C:\Users\Hp\AppData\Local\Temp\msoE927.tmp


 

 

Bangladesh Journal of Pharmacology 

Research Article 

%-3 



 

Introduction 

Ferulago W. Koch. is a perennial genus of Apiaceae and 
is represented by approximately 50 taxa throughout the 
world and 35 taxa (18 of them are endemics) in Turkey. 
Hence Anatolia is considered as the gene center of this 
genus (Güner et al., 2012). F. blancheana Post ex Boiss. 
and F. pachyloba (Fenzl) Boiss. are endemic perennial 
species, growing only in Niğde-Central Anatolia and 
Kayseri-Central Anatolia, Turkey respectively, however 
F. trachycarpa Boiss. is not an endemic species, growing 
in Antalya-Southeastern Anatolia, Turkey (Peşmen, 
1972; Troia et al., 2012)  

Ferulago species have been used in folk medicine as 
digestive, carminative, tonic, sedative, vermifuge and 
aphrodisiac. It is also used to relieve headache, ulcers, 
hemorrhoids, snake bites, and spleen diseases. Ferulago 
species are used as salad or spice and food for goats 
and deers (Erdurak, 2003). 

Coumarins, indicated as the common metabolites of 
Ferulago species (Erdurak, 2003), have various biological 
activities such as antihyperglycemic (Tchamadeu et al., 
2010), antidiabetic (Patel et al., 2012), anti-hypertensive 
(Gantimur et al., 1986), antiadipogenic (Shin et al., 
2010), anticoagulant, anti-inflammatory, antibacterial, 

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Eleven coumarins named osthole (1), imperatorin (2), bergapten (3), prants-
chimgin (4), grandivitinol (5), suberosin (6), xanthotoxin (7), felamidin (8), 
marmesin (9), umbelliferone (10), ulopterol (11), and a sterol mixture 
consisted of stigmasterol (12), β-sitosterol (13) were isolated from the roots of 
Ferulago blancheana, F. pachyloba and F. trachycarpa through in vitro bioassay-
guided fractionation processes. The extracts and bioactive compounds were 
evaluated for their α-amylase and α-glucosidase activities. Among the tested 
compounds, felamidin and suberosin showed significant α-glucosidase 
inhibitory activity with IC50 values of 0.4 and 0.9 mg/mL, respectively, when 
compared to the reference standard acarbose (IC50 = 4.9 mg/mL). Grandivi-
tinol (IC50 = 20.0 mg/mL) had the lowest inhibitory effect. On the other hand, 
none of the tested extracts were found to be active on α-amylase inhibition. 
This is the first report on isolation, characterization of the bioactive com-
pounds and evaluation the α-amylase and α-glucosidase inhibitory activities 
of these species.  

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Received:  23 August 2017 
Accepted:  18 January 2018 
Available Online:   5 February 2018  

 

DOI: 10.3329/bjp.v13i1.33668 
 
 
 
 

Cite this article: 
Karakaya S, Özbek H, Gözcü S, 
Güvenalp Z, Yuca H, Duman H, Ka-
zaz C, Kiliç CS. α-Amylase and α-
glucosidase inhibitory activities of the 
extracts and constituents of Ferulago 
blancheana, F. pachyloba and F. trachy-
carpa roots. Bangladesh J Pharmacol. 
2018; 13: 35-40. 

α-Amylase and α-glucosidase inhibitory activities of the extracts 
and constituents of Ferulago blancheana, F. pachyloba and F. 
trachycarpa roots 
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'XPDQ���&DYLW�.D]D]��DQG�&H\GD�6LEHO�.LOLo� 

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This work is licensed under a Creative Commons Attribution 4.0 License. You are free to copy, distribute and perform the work. You must attribute 
the work in the manner specified by the author or licensor.  



 

antifungal, antiviral (Venugopala et al., 2013),  anti-
tubercular (Chiang et al., 2010), anti-cancer (Luo et al., 
2011), anti-oxidant (Basile et el., 2009), anti-convulsant 
(Luszczki et al., 2009) and neuroprotective (Wang et al., 
2012).  

