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Isolation and Identification of Components from Wasabi (Wasabia japonica Matsumura) Flowers and Investigation of Their Antioxidant and Anti-inflammatory Activities

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Abstract

Wasabi (Wasabia japonica Matsumura) is a perennial plant, and its rhizome is widely used as a pungent spice. Wasabi rhizome has been reported to have various physiological activities, but the flower has not been studied in depth. The aim of the present study was to isolate compounds from wasabi flowers and clarify their antioxidant and anti-inflammatory activities. Three phenylpropanoids, one alkaloid and seven flavonoids were isolated from wasabi flowers. Among them, 2″-O-trans sinapoyl isovitexin was identified as a novel compound. Five compounds inhibited 2,2-diphenyl-1-picrylhydrazyl radical scavenging activity, with IC50 values of less than 100 µM. Luteolin isolated in this study was found to inhibit nitric oxide production in macrophage-like J774.1 cells, with an IC50 value of 24.1 ± 4.4 µM. Our results indicate that the phenolic compounds in wasabi flowers are effective ingredients for antioxidant and anti-inflammatory activities. For these reasons, wasabi flowers are expected to be used effectively as a functional food.

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... However, ten flavonoids (namely, isovitexin, isosaponarin, apigenin, luteolin, isoorientin, 7-O-trans-sinapoylisovitexin, 6"-O- [9]. Using the HPLC method, Kurata et al. [10] identified luteolin, isorhamnetin-3-glucoside, astragalin, isovitexin, isoorientin, and rutin in the flowers of W. japonica. Moreover, from the leaves of W. japonica cultivated in Japan, isosaponarin [12,20] and isoorientin were isolated [12]. ...
... Therefore, our results were in good agreement with previous investigations on the identification of isosaponarin and ferulic acid in the leaves [11,20], isorhamnetin-3-glucoside and astragalin in the flowers [10], and trans-ferulic acid, as well as trans-pcoumaric acid, in the roots [27] of E. japonicum. To the best of our knowledge, the other phenolic acids and flavonoids were identified for the first time in the investigated species. ...
... Ferulic acid, luteolin, isoorientin, and rutin showed a significant inhibitory activity. Importantly, luteolin (IC 50 = 4.09 ± 0.28 µg/mL) and isoorientin (IC 50 = 6.73 ± 0.45 µg/mL) showed a stronger activity compared to Trolox (IC 50 = 6.48 ± 0.73 µg/mL) [10]. ...
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Each tea catechin was reacted with 1,1-diphenyl-2-picrylhydrazyl (DPPH), and the reaction mixture was subjected to NMR analysis. The antioxidation mechanism of (+)-catechin [(+)-C] is considered to be due to the change of the B-ring to an o-quinone structure at first because of the appearance of two carbonyl signals. This is substantiated by trapping the compound as an adduct of a 1,2-phenylenediamine to an o-quinone. (-)-Epicatechin [(-)-EC] was also confirmed to give a similar result, but in the case of (-)-epigallocatechin [(-)-EGC] and ethyl gallate (EG) no carbonyl signals were observed. The antioxidation mechanisms of (-)-EGC and EG are different from those of (+)-C and (-)-EC. This may be one of the reasons for the differences of the antioxidative activities between the two types of catechins.
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6-Methylsulfinylhexyl isothiocyanate (MS-ITC) was isolated from wasabi (Wasabia japonica, Japanese domestic horseradish) as a potential inhibitor of human platelet aggregation in vitro through our extensive screening of vegetables and fruits. In the course of an another screening for the induction of glutathione S-transferase (GST) activity in RL34 cells, MS-ITC was inadvertently isolated from wasabi as a potential inducer of GST. MS-ITC administered to rats or mice also showed both activities in vivo. As a result from elucidation of the platelet aggregation inhibition and the GST induction mechanisms of MS-ITC, the isothiocyanate moiety of MS-ITC plays an important role for antiplatelet and anticancer activities because of its high reactivity with sulfhydryl (RSH) groups in biomolecules (GSH, cysteine residue in a certain protein, etc.).
Article
