Structures of New Erythrinan Alkaloids and Nitric Oxide Production Inhibitors from Erythrina crista-galli

Ozawa, Masaaki; Kawamata, S.; Etoh, Tadahiro; Hayashi, Masahiko; Komiyama, Kanki; Kishida, Akio; Kuroda, Chiaki; Ohsaki, Ayumi

doi:10.1248/cpb.58.1119

Cited by 45 publications

(22 citation statements)

References 20 publications

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“…2) In the present study, we pharmacologically analyzed its mechanism of action in TLR signaling pathways. Firstly, we should mention that erythraline at various concentrations (3, 10, and 30 µm) did not affect cell viability of RAW264.7 cells following the 20 h incubation ( Fig.…”

Section: Discussionmentioning

confidence: 99%

Inhibitory Effect of Erythraline on Toll-Like Receptor Signaling Pathway in RAW264.7 Cells

Etoh

Kim

Ohsaki

et al. 2013

Biological & Pharmaceutical Bulletin

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Erythraline, isolated from the bark of Erythrina crista-galli which are used as Brazilian medicine plant for the treatment of inflammation diseases, suppressed nitric oxide (NO) production and induction of inducible nitric oxide synthase (iNOS) expression in RAW264.7 cells stimulated by lipopolysaccharide (LPS). Because of Toll-like receptor (TLR) 4 and its signal transduction are indispensable to the production of NO and iNOS expression by LPS, we investigated the effects of erythraline on TLR signaling molecules. Western blot analysis revealed that the degradation of inhibitor of nuclear factor (NF)-κB (IκB) by LPS was suppressed by erythraline. Moreover, erythraline inhibited not only LPS-induced phosphorylation of IκB kinase (Ikk) but also phosphorylation of mitogen-activated protein kinases (MAPKs). However, it showed no effect on LPS -induced phosphorylation of transforming growth factor (TGF)-β-activated kinase (TAK) 1 that exists upstream of Ikk and MAPKs, and is required for the activation of these signaling molecules on TLR signaling pathway. These results suggested that erythraline might have inhibited the kinase activity of TAK1. Furthermore, these results were supported from the inhibitory pattern of erythraline on TLR signaling molecules when the cells were stimulated by TLR2 ligand, peptidoglycan which activates the same pathway as LPS on TLR signal transduction.Key words erythraline; transforming growth factor-β activated kinase 1; anti-inflammation; toll-like receptorThe Erythrina genus (Leguminosae) includes more than 100 species and is distributed in South America and tropical and subtropical regions of South Asia. Erythrina crista-galli L. is commonly known as the cockspur coral tree. It is also called "Corticeira" in Brazil and its bark is used for the treatment of rheumatism, hepatitis, sedation, and hypnogenesis.

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Section: Discussionmentioning

confidence: 99%

Inhibitory Effect of Erythraline on Toll-Like Receptor Signaling Pathway in RAW264.7 Cells

Etoh

Kim

Ohsaki

et al. 2013

Biological & Pharmaceutical Bulletin

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“…Many of these species are used indigenously as traditional medicines to treat various diseases, such as infection, cough, malaria, inflammation, and asthma. This genus has been shown to produce a number of phenolic compounds, particularly alkaloids [1], flavonoids [2,3], pterocarpans [4,5] and stilbenoids [6]. In continuation of our research into the phenolic compound in this medicinal plant, we report the isolation of methyl 2,5-dihydroxy-4-(3 1 -methyl-2 1 -butenyl)benzoate (1) from the methanol extract of the the root of Erythrina subumbrans.…”

Section: Introductionmentioning

confidence: 93%

Methyl 2,5-Dihydroxy-4-(3′-methyl-2′-butenyl)benzoate

Tjahjandarie

Saputri

Tanjung

2016

Molbank

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“…Erythraline ( 40 ), erythrinine ( 42 ), and hypaphorine ( 81 ) showed a significant inhibitory activity with IC 50 values of 8.8, 3.4, and 11.2 μg/ml, respectively. Additionally, these alkaloids did not affect cell viability of RAW264.7 macrophages (Ozawa et al, ).…”

Section: Preclinical Studiesmentioning

confidence: 99%

The genus Erythrina L.: A review on its alkaloids, preclinical, and clinical studies

Rambo

Biegelmeyer

Toson

et al. 2019

Phytotherapy Research

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Erythrina L. genus (Fabaceae) comprises about 115 species, and it has been extensively studied, mainly because of its alkaloids, which have pharmacological properties. References demonstrated that Erythrina spp. have a potential to act in the central nervous system, presenting anxiolytic and anticonvulsant properties already established. Phytochemical investigations confirmed the presence of tetracyclic alkaloids as the major compounds. However, other alkaloid classes have also been reported, including dimeric and trimeric substances, coupled through direct polymerization or two erythrinine units via an acetyl glucose. The present review covers the relevant literature from 1990 until 2017 and outlines the current data on chemical composition and preclinical and clinical studies on Erythrina species. Additionally, the quite striking analogy in the biosynthetic route of erythrin, morphinans, and Amaryllidaceae family alkaloids was also discussed.

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Structures of New Erythrinan Alkaloids and Nitric Oxide Production Inhibitors from Erythrina crista-galli

Cited by 45 publications

References 20 publications

Inhibitory Effect of Erythraline on Toll-Like Receptor Signaling Pathway in RAW264.7 Cells

Inhibitory Effect of Erythraline on Toll-Like Receptor Signaling Pathway in RAW264.7 Cells

Methyl 2,5-Dihydroxy-4-(3′-methyl-2′-butenyl)benzoate

The genus Erythrina L.: A review on its alkaloids, preclinical, and clinical studies

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