Coumarins may be a potential source of new anti-
diabetic agents and may also be useful for peripheral 
tissues by improving the insulin resistance and the 
increasing glucose uptake (Zhang et al., 2017). 
Peucedanol 7-O-β-D-glucopyranoside (Lee et al., 2004), 
coumarin (1,2-benzopyrone) (Pari and Rajarajeswari, 
2009), umbelliferone (Ramesh and Pugalendi, 2005), 
imperatorin, psoralen, 5-methoxypsoralen, 8-methoxy-
psoralen, iso-oxypeucedanin, pabulenol, oxypeuceda-
nin methanolate, oxypeucedanin hydrate (Shalaby et 
al., 2014), iso-bergapten, pimpinellin, isopimpinellin, 
sphondin, scopoletin, phellopterin, byakangelicin and 
daucosterol (Zhang et al., 2017) were isolated from 
various plants belonging to the Apiaceae family and 
they were found to be antidiabetic. So, it may be a good 
approach in the treatment of type 2 diabetes.  

This is the first report of the isolation and structure 
elucidation study on the roots of F. blancheana, F. 
pachyloba and F. trachycarpa to afford 11 coumarins (1-
11) and a sterol mixture (12-13). The α-amylase and α-
glucosidase inhibitory activities of the isolated couma-
rins were also evaluated.� 

 

Materials and Methods 
General experimental procedures  

NMR spectra were recorded on a Varian Mercury Plus 
at 400 MHz for 1H NMR and 100 MHz for 13C NMR by 
using TMS as the internal standard. The solvents were 
CDCl3. ESI-MS was performed on Waters Micromass 
ZQ mass spectrometer. Column chromatographies were 
performed on silica gel 60 (0.063-0.200 mm, Merck) and 
sephadex LH-20 (Fluka). Thin layer chromatography 
(TLC) was carried out on pre-coated Kieselgel 60 F254  

aluminum sheets (Merck).  

Plant material  

Flowering plants of F. blancheana, F. pachyloba and F. 

trachycarpa were collected in 2014 from the Antalya, 
Niğde and Kayseri (Turkey), respectively and identified 
by one of the authors (Hayri Duman). The voucher 
specimens were kept in the Herbarium of Ankara 
University, Faculty of Pharmacy (Herbarium numbers: 
AEF 26677, AEF 26674 and AEF26673, respectively). 

Extraction and isolation  

Air-dried roots of F. blancheana (750 g), F. pachyloba (600 
g) and F. trachycarpa (450 g) were powdered and 
macerated three times with methanol for 8 hours in a 
water bath not exceeding 45°C (4 × 2 L) using a mecha-
nical mixer at 300 rpm. The combined extracts were 
filtered and concentrated till dryness, then dispersed in 
methanol-water (1:9) and fractionated four times with 
400 mL of dichloromethane, ethyl acetate and n-buta-
nol, respectively. The same extraction and fractionation 
procedure were applied for the aerial parts of the 
plants. On the other hand, 50 g of roots and aerial parts 
were grounded and macerated with 500 mL of distilled 
water for 8 hours/3 days at 30 to 35°C. The amounts of 
the powdered plants and obtained extracts are shown 
in Table I.  

As a result of the bioguided fractionation study, the 
effective dichloromethane extracts of the roots of all 
species were first submitted to a silica gel column and 
eluted with a gradient of n-hexane:ethyl acetate (100:0 
→ 0:100, v/v) and ethyl acetate:methanol (100:0 → 
0:100, v/v), and nine fractions (Fr. A-I) were obtained. 
Fr. A was subjected to a silica gel column which was 
eluted with a mixture of n-hexane:ethyl acetate (95:5) 
and compounds 12 and 13 were obtained as a mixture 
(217 mg). Repetitive silica gel column chromatography 
with n-hexane-ethyl acetate (90:10 and 95:5) solvent 
system on Fr. B gave the compound 1 (220 mg). Fr. C 
was applied to the silica gel column eluting with n-
hexane:ethyl acetate (85:15) and sephadex LH-20 
column eluting with ethyl acetate to give the com-
pounds 2 (125 mg) and compound 3 (130 mg). Eluting 
with n-hexane-ethyl acetate (90:10) over silica gel 
column of Fr. D gave the compound 4 (400 mg) and Fr. 
E gave the compounds 5 (150 mg) and compound 6 (330 
mg). Fr. F eluted with 25% ethyl acetate in n-hexane and 
rechromatographed with 25% ethyl acetate in n-hexane 
on the silica gel column to obtain compound 7 (110 mg). 