Cardiac hypertrophy occurs in pathological conditions associated with chronic increases in hemodynamic load. Although hypertrophy can initially be viewed as a salutary response, ultimately, it often enters a phase of pathological remodeling that may lead to heart failure and premature death. A prevailing concept predicts that changes in gene expression in hypertrophied cardiac myocytes and cardiac myocyte loss by apoptosis contribute to the transition from hypertrophy to failure. In recent years, nitric oxide (NO) has emerged as an important regulator of cardiac remodeling. Specifically, NO has been recognized as a potent antihypertrophic and proapoptotic mediator in cultured cardiac myocytes. Studies in genetically engineered mice have extended these findings to the in vivo situation. It appears that low levels and transient release of NO by endothelial NO synthase exert beneficial effects on the remodeling process by reducing cardiac myocyte hypertrophy, cavity dilation and mortality. By contrast, high levels and sustained production of NO by inducible NO synthase seem to be maladaptive by reducing ventricular contractile function, and increasing cardiac myocyte apoptosis, and mortality. In the future, these novel insights into the role of NO in cardiac remodeling should allow the development of novel therapeutic strategies to treat cardiac remodeling and failure.
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Interleukin (IL)-8 plays a central role in the initiation and maintenance of inflammatory responses in the inflammatory bowel disease. The proinflammatory cytokine-mediated production of IL-8 requires activation of various kinases, which leads to the IkappaB degradation and NF-kappaB activation. In this study, we investigated the role of luteolin, a major flavonoid of Lonicera japonica, on TNF-alpha-induced IL-8 production in human colonic epithelial cells. HT29 cells were stimulated with TNF-alpha in the presence or absence of luteolin. IL-8 production was measured by enzyme-linked immunosorbent assay (ELISA) and reverse transcriptase-polymerase chain reaction (RT-PCR) analysis, and the mitogen-activated protein kinases (MAPKs) activation and IkappaB degradation were determined by Western blot analysis. NF-kappaB activation was assessed by the electrophoretic motility shift assay (EMSA). Luteolin suppressed TNF-alpha-induced IL-8 production in dose-dependent manner. In addition, luteolin inhibited TNF-alpha-induced phosphorylation of p38 MAPK and extracellular-regulated kinases (ERK), IkappaB degradation, and NF-kappaB activation. These results suggest that luteolin has the inhibitory effects on TNF-alpha-induced IL-8 production in the intestinal epithelial cells through blockade in the phosphorylation of MAPKs, following IkappaB degradation and NF-kappaB activation.
Article
6-(Methylsulfinyl)hexyl isothiocyanate (6-MITC) is an active ingredient of Wasabi (Wasabia japonica (Miq.) Matsumura), which is a very popular pungent spice in Japan. To clarify the cellular signaling mechanism underlying the anti-inflammatory action of 6-MITC, we investigated the effects of 6-MITC on the expression of inducible nitric oxide synthase (iNOS) in lipopolysaccharide (LPS)-activated murine macrophage RAW264 cells. 6-MITC showed a dose-dependent inhibition of LPS-induced nitric oxide (NO), iNOS mRNA and protein. LPS caused the c-Jun phosphorylation (a major component of AP-1) and IkappaB-alpha degradation. 6-MITC suppressed LPS-induced c-Jun phosphorylation, but did not inhibit IkappaB-alpha degradation. Cellular signaling analysis using MAPK-(U0126 for MEK1/2, SB203580 for p38 kinase and SP600125 for JNK) and Jak2-specific (AG490) inhibitors demonstrated that LPS stimulated iNOS expression via activating Jak2-mediated JNK, but not ERK and p38, pathway. 6-MITC suppressed iNOS expression through the inhibition of Jak2-mediated JNK signaling cascade with the attendant to AP-1 activation. In addition, the structure-activity study revealed that the inhibitory potency of methylsulfinyl isothiocyanates (MITCs) depended on the methyl chain length. These findings provide the molecular basis for the first time that 6-MITC is an effective agent to attenuate iNOS production.
Article
Many hydroxyflavone derivatives have been found in nature and shown to have many biological functions. Because their function is changed by the position and number of hydroxyl group, their structural identification is a fundamental and necessary step for understanding their functions. In the present study, the complete 1H and 13C NMR spectral assignments were presented for 6 hydroxyflavones, and NMR data of additional 14 hydroxyflavone derivatives were compared with those of the 6 hydroxyflavones. In addition, the partially incorrect NMR data of two of the dihydroxyflavones whose NMR data were previously reported were corrected.
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From the MeOH extract of the leaves of W. japonica, seven phenylpropanoid gentiobiosides (1-7) were isolated along with eight known phenylpropanoids (8-15). Structures of 1-7 were determined based on spectroscopic data and chemical evidence. The activity of compounds 1-15 to scavenge superoxide anion radicals was investigated using an electron spin resonance (ESR) method.
  • G R Augusto
  • F Maróstica
  • M R De Lima
G.R., Augusto, F., Maróstica Jr, M.R., and de Lima, Z.R. (2013).