Antimicrobial activity of rhizomes of Ferulago trachycarpa Boiss. and bioguided isolation of active coumarin constituents

doi:10.1016/j.indcrop.2018.06.072

Industrial Crops and Products

Volume 123, 1 November 2018, Pages 762-767

https://doi.org/10.1016/j.indcrop.2018.06.072 Get rights and content

Highlights

•
Antimicrobial activities of plant-derived coumarin compounds were investigated.
•
Coumarins are major compounds on Ferulago species.
•
Antimicrobial activity-guided isolation were firstly made from Ferulago trachycarpa.
•
Crenulatin, suberosin, marmecin senecioate demonstrated antifungal activity.

Abstract

Ferulago trachycarpa (Apiaceae) is a plant used traditionally for its sedative, digestive, carminative and aphrodisiac properties with distribution in West, Southwest and South Anatolian part of Turkey. In this study the antimicrobial activities of fractionally n-hexane, dichloromethane, methanol and only methanol extracts from rhizomes of F. trachycarpa were screened 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 fungal strains such as Candida albicans ATCC 10231, C. tropicalis ATCC 750 and C. parapsilosis ATCC 22019 by microdilution method. All extracts have been shown to possess antimicrobial activities against bacteria and fungal strains and according to the antimicrobial results, the isolation of the active constituents was made from the most active n-hexane and dichloromethane extracts. So, four pure compounds are known as coumarin derivatives, crenulatin (6-formyl-7-methoxycoumarin), suberosin (7-methoxy-6-prenylcoumarin), marmesin senecioate ((-)-prantschimgin) as dihydrofuranocoumarin derivative and ulopterol [6- (2’, 3’-dihydroxy-3’-methylbutyl)-7-methoxy-coumarin] were isolated. Crenulatin (6-formyl-7-methoxycoumarin), suberosin (7-methoxy-6-prenylcoumarin), marmesin senecioate ((-)-prantschimgin) which are pure compounds demonstrated antifungal activity with 625 mg/L MIC against C. albicans and antibacterial activity with 1250 mg/L MIC against S. aureus (MRSA). These results indicate that extracts and pure compounds obtained from Ferulago trachycarpa could be a potential for pharmaceutical products which have antimicrobial activity.

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).

