Antimicrobial activity of rhizomes of Ferulago trachycarpa Boiss. and bioguided isolation of active coumarin constituents
Introduction
Plants have a wide variety of phytochemicals which have traditionally used for centuries in ethnomedicines and these chemicals can be used to treat infectious diseases causing by microorganisms (Patra, 2012; Kapoor et al., 2015). The discovery of antibiotic in the early 20th century was seen an important step against bacterial diseases (Kapoor et al., 2015).
Recently, the emergence of multi-drug resistant to bacterial strains with decreased susceptibility to antibiotics has led to the discovery of new antimicrobial agents from natural sources for therapeutic purposes against microbial diseases (Patra, 2012). Therefore, the studies are important to find new antimicrobial agents from plant-derived natural products and provide to exploit new antimicrobial drugs.
The genus Ferulago W. Koch. which belongs to the Umbelliferae (Apiaceae) family consists of 49 species in the world. Eighteen Ferulago species of which 34 existing in Turkey are endemic (Akalın and Kızılarslan, 2013). Anatolia is acknowledged to the main center of the biodiversity of genus Ferulago (Ozhatay and Akalın, 2000) and as taxonomically, it is closely related to Ferula, Peucedanum and Prangos genus (Ozhatay and Akalın, 2000; Akalın and Koçyiğit, 2010–2011).
In folk medicine, Ferulago species have been used as sedative, tonic, digestive, carminative, aphrodisiac and in treatment of the intestinal worms and hemorrhoids (Akalın and Koçyiğit, 2010–2011).
The distribution of Ferulago trachycarpa have been seen in West, Southwest and South Anatolia of Turkey and while it is known as “Kişniş’’, “Kuzukulağı’’, “Kurtkulağı’’, “Kurtkemirdi’’, “Kuzubaşı’’ in Konya, “Kimyon otu’’ name is called by people in Balıkesir-Edremit region. The fresh leaves of plant are sold in the bazaar and used as a salad in Konya. The mature seeds of the plant are used as a spice in Balıkesir (Akalın and Alpınar, 1994; Akalın and Koçyiğit, 2010–2011).
Previous phytochemical studies have shown that coumarins are the main compound on Ferulago (De Pascual et al., 1979; Jiménez et al., 2000; Erdurak-Kılıç et al., 2006; Khalighi-Sigaroodi et al., 2006; Basile et al., 2009; Naseri et al., 2013). Coumarins have many pharmacological activities such as antibacterial, antifungal, anticoagulant, anti-inflammatory, anticancer, antihypertensive, antihyperglycemic, antioxidant and anti-inflammatory (Venugopala et al., 2013). There are studies showing that coumarins isolated from Ferulago species have antimicrobial activity (Basile et al., 2009; Golfakhrabadi et al., 2016).
The aim of this study is to provide a scientific basis for the antimicrobial activities of isolated coumarins from F. trachycarpa rhizomes being the major phytochemical group against various bacteria and fungi.
Section snippets
Chemical materials and instruments
For column chromatography, silica gel (0.2–0.5 mesh, Merck), column (length: 60 cm, size: 3 cm), Sephadex column chromatography LH-20 (Sigma Aldrich), TLC and pTLC plates (Merck 1.05554.001 TLC Kieselgel 60 F254 20x20, aluminium and glass plates) were used.
1H and 13C NMR spectra were recorded on a Bruker Avance III, 500 MHz instrument Shimadzu UV-1800 spectrophotometer was used for UV spectra.
Plant material
F. trachycarpa Boiss. was collected in June 2015 from Konya-Taşkent, Turkey. It was identified by Prof.
Result and discussion
The extracts (fractionally n-hexane-FTH, dichloromethane-FTD, methanol-FTM, and methanol-FTM-s) were obtained from rhizomes of F. trachycarpa and the antimicrobial activities of them were investigated against Stapylococcus aureus ATCC 6538, S. epidermidis ATCC 12228, Escherichia coli ATCC 8739, Klebsiella pneumoniae ATCC 4352, Pseudomonas aeruginosa ATCC 27853, Proteus mirabilis ATCC 14153, Enterococcus feacalis ATCC 29212 bacterial strains and Candida albicans ATCC 10231, C. tropicalis ATCC
Conclusion
According to the previously isolated coumarin compounds from Ferulago species, it has been noticed that F. trachycarpa has differences. This study is the first report about antimicrobial activity guided isolation from F. trachycarpa. Crenulatin compound was firstly isolated from Ferulago species and also, isolated compounds were found that have the antimicrobial activity against some bacteria and fungi strains. The study has contributed to the investigation potentially new sources of good
Conflict of interests
The authors declare no conflicts of interest.
Acknowledgment
This study was supported by Marmara University Scientific Research Project Coordination Unit (BAPKO) (Project number: SAG-C-YLP-130116-0001).
References (47)
- et al.
Coumarins from Amyris balsamiferae
Phytochemistry
(1979) Flavonoids, coumarins and acridone alkaloids from the root bark of Citrus limonia
Phytochemistry
(1990)- et al.
Coumarins in Eremocitrus glauca
Phytochemistry
(1974) - et al.
Alkaloids and coumarins from the stem bark of Citrus grandis
Phytochemistry
(1989) - et al.
Antimicrobial activity of ulopterol isolated from Toddalia asiatica (L.) Lam.: a traditional medicinal plant
J. Ethnopharmacol.
(2012) - et al.
