A new xanthone and a biphenyl from the flower and twig extracts of <i>Garcinia mckeaniana</i>

Auranwiwat, Chiramet; Limtharakul, Thunwadee; Pyne, Stephen G.; Rattanajak, Roonglawan; Kamchonwongpaisan, Sumalee

doi:10.1080/14786419.2019.1700505

Cited by 10 publications

(8 citation statements)

References 22 publications

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“…G. mckeaniana Craib, locally named Xen mu, is found in secondary forests, especially in Sapa mountain and Thuan Chau‐Son La [4] . To date, phytochemical and biological studies on G. mckeaniana are quite limited [5–9] . This current study is the first to report the phytochemical isolation and structural elucidation of the new xanthone 1 and eight known analogs 2 – 9 from the AcOEt extract of G. mckeaniana leaves, together with their cytotoxic and α‐glucosidase inhibitory activities.…”

Section: Introductionmentioning

confidence: 83%

Cytotoxic and α‐Glucosidase Inhibitory Xanthones from Garcinia mckeaniana Leaves and Molecular Docking Study

Thu

Minh²,

Van

et al. 2021

Chemistry & Biodiversity

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A new racemic xanthone, garmckeanin A (1), and eight known analogs 2–9 were isolated from the ethyl acetate (AcOEt) extract of the Vietnamese Garcinia mckeaniana leaves. Their structures were determined by MS and NMR spectral analyses and compared with the literature. The AcOEt extract showed good cytotoxicity against cancer cell lines KB, Lu, Hep‐G2 and MCF7, with IC50 values of 5.40–8.76 μg/mL, and it also possessed α‐glucosidase inhibitory activity, with an IC50 value of 9.17 μg/mL. Garmckeanin A (1) exhibited inhibition of all cancer cell lines, with an IC50 value of 7.3–0.9 μM. Allanxanthone C (5) successfully controlled KB growth, with an IC50 value of 0.54 μM, higher than that of the positive control, ellipticine (IC50 1.22 μM). Norathyriol (8) was a promising α‐glucosidase inhibitor, with an IC50 value of 0.07 μM, much higher than that of the positive control, acarbose (IC50 161.0 μM). The interactions of the potential α‐glucosidase inhibitors with the C‐ and N‐terminal domains of human intestinal α‐glucosidase were also investigated by molecular docking study. The results indicated that bannaxanthone D (2), garcinone E (4), bannaxanthone E (6), and norathyriol (8) exhibit higher binding affinity to the C‐terminal than to the N‐terminal domain through essential residues in the active sites. In particular, compound 8 could be assumed to be the most potent mixed inhibitor.

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Section: Introductionmentioning

confidence: 83%

Cytotoxic and α‐Glucosidase Inhibitory Xanthones from Garcinia mckeaniana Leaves and Molecular Docking Study

Thu

Minh²,

Van

et al. 2021

Chemistry & Biodiversity

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“…The n -hexane extract of the Garcinia bancana leaves showed antioxidant activity according to 1,1-diphenyl-2-picrylhydrazyl (DPPH) and ferric reducing antioxidant power (FRAP) tests ( Putri et al, 2018 ). In the research of Auranwiwat and co-workers, cytotoxicity against KB cells of 1 was tested, but 1 was inactive to both cells with IC 50 > 50 µM ( Table 1 ) ( Auranwiwat et al, 2021 ).…”

Section: Diverse Biphenyls From Clusiaceae and Their Bioactivitymentioning

confidence: 99%

“…For the aim of searching for undiscovered natural products of Garcinia mckeaniana Craib, the constituents belonging to the flower and twig extracts of this plant were investigated by Auranwiwat and others and a biphenyl ( 19 ) was found ( Figure 3 ) in 2021 ( Auranwiwat et al, 2021 ). Garcinia mckeaniana , also called Xen mu, is a common plant that is widespread in the tropical secondary forests of Sapa town and Son La province of Vietnam in particular.…”