36 Bangladesh J Pharmacol 2018; 13: 35-40                                                                

Table I 

Amounts of the powdered plants and obtained extracts 

Species Used parts Powdered 
(g) 

MeOH 
(g) 

CH2Cl2 
(g) 

EtOAc 
(g) 

BuOH 
(g) 

Aqueous residue 
(g) 

Lyophilized 
(g) 

F. blancheana 
    

Root 750 86.6 28.5 2.3 12.2 23.4 5.8 
Aerial part 50 3.2 1.9 0.5 0.6 0.4 1.8 

F. pachyloba   Root 600 83.3 23.6 1.5 13.1 21.3 5.0 
Aerial part 50 3.3 1.8 0.5 0.6 0.5 2.0 
Root 450 86.8 26.3 2.4 13.5 22.1 4.8 
Aerial part 50 3.4 1.7 0.5 0.6 0.6 1.7 

F. trachycarpa  



 

Fr. G was fractioned by column chromatography over 
silica gel using n-hexane:ethyl acetate mixtures (70:30 
and 90:10) consecutively and compound 8 was obtained 
(325 mg). Fr. H was submitted on a silica gel column 
using n-hexane:ethyl acetate (65:35) to yield compound 
9 and the resulting fraction was chromatographed on 
the silica gel column using n-hexane:ethyl acetate 
(90:10) to give the compound 10. Fr. I gave the 
compound 11 (320 mg). Compounds 1-4, 5, 7, 8, 10 and 
12-13 were isolated by the same chromatographic 
methods in all species. Compounds 6 and 11 were 
isolated only from the dichloromethane fraction of the 
roots from F. trachycarpa. Compound 9 was isolated 
only from the dichloromethane fraction of the roots 
from F. blancheana (Figure 1). 

α-Amylase inhibitory activity  

α-Amylase inhibitory activity was established in accor-
dance with the reported method (Nampoothiri et al., 
2011) with slight modifications. 1% Starch solution (100 
µL) in 20 mM sodium phosphate buffer (pH 6.9 with 
6 mM sodium chloride) and sample solutions (100 µL) 
were incubated at 25°C for 10 min in 24-well micro-
plate. Afterwards incubation, 100 μL α-amylase solution 
(0.5 mg/mL) was added to each well and the reaction 

mixtures were incubated at 25°C for 10 min. In order to 
stop the reaction after the incubation, dinitrosalicylic 
acid color reagent (200 μL) was added and then the 
microplate was incubated in a boiling water bath for 
5 min and cooled at room temperature. It was taken 50 
μL from each well and then was added to 96-well 
microplate. The reaction mixture was diluted by adding 
200 μL distilled water and the absorbance was mea-
sured at 540 nm. Each assay for all samples was carried 
out in triplicate. Percentage inhibitions of all samples 
were calculated using the equation at following: 

                                 rAsample 
%Inhibition = (1 -                    ) x 100 
                                 rAcontrol 
   

α-Glucosidase inhibitory activity  

α-Glucosidase inhibitory activity was established by 
using a 96-well microtiter plate in accordance with the 
described method (Tao et al., 2013) with slight modifi-
cations. p-Nitro-phenyl-α-D-glucopyranoside (p-NPG) 
was used as the substrate and was prepared in 0.1 M 
potassium phosphate buffer (pH 6.8). α-Glucosidase (0.1 
unit/mL, enzyme solution) was dissolved in the same 
buffer. The samples were dissolved in dimethyl sulfo-

Figure 1: Chemical structures of compounds 1-13 

 Bangladesh J Pharmacol 2018; 13: 35-40                                                                 37 