Coumarins and other constituents of Hesperathusa crenulata
Phytochemistry
(1972) - et al.
A new species of Ferulago W. Koch (Umbelliferae) from north-west Turkey
Bot. J. Linn. Soc.
(2000) - et al.
Coumarins and γ-pyrone derivatives from Prangos pabularia: antibacterial activity and inhibition of cytokine release
Phytochemistry
(2002) - et al.
The coumarin composition of the roots of Prangos uloptera
Chem. Nat. Compd.
(1973) - et al.
The structure of ulopterol
Chem. Nat. Compd.
(1970)
Tekirdağ’ın tıbbi ve yenen bitkileri hakkında bir araştırma
Ege Ünv. Ecz. Fak. Derg.
Fruit anatomy of some Ferulago (Apiaceae) species in Turkey
Turk. J. Bot.
Phenolic contents, antibacterial and antioxidant activities of flower, leaf and stem extracts of Ferulago angulata
Int. J. Pharm. Pharm. Sci.
Crenulatin, a formyl coumarin from Hesperathusa crenulata (Rutaceae)
Aust. J. Chem.
Antimicrobial and antioxidant activities of coumarins from the roots of Ferulago campestris (Apiaceae)
Molecules
Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically: Approved Standard M7-A5
Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts; Approved Standart M27-A NCCLS
Coumarins from Ferulago granatensis group: isovaleryl marmesin
An. Quim.
Antibacterial activity of coumarins
Z. Naturforsch.
Chemical constituents from lipophilic parts in roots of Angelica dahurica var. formusana cv. Chuanbaizhi
J. Chin. Mater. Med.
The Phytochemical Research on Ferulago aucheri, Ferulago humulis and Ferulago asparagifolia Growing in Turkey
New furanocoumarins isolated from the roots of Ferulago isaurica Pesmen growing in Turkey
Heterocycles
Cited by (21)
The ethnobotany, phytochemistry and biological properties of genus Ferulago – A review
2021, Journal of EthnopharmacologyCitation Excerpt :demonstrated antifungal activity against C. albicans (ATCC 10231), C. tropicalis (ATCC 750) and C. parapsilosis (ATCC 22019). However, only the hexane extract showed superior activity, with MIC values 4.8 mg/L and 4.8 mg/L, against C. albicans and C. tropicalis fungal strains, respectively, when compared with the drug Clotrimazole (Dikpınar et al., 2018). Golfakhrabadi et al. (2016a; 2016b) tested suberosin (7), suberenol (8), xanthotoxin (24), bergapten (25), isopimpinellin (26), prantschimgin (40) and hesperetin (63) against a fungal strain (Candida albicans ATCC 1023) by a microdilution method.
Antihyperglycemic activity of crude extract and isolation of phenolic compounds with antioxidant activity from Moringa oleifera Lam. leaves grown in Southern Brazil
2021, Food Research InternationalCitation Excerpt :For Ahangarpour et al (2019) the structure of chlorogenic acid enables its activity similar to metformin in potentiating insulin action while Rey et al (2019) suggest that astragalin can contribute to glucose homeoastase through the influx of calcium into the K+ATP, L-VDCC channels, mobilizing calcium from intracellular reserves and activating the PKC and PKA kinase proteins, leading to insulin secretion. The isolation of bioactive compounds by using the bioguided fractionation technique is an important tool to separate components which present some biological activity and the main advantage is the rationalization of the process used to isolate biologically bioactive substances from complex natural extracts (Chen et al., 2017; Dikpınar et al., 2018; Oldoni et al., 2016; Ortiz et al., 2019). In studies that use isolation at random it is not possible to ensure that the compounds responsible for the activity of interest were, in fact, isolated.
Phytochemical evaluation of the Ferulago genus and the pharmacological activities of its coumarin constituents
2021, Journal of Herbal MedicineCitation Excerpt :The results showed some differences in the bacterial strains. Golfakhrabadi et al. (2016a) found activity against S. aureus ATCC 6538 with an MIC > 7.5 mg/mL, while Dikpınar et al. (2018) did not find activity against this bacteria but did find activity against MRSA, with an MIC of 1250 mg/L. Karakaya et al. (2018e) found activity against S. aureus ATCC 25923 with an MIC of 500 μg/mL. This compound was not active against Escherichia coli ATCC 8739 or P. aeruginosa ATCC 9027 (Golfakhrabadi et al., 2016a) but was active against E. coli ATCC 25922, P. aeruginosa ATCC 27853 and Bacillus subtilis ATCC 6633, with MIC values of 250 μg/mL (Karakaya et al., 2018e).
Chemical profile, antioxidant, antimicrobial, enzyme inhibitory, and cytotoxicity of seven Apiaceae species from Turkey: A comparative study
2020, Industrial Crops and ProductsCitation Excerpt :Also, a better antimicrobial profile (against eight bacterial and two fungal strains) for Laserpitium zernyi was described by Popovic et al. (2017). However, the methanol extract of Ferulago trachycarpa was not active against the tested bacterial strains including S. aureus and E. coli (Dikpınar et al., 2018). In addition, the methanol extract from C. aromaticum exhibited no antibacterial abilities against six bacterial strains (Petrović et al., 2017).
Sardinian plants with antimicrobial potential. Biological screening with multivariate data treatment of thirty-six extracts
2019, Industrial Crops and Products