A new anti-Helicobacter pylori juglone from Reynoutria japonica

Khalil, Atif Ali Khan; Park, Woo Sung; Lee, Jeehoon; Kim, Hye-Jin; Akter, Kazi-Marjahan; Goo, Youn‐Kyoung; Bae, Ji‐Yeong; Man‐Seog, Chun; Kim, Junghwan; Ahn, Mi‐Jeong

doi:10.1007/s12272-019-01160-x

Cited by 24 publications

(13 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…In medicinal plants, naphthoquinone, including juglone and its derivatives, exhibit antibacterial activity [21,33]. In the previous report, MA, among other juglone derivatives, showed a strong anti- H. pylori activity [25]. Since oxidative stress induced by H. pylori can lead to damage of gastric epithelial cells [34], we conclude that MA can be used for chemoprevention or chemotherapeutic purposes.…”

Section: Discussionmentioning

confidence: 72%

“…Four derivatives of juglone, 2-methoxy-7-acetonyljuglone (MA), 2-ethoxy-6-acetyl-7-methyljuglone (EAM), 2-methoxy-6-acetyl-7-methyljuglone (MAM) and 2-methyl-3-acetyl-7-methoxyjuglone (MAMO) were isolated from R. japonica in our laboratory according to the method as previously described [25]. Anti-NRF2 (ab137550) and anti-HO-1 (ab68477) antibodies were obtained from Abcam (Cambridge, MA).…”

Section: Methodsmentioning

confidence: 99%

“…Juglone and its derivatives from Reynoutria japonica have been reported to exert antimicrobial [21,22,23] and anticancer [24] activities. We previously reported that a new natural juglone isolated from this plant, 2-methoxy-7-acetonyljuglone (MA) showed potent anti- Helicobacter pylori activity [25]. In this study, we further investigated the effect of MA on NRF2 activation in HeLa cells.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

2-Methoxy-7-Acetonyljuglone Isolated from Reynoutria japonica Increases the Activity of Nuclear Factor Erythroid 2-Related Factor-2 through Inhibition of Ubiquitin Degradation in HeLa Cells

Kim

et al. 2019

Antioxidants

Self Cite

View full text Add to dashboard Cite

The nuclear factor erythroid-derived 2-related factor 2 (NRF2) is a key transcription factor for the activation of genes responsible for oxidative stress and drug detoxification. Thus, it is important to identify NRF2 activators, which can be used to protect the cells from oxidative damage. Here, we investigated the effect of juglone derivatives isolated from Reynoutria japonica on the activity of NRF2 in HeLa cells. We demonstrated that among the juglone derivatives, 2-methoxy-7-acetonyljuglone (MA) strongly stimulated the antioxidant response element (ARE)-luciferase activity in a dose-dependent manner. In addition, MA significantly increased the nuclear localization of NRF2 and, consequently, increased the expression of NRF2 target genes, including heme oxygenase-1(HO-1), NAD(P)H: quinine oxidoreductase-1 (NQO-1), and glutamate-cysteine ligase catalytic (GCLC). To gain insights into the NRF2 signaling mechanism by MA, we measured the activities of RAC-alpha serine/threonine-protein kinase (AKT) and mitogen-activated protein (MAP) kinase family proteins, including extracellular signal-regulated kinase (ERK) and p38. Our results showed that MA induced NRF2 activity through p38 and AKT signaling. Subsequently, we found that MA significantly enhanced NRF2 stability by inhibiting ubiquitin-dependent proteasomal degradation. Thus, MA might protect cells by enhancing the activity and stability of NRF2 through inhibition of the proteasomal degradation pathway.

show abstract

Section: Discussionmentioning

confidence: 72%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

2-Methoxy-7-Acetonyljuglone Isolated from Reynoutria japonica Increases the Activity of Nuclear Factor Erythroid 2-Related Factor-2 through Inhibition of Ubiquitin Degradation in HeLa Cells

Kim

et al. 2019

Antioxidants

Self Cite

View full text Add to dashboard Cite

show abstract

“…Os extratos de metanol dos rizomas de Bergenia ciliata, com CIM = 12.50 µg/µL inibiram o crescimento de H. pylori, e o autor descreve possíveis mecanismos da propriedade anti-úlcera da planta (ALI et al, 2020). Foi demonstrada interessante ação antibacteriana por Khalil et al (2019), do composto 3-acetil-7metoxi-2-metiljuglona, obtido do extrato de etanol da raiz de Reynoutria japônica sendo eficaz contra três cepas de H. pylori com a CIM de 0,06 -0.13 μM, considerada ótima, tendo o metronidazol de controle positivo.…”

