Isolation and structure elucidation of two antiprotozoal bisbenzylisoquinoline alkaloids from Triclisia gilletii stem bark

Kanyanga, R. Cimanga; Munduku, C. Kikweta; Lumpu, S. Nsaka; Ehata, M. Tshodi; Bool-Miting, F. Makila; Kabangu, O. Kambu; Maya, B. Mbamu; Cos, Paul; Maes, Louis; Vlietinck, A. J.; Tuenter, Emmy; Foubert, Kenn; Pieters, Luc

doi:10.1016/j.phytol.2018.09.008

Cited by 5 publications

(4 citation statements)

References 23 publications

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“…We isolated 3 compounds from the plant extract, which included 2 DBBI (dibisbenzylisoquinoline) alkaloids. The compounds were identified as phaeanthine (80 mg, 0.004% yield), cycleanine (50 mg, 0.0025% yield), and N-methylcorydaldine (30 mg, 0.0015% yield) (Figure 1) based on extensive characterization using the NMR technique ( 1 H, 13 C, 2D) and HRMS analysis, which were in good agreement with the reported data 17,19,20 (…”

Section: ■ Results and Discussionsupporting

confidence: 86%

“…Phaeanthine has not been explored much in terms of its anticancer potential. Some other activities are reported for the compound, such as antiplasmodial activity, 16 antiprotozoal activity, 17 and acetylcholinesterase inhibitory potential. 18 Considering the reports, we investigated the effect of phytomolecules isolated from the plant on anticancer profiling with a focus on the most common cancer of the female reproductive system, i.e., cervical cancer.…”

Section: ■ Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Exploration of Phaeanthine: A Bisbenzylisoquinoline Alkaloid Induces Anticancer Effect in Cervical Cancer Cells Involving Mitochondria-Mediated Apoptosis

et al. 2023

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Natural-product-based pharmacophores possess considerably more structural diversity, attractive physicochemical features, and relatively less toxicity than synthesized drug entities. In this context, our studies on phaeanthine, a bisbenzylisoquinoline alkaloid isolated from the rhizomes of Cyclea peltata (Lam) Hook.f & Thoms., showed selective cytotoxicity toward cervical cancer cells (HeLa) with an IC50 of 8.11 ± 0.04 μM. Subsequent investigation with in silico molecular docking of phaeanthine displayed preferential binding to the antiapoptotic protein Akt as reflected by a docking score of −5.023. Interestingly, the follow-up in vitro assessment of the compound correlated with mitochondria-mediated apoptosis specifically by downregulating the expression of Akt and p-Akt, including other antiapoptotic proteins MCl-1, IGF-2, and XIAP. In the complementary in vitro assessment, mitochondrial membrane polarization and dynamics of intercellular cytochrome c validated the intrinsic mechanism of the apoptotic phenomenon. To the best of our knowledge, this is the first comprehensive anticancer profiling study of phaeanthine against HeLa cells.

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Section: ■ Results and Discussionsupporting

confidence: 86%

Section: ■ Introductionmentioning

confidence: 99%

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Exploration of Phaeanthine: A Bisbenzylisoquinoline Alkaloid Induces Anticancer Effect in Cervical Cancer Cells Involving Mitochondria-Mediated Apoptosis

et al. 2023

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“…To the best of our knowledge, presented in this paper, combinations of EOs, acids and metal ions were tested for the first time. The object of investigations that have been conducted, are usually combinations of two or more essential oils [43], metals [38,42], antibiotics [44,45], organic acids [46], active compounds occurring in essential oil [22], essential oils with other compounds of natural origin [47] or other compounds of plant origin e.g., alkaloids [48][49][50], triterpene saponins [51] or chalcones and flavonoids [41]. The proposed combination is characterized by innovation and, most importantly, high efficiency.…”

Section: Discussionmentioning

confidence: 99%

Novel Formula of Antiprotozoal Mixtures

et al. 2022

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Antimicrobial resistance (AMR) is becoming more common in both bacteria and pathogenic protozoa. Therefore, new solutions are being sought as alternatives to currently used agents. There are many new ideas and solutions, especially compounds of natural origin, including essential oils. In the present study, the antiprotozoal activity of a mixture of essential oils (eucalyptus, lavender, cedar and tea tree), organic acids (acetic acid, propionic acid and lactic acid) and metal ions (Cu, Zn, Mn) were tested. As a model, protozoans were selected: Euglena gracilis, Gregarina blattarum, Amoeba proteus, Paramecium caudatum, Pentatrichomonas hominis. The tested concentrations of mixtures were in the range of 0.001–1.5%. The analyses show unexpected, very strong protozoicidal activity of combinations, presenting the synergy of compounds via determination of LD50 and LD100 values. Obtained mixtures showed significantly higher activity against protozoans, compared to chloramphenicol and metronidazole. Most of the analyzed samples show high antiprotozoal activity at very low concentration, in the range of 0.001–0.009%. The most effective combinations for all analyzed protozoans were the cedar essential oil and tea tree essential oil with a mixture of acids and manganese or zinc ions. Innovative combinations of essential oils, organic acids and metal ions are characterized by very high antiprotozoal activity at low doses, which, after further investigation, can be applicable for control of protozoan pathogens.

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Antimalarial Natural Products

Kingston

Cassera

2022

Antimalarial Natural Products

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Isolation and structure elucidation of two antiprotozoal bisbenzylisoquinoline alkaloids from Triclisia gilletii stem bark

Cited by 5 publications

References 23 publications

Exploration of Phaeanthine: A Bisbenzylisoquinoline Alkaloid Induces Anticancer Effect in Cervical Cancer Cells Involving Mitochondria-Mediated Apoptosis

Exploration of Phaeanthine: A Bisbenzylisoquinoline Alkaloid Induces Anticancer Effect in Cervical Cancer Cells Involving Mitochondria-Mediated Apoptosis

Novel Formula of Antiprotozoal Mixtures

Antimalarial Natural Products

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