Biologically Active Constituents of Magnolia salicifolia: Inhibitiors of Induced Histamine Release from Rat Mast Cells.

Tsuruga, Tomoko; Ebizuka, Yutaka; Nakajima, Junko; Chun, Yiu-To; Noguchi, Hiroshi; Iitaka, Yōichi; Sankawa, Ushio

doi:10.1248/cpb.39.3265

Cited by 30 publications

(20 citation statements)

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“…An affinity to Roridula, essentially inspired by a common placement in Droseraceae, was assumed for similar reasons (Domin 1922) and can likewise be discounted due to ultrastructural differences. Similarities in floral structure already mentioned by Planchon (1848) led a large number of Takeda et al 1995Franzyk et al 2000Hegnauer 1990Hegnauer 1990Hegnauer 1990Rodriguez and Castro 1996Hegnauer 1990von Poser et al 1998Rasoanaivo et al 1989van Heerden et al 2002Tsuruga et al 1991 Apiales), and inclusion in a common monophyletic clade with Lamiaceae, Scrophulariaceae, and Lentibulariaceae comprising the order Scrophulariales (syn. Lamiales, Bignoniales).…”

Section: Resultsmentioning

confidence: 52%

Acteoside and related phenylethanoid glycosides in Byblis liniflora Salisb. plants propagated in vitro and its systematic significance

Schlauer

Budzianowski

Kukulczanka³

et al. 2011

Acta Soc Bot Pol

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From plantlets of Byblis liniflora Salisb. (Byblidaceae), propagated by in vitro culture, four phenylethanoid glycosides - acteoside, isoacteoside, desrhamnosylacteoside and desrhamnosylisoacteoside were isolated. The presence of acteoside substantially supports a placement of the family Byblidaceae in order Scrophulariales and subclass Asteridae. Moreover, the genera containing acteoside are listed; almost all of them appear to belong to the order Scrophulariales

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Section: Resultsmentioning

confidence: 52%

Acteoside and related phenylethanoid glycosides in Byblis liniflora Salisb. plants propagated in vitro and its systematic significance

Schlauer

Budzianowski

Kukulczanka³

et al. 2011

Acta Soc Bot Pol

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“…p-Hydroxybenzoic acid (6) and scopoletin (9) did not showed significant inhibitory effects. However, as the inhibitory effects of 7 and 9 on histamine release from mast cells have been previously reported 14,15) in an in vitro assay, in the future experiments should be conducted using other routes, time schedules, and doses. In natural product pharmacy therapeutic studies, in vivo assays usually yield more information for actual application.…”

Section: Resultsmentioning

confidence: 97%

Antipruritic Effects of 1,4-Naphthoquinones and Related Compounds.

Oku

Kato²,

Ishiguro

2002

Biological & Pharmaceutical Bulletin

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The number of patients with allergic disease has recently been increasing. To treat such diseases, we have isolated natural compounds with antianaphylactic, 1,2) antihistaminic, 3) and anti-platelet-activating factor (PAF) 4) activity using in vivo assay systems that we have developed. However, in cases of allergic disease with chronic and severe pruritus, such as atopic dermatitis, not only treatment of the allergy but also inhibition of scratching at the lesion is very important. We therefore searched for natural compounds with antipruritic activity using our in vivo assay systems.5) We discovered that a 2-hydroxy-1,4-naphthoquinone (lawsone) (1) isolated from Impatiens balsamina L., could significantly inhibit scratching behavior 5) induced in mice by histamine-releasing agents, such as Dextran T40 and compound 48/80 (COM). We were also able to show that 1 can be effective as an antipruritic agent against atopic dermatitis, because it inhibited 6) chronic and serious scratching behavior in atopic dermatitis model NC mice with dermatitis.Here we report the antipruritic effects of natural and synthesized 1,4-naphthoquinones and related compounds for new antipruritic medicines that can be effective for the treatment of allergic disease. MATERIALS AND METHODS General Experimental ProceduresMelting points were determined with a Yanagimoto micro melting point apparatus. IR spectra were recorded on a Shimadzu 435 spectrometer and UV absorption spectra with a Hitachi 323 spectrometer.1 H-NMR and 13 C-NMR spectra were recorded with JEOL JNM-GSX 400 spectrometers (using tetramethylsilane (TMS) as an internal reference). Electron-impact (EI)-MS spectra (70 eV) were obtained with a JEOL JMS-DX 303 spectrometer.Materials COM was obtained from Sigma. 2,3-Dihydroxy-1,4-naphthoquinone (2), 2-hydroxy-3-methoxy-1,4-naphthoquinone (3), and 2-hydroxy-3-(2-hydroxyethyl)-1,4-naphthoquinone (4) were synthesized by known methods. 7,8) Compound 1, p-hydroxybenzoic acid (6), p-coumaric acid (7), ferulic acid (8), scopoletin (9), 2,2Ј-methylenebis(3-hydroxy-1,4-naphthoquinone) (10), and 2,2Ј-ethylidenebis(3-hydroxy-1,4-naphthoquinone) (impatienol) (11) were isolated from I. balsamina using methods described previously. 1,9,10) Balsaquinone (5) was isolated from the pericarp of I. balsamina as described in the following section.Isolation and Identification of Compound 5 Fresh pericarp (75 g) of I. balsamina was extracted with 50% ethanol 400 ml over 3 d at room temperature and filtered. The extract (2.9 g) was subjected to silica gel chromatography using a CHCl 3 -MeOH gradient system followed by TLC to give compound 5 (6 mg). The UV spectrum showed characteristic absorption maxima of 1,4-naphthoquinone. The IR spectrum suggested the presence of a hydroxyl group and an a,b-unsaturated function. The EI-MS spectrum exhibited a [M] ϩ at m/z 232. The 1 H-and 13 C-NMR spectral data were similar to those of 2-methoxy-1,4-naphthoquinone except for the presence of the hydroxyethyl group and absence of 3-H, suggesting that 5 is 2-methoxy-1,4-n...

