Abstract
Seven free-radical-scavenging phenolic compounds including five flavonoids, rutin (1), chrysoeriol 7-O-rutinoside (2), kaempferol 3-O-glucoside (3), chrysoeriol 7-O-glucoside (4) and naringenin (5), and two phenylethanoid glycosides, forsythoside B (6) and acteoside (7) were isolated from the methanol extract of the aerial parts of the Iranian medicinal plant Phlomis caucasica by reversed-phase preparative high-performance liquid chromatography (HPLC), and the structures of these compounds were elucidated by spectroscopic means. The free-radical-scavenging properties of 1–7 were assessed by 2,2-diphenyl-1-picryl hydrazyl (DPPH) assay. Among these compounds, forsythoside B (6) and acteoside (7) were found to be the most potent antioxidants with the RC50 values of 4.97 and 4.27 μg/ml, respectively.
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Rechinger KH (1982) Flora Iranica. Graz-Austria: Akademic Druck-u. Verlagsanstalt 150:292–313
Mohajer M, Sarkhail P, Hajarolasvadi N, Zamani MJ, Khorasani R, Shafiee A, Amin G, Abdollahi M (2005) Antiinflammatory and analgesic effects of Phlomis lanceolata Boiss and Hohen. Extracts and examination of their components. Int J Pharmacol 2:50–54
Sarkhail P, Amin G, Surmaghi MHS, Shafiee A (2005) Composition of the volatile oils of Phlomis lanceolata Boiss. & Hohen., Phlomis anisodonta Boiss. and Phlomis bruguieri Desf. from Iran. Flavour Fragrance J 20:327–329
Nazemiyeh H, Rahman MM, Gibbons S, Nahar , Delazar A, Ghahramani M-A, Talebpour A-H, Sarker SD (2008) Assessment of the antibacterial activity of phenylethanoid glycosides from Phlomis lanceolata against multiple-drug-resistant (MDR) strains of Staphylococcus aureus. J Nat Med 62:91–95
Delazar A, Biglari F, Nazemiyeh H, Talebpour A, Imani Y, Nahar L, Sarker SD (2006) GC-MS analysis of the essential oils, and the isolation of phenylpropanoid derivatives from the aerial parts of Pimpinella aurea. Phytochemistry 67:2176–2181
Delazar A, Gibbons S, Kumarasamy Y, Nahar L, Shoeb M, Sarker SD (2005) Antioxidant phenylethanoid glycosides from the rhizomes of Eremostachys glabra (Lamiaceae). Biochem Syst Ecol 33:87–90
Delazar A, Talicgi B, Nazemiyeh Z, Rezazadeh H, Nahar L, Sarker SD (2006) Chrozophorin: a new acylated flavone glucoside from Chrozophora tinctoria. Revista Brasileira de Farmacognosia (Braz J Pharmacognosy) 16:286–290
Delazar A, Reid RG, Sarker SD (2004) GC-MS analysis of essential oil of the oleoresin from Pistacia atlantica var mutica. Chem Nat Comp 40:24–27
Delazar A, Gibbons S, Kosari AR, Nazemiyeh H, Modarresi M, Nahar L, Sarker SD (2006) Flavonoid C-glycosides and cucurbitacin glycosides from Citrullus colocynthis. DARU 14:109–114
Delazar A, Gibbons S, Kumarasamy Y, Nahar L, Shoeb M, Sarker SD (2005) Antioxidant phenylethanoid glycosides from the rhizomes of Eremostachys glabra (Lamiaceae). Biochem Syst Ecol 33:87–90
Nazemiyeh H, Razavi SM, Delazar A, Hajiboland R, Mozaffarian V, Nahar L, Sarker SD (2007) Essential oil composition of the umbels and fruits of Prangos uloptera DC. Nat Prod Commun 2:89–91
Nazemiyeh H, Bahadori F, Delazar A, Ay M, Topcu G, Kolak U, Nahar L, Auzi AA, Sarker SD (2007) Tricetin 4’-O-α-L-rhamnopyranoside: a new flavonoid from the aerial parts of Erica arborea. Chem Nat Comp (in press)
