The Influence of Different Extraction Methods/Solvents on Composition, Biological Activities and ADMET Predictions of Phenolics in Tribulus terrestris

Taşkın, Duygu; Yılmaz, Beyza Nur; Taşkın, Turgut; Omurtag, Gülden Zehra

doi:10.1590/1678-4324-2021210249

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Article - Biological and Applied Sciences • Braz. arch. biol. technol. 64 • 2021 • https://doi.org/10.1590/1678-4324-2021210249 copy

The Influence of Different Extraction Methods/Solvents on Composition, Biological Activities and ADMET Predictions of Phenolics in Tribulus terrestris

Authorship SCIMAGO INSTITUTIONS RANKINGS

HIGHLIGHTS

The effects of different extraction methods/solvents on the plant's biological activity

The effect of various extraction methods/solvents on the chemical components of the plant

Biological activities of different extracts from the plant

Analysis of major phenolic compounds and in-silico ADMET prediction

Abstract

Tribulus terrestris is a plant that has medical importance in treating diseases such as cancer, urinary tract infections, kidney stones, rheumatism, and hypertension. The aim of this study is to examine the effects of extraction methods/solvents on the biological activity and chemical content of the plant and then to determine ADMET predictions of phenolics that were analysed quantitatively using HPLC-DAD in the plant. Maceration methanol (IC₅₀:0.277 mg/mL) and chloroform (0.263 mMFeSO₄/mg extract) extracts were found to have the strongest DPPH radical scavenging and iron (III) ion reducing activity, respectively. It was determined that Soxhlet methanol (0.0225 mMTE/mg extract) and Soxhlet chloroform (1.360 mMTE/mg extract) extracts exhibited stronger radical cation (ABTS^.+) scavenging and cupric ion reducing activity compared to other extracts, respectively. It was found that ultrasonic bath methanol extracts showed the highest anti-urease (21.47%) and calcium oxalate anti-crystallization (71.54%, 80.52%) activity. It was also found that Soxhlet methanol extract (66.763%) has strong acetylcholinesterase enzyme inhibition capacity compared to other extracts. Pyrocatechol, vanillic acid, vanillin, rutin and rosmarinic acid were analysed by HPLC-DAD in the plant. Moreover, it was determined that methanol extracts obtained using soxhlet, ultrasonic bath, and maceration contained the highest amount of rutin, pyrocatechol, and rutin, respectively. ADMET predictions of phenolics show that these compounds are easily absorbed and do not have toxic effects, suggesting that this species may be used as a natural medicinal and nutritional source in the future after detailed analysis tests.

Keywords:
antioxidant; enzyme inhibition; anti-crystallization; HPLC-DAD

Compounds	Regression equation	R²	Linear range (μg/mL)	LOD (μg/mL)	LOQ (μg/mL)
Pyrocatechol	Y=113.1x-648.6	0.9881	20-100	1.55	4.70
Vanillic acid	Y=308.8x-98.34	0.9962	4-20	0.25	0.76
Vanillin	Y=420.3x+22.18	0.9757	2-10	0.02	0.06
Rutin	Y=38.59x-116.5	0.9998	50-250	1.42	4.74
Rosmarinic acid	Y=410.1x-453.2	0.9873	4-20	0.8	2.6

Extracts	DPPH (IC₅₀: mg/mL)			FRAP (mMFeSO₄/mg extract)			CUPRAC (mMTE/mg extract)			ABTS/TEAC (mMTE/mg extract)
	Ultrasonic bath	Maceration	Soxhlet	Ultrasonic bath	Maceration	Soxhlet	Ultrasonic bath	Maceration	Soxhlet	Ultrasonic bath	Maceration	Soxhlet
Petroleum ether	0.724±0.419^a	0.48±0.2436^a	0.529±0.407^a	0.227±0.0203^a	0.117±0.0169^a	0.216±0.0148^a	0.643±0.0193^a	0.034±0.7705^a	0.995±0.0321^a	NA	0.0032±0.0013^a	NA
Chloroform	0.556±0.376^b	0.712±0.406^b	2.367±1.539^b	0.259±0.0303^a	0.263±0.0319^b	0.169±0.0316^b	0.951±0.0268^b	1.277±0.0150^b	1.36±0.0237^b	0.0037±0.0008^a	0.0094±0.0009^b	0.0209±0.0078^a
Methanol	0.36±0.232^c	0.277±0.145^c	0.372±0.189^c	0.055±0.0146^c	0.005±0.0057^c	0.008±0.0006^c	0.602±0.0116^a	0.671±0.025^c	0.708±0.0119^c	0.0185±0.0012^b	0.0216±0.0009^c	0.0225±0.0051^a
AA	0.0028±0.0004									0.132±0,001
BHA							1.83±0.0002
BHT				1.10±0.001

