Antioxidant and Vasorelaxant Activities of Flavonoids from Amygdalus lycioides var. horrida

Amygdalus lycioides var. horrida (Spach) Browicz (Rosaceae), also known as Prunus lycioides (Spach.) Schneid., is an endemic Iranian species of the genus Amygdalus. In Iranian traditional medicine, the aerial parts and roots of A. lycioides are used in the treatment of diabetes. Six flavonoids, i.e. quercetin 3-O-rhamnoside (1), luteolin 7-O-rhamnoside (2), isorhamnetin 3-O-rutinoside (3), kaempferol 3-O-rhamnoside (4), apigenin (5), and naringenin (6), have been isolated from the aerial parts of this plant. The structures of these compounds were elucidated by UV, MS, and NMR spectroscopic data analyses. While the antioxidant activity of these compounds was assessed by the 2,2-diphenyl-1-picryl-hydrazyl (DPPH) assay, the vasorelaxant effect was determined using the rat aortic vascular smooth muscle. Compounds 1-6 displayed significant antioxidant activity, with the RC50 values ranging from 0.0033 to 0.5186 mg/ml. Compound 2 showed a considerable vasorelaxant activity on rat aortic vascular smooth muscle in a dose-dependent manner.

Antioxidant and Vasorelaxant Activities of Flavonoids from Amygdalus lycioides var. horrida

Amygdalus lycioides var. horrida (Spach) Browicz (Rosaceae), also known as Prunus lycioides (Spach.) Schneid., is an endemic Iranian species of the genus Amygdalus. In Iranian traditional medicine, the aerial parts and roots of A. lycioides are used in the treatment of diabetes. Six flavonoids, i.e. quercetin 3-O-rhamnoside (1), luteolin 7-O-rhamnoside (2), isorhamnetin 3-O-rutinoside (3), kaempferol 3-O-rhamnoside (4), apigenin (5), and naringenin (6), have been isolated from the aerial parts of this plant. The structures of these compounds were elucidated by UV, MS, and NMR spectroscopic data analyses. While the antioxidant activity of these compounds was assessed by the 2,2-diphenyl-1-picryl-hydrazyl (DPPH) assay, the vasorelaxant effect was determined using the rat aortic vascular smooth muscle. Compounds 1-6 displayed significant antioxidant activity, with the RC50 values ranging from 0.0033 to 0.5186 mg/ml. Compound 2 showed a considerable vasorelaxant activity on rat aortic vascular smooth muscle in a dose-dependent manner.