 

xide (DMSO) and all samples (20 μL) together with the 
enzyme solution (20 μL) were mixed in the plate. 
Afterward, the substrate (40 μL) was added for initia-
tion of the reaction and the mixture was incubated at 
37°C for 40 min. After incubation, 0.2 M sodium carbo-
nate (80 µL) in phosphate buffer (pH 6.8) was added to 
all wells in order to quench the reaction. The amount of 
released p-nitrophenol (pNP) was measured at 405 nm 
using a 96-well microplate reader. Each assay for all 
samples was carried out in triplicate. Percentage 
inhibitions of all samples were calculated using the 
equation at following: 

                                 rAsample 
%Inhibition = (1 -                    ) x 100 
                                 rAcontrol 
   

Results and Discussion 

Methanol extracts of the roots of three Ferulago species 
were fractionated using solvents with different polari-
ties (dichloromethane, ethyl acetate and n-butanol) and 
the obtained fractions were evaluated for their α-
amylase and α-glucosidase inhibitory activities. The 
active dichloromethane extracts were subjected to 
column chromatography over silica gel and sephadex 
LH-20. As the result, eleven coumarins osthole (1) 
(Sajjadi et al., 2009), imperatorin (2) (Muller et al., 2004), 
bergapten (3) (Stevenson et al., 2003), prantschimgin (4) 
(Sajjadi et al., 2015), grandivitinol (5) (Abyshe et al., 
1977), suberosin (6) (Tabanca et al., 2016), xanthotoxin 
(7) (Stevenson et al., 2003), felamidin (8) (Kilic et al., 
2006), marmesin (9) (Abreu et al., 2010), umbelliferone 
(10) (Singh et al., 2010), ulopterol (11) (Doganca et al., 
1979) and a sterol mixture consisted of stigmasterol 
(12), β-sitosterol (13) (Woldeyes et al., 2012) (Figure 1) 
were isolated and identified.   

The extracts and compounds 1-11, obtained via bio-
assay guided fractionation and isolation process, were 
evaluated for their in vitro α-amylase and α-glucosidase 
inhibitory activities. The IC50 values and inhibitory 
effects (%) are given in Table II. Acarbose was used as a 
reference standard for both assays. Dichloromethane 
extracts of roots from F. blancheana, F. pachyloba and F. 
trachycarpa showed significant activities against α-
glucosidase with IC50 value of 2.0, 2.0 and 0.3 mg/mL, 
respectively. Among the tested compounds felamidin 
(IC50 0.4 mg/mL) possessed the best inhibitory activity 
which was more potent than acarbose (IC50 5.0 mg/
mL). Suberosin, osthole, imperatorin, prantschimgin 
and marmesin also showed α-glucosidase inhibitory 
activity (IC50 0.9, 1.0, 1.2, 1.9, 3.0 mg/mL, respectively) 
which had lower effect than felamidin but stronger than 
acarbose. On the other hand, none of the extracts 
showed meaningful α-amylase inhibitory activity, while 
acarbose indicated 82.3% inhibition at a concentration 
of 1 mg/mL. These results indicate that felamidin was 
eleven times more effective than acarbose against α-

glucosidase. To our knowledge, no previous study have 
been reported on α-glucosidase and α-amylase inhibi-
tory activities of F. blancheana, F. pachyloba and F. 
trachycarpa and the isolated coumarins prantschimgin, 
felamidin, grandivitinol and suberosin. Also this is the 
first report on phytochemical analysis of these species. 
Our results are similar to the previous studies 
performed on related coumarins. Shalaby et al. (2014) 
found that imperatorin (at 1000 µg/mL α-glucosidase 
inhibition% was found to be 69.7 ± 3.7 and we found an 
inhibition of 89.9 ± 0.9% at a concentration of 5000 µg/
mL) showed appreciable antidiabetic activity. Compa-
ring these results with previous studies in which α-
glucosidase IC50 value of umbelliferone was found to be 
7.8 ± 0.1 μg/mL, we have found a higher inhibitory 
activity with 9.3 mg/mL (Ramith et al., 2014). Compa-
ring these results with another previous study in which 
α-glucosidase IC50 value of umbelliferone was 0.5 mg/
mL at 0.5 mg/mL, the inhibitory activity that we have 
found was again higher (Ayyasamy and Rajamanickam, 
2015).  

