Extraction and Structural Characterization of Flavonoids from Twigs of Sophora japonica

Flavonoids represent a large group of polyphenols that have been recognized to exert a wide range of biological effects, such as anticancer, inflammation inhibition, anti-aging, and neuroprotective activities. In the forest industry, tree twigs have been treated as residues; however, tree twigs could be a rich source of high-value added compounds, which have been relatively unexplored. In this study, an investigation into the chemical constituent of extractives from S. japonica twigs resulted in the isolation of a new (Z)-caffeoyl flavonol glycoside that was elucidated as myricetin 3-O-(4′′-(Z)-caffeoyl)-α-rhamnopyranoside (IV). The structure of the new compound was established mostly on the basis of extensive spectroscopic techniques and other physiochemical evidences. Among the three known flavonoids extracted in this work, including isoquercitrin (I), isorhamnetin 3′-O-β-D-glucopyranoside (II), and myricitrin (III), II and III have never been previously reported in the Sophora genus.

[1]  R. Maronpot,et al.  Genotoxicity evaluation of the flavonoid, myricitrin, and its aglycone, myricetin. , 2015, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[2]  A. Shafaghat,et al.  Luteolin derivatives and antimicrobial activity of Achillea tenuifolia Lam. methanol extract , 2014 .

[3]  T. Shen,et al.  Recovery of Low-molecular Weight Galloyltannins from Agricultural Residue of Juglans sigillata Dode Seed Husks and their Tyrosinase Inhibitory Effect , 2014 .

[4]  Hai-yan Hu,et al.  A new lignan glycoside and phenolics from the branch wood of Pinus banksiana Lambert , 2013 .

[5]  C. Kong,et al.  Antiadipogenic activity of isohamnetin 3-O-β-D-glucopyranoside from Salicornia herbacea , 2012, Immunopharmacology and immunotoxicology.

[6]  S. Kitanaka,et al.  Flavonol acylglycosides from flower of Albizia julibrissin and their inhibitory effects on lipid accumulation in 3T3-L1 cells. , 2012, Chemical & pharmaceutical bulletin.

[7]  Martin M. F. Choi,et al.  In vivo antioxidative effect of isoquercitrin on cadmium-induced oxidative damage to mouse liver and kidney , 2011, Naunyn-Schmiedeberg's Archives of Pharmacology.

[8]  S. Jachak,et al.  Recent developments in anti‐inflammatory natural products , 2009, Medicinal research reviews.

[9]  J. Duan,et al.  Two new isoflavone triglycosides from the small branches of Sophora japonica , 2008, Journal of Asian natural products research.

[10]  C. Jankowski,et al.  Isoquercitrin from Argemone platyceras inhibits carbachol and leukotriene D4-induced contraction in guinea-pig airways. , 2005, European journal of pharmacology.

[11]  Yu-Ping Tang,et al.  A flavonol tetraglycoside from Sophora japonica seeds. , 2003, Phytochemistry.

[12]  N. Semmar,et al.  New flavonol tetraglycosides from Astragalus caprinus. , 2002, Chemical & pharmaceutical bulletin.

[13]  C. Williams,et al.  Advances in Flavonoid Research Since 1992 , 2001 .

[14]  Samir Samman,et al.  Flavonoids—Chemistry, metabolism, cardioprotective effects, and dietary sources , 1996 .

[15]  T. Nakabayashi Isolation of Astragalin and Isoquercitrin from Bracken, Pteridium aquilinum , 1955 .

[16]  B. Konuklugil,et al.  Phytochemical study of Algerian Foeniculum vulgare Mill (Apiaceae) , 2013 .

[17]  Y. Imakura,et al.  Bitter phenyl propanoid glycosides from campsis chinensis , 1985 .