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Itosides A – I, New Phenolic Glycosides from Itoa orientalis
Author(s) -
Chai XingYun,
Xu ZhengRen,
Ren HongYan,
Shi HaiMing,
Lu YaNan,
Li FeiFei,
Tu PengFei
Publication year - 2007
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200790225
Subject(s) - chemistry , moiety , hydroxymethyl , glycoside , alcohol , stereochemistry , benzene , diol , organic chemistry , bark (sound) , physics , acoustics
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.