 

Conclusion 

Among the compounds isolated from CH2Cl2 fractions 
of F. blancheana, F. pachyloba and F. trachycarpa roots, 
coumarins were determined the main chemical consti-
tuents of these fractions. The most potent compounds 
were felamidin and suberosin.   

 

Conflict of Interest 

The authors declare that they have no conflict of interest. 

 

Acknowledgement 
This study was supported by the Scientific and Techno-logical 
Research Council of Turkey (TUBITAK 115S009).  

 

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38 Bangladesh J Pharmacol 2018; 13: 35-40                                                                



 

Table II 

α-Glucosidase inhibitory activities of extracts, fractions and compounds from Ferulago blancheana, F. pachyl-
oba and F. trachycarpa 

Species Extracts/fractions/ 
compounds 

Concentration       
(µg/mL) 

α-Glucosidase inhibi-
tion (%) 

IC50 value 
(mg/mL) 

F. blancheana  Methanol extract 5000 77.3 ± 0.1 2.2 

Methanol extract 2000 49.2 ± 0.5 2.2 
Dichloromethane fraction 5000 79.8 ± 1.0 2.0 
Dichloromethane fraction 2000 50.2 ± 0.6 2.0 
Ethyl acetate fraction 5000 ND ND 
n-Butanol fraction 5000 ND ND 
Aqueous residue fraction 5000 ND ND 

F. pachyloba  Methanol extract 5000 68.2 ± 0.7 3.2 
Methanol extract 2000 40.7 ± 0.1 3.2 
Dichloromethane fraction 5000 89.9 ± 0.5 2.0 
Dichloromethane fraction 2000 52.8 ± 0.1 2.0 
Ethyl acetate fraction 5000 72.1 ± 0.2 3.0 
Ethyl acetate fraction 2000 40.1 ± 0.1 3.0 
n-Butanol fraction 5000 ND ND 
Aqueous residue fraction 5000 ND ND 
Aqueous extract 5000 ND ND 

F. trachycarpa  Methanol extract 5000 88.7 ± 0.7 0.4 
Methanol extract 2000 82.1 ± 0.2 0.4 
Dichloromethane fraction 5000 89.1 ± 0.2 0.3 
Dichloromethane fraction 2000 85.3 ± 0.4 0.3 
Ethyl acetate fraction 5000 ND ND 
n-Butanol fraction 5000 ND ND 
Aqueous residue fraction 5000 ND ND 
Aqueous extract 5000 ND ND 

Osthole   5000 93.3 ± 0.3 1.0 
2000 84.3 ± 1.7 1.0 

Imperatorin   5000 89.0 ± 0.9 1.2 
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Bergapten   5000 42.3 ± 0.4 6.1 
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Prantschimgin   5000 68.2 ± 0.4 1.9 
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Grandivitinol   5000 12.3 ± 0.4 20.0 
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Suberosin  5000 88.9 ± 1.1 0.9 
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Xanthotoxin  5000 45.8 ± 4.8 5.4 
2000 38.0 ± 8.6 5.4 

Felamidin  5000 94.6 ± 0.1 0.4 
2000 64.9 ± 2.1 0.4 

Marmesin  5000 84.8 ± 3.2 3.0 
2000 32.8 ± 2.2 3.0 

Umbelliferone  5000 10.3 ± 0.5 9.3 
2000 8.8 ± 0.0 9.3 

Ulopterol  5000 50.6 ± 2.8 5.1 
2000 42.9 ± 3.1 5.1 
5000 50.8 ± 2.5 5.0 
2000 29.4 ± 1.7 5.0 

Acarbose  

 Bangladesh J Pharmacol 2018; 13: 35-40                                                                 39 



 

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40 Bangladesh J Pharmacol 2018; 13: 35-40                                                                


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