Bioactive Triterpene Saponins from the Roots of <i>Phytolacca americana</i>

Wang, Liyan; Bai, Liming; Nagasawa, Takashi; Hasegawa, Toshiaki; Yang, Xiaoyang; Sakai, Jun‐ichi; Bai, Yuhua; Kataoka, Takao; Oka, Seiko; Hirose, Katsutoshi; Tomida, Akihiro; Tsuruo, Takashi; Andô, Masataka

doi:10.1021/np078012m

Cited by 45 publications

(32 citation statements)

References 26 publications

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“…Among these compounds, odoroside A (Figure 7a) was found to inhibit ICAM-1 expression induced by TNF-a or IL-1 at IC 50 values o1 mM. [119][120][121][122][123] Odoroside A has been shown to directly inhibit the ATP-hydrolyzing activity of Na + /K + -ATPase as potently as ouabain. 124 However, in contrast to previous studies, we have found that odoroside A and ouabain affect neither TNF-a-induced early NF-kB signaling pathway nor mRNA expression, but rather prevent NF-kB-inducible protein expression by blocking Na + -dependent amino acid transport.…”

Section: Cardenolide Glycosidesmentioning

confidence: 99%

Chemical biology of inflammatory cytokine signaling

Kataoka

2009

J Antibiot

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Pro-inflammatory cytokines, such as tumor necrosis factor-a and interleukin-1, trigger the signal transduction pathway leading to the activation of the transcription factor, nuclear factor-jB (NF-jB). NF-jB induces a large number of target genes involved in many biological processes, such as inflammation, immunity, cell survival, cell death and carcinogenesis. As therapeutic agents for inflammatory diseases and cancer, as well as bioprobes for the characterization of intracellular biological response and cell function, a large number of natural and synthetic small molecules have been identified to inhibit the activation of the NF-jB signaling pathway. This review focuses on recent progress in the identification and biological properties of small molecules targeting the NF-jB signaling pathway induced by pro-inflammatory cytokines.

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Section: Cardenolide Glycosidesmentioning

confidence: 99%

Chemical biology of inflammatory cytokine signaling

Kataoka

2009

J Antibiot

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“…EsA, which can inhibit cell growth and ICAM-1 induction, accumulate calcein in cells (Wang et al, 2008) and treat nephritis (Ju et al, 1999), did not show obvious proinflammatory or irritating effects herein. Since the content of EsA remained constant while that of EsC reduced appreciably after vinegar processing, the toxicity of P. americana may be associated more with EsC than with EsA.…”

Section: Discussionmentioning

confidence: 71%

Rabbit conjunctivae edema and release of NO, TNF-α, and IL-1β from macrophages induced by fractions and esculentosides isolated fromPhytolacca americana

Yu¹,

Gong²,

Wang³

et al. 2015

Pharmaceutical Biology

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Context: The roots of Phytolacca americana L. (Phytolaccaceae) may be toxic. Despite heated controversy over the toxic compounds of P. americana, especially esculentosides, relevant studies remain scarce. Objective: The objective of this study is to screen the toxic fractions and compounds of P. americana, to determine the controlling indices, and to provide evidence for unraveling the mechanism. Materials and methods: Petroleum ether (PE), CH 2 Cl 2 , n-BuOH, and water fractions were isolated from 70% ethanol extract of P. americana. The n-BuOH fraction was dissolved in 50% ethanol and precipitated by adding ethyl ether. The resultant supernatants and precipitates were referred to as SUPs and SEDs fractions, respectively. SUPs fraction was separated by column chromatography into four main stimulating esculentosides that were identified by HR-ESI/MS and NMR as EsA, EsB, EsC, and EsF. The irritating effects of esculentosides on rabbit conjunctivae (500 mg/eye) was observed by pathological examination and those on macrophages (5, 25, 50 and 100 mg/mL) were evaluated by detecting changes of NO, TNF-a, and IL-1b levels. Results and discussion: n-BuOH, SUP fractions, and EsC induced severe conjunctival edema. The four esculentosides induced dose-dependent releases of proinflammatory mediators NO, TNF-a, and IL-1b from macrophages, and releasing amounts peaked after 2 h of treatment. EsC and EsF induced macrophages to release mediators most significantly. EsC (50 mg/mL) functioned more effectively than EsF did, and similarly n-BuOH and SUPs fractions functioned more effectively than the esculentoside mixture. Thus, the four esculentosides exerted proinflammatory effects synergistically. Conclusion: All extracted esculentosides, especially EsC, induced inflammatory stimulation. Phytolacca americana-induced irritation of the gastrointestinal tract may be associated with esculentosides such as EsC.

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“…Although the plant is toxic, it is used as a traditional herbal medicine in China [17,18]. The following compounds have been identified in the leaves of P. americana:…”

Section: Introductionmentioning

confidence: 99%

“…The glucosides of triterpene saponins (e.g., esculentoside B, phytolaccoside E, and esculentoside G) were extracted from the root of P. americana, and their structures were established on the basis of spectroscopic analysis [18]. Since these triterpene saponin glucosides were also obtained from cell cultures of P.…”

Section: Introductionmentioning

confidence: 99%

Glucosylation of hydroxyflavones by glucosyltransferases from Phytolacca americana

Iwakiri

Mase

Murakami

et al. 2013

Journal of Molecular Catalysis B: Enzymatic

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Cell suspension cultures of Phytolacca americana can glucosylate 6-and 7-hydroxyflavone, but not 5-hydroxyflavone. In order to identify the enzymes responsible for these transformations, glucosyltransferases (GTs) from P. americana were overexpressed in Escherichia coli and purified. The purified PaGT3 enzyme could glucosylate 6-and 7-hydroxyflavone when incubated with UDP-glucose, a glucosyl donor molecule, but PaGT2 could conjugate a glucose moiety only to 6-hydroxyflavone. E. coli cells expressing PaGT2 and 3 could also be utilized for the glucosylation of hydroxyflavones. The glucoside products which had accumulated in the medium of overnight E. coli cell cultures were isolated using hydrophobic resins. This methodology might be suitable for the glucosylation of aglycones with important health-related properties.

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Bioactive Triterpene Saponins from the Roots of Phytolacca americana

Cited by 45 publications

References 26 publications

Chemical biology of inflammatory cytokine signaling

Chemical biology of inflammatory cytokine signaling

Rabbit conjunctivae edema and release of NO, TNF-α, and IL-1β from macrophages induced by fractions and esculentosides isolated fromPhytolacca americana

Glucosylation of hydroxyflavones by glucosyltransferases from Phytolacca americana

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