___

  • 1. Browicz K, Zohary D. The genus Amygdalus L. (Rosaceae): species relationships, distribution and evolution under domestication. Genetic Resources and Crop Evolution 43: 229-247, 1996.
  • 2. GRIN Database. USDA, ARS, National Genetic Resources Program, Germplasm Resources Information Network - (GRIN) [Online Database], National Germplasm Resources Laboratory, Beltsville, Maryland. Available on-line at: http://www.ars-grin.gov/cgibin/npgs/html/taxon.pl?3027, 2008.
  • 3. Siami A, Heidari R, Mohseni M. Comparative study of amygdalin, fat and total protein of 7 species of wild almond in West Azerbaijan (Iran). Proceedings of the 3rd International Symposium on Pistachios and Almond 591: 181-187, 2002.
  • 4. Delazar A, Naseri M, Nazemiyeh H et al. Flavonol 3-methyl ether glucosides and a tryptophylglycine dipeptide from Artemisia fragrans (Asteraceae). Biochem Syst Ecol 35: 52-56, 2007.
  • 5. Delazar A, Naseri M, Nahar L et al. GC-MS analysis and antioxidant activities of essential oils of two cultivated Artemisia species. Chemistry of Natural Compounds 43: 112-114, 2007.
  • 6. Delazar A, Biglari F, Nazemiyeh H et al. GC-MS analysis of the essential oils, and the isolation of phenylpropanoid derivatives from the aerial parts of Pimpinella aurea. Phytochemistry 67: 2176-2181, 2006.
  • 7. Delazar A, Modarresi M, Shoeb M et al. Eremostachiin: A new furanolabdane diterpene glycoside from Eromostachys glabra. Natural Product Research 20: 167-172, 2006.
  • 8. Delazar A, Talischi B, Nazemiyeh Z et al. Chrozophorin: a new acylated flavone glucoside from Chrozophora tinctoria. Revista Brasileira de Farmacognosia (Brazilian Journal of Pharmacognosy) 16: 286-290, 2006.
  • 9. Delazar A, Gibbons S, Kosari AR et al. Flavonoid C-glycosides and cucurbitacin glycosides from Citrullus colocynthis. DARU 14: 109- 114, 2006.
  • 10. Delazar A, Celik S, Gokturk RS et al. Two acylated flavonoids from Stachys bombycina and their free radical scavenging activity. Die Pharmazie 60: 878-880, 2005.
  • 11. Delazar A, Reid RG, Sarker SD. GC-MS analysis of essential oil of the oleoresin from Pistacia atlantica var mutica. Chemistry of Natural Compounds 40: 24-27, 2004.
  • 12. Delazar A, Byres M, Gibbons S et al. Iridoid glycosides from Eremostachys glabra. J Nat Prod 67: 1584-1587, 2004.
  • 13. Nazemiyeh H, Delazar A, Ghahramani MA et al. Phenolic glycosides from Phlomis lanceolata (Lamiaceae). Natural Product Communications 3: 53-56, 2008.
  • 14. Nazemiyeh H, Maleki N, Mehmani F et al. Assessment of antiinflammatory properties ethyl acetate extract of Stachys schtschegleevii Sosn. DARU 4: 174-182, 2007.
  • 15. Mabry TJ, Markham KR, Thomas MB. The Systematic Identification of Flavonoids, Springer-Verlag, New York, 1970. 16. Markham KR. Techniques of Flavonoid Identification, Academic Press, London, 1982.
  • 17. Harborne JB, Mabry TJ. The Flavonoids: Advances in Research, Chapman and Hall, London, 1982. 18. Agrawal PK. Carbon-13 NMR of Flavonoids, Elsevier, Amsterdam, 1989.
  • 19. Takao T, Watanabe N, Yagi I et al. 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, 1994.
  • 20. Kumarasamy Y, Fergusson M, Nahar L et al. Biological activity of moschamindole from Centaurea moschata. Pharm Biol 40: 307- 310, 2002.
  • 21. Kumarasamy Y, Byres M, Cox PJ et al. Isolation, structure elucidation and biological activity of flavone C-glycosides from the seeds of Alliaria petiolata. Chemistry of Natural Compounds 40: 122-128, 2004.
  • 22. Chan EC, Pannangpetch P, Woodman OL. Relaxation to flavones and flavonols in rat isolated thoracic aorta: mechanism of action and structure-activity relationships. J Cardiovasc Pharmacol 35: 326-333, 2000.
  • 23. Kim TJ, Kim JH, Jin YR et al. The inhibitory effect and mechanism of luteolin 7-glucoside on rat aortic vascular smooth muscle cell proliferation. Arch Pharm Res 29: 67-72, 2006.
  • 24. Combined Chemical Dictionary. Chapman & Hall/CRC Press LLC. URL: http://www.chemnetbase.com/, 2008.
  • 25. ISI database. ISI Web of Knowledge, Thomson ISI, London. Available on-line at http://wok.mimas.ac.uk/, 2008.
  • 26. Milbury PE, Chen CY, Dolnikowski GG et al. Determination of flavonoids and phenolics and their distribution in almonds. Journal of Agriculture and Food Chemistry 54: 5027-5033, 2006.
  • 27. Lemos VS, Cotes SF, dos Santos MH et al. Structure and vasorelaxant activity of floranol, a flavonoid isolated from the roots of Dioclea grandiflora. Chemistry and Biodiversity 3: 635- 645, 2006.
  • 28. Morello S, Vellecco V, Alfieri A et al. Vasorelaxant effect of the flavonoid galangin on isolated rat thoracic aorta. Life Sciences 78: 825-830, 2006.
Turkish Journal of Biology-Cover
  • ISSN: 1300-0152
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

Gamma ray-and EMS-induced bold high-yielding mutants in chickpea (Cicer arietnum L.)

Mohammad ANIS, Aijaz A. WANI

Sensitivity of Kinetoplastids to Aminoglycoside: Correlation with the 3’ Region of the Small Subunit rRNA Gene

A. S. Hamad ELGAZWY, Masoom M. YASINZAI

Comparative Antioxidant Activity of Some Edible Plants

Zaha A. EL-AGBAR, Ashok K. SHAKYA, Nooman A. KHALAF, Makbula AL-HAROON

The Antioxidant Activity of Some Medicinal Plants

Prateek Kumar JAIN, Veerasamy RAVICHANDRAN, Simant SHARMA, Ram K. AGRAWAL

The effect of hperosmotic stress and nitrogen starvation growth and $ Beta$-galactosidase synthesis in kluyveromyces lactis and kluyveromyces marxianus

Sezai TÜRKEL, Elif ARIK, Sinem GÜZELVARDAR

The Effect of Hyperosmotic Stress and Nitrogen Starvation on Growth and b-Galactosidase Synthesis in Kluyveromyces lactis and Kluyveromyces marxianus

Sezai TÜRKEL, Elif ARIK, Sinem GÜZELVARDAR

Sensitivty of kinetoplastids to aminoglycoside: Correlation with the 3' region of the small subunit rRNA gene

A.S. Hamad ELGAZWY, Massom M. YASINZAI

Sensitivity of Kinetoplastids to Aminoglycoside: Correlation with the 3’ Region of the Small Subunit rRNA Gene

A. S. Hamad ELGAZWY, Masoom M. YASINZAI

Gamma Ray- and EMS-Induced Bold-Seeded High-Yielding Mutants in Chickpea (Cicer arietinum L.)

Aijaz A. WANI, Mohammad ANIS

Bioactivities of the Various Extracts and Essential Oils of Salvia limbata C.A.Mey. and Salvia sclarea L.

Hatice ÖĞÜTÇÜ, Atalay SÖKMEN, Münevver SÖKMEN, Moschos POLISSIOU, Julia SERKEDJIEVA, Dimitra DAFERERA, Fikrettin ŞAHİN, Özlem BARIŞ, Medine GÜLLÜCE