Bioactive Terpenoids and Flavonoids from Daucus littoralis Smith subsp. hyrcanicus Rech.f, an Endemic Species of Iran

Abstract

BackgroundDaucus littoralis Smith subsp. hyrcanicus Rech.f. (Apiaceae) is an endemic species in northern parts of Iran where it is commonly named Caspian carrot. The fruits have been used as condiment.MethodsIn a series of in vitro assays, antioxidant (DPPH and FRAP assays), cytotoxic and antimicrobial activities of different extracts of roots and fruits were evaluated for the first time. The separation and purification of the compounds were carried out on the most potent extracts using various chromatographic methods and identified by spectroscopic data (1H and 13C NMR).ResultsThe results showed that among the extracts only fruit methanol extract (FME) has significant antioxidant activity (IC50 = 145.93 μg.ml-1 in DPPH assay and 358 ± 0.02 mmol FeII/g dry extract in FRAP assay). The radical scavenging activity of FME at 400 μg.ml-1 was comparable with α-tocopherol (40 μg.ml-1) and with BHA (100 μg.ml-1) (p > 0.05). FME did not show any toxicity against cancerous and normal cell lines. Fruit ethyl acetate extract (FEE) had cytotoxic activity against breast carcinoma and hepatocellular carcinoma cells (IC50 168.4 and 185 μg.ml-1, respectively), while it did not possess antioxidant activity in comparison with α-tocopherol and BHA as standard compounds. Ethyl acetate and methanol extract of fruits showed antimicrobial activity against Staphylococcus aureus (MIC: 3.75 mg.ml-1) and Candida albicans (MIC: 15.6 and 7.8 mg.ml-1, respectively). Four terpenoids were isolated form FEE including: β-sitosterol (1), stigmasterol (2), caryophyllene oxide (3), β-amyrin (4). Also, three flavonoids namely quercetin 3-O-β-glucoside (5), quercetin 3-O-β-galactoside (6) and luteolin (7) were isolated from FME.ConclusionThis study showed that FEE and FME of D. littoralis Smith subsp. hyrcanicus Rech.f. had the highest biological activities which may be correlated with in vitro cytotoxic, antimicrobial and antioxidant activities of terpenoids and flavonoids components of the extracts.

Phytochemical Investigation and Antifungal Activity of Daucus littoralis Smith sub sp. hyrcanicus Rech.f

“…This compound has been identified in the essential oil of D. littoralis subsp. hyrcanicus as a major compound (Yousefbeyk et al, 2014b). In a study, the antimicrobial, anti-inflammatory, antioxidant, antidiarrheal, antiulcer, antispasmodic, immunosuppressant and mitogen inhibitor activities of Acorus calamus are referred to acorenone and other constituents in the essential oil (Divya et al, 2011).…”

“…Sesquiterpene hydrocarbons like germaceren D (22-36%) and acorenone B (19.7-57.5%) were reported as major components. Also high amount of myristicin was identified in leaves/stems, roots and fruits essential oils (8.6, 9.5 and 15.2%, respectively) (Yousefbeyk et al, 2014b). Phytochemical investigation of fruits eventuated in identification of β-sitosterol, stigmasterol, caryophyllene oxide, β-amyrin, quercetin 3-O-β-glucoside, quercetin 3-O-β-galactoside and luteolin in this plant (Yousefbeyk et al, 2014a).…”

“…Fungicidal Concentration (MFC) of the extracts were evaluated by broth microdilution method with visible growth observed by using 96 U-shaped wells plates (Yousefbeyk et al, 2014b). A stock concentration of 200 mg mLG 1 from each extract was prepared in DMSO.…”

“…hyrcanicus Rech.f. (Apiaceae), well known as Caspian carrot, is an annual or perennial plant growing exclusively in the north of Iran (Mazandaran and Guilan provinces) (Yousefbeyk et al, 2014b). The genus Daucus is distributed in Europe, Africa, West Asia, North America and Australia.…”

In vitro Propagation and Essential Oils Composition with Cytotoxicity of Daucus capillifolius Gilli (Apiaceae)

“…It includes 60 species which are mainly distributed in the Mediterranean regions, extending to East Asia, tropical and South Africa and Australia . Chemically, the genus Daucuswas reported as one of the rich sources in essential oil [2][3][4][5] , sesquiterpens 6,7 , sterols and triterpenes 8 , polyacetylenic compounds 9,10 , sesquiterpene lactones 11,12 , flavonoids and phenylpropanoids 13 . Biologically, the essential oils from many Daucus species were reported to possess a wide range of activities including cytotoxicity 8,12 antimicrobial 8,14 , insecticidal 15 , anti-inflammatory 16 and antioxidant 17 .…”