Naturally Occurring 5-Lipoxygenase Inhibitor. II. Structures and Syntheses of Ardisianones A and B, and Maesanin, Alkenyl-1,4-benzoquinones from the Rhizome of Ardisia japonica.

Kiriyama, Yuuko; Okino, Junko; Kodama, Masashi; Iwaki, Hideyuki; Hosozawa, Sigeki; Matsui, Kuniaki

doi:10.1248/cpb.41.561

Cited by 36 publications

(27 citation statements)

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“…Schemes for the straightforward synthesis of maesanin and its derivatives have already been reported (Kubo et al, 1987;Fukuyama et al, 1993), and a further study will be pursued in that direction. …”

Section: Resultsmentioning

confidence: 99%

“…However, earlier investigations reported that maesanin possesses non-specific host defense stimulatory and anti-5-LO activities (Kubo et al, 1987;Fukuyama et al, 1993), and it also inhibits the mitochondrial oxidative phosphorylation (Makawiti et al, 1990). In addition, recent investigations have reported on the antiviral, haemolytic and molluscicidal activities of triterpenoid saponins, isolated from leaves of this plant 2001).…”

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confidence: 99%

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Cytotoxic and antioxidant activities of alkylated benzoquinones from Maesa lanceolata

Muhammad

Takamatsu

Walker

et al. 2003

Phytotherapy Research

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The natural and semi-synthetic analogs of substituted 1,4-benzoquinones were evaluated for in vitro cytotoxic and antioxidant activities. Maesanin, dihydromaesanin, maesanin dimethyl ether and isomeric mixtures of 3-[(Z)-10'-pentadecenyl]-benzoquinone derivatives exhibited cytotoxic activity against HL-60 cell line (IC50 values 4.5, 2.2, 0.43 and 2.8 microg/mL, respectively), while it was found to be inactive against ROS (Reactive Oxygen Species) generation in HL-60. In contrast, the isomeric acylated benzoquinones with shorter alkyl substituents, namely, 2-acetoxy-5-hydoxy-6-methyl-3-tridecyl-1,4-benzoquinone and 2-hydoxy-5-acetoxy-6-methyl-3-tridecyl-1,4-benzoquinone showed most prominent antioxidant and antiproliferative effect on HL-60 (IC50 values 6.2 and 2.2 microg/mL, respectively), as well as cytotoxicities against SK-MEL, KB, BT-549 and SK-OV-3 carcinomas (IC50 values <1.1-4.2 microg/mL). All benzoquinones were found to be inactive against cell aggregation and cell adhesion assays, thus showing no effect on immune responses and inflammation.

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Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

Cytotoxic and antioxidant activities of alkylated benzoquinones from Maesa lanceolata

Muhammad

Takamatsu

Walker

et al. 2003

Phytotherapy Research

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“…This [142] and subsequent studies [143], [144], [145], [146] identified ardisianone A 76, ardisiaquinones A 74, B 75a, D 75b, E 75c, and F 75d, as well as maesanin 83 (Table 5) as potent inhibitors of 5-LO in cell-free assays with IC 50 values = 0.2 ± 1 mM. In intact cells, ardisiaquinone A 74, the most potent analogue in cell-free assays was less efficient (IC 50 = 5.56 mM) [146].…”

Section: Quinonesmentioning

confidence: 96%

Inhibition of 5-Lipoxygenase Product Synthesis by Natural Compounds of Plant Origin

Werz¹

2007

Planta Med

153

135

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The biosynthesis of leukotrienes (LTs) is initiated by the transformation of free arachidonic acid to LTA 4 by 5-lipoxygenase (5-LO). Subsequent enzymatic conversion of LTA 4 yields LTB 4 and the cysteinyl-LTs C 4 , D 4 and E 4 . LTs have prominent functions in pathophysiology and are connected to numerous disorders including bronchial asthma, allergic rhinitis, inflammatory bowel and skin diseases, rheumatoid arthritis, cancer, osteoporosis and cardiovascular diseases. Pharmacological and genetic interruption of the 5-LO pathway or blockade of LT receptors, serving as means for intervention with LTs, may be of therapeutic value for certain related disorders. Natural or plant-derived substances were among the first 5-LO inhibitors identified in the early 1980 s. To date, a huge number of diverse plant-derived compounds have been reported to interfere with 5-LO product synthesis. However, many investigations have addressed the efficacy of a given compound solely in cellular test systems and analysis of direct interference with 5-LO has been neglected. In the first part of this review, the biology and molecular pharmacology of the 5-LO pathway is summarized in order to understand its overall regulation and complexity as well as to comprehend the possible points of attack of compounds that eventually lead to inhibition of 5-LO product formation in intact cells. In the second part, natural compounds that interfere with 5-LO product formation are compiled and grouped into structural classes, and the underlying molecular mechanisms and structureactivity relationships are discussed.

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“…Ardisia japonica can be also used to improve circulation and the respiratory system (Anonymous, 1973). Moreover, phytochemical investigation of Ardisia japonica has resulted in the discovery of compounds that are 5-lipoxygenase inhibitors (Fukuyama et al, 1993;Fukuyama et al, 1994), anti-HIV (Piacente et al, 1996), anti-tubercular (Hu et al, 1979), and PTP1B inhibitors (Li et al, 2003).…”

Section: Food and Medicinal Usagesmentioning

confidence: 99%

The genus Ardisia: a novel source of health-promoting compounds and phytopharmaceuticals

Kobayashi

Mejía

2005

Journal of Ethnopharmacology

123

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Naturally Occurring 5-Lipoxygenase Inhibitor. II. Structures and Syntheses of Ardisianones A and B, and Maesanin, Alkenyl-1,4-benzoquinones from the Rhizome of Ardisia japonica.

Cited by 36 publications

References 1 publication

Cytotoxic and antioxidant activities of alkylated benzoquinones from Maesa lanceolata

Cytotoxic and antioxidant activities of alkylated benzoquinones from Maesa lanceolata

Inhibition of 5-Lipoxygenase Product Synthesis by Natural Compounds of Plant Origin

The genus Ardisia: a novel source of health-promoting compounds and phytopharmaceuticals

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