Synthesis and antioxidant activity of a novel class of fluorescein-based β-C-glycosides

被引:11
作者
Rajasekar, Mani [1 ]
Das, Thangamuthu Mohan [1 ,2 ]
机构
[1] Univ Madras, Dept Organ Chem, Madras 600025, Tamil Nadu, India
[2] CUTN, Sch Basic & Appl Sci, Dept Chem, Thiruvarur 610004, India
关键词
Fluorescein derivatives; beta-C-glycosides; Aldol condensation; Antioxidant activity; CONDENSATION; ANALOG;
D O I
10.1016/j.carres.2013.06.016
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A series of fluorescein-based beta-C-glycosyl ketones were synthesized through aldol condensation of beta-C-glycosyl ketones with fluorescein monoaldehyde under ambient reaction conditions in good yields. Formation of the expected product has been confirmed through different spectral techniques. Fluorescein-based beta-C-glycosides show moderate anti-oxidant activities with maximum inhibitory activity of 60%. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:38 / 42
页数:5
相关论文
共 37 条
[1]   Effect of antioxidant oxidation potential in the oxygen radical absorption capacity (ORAC) assay [J].
Bisby, Roger H. ;
Brooke, Rachel ;
Navaratnam, Suppiah .
FOOD CHEMISTRY, 2008, 108 (03) :1002-1007
[2]   Aldol reaction of β-C-glycosylic ketones:: synthesis of C-(E)-cinnamoyl glycosylic compounds as precursors for new biologically active C-glycosides [J].
Bisht, Surendra Singh ;
Pandey, Jyoti ;
Sharma, Anindra ;
Tripathi, Rama Pati .
CARBOHYDRATE RESEARCH, 2008, 343 (09) :1399-1406
[3]   One-step synthesis of β-C-glycosidic ketones in aqueous media:: The case of 2-acetamido sugars [J].
Bragnier, N ;
Scherrmann, MC .
SYNTHESIS-STUTTGART, 2005, (05) :814-818
[4]   SGLT2 inhibition - a novel strategy for diabetes treatment [J].
Chao, Edward C. ;
Henry, Robert R. .
NATURE REVIEWS DRUG DISCOVERY, 2010, 9 (07) :551-559
[5]   A tandem Aldol condensation/dehydration co-catalyzed by acylase and N-heterocyclic compounds in organic media [J].
Chen, Xiang ;
Liu, Bo-Kai ;
Kang, Hong ;
Lin, Xian-Fu .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2011, 68 (01) :71-76
[6]   A thiol-specific fluorescent probe and its application for bioimaging [J].
Chen, Xiaoqiang ;
Ko, Sung-Kyun ;
Kim, Min Jung ;
Shin, Injae ;
Yoon, Juyoung .
CHEMICAL COMMUNICATIONS, 2010, 46 (16) :2751-2753
[7]   Enrichment and Purification of Total Flavonoid C-Glycosides from Abrus mollis Extracts with Macroporous Resins [J].
Du, Huibin ;
Wang, Hao ;
Yu, Jia ;
Liang, Chunyi ;
Ye, Wencai ;
Li, Ping .
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2012, 51 (21) :7349-7354
[8]   Application of butenonyl-C-glucosides in the synthesis of pyrazolinyl-, aminopyrimidinyl- and biphenyl methyl-β-D-C-glucopyranosides [J].
Fatima, Seerat ;
Pandey, Vivek Parashar ;
Bisht, Surendra Singh ;
Tripathi, Rama P. .
MOLECULAR DIVERSITY, 2011, 15 (03) :759-768
[9]   Stereo- and regioselective glycosylations to the Bis-C-arylglycoside of kidamycin [J].
Fei, ZhongBo ;
McDonald, Frank E. .
ORGANIC LETTERS, 2007, 9 (18) :3547-3550
[10]   Concise total synthesis of flavone C-glycoside having potent anti-inflammatory activity [J].
Furuta, T ;
Kimura, T ;
Kondo, S ;
Mihara, H ;
Wakimoto, T ;
Nukaya, H ;
Tsuji, K ;
Tanaka, K .
TETRAHEDRON, 2004, 60 (42) :9375-9379