Characterized mechanism of α-mangostin-induced cell death: Caspase-independent apoptosis with release of endonuclease-G from mitochondria and increased miR-143 expression in human colorectal cancer DLD-1 cells

Nakagawa, Yoshihito; Iinuma, Munekazu; Naoe, Tomoki; Nozawa, Yoshinori; Akao, Yukihiro

doi:10.1016/j.bmc.2007.04.071

Cited by 160 publications

(149 citation statements)

References 24 publications

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“…5) As examples, inhibition of the cell proliferation of DLD-1 cells by 1 was observed at concentrations above 2 mM with an IC 50 value at 7.5 mM. 6) This value corresponds to the activity observed in HL-60 cells. 7) 3 seems to have a stronger effect compared with 1 and 2 8) but this is not confirmed by all reports.…”

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confidence: 84%

Cytotoxic Geranylated Xanthones and O-Alkylated Derivatives of .ALPHA.-Mangostin

Hansen

Vang

et al. 2009

Chem. Pharm. Bull.

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Xanthones are widely distributed in the genus Garcinia (Guttiferae), which provides compounds with a wide range of pharmacological effects such as cytotoxic, anti-bacterial, antioxidant and anti-human immunodeficiency virus (HIV) activities.1-3) The diverse substitution patterns of xanthones provide a good basis for different biological activity and for structure-activity relationship studies. 4)a-Mangostin (1), the dominating constituent of the fruit hulls of Garcinia mangostana, together with b-mangostin (2) and g-mangostin (3) (Fig. 1), have exhibited various biological activities, such as cytotoxicity in different cell lines together with anti-oxidative, anti-inflammatory, and anti-bacterial activities.5) As examples, inhibition of the cell proliferation of DLD-1 cells by 1 was observed at concentrations above 2 mM with an IC 50 value at 7.5 mM.6) This value corresponds to the activity observed in HL-60 cells.7) 3 seems to have a stronger effect compared with 1 and 2 8) but this is not confirmed by all reports. [7][8][9] Besides their slightly different potencies, three mangostins (1-3) differ in their mechanism of action. 3 caused accumulation of the cells in S-phase, whereas the cells treated with 1 and 2 showed G 0 /G 1 accumulation. Furthermore, the three mangostins (1-3) showed different expression profiles for proteins involved in the cell cycle regulation.8) The cytotoxic activity of 1 is only partly explained by apoptosis, as higher concentrations are needed for apoptosis than necessary for cytotoxicity.6) Apoptosis seems to be caused by 1-induced dysfunction of mitochondria. 10)Beside 1-3, several other xanthones have been tested for their cytotoxic activity and a structure-activity relationship can partly be elucidated. In all such experiments, the mangostins showed the strongest effect.7-9) Analysis of the cytotoxic effect of 6-methoxy-b-mangostin 8) indicated that the free hydroxyl group at C-6 was necessary for the cytotoxic activity. Furthermore, the apoptosis activity also depends on the number of free hydroxyl groups. 7,9,10) Pyranoxanthones, produced naturally or synthetically from 1 by acid-catalysed cyclisation of the prenyl group, have been found to have reduced cytotoxic potency compared with 1. 9) For 3,6-di-O-alkylated a-mangostin, the inhibitory effects on antifungal activity were reduced dramatically as compared with a-mangostin.11) However, the cytotoxic effects of these derivatives on MCF-7 cells (human breast cancer cells) or DLD-1 (human colon cancer cells) have not been investigated yet.In this paper, we report the isolation of two new geranylated xanthones (4, 5) and five known compounds (2, 6-9) from the bark of Garcinia oliveri PIERRE, a Vietnamese tall tree whose young buds and sour fruit are used for soup cooking. However, no use in folk medicine nor identification of specific compounds has been previously reported.12) Furthermore, conversion of a-mangostin into O-alkylated a-mangostin derivatives (10-17) is described. Cytotoxic activity for compounds 1-3 and 6-17 was analy...

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confidence: 84%

Cytotoxic Geranylated Xanthones and O-Alkylated Derivatives of .ALPHA.-Mangostin

Hansen

Vang

et al. 2009

Chem. Pharm. Bull.

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“…Plant extracts with these properties are rich in phenolic compounds such as phenolic acids, flavonoids, flavonol glycosides, anacardic acids, proanthocyanidins, phenylcoumarins, theaflavins, cannabinoids, phenolic amides, curcuminoids, stilbene oligomers, xanthones, phenolic oils and flavonoligans (Anilkumar 2010). Specific phenolic compounds include quercetin (Dajas 2012), anacardic acid (Sun et al 2006;Hsieh & Hernández-Ledesma 2011), epigallocatechin gallate (EGCg) (Khan & Mukhtar 2008), gallic acid (Verma et al 2013), proanthocyanidins (Nandakumar et al 2008), curcumin (Goel et al 2008), cannabinoids (Alexander et al 2009), mangostin (Nakagawa et al 2007;Johnson et al 2012), gossypin (Kim et al 2008;Shi et al 2012), silymarin (Ramasamy & Agarwal 2008), gingerols and shagoals Sang et al 2009). In addition, anticancer effects can also include inhibition of cell growth, cell-cycle arrest, induction of apoptosis, inhibition of topoisomerase enzymes and matrix metalloproteinases as well as angiogenesis.…”

