Enzymatic assays and molecular modeling studies of Schisandra chinensis lignans and phenolics from fruit and leaf extracts

Figures & data

Table 1. Bioactive compounds in Schisandra chinensis fruits and leaves: identification and quantification (mg/g d.w. material) – mean ± SD.

Compound	MW(g/mol)	Leaves(mg/g dw)	Fruits(mg/g dw)
Schisandrol A*	432	1.29 ± 0.02	4.24 ± 0.21
Schisandrol B*	416	0.63 ± 0.01	1.45 ± 0.14
Schisandrin A*	416	0.23 ± 0.00	0.89 ± 0.09
γ-Schisandrin*	400	1.01 ± 0.01	2.27 ± 0.09
Cinnamic acid*	148	3.54 ± 0.06	ND
Protocatechuic acid*	154	0.53 ± 0.01	0.34 ± 0.01
3-O-Caffeoylquinic acid (neo-chlorogenic acid)	354	2.95 ± 0.02	ND
4-O-p-Coumaroylquinic acid	338	0.26 ± 0.01	ND
3-O-p-Coumaroylquinic acid	338	0.87 ± 0.04	ND
5-O-Caffeoylquinic acid* (chlorogenic acid)	354	4.99 ± 0.22	ND
3-O-Ferruloylquinic acid	368	0.19 ± 0.01	ND
4-O-Caffeoylquinic acid (crypto-chlorogenic acid)	354	0.15 ± 0.01	ND
trans-5-O-p-Coumaroylquinic acid	338	1.05 ± 0.05	ND
cis-5-O-p-Coumaroylquinic acid	338	0.41 ± 0.02	ND
Rutin*	610	0.38 ± 0.01	ND
Quercetin-3-O-glucoside-7-O-rhamnoside	610	1.70 ± 0.12	ND
Quercetin-3-O-galactoside	464	2.49 ± 0.05	ND
Quercetin-3-O-glucoside*	464	3.68 ± 0.01	ND
Quercetin-3-O-dirhamnoside	594	0.42 ± 0.01	ND
Quercetin-3-O-xyloside	434	0.49 ± 0.02	ND
Kaempferol-3-O-glucoside-7-O-rhamnoside	594	5.68 ± 0.09	ND
Kaempferol-3-O-glucoside	448	5.12 ± 0.07	ND
Kaempferol-3-O-arabinose	418	0.48 ± 0.01	ND
Cinnamic acid*	148	3.54 ± 0.06	ND
Quercetin*	302	0.29 ± 0.01	ND
Kaempferol*	286	0.63 ± 0.02	ND

Compounds with* were identified with references accurately. Data according to Mocan et al.²³

Scheme 1. Chemical structures of compounds cp1, cp4, cp24, and cinnamic acid (CA) employed for docking and molecular dynamic experiments.

Figure 1. (A and C) best pose of compound cp1 in complex to acetylcholinesterase (GoldScore); (B and D) best pose of compound cp4 in complex to acetylcholinesterase (PLP).

Figure 2. RMSD in Angstrom of 26 ns MD simulation of compounds cp1 (GoldScore) (yellow), cp4 (PLP) (blue) in complex to acetylcholinesterase compared to the simulation of the crystallographic ligand tacrine-nicotinamide (light red).

Figure 3. (A and C) best pose of cp1 (PLP) in complex to glucosidase; (B and D) best pose of cp4 (PLP) in complex to glucosidase.

Figure 4. (A and B) best pose of cp1 (PLP) in complex to amylase; (C) RMSD in Angstrom of 26 ns MD simulation of compound cp1 (PLP) in complex to amylase.

Figure 5. (A and B) best pose of cp4 (GoldScore) in complex to tyrosinase; (C and D) best pose of CA (GoldScore) in complex to tyrosinase.

Figure 6. RMSD in Angstrom of 26 ns MD simulation of compounds cp4 (GoldScore), cp24 (ChemScore) and CA (GoldScore) in complex to tyrosinase.

Table 2. Enzyme inhibitory effects of Schisandra chinensis leave and fruit extracts.

Samples	AChE inhibition (mg GALAE/g extract)	BChE inhibition (mg GALAE/g extract)	Amylase inhibition (mmol ACAE/g extract)	Glucosidase inhibition (mmol ACAE/g extract)	Tyrosinase inhibition (mg KAE/g extract)
Leaves	0.97 ± 0.01*	NA	0.36 ± 0.02	8.54 ± 0.02	15.53 ± 0.12
Fruits	0.98 ± 0.01	1.78 ± 0.01	0.46 ± 0.01	0.31 ± 0.04	10.24 ± 0.34

*Three parallel experiments ± SD.

GALAE: galanthamine equivalents; ACAE: acarbose equivalents; KAE: kojic acid equivalents; NA: not active.

Mocan A, Schafberg M, Crişan G, Rohn S. Determination of lignans and phenolic components of Schisandra chinensis (Turcz.) Baill. using HPLC-ESI-ToF-MS and HPLC-online TEAC: contribution of individual components to overall antioxidant activity and comparison with traditional antioxidant assays. J Funct Foods 2016;24:579–94

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