A new cis-p-coumaroyl flavonol glycoside from the inner barks of Sophora japonica L.

Abstract Tree barks could be a rich source of novel bioactive compounds, which are not well explored. In this work, the chemical constituent investigation of extractives from the inner barks of Sophora japonica L. (Leguminosae) led to the isolation of a new cis-p-coumaroyl flavonol glycoside, which was elucidated as kaempferol 3-O-(4″-cis-p-coumaroyl)-α-rhamnopyranoside (IV). The structure of the new compound was established mainly based on extensive spectroscopic techniques. In addition, among the four known phenolics purified in this study, including three flavonol glycosides [rutin (I), kaempferol-3-O-(6″-galloyl)-β-glucopyranoside (II), and quercitrin (V)], as well as a phenolic acid [trans-ferulic acid (III)], compounds II and III have never been reported in S. japonica previously.

[1]  Liangliang An,et al.  Isolation and Structure Elucidation of a New Flavonol Glycoside from Sophora japonica , 2016, Chemistry of Natural Compounds.

[2]  A. Ugur,et al.  Antimicrobial, antioxidant, antimutagenic activities, and phenolic compounds of Iris germanica☆☆☆ , 2014 .

[3]  R. Sahane,et al.  Evaluation of wound healing activity of ferulic acid in diabetic rats , 2014, International wound journal.

[4]  M. Monjo,et al.  Identification of quercitrin as a potential therapeutic agent for periodontal applications. , 2014, Journal of periodontology.

[5]  I. Krasnyuk,et al.  Mechanisms of Rutin Pharmacological Action (Review) , 2014, Pharmaceutical Chemistry Journal.

[6]  Mi Ae Kim,et al.  Phytoestrogenic activity of Aceriphyllum rossii and rapid identification of phytoestrogens by LC–NMR/MS and bioassay-guided isolation , 2014, European Food Research and Technology.

[7]  A. Cavalheiro,et al.  A new flavonoid derivative from leaves of Oxandra Sessiliflora R. E. Fries , 2014 .

[8]  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 .

[9]  N. Baek,et al.  Iridoids from the stems of Viburnum erosum , 2014 .

[10]  B. Hinterstoisser,et al.  Extractives of mechanically wounded wood and knots in beech , 2014 .

[11]  H. Häggman,et al.  Condensed conifer tannins as antifungal agents in liquid culture , 2013 .

[12]  Tae-Il Jeon,et al.  Coumaroyl quinic acid derivatives and flavonoids from immature pear (Pyrus pyrifolia nakai) fruit , 2013, Food Science and Biotechnology.

[13]  Jie-li Lv,et al.  Japonicasins A and B, two new isoprenylated flavanones from Sophora japonica. , 2013, Fitoterapia.

[14]  Carlos M. Silva,et al.  Lipophilic extractives from the bark of Eucalyptus grandis x globulus, a rich source of methyl morolate: Selective extraction with supercritical CO2 , 2013 .

[15]  Walaa El-Kashak,et al.  Secondary metabolites and bioactivities of Albizia anthelmintica , 2013, Pharmacognosy research.

[16]  P. Saranpää,et al.  Root neck of Norway spruce as a source of bioactive lignans and stilbenes , 2013 .

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

[18]  A. Rabello,et al.  Chemical constituents and leishmanicidal activity from leaves of Kielmeyera variabilis , 2012 .

[19]  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.

[20]  N. Baek,et al.  New diarylpropanoids from Lindera glauca Bl. heartwood , 2012 .

[21]  K. E. Malterud,et al.  Bioactive polyphenols in Ximenia americana and the traditional use among Malian healers. , 2012, Journal of ethnopharmacology.

[22]  Jez Willian Batista Braga,et al.  Assessment of total phenols and extractives of mahogany wood by near infrared spectroscopy (NIRS) , 2012 .

[23]  M. Ek,et al.  Analysis of lignin and extractives in the oak wood of the 17th century warship Vasa , 2014 .

[24]  P. Eklund,et al.  Chemical characterization of polymerized products formed in the reactions of matairesinol and pinoresinol with the stable radical 2,2-diphenyl-1-picrylhydrazyl , 2012 .

[25]  M. Helander,et al.  Characterization of phenolic compounds from inner bark of Betula pendula , 2012 .

[26]  Hao Li,et al.  Preparative isolation and purification of senkyunolide-I, senkyunolide-H and ferulic acid from Rhizoma Chuanxiong using counter-current chromatography. , 2011, Journal of separation science.

[27]  S. Tian,et al.  Isolation and identification of phenolic compounds from Gynura divaricata leaves , 2011, Pharmacognosy magazine.

[28]  Myong-Jo Kim,et al.  A new isoflavone glycoside from the stem bark of Sophora japonica , 2010, Archives of pharmacal research.

[29]  Sang-Un Choi,et al.  A new phenylpropane glycoside from the rhizome of Sparganium stoloniferum , 2010, Archives of pharmacal research.

[30]  Shu‐Ming Li,et al.  Phenolic Compounds in the Leaves of Populus ussuriensis and their Antioxidant Activities , 2009, Planta medica.

[31]  Y. Dai,et al.  TG-DTG as an effective method for the characterization of rutin extracted from the buds of Sophora japonica L. , 2009 .

[32]  H. Yun-Choi,et al.  Anti-platelet effects of flavonoids and flavonoid-glycosides from Sophora japonica , 2008, Archives of pharmacal research.

[33]  Y. Bae,et al.  Structure elucidation of phenylethanoid glycosides from Paulownia tomentosa Steud. var. tomentosa wood , 2008 .

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

[35]  A. Morel,et al.  Quercitrin, a glycoside form of quercetin, prevents lipid peroxidation in vitro , 2006, Brain Research.

[36]  R. Nicholson,et al.  Phenolic Compound Biochemistry , 2006 .

[37]  M. De Leo,et al.  Phenolic compounds from Baseonema acuminatum leaves: isolation and antimicrobial activity. , 2004, Planta medica.

[38]  T. Tsuno,et al.  Antioxidant activity and hypoglycemic effect of ferulic acid in STZ‐induced diabetic mice and KK‐Ay mice , 2004, BioFactors.

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

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

[41]  J. Cavaleiro,et al.  Lipophilic Extractives of the Inner and Outer Barks of Eucalyptus globulus , 2002 .

[42]  Xiangjun Li,et al.  Separation and determination of rutin and quercetin in the flowers ofSophora japonica L. by capillary electrophoresis with electrochemical detection , 2002 .

[43]  D. Choi,et al.  Extractives from the Bark of Sophora japonica , 2002 .

[44]  Y. Tang,et al.  Four new isoflavone triglycosides from Sophora japonica. , 2001, Journal of natural products.

[45]  T. Mason,et al.  The extraction of rutin from flower buds of Sophora japonica. , 2001, Ultrasonics sonochemistry.

[46]  A. Zarzuelo,et al.  Antidiarrhoeic activity of quercitrin in mice and rats , 1993, The Journal of pharmacy and pharmacology.

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