Biologically active thiosulphinates and α-sulphinyldisulphides from Allium cepa

Bayer, Th.; Breu, W.; Seligmann, Otto; Wray, V.; Wagner, Hildebert

doi:10.1016/s0031-9422(00)97987-1

Cited by 56 publications

(42 citation statements)

References 22 publications

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“…Cepaenes and thiosulfinates have been identified as biologically active compounds in onion juice [1][2][3][4][5][6][7]. These compounds are not present in the intact plant.…”

Section: Onionsmentioning

confidence: 99%

New Antiasthmatic Drugs from Traditional Medicine?

Dorsch

Wagner²

1991

Int Arch Allergy Immunol

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Several plants are used in traditional medicine for the treatment of bronchial asthma. We are trying to identify the active compound(s) and their mode of action. For the isolation and identification of the active principles, different chromatographic methods, HPLC, MPLC, elementary analysis, UV, mass, ¹H- and ¹³C-NMR spectroscopy are used. Whole plant extracts, fractionated extracts and pure compounds are tested in the following pharmacological systems: cyclooxygenase and lipoxygenase pathway of arachidonic acid metabolism, bronchial obstruction of guinea pigs after inhalation of allergens, platelet-activating factor (PAF), histamine or acetylcholine, PAF-induced bronchial hyper-reactivity of guinea pigs, histamine release, chemoluminescence and chemotaxis of human polymorphonuclear leukocytes as well as thromboxane biosynthesis of human platelets. As active compounds in onion extracts, thiosulfinates and cepaenes could be identified. They exert a wide spectrum of pharmacologic activities, both in vitro and in vivo. Tetragalloyl quinic acid from Galphimia glauca, suppressed allergen- and PAF-induced bronchial obstruction, PAF-induced bronchial hyperreactivity (5 mg/kg orally) in vivo and thromboxane biosynthesis in vitro. Hitherto unknown alkaloids from Adhatoda vasica showed pronounced protection against allergen-induced bronchial obstruction in guinea pigs (10 mg/ml aerosol). Androsin from Picrorhiza kurroa prevented allergen- and PAF-induced bronchial obstruction (10 mg/kg orally; 0.5 mg inhalative). Histamine release in vitro was inhibited by other compounds of the plant extract yet to be identified. Pharmacological effects of plant extracts and pure compounds in man are under investigation.

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“…Cepaenes and thiosulfinates have been identified as biologically active compounds in onion juice [1][2][3][4][5][6][7]. These compounds are not present in the intact plant.…”

Section: Onionsmentioning

confidence: 99%

New Antiasthmatic Drugs from Traditional Medicine?

Dorsch

Wagner²

1991

Int Arch Allergy Immunol

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“…In order to then determine the composition and ratio of compounds, we anal yzed each extract as described [11] using the following high-per formance liquid chromatographic method: LiChrospher RP 18 col umn, acetonitrile/water gradient 20-80% in 30 min and ultraviolet detection at 210 nm. (We gratefully acknowledge the kind support of Dr. Cully, Trostberg, FRG.…”

Section: Preparation and Analysis O F Onion Extractsmentioning

confidence: 99%

“…T he sym m etrically su b stitu ted th io su lfin a te s were synthesized by one of us [11] according to Small at al. [12], The asymmetrically substituted thiosulfinates were produced similarly.…”

Section: Synthesis Ofthiosulfinatesmentioning

confidence: 99%

Anti-Inflammatory Effects of Onions: Inhibition of Chemotaxis of Human Polymorphonuclear Leukocytes by Thiosulfinates and Cepaenes

Dorsch

Schneider

Bayer

et al. 1990

Int Arch Allergy Immunol

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Seven different synthetic thiosulfinates, and cepaene- and/or thiosulfinate-rich onion extracts were found to inhibit in vitro the chemotaxis of human granulocytes induced by formyl-methionine-leucinephenylalanine in a dose-dependent manner and at a concentration range of 0.1–100 μM. Diphenylthiosulfinate showed the highest activity and was found to be more active than prednisolone. The anti-inflammatory properties of onion extracts are related, at least in part, to the inhibition of inflammatory cell influx by thiosulfinates and cepaenes.

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“…The compounds characterised by a fresh onion-like Ñavour appear Ðrst in the solvent (Bayer et al 1989 ;Block et al 1992a,b) and extracts (Sinha et al SC-CO 2 1992 ;Calvey et al 1994).…”

Section: Introductionmentioning

confidence: 99%