Flavone Glycosides from the Aerial Parts of Stachys lavandulifolia Vahl

Background: Stachys lavandulifolia Vahl is an herbaceous perennial plant which its flowering aerial parts are used traditionally as gastrotonic, spasmolytic, sedative and for the treatment of gastrointestinal disorders. In the present study the aerial parts of this medicinal plant was investigated for its flavonoid glycosides content. Methods: n-butanol fraction derived from hydroalcoholic extract of S. lavandulifolia was subjected to phytochemical analysis using chromatography on Sephadex LH-20 and RP-18 silica gel columns. The structures of isolated compounds were identified using 1H-NMR, 13C-NMR and UV spectral analysis. Results: Four flavone glycosides, chrysoeriol-7-O-β-D-glucopyranoside (1), apigenin-7-O-(6″-O-acetyl)-β-D-glucopyranoside (2), luteolin-7-O-β-D-glucopyranoside (3), apigenin-7-O-β-D-glucopyranoside (4), along with apigenin (5) and chlorogenic acid (6) were isolated from S. lavandulifolia aerial parts. Conclusion: Identification of these phenolic compounds with some known biological activities in S. lavandulifolia explains some medicinal properties reported for this species and make scientific rationale for its traditional uses.

[1]  P. Saiyarsarai,et al.  Cytotoxic Flavonoids from the Aerial Parts of Stachys lavandulifolia Vahl , 2018, Pharmaceutical Sciences.

[2]  Jong-Choon Kim,et al.  Beneficial Effects of Cynaroside on Cisplatin-Induced Kidney Injury In Vitro and In Vivo , 2018, Toxicological research.

[3]  M. Rabbani,et al.  Bioactivity guided isolation of apigenin from Stachys lavandulifolia Vahl. in mice with anxiolytic effects , 2018 .

[4]  P. Enck,et al.  The potential effects of chlorogenic acid, the main phenolic components in coffee, on health: a comprehensive review of the literature , 2017, European Journal of Nutrition.

[5]  M. Rabbani,et al.  Isolation and Identification of Secondary Metabolites from the Aerial Parts of Stachys lavandulifolia Vahl. , 2017, Iranian journal of pharmaceutical research : IJPR.

[6]  S. A. H. Goli,et al.  Evaluation of antioxidant activity, total phenolics, total flavonoids and LC–MS/MS characterisation of phenolic constituents in Stachys lavandulifolia , 2017, Natural product research.

[7]  A. Alshatwi,et al.  Experimental study on gastroprotective efficacy and mechanisms of luteolin-7-O-glucoside isolated from Ophiorrhiza mungos Linn. in different experimental models , 2016 .

[8]  M. Serafini,et al.  Phytochemical Study of a Species with Ethnopharmacological Interest: Sideritis romana L. , 2016 .

[9]  A. Delazar,et al.  Phenolic Derivatives of Artemisia Spicigera C. Koch Growing in Iran , 2015, Iranian journal of pharmaceutical research : IJPR.

[10]  Z. A. Bhat,et al.  Apigenin 7-glucoside from Stachys tibetica Vatke and its anxiolytic effect in rats. , 2014, Phytomedicine : international journal of phytotherapy and phytopharmacology.

[11]  M. Bonesi,et al.  Tyrosinase , Acetyl-and Butyryl-Cholinesterase Inhibitory Activity of Stachys lavandulifolia Vahl ( Lamiaceae ) and Its Major Constituents , 2014 .

[12]  C. Park,et al.  Luteolin and luteolin-7-O-glucoside inhibit lipopolysaccharide-induced inflammatory responses through modulation of NF-κB/AP-1/PI3K-Akt signaling cascades in RAW 264.7 cells , 2013, Nutrition research and practice.

[13]  M. Bozorgmanesh,et al.  Phytotherapeutic Management of Polycystic Ovary Syndrome: Role of Aerial Parts of Wood Betony (Stachys lavandulifolia) , 2013, Phytotherapy research : PTR.

[14]  F. Satıl,et al.  Traditional uses of medicinal plants in Solhan (Bingöl-Turkey). , 2013, Journal of ethnopharmacology.

[15]  M. Abdollahi,et al.  Anti-Oxidative Stress Activity of Stachys lavandulifolia Aqueous Extract in Human , 2013, Cell journal.

[16]  L. Jafarzadeh,et al.  Teratogenic effects of hydroalcoholic extract of Stachys lavandulifolia Vahl on the skeletal system and fetal growth in Balb/c mice , 2012 .

[17]  B. Demirci,et al.  Antimicrobial and Antioxidant Activities of Stachys lavandulifolia subsp. lavandulifolia Essential Oil and its Infusion , 2012, Natural product communications.

[18]  S. Rezaee,et al.  Spasmolytic Effect of Stachys Lavandulifolia Vahl. Crude Methanolic Extract and Fractions on Rat Ileum , 2011, Iranian journal of pharmaceutical research : IJPR.

[19]  A. Alizadeh,et al.  Gastroprotective effects of Stachys Lavandulifolia extract on experimental gastric ulcer , 2011 .

[20]  A. Delazar,et al.  Lavandulifolioside B: a new phenylethanoid glycoside from the aerial parts of Stachys lavandulifolia Vahl , 2011, Natural product research.

[21]  A. G. Pirbalouti,et al.  Wound Healing Activity of Extracts of Malva sylvestris and Stachys lavandulifolia , 2010 .

[22]  F. Iranpour,et al.  ABORTIFICIENT EFFECTS OF STACHYS LAVANDULIFOLIA VAHL IN MICE , 2010 .

[23]  Z. Güvenalp,et al.  Secondary metabolites from Nepeta heliotropifolia , 2009, Turkish Journal of Chemistry.

[24]  A. Ghannadi,et al.  Analgesic and anti-inflammatory properties of the hydroalcoholic, polyphenolic and boiled extracts of Stachys lavandulifolia , 2007 .

[25]  C. Pereira-Wilson,et al.  Phenolic compounds protect HepG2 cells from oxidative damage: relevance of glutathione levels. , 2006, Life sciences.

[26]  İ. Çalış,et al.  Secondary Metabolites from Phlomis syriaca and Their Antioxidant Activities , 2006 .

[27]  Z. Güvenalp,et al.  Iridoid, Flavonoid, and Phenylethanoid Glycosides from Wiedemannia orientalis , 2006 .

[28]  Gang Li,et al.  Mechanisms of apigenin-7-glucoside as a hepatoprotective agent. , 2005, Biomedical and environmental sciences : BES.

[29]  D. Kitts,et al.  Luteolin and luteolin-7-O-glucoside from dandelion flower suppress iNOS and COX-2 in RAW264.7 cells , 2004, Molecular and Cellular Biochemistry.

[30]  P. Kroon,et al.  Isolation, identification and stability of acylated derivatives of apigenin 7-O-glucoside from chamomile (Chamomilla recutita [L.] Rauschert). , 2004, Phytochemistry.

[31]  Xubo,et al.  Protective effects of luteolin-7-glucoside against liver injury caused by carbon tetrachloride in rats. , 2004, Die Pharmazie.

[32]  M. Rabbani,et al.  Anxiolytic effects of Stachys lavandulifolia Vahl on the elevated plus-maze model of anxiety in mice. , 2003, Journal of ethnopharmacology.

[33]  K. Mate Medicinal Herbs , 1941, Nature.