UHPLC-QQQ-MS and RP-HPLC Detection of Bioactive Alizarin and Scopoletin Metabolites from Morinda citrifolia Root Extracts and Their Antitubercular, Antibacterial, and Antioxidant Activities

Abstract

Morinda citrifolia is a medicinal plant that has been traditionally used in various therapeutic applications. All parts of M. citrifolia including fruits, leaves, stems, roots, and flowers contain various biologically active phytochemicals. This study aimed to evaluate the antitubercular, antibacterial, and antioxidant activities of M. citrifolia root extracts and spectroscopically analyze the bioactive metabolites. M. citrifolia root extracts were prepared via maceration. The minimum inhibitory concentration (MIC) for antitubercular activity, the inhibition zone for antibacterial activity, and the antioxidant activities in terms of half-maximal inhibitory concentration (IC50) values were determined. 1H-NMR, RP-HPLC, and UHPLC-QQQ-MS analyses were performed to evaluate the secondary metabolites. The results showed that the dichloromethane root extract exhibited relatively good inhibition of M. tuberculosis with an MIC value of 50 μg/mL. All extracts were mostly active against five tested bacterial strains. The ethanolic and dichloromethane root extracts showed the highest antioxidant power against DPPH (IC50 = 0.82 mg/mL) and NO (IC50 = 0.64 mg/mL) radicals, respectively. The 1H-NMR-based screening of the secondary metabolites of all M. citrifolia root extracts confirmed the presence of triterpenes, steroids, phenolics, flavonoids, tannins, and anthraquinones as major bioactive components. Alizarin and scopoletin were detected in the extracts via UHPLC-QQQ-MS, and the alizarin (0.552–3.227 g/100 g dry weight) and scopoletin (0.092–0.554 g/100 g dry weight) contents were quantified via RP-HPLC. The antimicrobial and antioxidant activities of M. citrifolia root extracts and the identification of the main bioactive ingredients are the initial studies that can be beneficial for further in vivo studies and biomedical applications of its bioactive compounds.

Scopoletin: a review of its pharmacology, pharmacokinetics, and toxicity

“…Its mechanism of action is interference in the synthesis of essential fungal cell components, disruption of cell walls and plasma membranes, and impairment of C. tropicalis biofilm growth, formation, and proliferation (Lemos et al, 2020). Recent studies have reported that scopoletin has strong antitubercular activity; the compound isolated from Morinda citrifolia roots exhibits high activity against Mycobacterium tuberculosis with an MIC of 50 μg/mL (Sam-Ang et al, 2023). The MIC of the crude ethanol extract from the stem bark of Hymenodictyon floribundum BL Rob.…”

“…In addition, scopoletin shows antioxidant potential against DPPH (IC 50 = 0.82 mg/mL) and NO (IC 50 = 0.64 mg/mL) radicals (Sam-Ang et al, 2023).…”

Annulated Heterocyclic[g]Coumarin Composites: Synthetic Approaches and Bioactive Profiling

“…Moreover, the researchers created acylthiourea derivatives, including the production of a specific compound (23). Starting from compound (20), derived similarly to the method mentioned by Yu et al, [35] it underwent a reaction with oxalic dichloride in methylene dichloride, forming intermediate (21). The synthesis of compound (22) involved the reaction between intermediate (21) and ammonium sulfocyanate, using anhydrous ethanenitrile as the solvent.…”

“…Starting from compound (20), derived similarly to the method mentioned by Yu et al, [35] it underwent a reaction with oxalic dichloride in methylene dichloride, forming intermediate (21). The synthesis of compound (22) involved the reaction between intermediate (21) and ammonium sulfocyanate, using anhydrous ethanenitrile as the solvent. The final compound (23) was produced by reacting compound (22) with amine derivatives in the presence of anhydrous ethanenitrile.…”

“…Warfarin, nicouramol, and liquefaction are widely acknowledged as highly effective blood thinners [16,17] . While Armillarisinum A, Calanolide A, imecromone, and scopoletin are classified as antibiotics, [18] antiretrovirals, [19] spasmolytic, [20] and antiradical [21] agents, respectively. A well‐known coumarin derivative, esculinin, considerably improves mental acuity through modulating the neurotransmitter system [22] .…”