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Erectile dysfunction (ED) is the most common form of sexual dysfunction which has been the topic of great interest through the history by all cultures. It is now among the most treated health problems in men of all ages that develop under the influence of lifestyle factors and some diseases. Plants are extensively used to cure sexual dysfunction for centuries. Roots of Prangos sp. have been used to improve sexual performance in Anatolian traditional medicine and are rich of coumarin, furanocoumarin and their derivatives. Scientific research is necessary to support and validate the ethno-traditional uses of these plants.
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The roots of plants were extracted with chloroform, n-hexane and methanol. The compounds were isolated from the extract by column chromatography and structures were identified by NMR and MS. The relaxant effects of extracts (10⁻⁷-10⁻⁴ g/mL), (+)-oxypeucedanin (10⁻⁷-10⁻⁴ M) and Na₂S (10⁻⁷-3 × 10⁻³ M) were tested in MCC strips by DMT myograph. To investigate the mechanism, the synthesis inhibitors of aminooxyacetic acid (AOAA, 10⁻² M) and nitro-L-arginine methyl ester (L-NAME, 10⁻⁴ M) were used, respectively. H₂S formation was evaluated basal and L-cysteine (L-cyst)-stimulated conditions by H₂S microsensor.
All extracts relaxed MCC in a concentration dependent manner. The maximum relaxing effects were achieved with chloroform extracts. Chloroform extract of P. pabularia (Pp-CE) was more potent than the others. Pp-CE-induced relaxations were significantly decreased by AOAA and L-NAME. (+)-Oxypeucedanin, the major compound of Pp-CE, induced relaxant responses and this effect was inhibited by AOAA, but not L-NAME. The relaxation of (+)-oxypeucedanin was found to be similar in view of E_max to positive control H₂S donor Na₂S. (+)-Oxypeucedanin increased L-cyst-stimulated H₂S formation. Augmentation of H₂S synthesis with (+)-oxypeucedanin was inhibited by AOAA.
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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.
The genus Ferulago, belonging to the Apiaceae family, is found mainly in the Mediterranean area, Southwest and Middle Asia, the Caucasus and North Africa. Since ancient times, species of this genus have been largely employed in traditional medicine for their biological properties such as antimicrobial, anti-inflammatory, antispasmodic, insecticidal, and anti-malaria, cholinesterase inhibition effects, etc.
The scope of this paper is to present a comprehensive respect review of this interesting genus including traditional uses, chemical composition of volatile and non-volatile metabolites, and in vitro and in vivo biological properties either utilizing the crude extracts or essential oils, or the single isolated compounds. Furthermore, critical considerations of the published data have been highlighted by comparing them with the results obtained from species of other genus belonging to the Apiaceae family.
The available information on these genera was collected from scientific databases and cover from 1967 up to 2020. The following electronic databases were used: PubMed, SciFinder, Science Direct, Scopus, Web of Science and Google Scholar. The search terms used for this review included Ferulago, all the botanical names of the species, both accepted names or synonyms, essential oils, volatile components, traditional uses, activity, pharmacology, and toxicity. No limitations were set for languages. A total of 230 articles were included in the present review.
Researches performed on either crude extracts, solvent fractions or isolated pure compounds from species of genus Ferulago showed several biological properties such as antibacterial, antifungal, antioxidant, antidiabetic, enzymatic, cytotoxic, anticancer, hepatoprotective, nephroprotective, antileishmanial, antimalarial, anticoagulant, anti-inflammatory, insecticidal, etc. Activities. Phytochemical investigations of Ferulago species have revealed that coumarins are the main constituents of the genera. A large number of flavonoids, terpenoids and other metabolites were also identified. Furthermore, a complete review on the essential oil composition of all the taxa studied so far has been also included.
In the present study, we have provided scientific information and research developments on traditional uses, phytochemical profiles, biological activities and industrial practices on the Ferulago genus. The commercial use and the applications in agri-food sector of some of these species have been also considered. In fact, the various extracts and essential oils have been used as antioxidants and/or as antimicrobial agents, for the stabilization of sunflower and soybean oil, for food packagings, as antioxidants of mayonnaise and yogurt during their storage and, also, as economically valid source for obtaining single compounds, more expensive at a synthetic level.
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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.
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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).