Fathiazad F, Delazar A, Amiri R, Sarker SD (2006) Extraction of flavonoids and quantification of rutin from waste tobacco leaves. Iran J Pharm Res 3:222–227
Delazar A, Naseri M, Nahar L, Moghadam SB, Esnaashari S, Nazemiyeh H, Sarker SD (2007) GC-MS analysis and antioxidant activities of essential oils of two cultivated Artemisia species. Chem Nat Comp 43:112–114
Nazemiyeh H, Razavi SM, Hajiboland R, Delazar A., Esna-ashari S, Bamdadm R, Nahar L, Sarker SD (2007) Composition of the essential oils of Prangos scabra fruits and inflorescence from Iran. Chem Nat Comp 43:736–737
Delazar A, Modarresi M, Shoeb M, Nahar L, Reid RG, Majinda RRT, Sarker SD (2006) Eremostachiin: a new furanolabdane diterpene glycoside from Eromostachys glabra. Nat Prod Res 20:167–172
Mabry TJ, Markham KR, Thomas MB (1970) The systematic identification of flavonoids. Springer, New York
Agrawal PK (1989) Carbon-13 NMR of flavonoids. Elsevier, Amsterdam
Markham KR (1982) Techniques of flavonoid identification. Academic Press, London
Harborne JB, Mabry TJ (1982) The flavonoids: advances in research. Chapman and Hall, London
Andary C, Wylde R, Laffite C, Privat G, Winternitz F (1982) Structures of verbascoside and orobanchoside, caffeic acid sugar esters from Orobanche rapum-genistae. Phytochemistry 21:1123–1127
Franzyk H, Husum T L, Jensen SR (1998) A caffeoyl phenylethanoid glycoside from Plantago myosuros. Phytochemistry 47:1161–1162
Calis I, Basaran AA, Saracoglu I, Sticher O, Rued P (1990) Phlinosides A, B and C, three phenylpropanoid glycosides from Phlomis linearis. Phytochemistry 29:1253–1257
Saracoglu I, Harput US, Calis I, Ogihara Y (2002) Phenolic constituents from Phlomis lycia. Turk J Chem 26:133–142
Ersoz T, Saracoglu I, Harput US, Calis I, Donmez AA (2002) Iridoid and phenylpropanoid glycosides from Phlomis grandiflora var. fimbrilligera and Phlomis fruticosa. Turk J Chem 26:171–178
ISI database (2008) ISI web of knowledge. Thomson ISI, London. Available at: http://wok.mimas.ac.uk/
Takao T, Watanabe N, Yagi I, Sakata K (1994) A simple screening method for antioxidants and isolation of several antioxidants produced by marine-bacteria from fish and shellfish. Biosci Biotech Biochem 58:1780–1783
Kumarasamy Y, Fergusson M, Nahar L, Sarker SD (2002) Biological activity of moschamindole from Centaurea moschata. Pharm Biol 40:307–310
Kumarasamy Y, Byres M, Cox PJ, Delazar A, Jaspars M, Nahar L, Shoeb M, Sarker SD (2004) Isolation, structure elucidation and biological activity of flavone C-glycosides from the seeds of Alliaria petiolata. Chem Nat Comp 40:122–128
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We thank the EPSRC National Mass Spectrometry Service Centre (Department of Chemistry, University of Wales Swansea, Swansea, Wales, UK) for MS analyses.
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Delazar, A., Sabzevari, A., Mojarrab, M. et al. Free-radical-scavenging principles from Phlomis caucasica . J Nat Med 62, 464–466 (2008). https://doi.org/10.1007/s11418-008-0255-y
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DOI: https://doi.org/10.1007/s11418-008-0255-y