Section: Resultsunclassified

Coinfecção entre Dengue e Covid-19 possíveis implicações: uma revisão narrativa

Santos¹,

Campos²,

Costa³

et al. 2021

Assistência Em Saúde Baseada Em Evidências

View full text Add to dashboard Cite

show abstract

“…The chemicals corresponding to each peak were determined to be three stilbenes, resveratroloside (1), polydatin (2) and trans-resveratrol (4); a naphthalene glucoside of 6-methoxy-3-methyl-1-hydroxy-2-naphthoic acid 8-O-β-D-glucopyranoside (5); a juglone of 2-methoxy-6-acetyl-7-methyljuglone (8); and five anthraquinones, emodin-1-O-β-D-glucoside (3), emodin-8-O-β-D-glucoside (6), physcion-8-O-β-D-glucoside (7), emodin (9) and physcion (10) (Figure 7) (see Supplementary data, Figures S1-S30). They were isolated from the root of R. japonica by our previously reported methods [26,27] and used as external standards for quantification. Compound 5 was isolated as a brownish powder for the first time from R. japonica (see Supplementary data), although this compound had been previously reported from Fallopia multiflora [28].…”

Section: Hplc-dad Profiles Of Reynoutria Plantsmentioning

confidence: 99%

Comparative Inner Morphological and Chemical Studies on Reynoutria Species in Korea

Akter

Kim

Park

et al. 2020

Plants

Self Cite

View full text Add to dashboard Cite

Reynoutria species are medicinal plants that belong to the family Polygonaceae and are widely distributed in eastern Asia, North America and Europe. Although the phylogeny and morphological and anatomical studies of some species in Korea have been previously reported, there are no discriminative anatomical and chemical data available. Therefore, anatomical characterization of the leaf, stem and root, and high performance liquid chromatography-diode array detector (HPLC-DAD) analyses were carried out to assess the differences in anatomical and chemical profiles among the Reynoutria plants in Korea, i.e., R. japonica, R. sachalinensis, R. forbesii and R. japonica for. elata. The anatomical evaluation showed discriminative characteristics, such as the shape of the stomata and the stomatal index of the lower leaf surface; the ratio of the adaxial/abaxial height, the size of the vascular bundles and the frequency of druse in the midrib, petiole, and stem; and the pericycle number in the root. For the HPLC analysis, ten compounds corresponding to each major peak were isolated from R. japonica roots and their structures were identified by comprehensive spectroscopic studies. Samples collected before the flowering season showed higher contents of these ten major compounds than those collected after the flowering season. The orthogonal projections to latent structures-discrimination analysis (OPLS-DA) with the inner morphological and HPLC quantification results, clearly discriminated these plants. These results provide anatomical parameters and HPLC profiling that can be used to distinguish the four Reynoutria plants, which supports quality control for their precise identification.Plants 2020, 9, 222 2 of 13 and the young stems have been used as a foodstuff [10]. R. sachalinensis and R. japonica for. elata are endemic plants on the Ulleung and Jeju islands of Korea, respectively [11]. R. sachalinensis, with its characteristic large leaves, is known to have antioxidant and anti-inflammatory activities [12,13]. The outer morphology of R. japonica for. elata is similar to R. japonica. The only differences are its smaller size, red flower and seeds [11]. Early works have reported many phytochemical constituents from the roots and leaves of Reynoutria species, including stilbenes (resveratrol and polydatin), flavonoids (rutin, apigenin, quercetin, quercitrin, isoquercitrin, hyperoside, reynoutrin and kaempferol), anthraquinones (emodin, citreorosein, physcion, fallacinol, chrysophanol, phylloquinones B and C, and anthraglycosides A and B), coumarins, essential oils, and others (lapathoside, 8-hydroxycalamenene, oleanolic acid, chlorogenic acid, protocatechuic acid, gallic acid, tachioside etc) [1][2][3][4][8][9][10][14][15][16].Although Reynoutria species are used as a folk medicine, their exact botanical origin is unclear. Previous studies have reported certain Reynoutria species with great ambiguity in their taxonomic classification, because of variabilities in their chromosome number and morphology [17]. In addition, taxono...

show abstract

A new anti-Helicobacter pylori juglone from Reynoutria japonica

Cited by 24 publications

References 34 publications

2-Methoxy-7-Acetonyljuglone Isolated from Reynoutria japonica Increases the Activity of Nuclear Factor Erythroid 2-Related Factor-2 through Inhibition of Ubiquitin Degradation in HeLa Cells

2-Methoxy-7-Acetonyljuglone Isolated from Reynoutria japonica Increases the Activity of Nuclear Factor Erythroid 2-Related Factor-2 through Inhibition of Ubiquitin Degradation in HeLa Cells

Coinfecção entre Dengue e Covid-19 possíveis implicações: uma revisão narrativa

Comparative Inner Morphological and Chemical Studies on Reynoutria Species in Korea

Contact Info

Product

Resources

About