	Urease inhibition (%) (12.5 μg/mL)			Acetylcholinesterase inhibition (%) (200 µg/mL)
	Ultrasonic bath	Maceration	Soxhlet	Ultrasonic bath	Maceration	Soxhlet
Petroleum ether	14.99±2.7321^a	4.34±2.8053^a	15.18±4.228^a	30.472±7.6575^a	22.286±4.0598^a	49.3±1.9217^a
Chloroform	15.73±1.1453^a	19.22±1.908^b	15.77±5.112^a	11.496±5.4245^b	14.608±3.1555^b	34.973±6.3418^b
Methanol	21.47±1.0112^b	9.58±2.7603^c	18.84±1.784^a	50.941±2.7496^c	60.843±1.0542^c	66.763±3.0125^c
Thiourea	70.05±0.007
Galantamine				85.289±0.06

	Nucleation (%)				Aggregation (%)
Concentration (mg/mL)	Maceration	Soxhlet	Ultrasonic bath	Potassium citrat	Maceration	Soxhlet	Ultrasonic bath	Potassium citrat
5	NA*	NA	71.54	97.94	78.21	70.71	80.52	98.41
2.5	NA	NA	63.48	64.23	44.88	48.49	74.89	72.73
1.25	NA	9.55	55.81	56.12	33.33	NA	45.74	57.72

Compounds	Ultrasonic Bath (Average amount ± SD)	Soxhlet (Average amount ± SD)	Maceration (Average amount ± SD)
Pyrocatechol	2.179 ±0.006	ND	ND
Vanillic acid	0.181±0.002	0.260±0.004	0.178±0.002
Vanillin	0.028±0.002	0.007±0.001	0.110±0.002
Rutin	1.581±0.029	4.391±0.021	2.638±0.044
Rosmarinic acid	ND	ND	0.400±0.001

Predicted Value
Property	Pyrocatechol	Vanillic acid	Vanillin	Rutin	Rosmarinic acid
Absorption
Water solubility (log mol/L)	-0.762	-1.838	-1.308	-2.892	-3.059
Caco2 permeability (log Papp in 10^-6 cm/s)	1.682	0.33	1.219	-0.949	-0.937
Intestinal absorption (human)(% Absorbed)	86.856	78.152	84.976	23.446	32.516
Skin Permeability (log Kp)	-2.618	-2.726	-2.832	-2.735	-2.735
P-glycoprotein substrate	No	No	No	Yes	Yes
P-glycoprotein I inhibitor	No	No	No	No	No
P-glycoprotein II inhibitor	No	No	No	No	No
Distribution
VDss (human) (log L/kg)	-0.022	-1.739	-0.152	1.663	0.393
Fraction unbound (human) (Fu)	0.62	0.518	0.43	0.187	0.348
BBB permeability^a (log BB)	-0.318	-0.38	-0.243	-1.899	-1.378
CNS permeability^b (log PS)	-2.076	-2.628	-2.236	-5.178	-3.347
Metabolism
CYP2D6 substrate	No	No	No	No	No
CYP3A4 substrate	No	No	No	No	No
CYP1A2 inhibitor	No	No	No	No	No
CYP2C19 inhibitor	No	No	No	No	No
CYP2C9 inhibitor	No	No	No	No	No
CYP2D6 inhibitor	No	No	No	No	No
CYP3A4 inhibitor	No	No	No	No	No
Excretion
Total Clearance (log ml/min/kg)	0.147	0.628	0.601	-0.369	0.25
Renal OCT2 substrate	No	No	No	No	No
Toxicity
AMES toxicity	No	No	No	No	No
Max. tolerated dose (human) (log mg/kg/day)	-0.017	0.719	1.285	0.452	0.152
hERG I inhibitor	No	No	No	No	No
hERG II inhibitor	No	No	No	Yes	No
Oral Rat Acute Toxicity (LD50) (mol/kg)	2.14	2.454	1.937	2.491	2.811
Oral Rat Chronic Toxicity (LOAEL) (log mg/kg_bw/day)	2.313	2.032	2.007	3.673	2.907
Hepatotoxicity	No	No	No	No	No
Skin Sensitization	Yes	No	No	No	No
T.Pyriformis toxicity (log µg/L)	0.105	0.265	-0.014	0.285	0.302
Minnow toxicity (log mM)	2.194	1.926	1.899	7.677	2.698

Compounds	MLP	TPSA
Pyrocatechol
Pyrocatechol	LogP= 1.0978	TPSA= 40.46
Vanillic acid
Vanillic acid	LogP= 1.099	TPSA= 66.76
Vanillin
Vanillin	LogP= 1.2133	TPSA= 46.53
Rosmarinic acid
Rosmarinic acid	LogP= 1.63	TPSA= 144.52
Rutin
Rutin	LogP= -1.06	TPSA= 269.43

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[1] *Correspondence: duygu.taskin@sbu.edu.tr; Tel.: +90-506 3069982 (D.T.).