title: Synthesis and antioxidant evaluation of (S,S)- and (R,R)-secoisolariciresinol diglucosides (SDGs).
abstract: Secoisolariciresinol diglucosides (SDGs) (S,S)-SDG-1 (major isomer in flaxseed) and (R,R)-SDG-2 (minor isomer in flaxseed) were synthesized from vanillin via secoisolariciresinol (6) and glucosyl donor 7 through a concise route that involved chromatographic separation of diastereomeric diglucoside derivatives (S,S)-8 and (R,R)-9. Synthetic (S,S)-SDG-1 and (R,R)-SDG-2 exhibited potent antioxidant properties (EC50=292.17±27.71 μM and 331.94±21.21 μM, respectively), which compared well with that of natural (S,S)-SDG-1 (EC50=275.24±13.15 μM). These values are significantly lower than those of ascorbic acid (EC50=1129.32±88.79 μM) and α-tocopherol (EC50=944.62±148.00 μM). Compounds (S,S)-SDG-1 and (R,R)-SDG-2 also demonstrated powerful scavenging activities against hydroxyl [natural (S,S)-SDG-1: 3.68±0.27; synthetic (S,S)-SDG-1: 2.09±0.16; synthetic (R,R)-SDG-2: 1.96±0.27], peroxyl [natural (S,S)-SDG-1: 2.55±0.11; synthetic (S,S)-SDG-1: 2.20±0.10; synthetic (R,R)-SDG-2: 3.03±0.04] and DPPH [natural (S,S)-SDG-1: EC50=83.94±2.80 μM; synthetic (S,S)-SDG-1: EC50=157.54±21.30 μM; synthetic (R,R)-SDG-2: EC50=123.63±8.67 μM] radicals. These results confirm previous studies with naturally occurring (S,S)-SDG-1 and establish both (S,S)-SDG-1 and (R,R)-SDG-2 as potent antioxidants and free radical scavengers for potential in vivo use.
authors: Department of Medicine, Pulmonary Allergy and Critical Care Division, University of Pennsylvania Perelman School of Medicine, Philadelphia, PA 19104, USA.
authors: Om P
authors: OP
authors: Mishra
authors: Nicholas
authors: N
authors: Simmons
authors: Sonia
authors: S
authors: Tyagi
authors: Ralph
authors: R
authors: Pietrofesa
authors: Vladimir V
authors: VV
authors: Shuvaev
authors: Roman A
authors: RA
authors: Valiulin
authors: Philipp
authors: P
authors: Heretsch
authors: K C
authors: KC
authors: Nicolaou
authors: Melpo
authors: M
authors: Christofidou-Solomidou
mesh_terms: D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry; D001547:Benzaldehydes / Q000737:chemistry; D002072:Butylene Glycols / Q000138:chemical synthesis* / Q000737:chemistry; D019597:Flax / Q000737:chemistry; D016166:Free Radical Scavengers / Q000737:chemistry*; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D000975:Antioxidants; D001547:Benzaldehydes; D002072:Butylene Glycols; D016166:Free Radical Scavengers; D005960:Glucosides; C100058:vanillin; C090142:secoisolariciresinol diglucoside
keywords: Antioxidant; Flaxseed lignans; Free radical scavenger; ROS; SDG
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