Itosides A – I, New Phenolic Glycosides from Itoa orientalis

Eight new benzoylated gentisyl alcohol (=2‐(hydroxymethyl)benzene‐1,4‐diol) glucosides, itosides A–H (1–8), together with the new pyrocatechol (=benzene‐1,2‐diol) glycoside itoside I (9) were isolated from the bark and twigs of Itoa orientalis (Flacourtiaceae). In itosides B–D (2–4), the gentisyl alcohol moiety was esterified by 1‐hydroxy‐6‐oxocyclohex‐2‐ene‐1‐carboxylic acid, while itosides E–H (5–8) contained instead an additional 2‐hydroxybenzoic acid moiety. The compounds were accompanied by the known derivatives 4‐hydroxytremulacin (10), poliothyrsoside (11), poliothyrsin (12), homaloside D (13), tremulacin, and pyrocatechol β‐D‐glucopyranoside. The structures of the new compounds were elucidated by spectral and chemical methods.