Garcinoic Acids and a Benzophenone Derivative from the Seeds of <i>Garcinia kola</i> and Their Antibacterial Activities against Oral Bacterial Pathogenic Organisms

Hioki, Yusuke; Onwona-Agyeman, Siaw; Kakumu, Yuya; Hattori, Hiroyuki; Yamauchi, Kosei; Mitsunaga, Tohru

doi:10.1021/acs.jnatprod.9b01045

Cited by 8 publications

(2 citation statements)

References 29 publications

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Section: Introductionmentioning

confidence: 99%

“…Hence, new effective NAFLD drugs are urgently needed. Phenyl ketone derivatives have received considerable interest because they exhibit multiple pharmacological activities such as hepatoprotective, anti-inflammatory [ 8 ], antimicrobial [ 9 ], antidiabetic [ 10 ], and anticancer [ 11 ]. From a hepatoprotective point of view, phenyl ketone derivatives demonstrate antioxidant [ 12 ] and antifibrotic potential [ 13 ].…”

Section: Introductionmentioning

confidence: 99%

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Highly Accessible Computational Prediction and In Vivo/In Vitro Experimental Validation: Novel Synthetic Phenyl Ketone Derivatives as Promising Agents against NAFLD via Modulating Oxidoreductase Activity

Qiao

Deng

Liu

et al. 2023

Oxidative Medicine and Cellular Longevity

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Nonalcoholic fatty liver disease (NAFLD) has reached epidemic proportions with no pharmacological treatment approved. Several highly accessible computational tools were employed to predict the activities of twelve novel compounds prior to actual chemical synthesis. We began our work by designing two or three hydroxyl groups appended to the phenyl ketone core, followed by prediction of drug-likeness and targets. Most predicted targets for each compound overlapped with NAFLD targets (≥80%). Enrichment analysis showed that these compounds might regulate oxidoreductase activity. Then, these compounds were synthesized and confirmed by IR, MS, 1H, and 13C NMR. Their cell viability demonstrated that twelve compounds exhibited appreciable potencies against NAFLD ( E C 50 values ≤ 13.5 μ M ). Furthermore, the most potent compound 5f effectively prevented NAFLD progression as evidenced by the change in histological features. 5f significantly reduced total cholesterol and triglyceride levels in vitro/in vivo, and the effects of 5f were significantly stronger than those of the control drug. The proteomic data showed that oxidoreductase activity was the most significantly enriched, and this finding was consistent with docking results. In summary, this validated presynthesis prediction approach was cost-saving and worthy of popularization. The novel synthetic phenyl ketone derivative 5f holds great therapeutic potential by modulating oxidoreductase activity to counter NAFLD.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Highly Accessible Computational Prediction and In Vivo/In Vitro Experimental Validation: Novel Synthetic Phenyl Ketone Derivatives as Promising Agents against NAFLD via Modulating Oxidoreductase Activity

Qiao

Deng

Liu

et al. 2023

Oxidative Medicine and Cellular Longevity

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Garcinia kola Heckel. (Clusiaceae): An Overview of the Cultural, Medicinal, and Dietary Significance for Sustainability

Ogwu,

Osawaru

et al. 2023

Reference Series in Phytochemistry

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Garcinia kola: a critical review on chemistry and pharmacology of an important West African medicinal plant

et al. 2023

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Garcinia kola Heckel (Clusiaceae) is a tree indigenous to West and Central Africa. All plant parts, but especially the seeds, are of value in local folklore medicine. Garcinia kola is used in treatment of numerous diseases, including gastric disorders, bronchial diseases, fever, malaria and is used to induce a stimulating and aphrodisiac effect. The plant is now attracting considerable interest as a possible source of pharmaceutically important drugs. Several different classes of compounds such as biflavonoids, benzophenones, benzofurans, benzopyran, vitamin E derivatives, xanthones, and phytosterols, have been isolated from G. kola, of which many appears to be found only in this species, such as garcinianin (found in seeds and roots), kolanone (fruit pulp, seeds, roots), gakolanone (stem bark), garcinoic acid, garcinal (both in seeds), garcifuran A and B, and garcipyran (all in roots). They showed a wide range of pharmacological activities (e.g. analgesic, anticancer, antidiabetic, anti-inflammatory, antimalarial, antimicrobial, hepatoprotective and neuroprotective effects), though this has only been confirmed in animal models. Kolaviron is the most studied compound and is perceived by many studies as the active principle of G. kola. However, its research is associated with significant flaws (e.g. too high doses tested, inappropriate positive control). Garcinol has been tested under better conditions and is perhaps showing more promising results and should attract deeper research interest (especially in the area of anticancer, antimicrobial, and neuroprotective activity). Human clinical trials and mechanism-of-action studies must be carried out to verify whether any of the compounds present in G. kola may be used as a lead in the drug development.

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Garcinoic Acids and a Benzophenone Derivative from the Seeds of Garcinia kola and Their Antibacterial Activities against Oral Bacterial Pathogenic Organisms

Cited by 8 publications

References 29 publications

Highly Accessible Computational Prediction and In Vivo/In Vitro Experimental Validation: Novel Synthetic Phenyl Ketone Derivatives as Promising Agents against NAFLD via Modulating Oxidoreductase Activity

Highly Accessible Computational Prediction and In Vivo/In Vitro Experimental Validation: Novel Synthetic Phenyl Ketone Derivatives as Promising Agents against NAFLD via Modulating Oxidoreductase Activity

Garcinia kola Heckel. (Clusiaceae): An Overview of the Cultural, Medicinal, and Dietary Significance for Sustainability

Garcinia kola: a critical review on chemistry and pharmacology of an important West African medicinal plant

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