A new ursane-type triterpene acid, named azarolic acid (1), along with four known phenolic compounds and four known triterpene acids, was isolated from the crude EtOAc extract of the leaves of Crataegus azarolus var. aronia L. The structure of 1 was determined from 1D and 2D NMR spectroscopic data. Euscaphic acid showed high anti-vasoconstriction effects on aortic rings, supporting the use of this medicinal plant in cardiovascular disease.
ShahbazS.E. (2010) Trees and Shrubs, A field guide to the trees and shrubs of Kurdistan region of Iraq.Duhok University Press.
2.
(a) ChristensenK.I. (1992) Revision of Crataegus sect. Crataegus and nothosect. Crataeguineae (Rosaceae-Maloidae) in the Old World. Systematic Botany Monographs, 35, 1–199; (b) Edwards JE, Brown PN, Talent N, Dickinson TA, Shipley PR. (2012) A review of the chemistry of the genus Crataegus. Phytochemistry, 79, 5-26.
3.
Bahri-SahloulR., AmmarS., FredjR.B., SaguemS., GrecS., TrotinF., SkhiriF.H. (2009) Polyphenol contents and antioxidant activities of extracts from flowers of two Crataegus azarolus L. varieties. Pakistan Journal of Biological Sciences, 12, 660–668.
4.
KeserS., CelikS., TurkogluS., YilmazO., Turkoglu (2014) The investigation of some bioactive compounds and antioxidant properties of hawthorn (Crataegus monogyna subsp. monogyna Jacq). Journal of Intercultural Ethnopharmacology, 3, 51–55.
5.
ÇalişkanO., GündüzK., SerçeS., TopluC., KamiloğluÖ, ŞengülM., ErcişliS. (2012) Phytochemical characterization of several hawthorn (Crataegus spp.) species sampled from the Eastern Mediterranean region of Turkey. Pharmacognosy Magazine, 8, 16–21.
6.
(a) WangJ., XiongX., FengB. (2013) Review article: Effect of Crataegus usage in cardiovascular disease prevention: An evidence-based approach. Evidence-Based Complementary and Alternative Medicine. Vol. 2013. Article ID 149363. http://dx.doi.org/10.1155/2013/149363; (b) Dood KP, Frey AD, Geisbuhler TP. (2013) The effect of hawthorn extract on coronary flow. Journal of Evidence-Based Complementary & Alternative Medicine, 18, 257–267.
7.
(a) KumarD., AryaV., BhatZ.A., KhanN.A., PrasadD.N. (2012) The genus Crataegus: chemical and pharmacological perspectives. Brazilian Journal of Pharmacognosy, 22, 1187–1200;(b) Attard E, Attard H. (2006) The potential angiotensin-converting enzyme inhibitory activity of oleanolic acid in the hydroethanolic extract of Crataegus monogyna Jacq. Natural Product Communications, 1, 381–385; (c) Al-Hallaq EK, Afifi FU, Abdalla SS. (2012) Evaluation of the hypocholesterolemic effect and phytochemical screening of the hydroethanolic extract of Crataegus aronia from Jordan. Natural Product Communications, 7, 35–38.
8.
HamahameenB.A., JamalB. (2013) Determination of flavonoids in the leaves of hawthorn (Crataegus azarolus) of Iraqi Kurdistan region by HPLC analysis. International Journal of Bioscience, Biochemistry and Bioinformatics, 3, 67–70.
9.
FooL.Y., LuY., HowellA.M., VorsaN. (2000) The structure of cranberry proanthocyanidins which inhibit adherence of uropathogenic P-fimbriated Escherichia coli in vitro.Phytochemistry, 54, 173–181.
10.
(a) NikolovN., SeligmannO., WagnerH., HorowitzR.M., GentiliB. (1982) Neue flavonoid-glykoside aus Crataegus mon ogyna und Crataegus pentagyna. Planta Medica, 44, 50–53;(b) Prinz S, Ringl A, Huefner A, Pemp E, Kopp B. (2007) 4″’-Acetylvitexin-2″-O-rhamnoside, isoorientin, orientin, and 8-methoxykaempferol-3-O-glucoside as markers for the differentiation of Crataegus monogyna and Crataegus pentagyna from Crataegus laevigata (Rosaceae). Chemistry & Biodiversity, 4, 2920–2931.
11.
ChengJ-J, ZhangL-J, ChengH-L, ChiouC.T., LeeI-J, KuoY-H. (2010) Cytotoxic hexacyclic triterpene acids from Euscaphis japonica. Journal of Natural Products, 73, 1655–1658.
12.
XuH-X, ZengF-Q, WanM., SimK-Y. (1996) Anti-HIV triterpene acids from Geum japonicum. Journal of Natural Products, 59, 643–645.
13.
D'AbroscaB., FiorentinoA., MonacoP., PacificoS. (2005) Radical-scavenging activities of new hydroxylated ursane triterpenes from cv. Annurca apples. Chemistry & Biodiversity, 2, 953–958.
14.
PonouB.K., TeponnoR.B., RicciutelliM., NguelefackT.B., QuassintiL., BramucciM., LupidiG., BarboniL., TapondjouL.A. (2011) Novel 3-oxo and 3,24-dinor-2,4-secooleanane-type triterpenes from Terminalia ivorensis A. Chev. Chemistry & Biodiversity, 8, 1301–1309.
15.
JohnsS.R., LambertonJ.A., MortonT.C., SuaresH., WillingR.I. (1983) Triterpenes of Lantana tiliaefolia. 24-Hydroxy-3-oxours-12-en-28-oic acid, a new triterpene. Australian Journal of Chemistry, 36, 2537–2547.
16.
YoshiokaI., SugawaraT., OhsukaA., KitagawaI. (1971) Soil bacterial hydrolysis leading to genuine aglycone. III. The structures of glycosides and genuine aglycone of Sanguisorbae Radix. Chemical and Pharmaceutical Bulletin, 19, 1700–1707.
17.
MahatoS.B., KunduA.P. (1994) 13C NMR spectra of pentacyclic triterpenoids-a compilation and some salient features. Phytochemistry, 37, 1517–1535.
18.
KonishiT., YamazoeK., KanzatoM., KonoshimaT., FujiwaraY. (2003) Three diterpenoids (excoecarins V1–V3) and a flavanone glycoside from the fresh stem of Excoecaria agallocha. Chemical and Pharmaceutical Bulletin, 51, 1142–1146.
19.
OcchiutoF., BusaG., RagusaS., De PasqualeA. (1991) Comparative antiarrhythmic and anti-ischaemic activity of some flavones in the guinea-pig and rat. Phytotherapy Research, 5, 9–14.
20.
OcchiutoF., CircostaC., CostaR., BriguglioF., TommasiniA. (1986) Comparative study of the cardiovascular activity of shoots, leaves and flowers of Crataegus oxyacantha: 2. Action of extracts and isolated pure active principles on the isolated rabbit heart. Plantes medicinales et phytotherapie, 20, 52–63.
21.
Al-HabibO.A.M., MahmudS.A., VidariG. (2015) Anti-contraction effects of euscaphic acid isolated from Crataegus azarolus var. aronia L on rat's aortic smooth muscle. Advances in Life Science and Technology, 33, 48–60.
22.
GilardoniG., ChiribogaX., Vita FinziP., VidariG. (2015) New 3,4-secocycloartane and 3,4-secodammarane triterpenes from the Ecuadorian plant Coussarea macrophylla. Chemistry & Biodiversity, 12, 946–954.