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“…Two major lignans of PN-ext, (Ϫ)-cubebin (1) and (Ϫ)-3,4-dimethoxy-3,4-desmethylenedioxycubebin (2), were already isolated from the ethyl acetate soluble fraction as described in the previous paper. 1,4) Because Tsuruga et al 15) reported that several cubebin-type lignans having 3,4-dibenzyltetrahydrofuran ring, such as matairesinol and trachelogenin, had significant histamine release inhibitory activities, we examined inhibitory effects of 1 and 2 on compound 48/80-induced histamine release from rat peritoneal mast cells. As shown in Table 3, the inhibitory activities of 1 and 2 were superior to that of SCG.…”

Section: Resultsmentioning

confidence: 99%

Histamine Release Inhibitory Activity of Piper nigrum Leaf

Hirata

Naruto

Inaba

et al. 2008

Biological & Pharmaceutical Bulletin

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During the course of our search for useful ingredients of cosmetics from natural resource, we have previously reported that Piper nigrum leaf extract showed both melanogenesis stimulation activity and testosterone 5a-reductase inhibitory activity and that (Ϫ)-cubebin (1) and (Ϫ)-3,4-dimethoxy-3,4-desmethylenedioxycubebin (2) were isolated as active lignan constituents. [1][2][3][4] It was suggested that these substances may be useful ingredients of hair-care cosmetics for prevention of gray hair and alopecia. As a part of our continuous study on P. nigrum leaf, we examined anti-allergic effect of the leaf, because hair care cosmetics having anti-allergic activity may be desirable. It has been reported that antiallergic effect of a botanical formulation 5) in which P. nigrum fruit was included. Anti-allergic activity of piperine, 6) a major alkaloid amide of P. nigrum fruit have been reported, but HPLC analysis revealed that the piperine content in the leaf was 0.00007%. 7) Moreover, we have not found any reports on anti-allergic effect of the leaf. In this paper, we describe in vivo anti-allergic effects of P. nigrum leaf extract against type I allergy model and type IV allergy model in mice. 2,4-Dinitrofluorobenzene (DNFB) has been shown to induce triphasic increase in ear thickness of mouse by the challenge after a passive sensitization with monoclonal antidinitrophenyl (DNP) IgE antibody. 8,9) This model serves as an animal model for type I allergy. 8,9) In addition, we used picryl chloride (PC)-induced contact dermatitis in mice as an animal model for type IV allergy.10) Inhibitory effects of Piper nigrum leaf extract, on histamine release were also examined by in vitro assay using compound 48/80-induced histamine release from rat peritoneal mast cells. MATERIALS AND METHODS Plant MaterialsPiper nigrum leaf was the same sample described in the previous paper. 1-4)Reagents 2,4-Dinitrofluorobenzene (DNFB), Ficoll, Hanks' balanced salt solution, olive oil, o-phthaldialdehyde, picryl chloride (PC), and sodium carboxymethyl cellulose (CMC · Na) were purchased from Nacalai Tesque (Tokyo, Japan). Sodium cromoglycate (SCG) was purchased from Funakoshi (Tokyo, Japan). Compound 48/80, dimethyl sodium salt (DMSO), prednisolone, monoclonal anti-DNP antibody and heparin sodium salt were purchased from Sigma (St. Louis, MO, U.S.A.). Other chemical reagents were reagent grade and were purchased from Wako Pure Chemical Industries, Ltd. unless otherwise noted.Preparation of PN-ext and Fractionation Methanolic extract of Piper nigrum leaf (PN-ext) was obtained according to the previous paper in yield of 14.0%. The powdered dry leaves (500 g) of P. nigrum were extracted with MeOH (5 lϫ3 times) for 1 h under reflux. Combined extracts were evaporated under reduced pressure to give a methanolic extract (PN-ext, 71.1 g). A part of PN-ext (69.6 g) was extracted with hexane (400 mlϫ3), and the organic layer was evaporated to give a hexane soluble fraction (17.3 g). The hexane insoluble part was extracted with EtOAc (300 mlϫ2). The E...

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Biologically Active Constituents of Magnolia salicifolia: Inhibitiors of Induced Histamine Release from Rat Mast Cells.

Cited by 30 publications

References 0 publications

Acteoside and related phenylethanoid glycosides in Byblis liniflora Salisb. plants propagated in vitro and its systematic significance

Acteoside and related phenylethanoid glycosides in Byblis liniflora Salisb. plants propagated in vitro and its systematic significance

Antipruritic Effects of 1,4-Naphthoquinones and Related Compounds.

Histamine Release Inhibitory Activity of Piper nigrum Leaf

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