Compounds from flowers of Daucus carota L. SSP. carota and their antioxidant activity

Abstract

UDC 547.972 Daucus carota L. ssp. carota, wild carrot, belongs to the family Apiaceae (Umbelliferae). It is a tall robust biennial spiny-fruited herb that grows in dried-out fields [1]. It is indigenous to Europe and has antibacterial, stumulant [2], antisteroidogenic [3], anti-flammatory [4], antiseptic, carminative, diuretic, and hepatoprotective properties [5]. Chemical studies on the seed oil and the root of Daucus carota L. have revealed a variety of chemical counstituents such as daucane-type sesquiterpenes [6-9], flavonoids [10], polyacetylenes [11], fatty oils [12], β-carotene [13], and essential oil [14].The dichloromethane-methanol (1:1) extract of the flowers of Daucus carota L. was partitioned between water and n-butanol. The n-butanol soluble portion was subjected to successive column chromatographic separations using silica gel to afford compounds 2-5. The water soluble fraction give compound 1. Identification of compounds 1-5 was performed using 1D ( 1 H, 13 C)-2D NMR (HMBC, HMQC, COSY), LC/MS-APCI, and literature data.Compound 1 was obtained as a white amorphous solid from the water soluble fraction. The positive LC/MS-APCI spectrum of 1 showed a molecular ion peak at m/z 183.10 [M+H] + corresponding to the molecular formula C 6 H 14 O 6 . The main fragment peaks were recorded at m/z [M-OH] + 165.10 and m/z [M-CH=OH] + 152.10. The 1 H NMR and 13 C NMR spectra revealed signals for eight aliphatic hydrogens at δ H 3.62 (2H), 3.71 (4H), and 3.77 (2H) and three carbons at δ C 63.51, 69.65, and 71.28. The melting point of compound 1 was not identified (decomposed above 149°C). The melting point of the acetylated derivative 1a was found to be 121°C. The 1 H NMR spectrum of 1a showed signals at δ H 5.42 (2H, d, J = 8.0 Hz), 5.06 (2H, m), 4.21 (2H, dd, J = 2.8, 2.8 Hz), 4.06

The Antioxidant and Anticancer Effects of Wild Carrot Oil Extract

“…In this study, DCOE showed considerable radical scavenging activity when compared to that of Trolox (61% vs 90.8%). This is consistent with a previously reported antioxidant effect of dichloromethane‐methanol extract of wild carrot (Akgul et al ., ). The FRAP values obtained suggested that DCOE might act as an electron donor and might react with free radicals transforming them into more stable compounds.…”

“…The chemical composition of the Daucus carota oil, extracted from different parts of the plant, consists mainly of phenylpropanoids, monoterpenes, sesquiterpenes and phenols in addition to polyphenols which include flavonoids (Gonny et al, 2004;Staniszewska et al, 2005;Rossi et al, 2007;Maxia et al, 2009;Wei Fu et al, 2009, 2010. A study on the dichloromethane-methanol extract of the flower of wild carrot from Turkey, using the 1,1-diphenyl-2-picryl hydrazyl (DPPH) method, revealed significant antioxidant activity (Akgul et al, 2009).…”

The Wild Carrot (Daucus carota): A Phytochemical and Pharmacological Review

“…This aligns with the historical utilization of wild carrots in folk medicine for the treatment different inflammatory disorders like pain, prostatitis, and cystitis [ 5 , 11 , 12 , 13 ]. The observed anti-inflammatory effect of the wild carrot may also be attributed to the existence of antioxidant compounds in the plant extract [ 24 , 37 , 66 , 67 , 108 , 109 ]. Notably, various terpenes including α-pinene, β-Caryophyllene, β-bisabolene, sabinene, limonene, and α-longipinene along with polyphenols like luteolin, kaempferol, apigenin, caffeic acid, and quercetin are recognized for their radical scavenging activities [ 110 , 111 , 112 , 113 , 114 , 118 , 119 , 121 ].…”

“…gummifer . Akgul et al [ 108 ] reported that oil extracted from D. carota L. ssp. carota flowers from Turkey possesses significant DPPH radical scavenging properties, and this effect was stronger than that of individual compounds extracted from the oil.…”