Section: Diverse Biphenyls From Clusiaceae and Their Bioactivitymentioning

confidence: 99%

“…The chemical compositions of these plants contain a variety of valuable natural products with associated beneficial and healing properties such as anti-tumor ( Fan et al, 2015 ), anti-obesity ( Hasegawa, 2001 ; Kim et al, 2004 ), antibacterial ( Negi et al, 2008 ; Auranwiwat et al, 2014 ), antioxidant ( Farombi et al, 2013 ), antimalarial ( Elfita et al, 2009 ), and so on ( Grossman and Yang, 2020 ; Spontoni do Espirito Santo et al, 2020 ; Kalita et al, 2021 ). As a result, a considerable bunch of studies have been conducted to evaluate all types of phytochemical compositions from Clusiaceae, including polycyclic polyprenylated acylphloroglucinols (PPAPs) ( Tian et al, 2016 ; Chen et al, 2020 ), xanthones ( Nilar and Harrison, 2002 ; Rukachaisirikul et al, 2003b ; Elfita et al, 2009 ), benzophenones ( Elya et al, 2006 ), flavonoids ( Nguyen et al, 2021 ), biphenyls ( Auranwiwat et al, 2021 ) and others ( Ly Dieu et al, 2012 ; Jiang et al, 2014 ).…”

Section: Introductionmentioning

confidence: 99%

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Biphenyls in Clusiaceae: Isolation, structure diversity, synthesis and bioactivity

et al. 2022

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Clusiaceae plants contain a wide range of biologically active metabolites that have gotten a lot of interest in recent decades. The chemical compositions of these plants have been demonstrated to have positive effects on a variety of ailments. The species has been studied for over 70 years, and many bioactive compounds with antioxidant, anti-proliferative, and anti-inflammatory properties have been identified, including xanthones, polycyclic polyprenylated acylphloroglucinols (PPAPs), benzophenones, and biphenyls. Prenylated side chains have been discovered in many of these bioactive substances. To date, there have been numerous studies on PPAPs and xanthones, while no comprehensive review article on biphenyls from Clusiaceae has been published. The unique chemical architectures and growing biological importance of biphenyl compounds have triggered a flurry of research and interest in their isolation, biological evaluation, and mechanistic studies. In particular, the FDA-approved drugs such as sonidegib, tazemetostat, daclatasvir, sacubitril and trifarotene are closely related to their biphenyl-containing moiety. In this review, we summarize the progress and development in the chemistry and biological activity of biphenyls in Clusiaceae, providing an in-depth discussion of their structural diversity and medicinal potential. We also present a preliminary discussion of the biological effects with or without prenyl groups on the biphenyls.

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“…Xanthone derivatives have been reported to have antimalarial activity [18][19][20]. Furthermore, hydroxyxanthone as a derivative of xanthone also exhibited effective antimalarial activity [21]. It was also reported that thioxanthone derivatives exhibit good antimalarial activity [22][23].…”

Section: ■ Introductionmentioning

confidence: 99%

Computational Design of Thioxanthone Derivatives as Potential Antimalarial Agents through <i>Plasmodium falciparum</i> Protein Inhibition

et al. 2021

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Plasmodium falciparum (P. falciparum) is the most fatal among the other Plasmodium parasites that infect humans with the malaria disease. Currently, the resistance of P. falciparum against some antifolate drugs has become a severe problem. On the other hand, xanthone and thioxanthone derivatives have been reported to have remarkable antimalarial activity. However, molecular docking studies have not evaluated thioxanthone derivative compounds as antimalarial agents. Accordingly, this research investigated the binding pose and inhibition mechanism of several thioxanthone derivatives against P. falciparum proteins DHFR (PDB ID: 1J3K) and DHODH (PDB ID: 1TV5) through molecular docking study. The compound structures were geometrically optimized using Gaussian 09 software and docked to the receptors using AutoDock4 software. The results showed that the free binding energy of thioxanthone derivatives ranged between -6.77 to -7.50 and -8.45 to -9.55 kcal mol–1 against pfDHFR and pfDHODH, respectively, with RMSD values of less than 2 Å. Compound F (4-iodo-3,4-dihydroxy-thioxanthone) gave the most substantial free binding energy against both proteins. Furthermore, the hydrogen bond interaction of compound F was the same as the native ligands of pfDHFR and pfDHODH. These results suggested that compound F has a more robust interaction in pfDHFR and pfDHODH. Thus, it is promising to further evaluate the compound as a candidate for a new antimalarial agent.

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A new xanthone and a biphenyl from the flower and twig extracts of Garcinia mckeaniana

Cited by 10 publications

References 22 publications

Cytotoxic and α‐Glucosidase Inhibitory Xanthones from Garcinia mckeaniana Leaves and Molecular Docking Study

Cytotoxic and α‐Glucosidase Inhibitory Xanthones from Garcinia mckeaniana Leaves and Molecular Docking Study

Biphenyls in Clusiaceae: Isolation, structure diversity, synthesis and bioactivity

Computational Design of Thioxanthone Derivatives as Potential Antimalarial Agents through <i>Plasmodium falciparum</i> Protein Inhibition

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