Section: Introductionmentioning

confidence: 99%

Anti-proliferative properties of commercial Pelargonium sidoides tincture, with cell-cycle G₀/G₁ arrest and apoptosis in Jurkat leukaemia cells

Pereira

Bester

Soundy

et al. 2016

Pharmaceutical Biology

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Context Pelargonium sidoides DC (Geraniaceae) is an important medicinal plant indigenous to South Africa and Lesotho. Previous studies have shown that root extracts are rich in polyphenolic compounds with antibacterial, antiviral and immunomodulatory activities. Little is known regarding the anticancer properties of Pelargonium sidoides extracts. Objective This study evaluates the anti-proliferative effects of a Pelargonium sidoides radix mother tincture (PST). Materials and methods The PST was characterized by LC-MS/MS. Anti-proliferative activity was evaluated in the pre-screen panel of the National Cancer Institute (NCI-H460, MCF-7 and SF-268) and the Jurkat leukaemia cell line at concentrations of 0-150 mg/mL. The effect on cell growth was determined with sulphorhodamine B and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assays after 72 h. The effect on cell cycle and apoptosis induction in Jurkat cells was determined by flow cytometry with propidium iodide and Annexin V: fluorescein isothiocyanate staining. Results Dihydroxycoumarin sulphates, gallic acid as well as gallocatechin dimers and trimers were characterized in PST by mass spectrometry. Moderate anti-proliferative effects with GI 50 values between 40 and 80 mg/mL were observed in the NCI-pre-screen panel. Strong activity observed with Jurkat cells with a GI 50 value of 6.2 mg/mL, significantly better than positive control 5-fluorouracil (GI 50 value of 9.7 mg/mL). The PST arrested Jurkat cells at the G 0 /G 1 phase of the cell cycle and increased the apoptotic cells from 9% to 21%, while the dead cells increased from 4% to 17%. Conclusion We present evidence that P. sidoides has cancer cell type-specific anti-proliferative effects and may be a source of novel anticancer molecules. ARTICLE HISTORY

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“…Xanthones are polyphenolic compounds with a chemical structure that contains a tricyclic aromatic ring. This structure has biologically active molecules such as antioxidants and anti-inflammatory, antibacterial and anticancer factors (Nakagawa et al, 2007). The antioxidant molecules of the skin of mangosteens are very strong as catchers of free radicals (radical scavenging) (IPB, 2009).…”

Section: Discussionmentioning

confidence: 99%

Effectiveness of Topical Mangosteen Pericarp Extract Against Angiogenesis in Mice Exposed to Ultra Violet B

Anwar¹,

Djawad²,

Fitri³

2016

Pakistan J. of Nutrition

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Exposure to ultraviolet B (UVB) can have an impact on the epidermis and dermis that triggers inflammatory processes that affect angiogenesis in the skin. Our study aimed to assess the effectiveness of mangosteen pericarp extract against angiogenesis in mouse skin after being exposed to UVB. This research was carried out with animals in the anatomic pathology laboratory of Hasanuddin University in Makassar. We used an animal experimental research design with a control group. A total of 24 mice were divided into the following 4 sample groups: normal group, UVB group, ethanol group and mangosteen group. In the mangosteen group, mangosteen pericarp extract with a concentration of 50% was smeared on the mice shortly after they were exposed to UVB. The amount of vascularization was significantly different among the groups. The greatest amount of vascularization was found in the ethanol group and the least amount was found in the normal group. The amount of vascularization in the mangosteen group was significantly lower than the UVB and ethanol groups but significantly higher than the normal group. In conclusion, the mangosteen pericarp extract concentration of 50% (2 mg/g of mouse weight) reduced the amount of angiogenesis, which is a marker of inflammation, in the skin of the mice that were exposed to UVB.

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Characterized mechanism of α-mangostin-induced cell death: Caspase-independent apoptosis with release of endonuclease-G from mitochondria and increased miR-143 expression in human colorectal cancer DLD-1 cells

Cited by 160 publications

References 24 publications

Cytotoxic Geranylated Xanthones and O-Alkylated Derivatives of .ALPHA.-Mangostin

Cytotoxic Geranylated Xanthones and O-Alkylated Derivatives of .ALPHA.-Mangostin

Anti-proliferative properties of commercial Pelargonium sidoides tincture, with cell-cycle G₀/G₁ arrest and apoptosis in Jurkat leukaemia cells

Effectiveness of Topical Mangosteen Pericarp Extract Against Angiogenesis in Mice Exposed to Ultra Violet B

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Characterized mechanism of α-mangostin-induced cell death: Caspase-independent apoptosis with release of endonuclease-G from mitochondria and increased miR-143 expression in human colorectal cancer DLD-1 cells

Cited by 160 publications

References 24 publications

Cytotoxic Geranylated Xanthones and O-Alkylated Derivatives of .ALPHA.-Mangostin

Cytotoxic Geranylated Xanthones and O-Alkylated Derivatives of .ALPHA.-Mangostin

Anti-proliferative properties of commercial Pelargonium sidoides tincture, with cell-cycle G0/G1 arrest and apoptosis in Jurkat leukaemia cells

Effectiveness of Topical Mangosteen Pericarp Extract Against Angiogenesis in Mice Exposed to Ultra Violet B

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Product

Resources

About

Anti-proliferative properties of commercial Pelargonium sidoides tincture, with cell-cycle G₀/G₁ arrest and apoptosis in Jurkat leukaemia cells