The genus Ferulago W. Koch is a member of the Apiaceae (Umbelliferae) family and consists of 49 species throughout the world. In traditional medicine, Ferulago species have been utilized as sedatives, carminatives, aphrodisiacs, for increasing milk secretion and for the treatment of bronchitis, skin diseases, and eye diseases. The authors aimed to evaluate the phytochemical constituents of Ferulago species and the pharmacological activities of its coumarins. In this review, literature searches were performed using scientific search engines and databases (Google Scholar, SciFinder, Science Direct, Scopus, PubMed.) for papers published in the past until June 2019. The molecular structures of all isolated compounds are shown in Tables 2, 3, and 4, and the main constituents of the essential oil (Table 5) are indicated with the identified number, characterization, and extraction method. Additionally, the pharmacological activities of the coumarins isolated from the Ferulago genus were investigated. The results demonstrated that coumarins have various pharmacological activities such as antimicrobial, antioxidant, antiproliferative, and anticholinesterase activities. Therefore this review may be considered to be an important scientific resource for future research.
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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).
Several Apiaceae species, used as both food and in complementary and alternative medicine, represents a rich source of potential valuable phytopharmaceuticals which necessitates scientific contemplation. In the present study, the antioxidant, enzyme inhibitory, antimicrobial, and cytotoxic properties of methanol extracts of seven Apiaceae species, (Chaerophyllum macrospermum (Willd. ex Spreng.) Fisch. & C.A.Mey. ex Hohen, Ferula rigidula Fisch. ex DC., Ferula orientalis L., Prangos ferulacea Lindl., Prangos peucedanifolia Fenzl., Ferulago setifolia K. Koch, and Pimpinella anthriscoides Boiss.) were evaluated. Species belonging to the Prangos genus exhibited the highest total phenolic content, namely P. peucedanifolia and P. ferulacea, with values of 47.90 and 44.44 mg gallic acid equivalent/g extract, respectively. P. peucedanifolia also displayed the highest radical scavenging capacity (81.53 and 102.70 mg Trolox equivalent [TE]/g extract for 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid (ABTS), respectively) and reducing power (165.87 and 100.09 mg TE/g extract for cupric reducing antioxidant capacity (CUPRAC) and ferric reducing antioxidant power (FRAP), respectively). C. macrospermum showed the most potent inhibition against Alzheimer’s disease related enzymes, namely acetylcholinesterase (4.53 mg galantamine equivalent [GALAE]/g extract) and butyrylcholinesterase (3.22 mg GALAE/g extract). P. ferulacea (131.94 mg kojic acid (KAE) equivalent/g extract) and P. peucedanifolia (4.97 mmol acarbose equivalent (ACAE)/g extract) were potent inhibitors of tyrosinase and α-glucosidase, respectively. In general, studied species were able to reduce cellular viabilities. P. peucedanifolia possessed promising antibacterial potential against Bacillus cereus (Minimum inhibition concentration (MIC): 0.37 mg/mL), L. monocytogenes (MIC: 0.56 mg/mL), P. aeruginosa and Escherichia coli (MIC: 0.27 mg/mL), Salmonella typhimurium and Enterobacter cloacae (MIC: 0.75 mg/mL). F. rigidula showed the highest antifungal effect against Aspergillus ochraceus and Trichoderma viride (MIC: 0.10 mg/mL). The present findings could be the scientific starting point towards the pharmaceutical and/or commercial utilization of these Apiaceae species.
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In this paper, thirty-six extracts from Sardinian plants were evaluated in vitro for their antimicrobial activity towards a panel of reference strains, Staphylococcus aureus, S. epidermidis, Klebsiella pneumoniae and Escherichia coli, and for their cytotoxicity on mammalian cells. The biological data, together with total phenolic and flavonoid content of the extracts, were treated by PCA (Principal Components Analysis), which highlighted the positive correlation among total phenolic content and increasing antibacterial activities, and a possible involvement of flavonoids in mitigate the cytotoxicity. Thirteen extracts displayed relevant IC₅₀ values (half maximal inhibitory concentration) on S. aureus (IC₅₀ from 1.4 to 153.6 μg/mL), ten out of them were active also against S. epidermidis (IC₅₀ from 3.9 to 150 μg/mL), seven against K. pneumoniae (IC₅₀ from 28.5 to 97.5 μg/mL), and two against E. coli (IC₅₀ 74.9 and 156.3 μg/mL). In particular, three extracts obtained from Pistacia terebinthus ssp. terebinthus, Cytinus hypocistis and Limonium morisianum emerged as promising antibacterial candidates. They exhibited remarkable inhibitory activity towards bacterial strains from clinical specimens and presenting different antibiotic-resistance profiles.

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Antimicrobial activity of rhizomes of Ferulago trachycarpa Boiss. and bioguided isolation of active coumarin constituents

Highlights

Abstract

Introduction

Section snippets

Chemical materials and instruments

Plant material

Result and discussion

Conclusion

Conflict of interests

Acknowledgment

Phytochemistry

Phytochemistry

Phytochemistry

Phytochemistry

J. Ethnopharmacol.

Phytochemistry

Bot. J. Linn. Soc.

Phytochemistry

The coumarin composition of the roots of Prangos uloptera

Chem. Nat. Compd.

The structure of ulopterol

Chem. Nat. Compd.

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