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Xanthones and Xanthone O ‐ β ‐D‐Glucosides from the Roots of Polygala azizsancarii Dönmez
Author(s) -
Çalış İhsan,
Ünlü Ayşe,
Uğurlu Aydın Zübeyde,
Dönmez Ali A.,
Soliman Yusufoğlu Hasan,
Jurt Simon,
Linden Anthony
Publication year - 2022
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.202200499
Subject(s) - xanthone , chemistry , stereocenter , stereochemistry , two dimensional nuclear magnetic resonance spectroscopy , heteronuclear single quantum coherence spectroscopy , moiety , dept , carbon 13 nmr , organic chemistry , enantioselective synthesis , catalysis
Nine xanthone derivatives ( 1 – 9 ) were isolated from the roots of Polygala azizsancarii , which is a narrow endemic species for the flora of Türkiye. Based on all of the evidence, the structures of 1 – 9 were established as two previously undescribed xanthone O ‐glucosides, 3‐ O ‐ β ‐D‐glucopyranosyloxy‐1,6‐dihydroxy‐2,5,7‐trimethoxyxanthone ( 1 ), 3‐ O ‐ β ‐D‐glucopyranosyloxy‐1,6‐dihydroxy‐2,7‐dimethoxyxanthone ( 2 ), and seven previously described xanthones, 1,3,6‐trihydroxy‐2,5,7‐trimethoxyxanthone ( 3 ), 1,3,6‐trihydroxy‐2,7‐dimethoxyxanthone ( 4 ), 1,2,3,4,7‐pentamethoxyxanthone ( 5 ), 1,3‐dihydroxy‐2,5,6,7‐tetramethoxyxanthone ( 6 ), 1,3‐dihydroxy‐4,7‐dimethoxyxanthone ( 7 ), 1,7‐dihydroxy‐3‐methoxyxanthone ( 8 ), and 1,7‐dihydroxy‐2,3‐methylenedioxyxanthone ( 9 ). The structures of the compounds were determined by spectroscopic methods, including 1D‐NMR ( 1 H‐NMR, 13 C‐NMR, DEPT‐135), 2D‐NMR (COSY, NOESY, HSQC, HMBC, INADEQUATE), and HR‐MS. The solid‐state structures of 1 – 4 , including the absolute configurations of the stereogenic carbons of the sugar moiety in 1 and 2 , were established by X‐ray crystal‐structure analyses. For the newly described compounds, the trivial names sancarosides A ( 1 ) and B ( 2 ) are proposed.