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. 2021 Dec;59(1):444-456.
doi: 10.1080/13880209.2021.1913189.

UPLC-PDA-ESI-QTOF-MS/MS fingerprint of purified flavonoid enriched fraction of Bryophyllum pinnatum; antioxidant properties, anticholinesterase activity and in silico studies

Joyce Oloaigbe Ogidigo  1   2 , Chioma Assumpta Anosike  1 , Parker Elijah Joshua  1 , Collins U Ibeji  3 , Daniel Emmanuel Ekpo  1 , Bennett C Nwanguma  1 , Okwesili Fred Chiletugo Nwodo  1   4
Affiliations

UPLC-PDA-ESI-QTOF-MS/MS fingerprint of purified flavonoid enriched fraction of Bryophyllum pinnatum; antioxidant properties, anticholinesterase activity and in silico studies

Joyce Oloaigbe Ogidigo et al. Pharm Biol. 2021 Dec.

Abstract

Context: Bryophyllum pinnatum (Lam.) Oken (Crassulaceae) is used traditionally to treat many ailments.

Objectives: This study characterizes the constituents of B. pinnatum flavonoid-rich fraction (BPFRF) and investigates their antioxidant and anticholinesterase activity using in vitro and in silico approaches.

Materials and methods: Methanol extract of B. pinnatum leaves was partitioned to yield the ethyl acetate fraction. BPFRF was isolated from the ethyl acetate fraction and purified. The constituent flavonoids were structurally characterized using UPLC-PDA-MS2. Antioxidant activity (DPPH), Fe2+-induced lipid peroxidation (LP) and anticholinesterase activity (Ellman's method) of the BPFRF and standards (ascorbic acid and rivastigmine) across a concentration range of 3.125-100 μg/mL were evaluated in vitro for 4 months. Molecular docking was performed to give insight into the binding potentials of BPFRF constituents against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE).

Results: UPLC-PDA-MS2 analysis of BPFRF identified carlinoside, quercetin (most dominant), luteolin, isorhamnetin, luteolin-7-glucoside. Carlinoside was first reported in this plant. BPFRF significantly inhibited DPPH radical (IC50 = 7.382 ± 0.79 µg/mL) and LP (IC50 = 7.182 ± 0.60 µg/mL) better than quercetin and ascorbic acid. Also, BPFRF exhibited potent inhibition against AChE and BuChE with IC50 values of 22.283 ± 0.27 µg/mL and 33.437 ± 1.46 µg/mL, respectively compared to quercetin and rivastigmine. Docking studies revealed that luteolin-7-glucoside, carlinoside and quercetin interact effectively with crucial amino acid residues of AChE and BuChE through hydrogen bonds.

Discussion and conclusions: BPFRF possesses an excellent natural source of cholinesterase inhibitor and antioxidant. The material could be further explored for the potential treatment of oxidative damage and cholinergic dysfunction in Alzheimer's disease.

Keywords: Alzheimer’s diseases; acetylcholinesterase; butyrylcholinesterase; carlinoside; docking studies; lipid peroxidation.

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Conflict of interest statement

No potential conflict of interest was reported by the author(s).

Figures

Figure 1.
Figure 1.
Bryophyllum pinnatum plant.
Figure 2.
Figure 2.
Overlay of UPLC chromatogram at 280 nm top and base peak intensity (BPI) chromatograms (bottom) of BPFRF.
Figure 3.
Figure 3.
Photodiode array detector (PDA) spectra and mass spectra (MS/MS) fragmentation pattern present in B. pinnatum flavonoid-rich fraction (BPFRF). Luteolin C-glucoside-C-arabinoside (carlinoside) (A). Quercetin (B). Luteolin (C). Quercetin-3-methyl ether (isorhamnetin) (D). Luteolin-7-glucoside (E).
Figure 4.
Figure 4.
2,2-Diphenyl-1-picrylhydrazyl free radical scavenging effect of BPFRF in comparison with ascorbic acid (3.125–100 μg/mL).
Figure 5.
Figure 5.
Fe2+-induced lipid peroxidation inhibitory activity of BPFRF and the ascorbic acid.
Figure 6.
Figure 6.
Cholinesterase inhibitory activity of BPFRF AChE (A). BuChE (B).
Figure 7.
Figure 7.
Illustrations of molecular interactions (left: 3D and right: 2D) between the/highest binding energies of BPFRF constituents and standard against AChE target. Luteolin-7-glucoside (red) (Ai, Aii). Quercetin (orange) (Bi, Bii). Rivastigmine (purple) (Ci, Cii).
Figure 8.
Figure 8.
Illustrations of molecular interactions (left: 3D and right: 2D) between the highest binding energies of BPFRF constituents and standard against BuChE target. Carlinoside (yellow) (Ai, Aii). Quercetin (grey) (Bi, Bii). Rivastigmine (purple) (Ci, Cii).
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