compound 13 , we showed for the first time that 2-HT is also a fungal metabolite. Furthermore, 2-HT was found to inhibit tyrosinase in this study.…”

“…From the spectral data including 1 H NMR, 13 C NMR, and MS, and the search results of SciFinder Scholar, 2-HT was identified to be the same as the known synthetic compound 4-(2-hydroxyethyl)-1,3-benzenediol ( Fig. 1 ) 13 . In this study, 2-HT was named as 2-hydroxytyrosol.…”

“…OB-0098. 2-HT was originally reported to be a synthetic compound 13 , but its biological activity has not been reported. In this study, tyrosinase inhibitory activities and melanin formation in mouse B16 melanoma cells of 2-HT were described.…”

New Isoflavones and Pterocarpane with Hepatoprotective Activity from the Stems ofErycibe expansa

“…int.) = 400 (M + , 11), 341 (14), 325 (15), 311 (100), 299 (14), 281 (10), 179 (6). MTPA esters (1b, 2b) and (S)-MTPA esters (1c, 2c) from 1a and 2a A solution of 1a or 2a (both 1.0 mg) in CH 2 Cl 2 (1.0 mL) was treated with (R)-a-methoxy-a-trifluoromethylphenylacetic acid [(R)-MTPA, 10.0 mg] in the presence of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC´HCl, 8.0 mg) and 4-dimethylaminopyridine (4-DMAP, 3.0 mg), and the mixture was stirred at room temperature for 12 h. The reaction mixture was poured into ice-water and the whole was extracted with EtOAc.…”

“…int.) = 336 (M + , 18), 321 (100), 203(19), 161(12), 152 (5), 118 (3); IR, UV, and 1 H-NMR data, see[13].Medicarpin(14): Colorless crystals; EI-MS: m/z (rel. int.)…”