Aromatic compound glucosides, alkyl glucoside and glucide from the fruit of anise

From the polar portion of the methanolic extract of the fruit of anise ( Pimpinella anisum L.), which has been used as a spice and medicine since antiquity, four aromatic compound glucosides, an alkyl glucoside and a glucide were isolated together with 24 known compounds. The structures of the new compounds were clarified as ( E)-3-hydroxyanethole β- d-glucopyranoside, ( E)-1′-(2-hydroxy-5-methoxyphenyl)propane β- d-glucopyranoside, 3-hydroxyestragole β- d-glucopyranoside, methyl syringate 4- O-β- d-glucopyranoside, hexane-1,5-diol 1- O-β- d-glucopyranoside and 1-deoxy- l-erythritol 3- O-β- d-glucopyranoside by spectral investigation. ( E)-3-hydroxyanethole β- d-glucopyranoside, ( E)-1′-(2-hydroxy-5-methoxyphenyl)propane β- d-gluco-pyranoside, 3-hydroxyestragole β- d-glucopyranoside, methyl syringate 4- O-β- d-glucopyranoside, hexane-1,5-diol 1- O-β- d-glucopyranoside and 1-deoxy- l-erythritol 3- O-β- d-glucopyranoside were isolated from the fruit of anise.