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. 2023 Jun 16;28(12):4816.
doi: 10.3390/molecules28124816.

Characterization of Polyphenols from Chenopodium botrys after Fractionation with Different Solvents and Study of Their In Vitro Biological Activity

Dimitar Bojilov  1 , Stanimir Manolov  1 , Angelika Nacheva  1 , Soleya Dagnon  1 , Iliyan Ivanov  1
Affiliations

Characterization of Polyphenols from Chenopodium botrys after Fractionation with Different Solvents and Study of Their In Vitro Biological Activity

Dimitar Bojilov et al. Molecules. .

Abstract

In the present work, we have investigated the polyphenolic composition of Chenopodium botrys from Bulgaria. The polyphenols were fractionated with solvents of varying polarity (n-hexane, chloroform, ethyl acetate, and n-butanol). The fractions were analyzed by HPLC-PDA and UHPLC-MS. The ethyl acetate fraction contained mono- and di-glycosides of quercetin, di-glycosides of kaempferol, and isorhamnetin and monoglycosides of hispidulin and jaceosidine. We found quercetin triglycosides in the butanol fraction. The ethyl acetate and butanol fractions contained 168.82 mg/g Extr and 67.21 mg/g Extr of quercetin glycosides, respectively. The main components of the polyphenolic complex in C. botrys were 6-methoxyflavones (355.47 mg/g Extr), which were found in the chloroform fraction. The flavonoids pectolinarigenin, demethylnobiletin, and isosinensetin, and the glycosides of quercetin (triglycosides, acylglycosides), kaempferol, isorhamnetin, hispidiulin, and jaceosidine, were discovered and reported in Chenopodium botrys for the first time. We used in vitro methods to assess the biological activity against oxidative stress (hydrogen peroxide scavenging activity (HPSA) and hydroxyl radical scavenging activity (HRSA)), nitrosative stress (nitric oxide scavenging activity (NOSA)), anti-inflammatory activity (IAD inhibition), and anti-tryptic activity (ATA). Quercetin mono- and di-glycosides exhibited greater HPSA and HRSA (IC50 = 39.18, 105.03 µg/mL), while 6-methoxyflavones had a greater NOSA (IC50 = 146.59 µg/mL). The same components showed the highest ATA (IC50 ranging from 116.23 to 202.44 µg/mL).

Keywords: 6-methoxy and polymethoxylated flavones; ATA; Chenopodium botrys; HPSA; HRSA; IAD; NOSA; flavonoid-glycosides; in vitro biological activity.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Yields (%) of the hexane, chloroform, ethyl acetate and butanol fractions. The experiments were performed in triplicate (A). Total phenolic content (TPC) and total tannin content (TTC) of different fractions obtained from C. botrys. The TPC and TTC results are presented as mg GAE/g Extr and mg TAE/g Extr, respectively (B).
Figure 2
Figure 2
Chromatographic profiles of the fractionated polyphenolic complex in Chenopodium botrys obtained by HPLC-PDA. The chloroform fraction contains mainly 6-methoxy and polymethoxylated flavones, the ethyl acetate fraction contains mono- and di-glycosides of quercetin, kaempferol, isorhamnetin, monoglycosides of hispidulin, jaceosidin and isorhamnetin, and the butanol fraction contains triglycosides of quercetin.
Figure 3
Figure 3
Total ion current (TIC) of flavonoids from C. botrys in chloroform fraction (A); mass spectrum of nepetin obtained by negative ion ESI-MS/MS (B).
Scheme 1
Scheme 1
Structures of 6-methoxyflavones (A); nomenclature for the different retro-cyclization cleavages in negative ESI-MS/MS mode (B).
Scheme 2
Scheme 2
Proposed fragmentation of deprotonated nepetin [M−H]− at CE 55 eV.
Figure 4
Figure 4
Total ion current (TIC) of flavonoids from C. botrys in EtOAc fraction (A); total ion current (TIC) of flavonoids from C. botrys in BuOH fraction (B). Mono- and di-glycosides of quercetin (Peaks—6–9, 11, 12, 15, 20, 21, 23–26) were identified in the EtOAc fraction (A), di-glycosides of kaempferol (Peaks—18, 22), mono- and di-glycosides of isorhamnetin (Peaks—10, 13, 16), monoglycosides of jaceosidine (Peaks—14, 19) and hispidulin (Peak—17). Triglycosides of quercetin were identified in the BuOH fraction (B) (Peaks—1–5).
Figure 5
Figure 5
HPSA (A) and HRSA (B) of the fractionated polyphenolic complex with differences in polarity solvents obtained from C. botrys. Ascorbic acid (AA) and quercetin (Qrc) were used as standards. The antioxidant activity results are presented as IC50 (µg/mL).
Figure 6
Figure 6
NOSA of the fractionated polyphenolic complex with different polar solvents obtained from C. botrys. Ascorbic acid (AA) and quercetin (Qrc) were used as standards. Antioxidant activity results are presented as IC50 (µg/mL).
Figure 7
Figure 7
IAD (A) and ATA (B) of the fractionated polyphenolic complex with differences in polarity solvents obtained from C. botrys. As controls, ibuprofen (Ibu) and ketoprofen (Ket) were utilized. The results are reported as IC50 (µg/mL).
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