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A non-pungent triprenyl phenol of fungal origin, scutigeral, stimulates rat dorsal root ganglion neurons <i>via</i> interaction at vanilloid receptors
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A non-pungent triprenyl phenol of fungal origin, scutigeral, stimulates rat dorsal root ganglion neurons via interaction at vanilloid receptors

Author: A Szallasi Affiliation: Department of Anatomy and Neurobiology, Washington University School of Medicine, St. Louis, Missouri, U.S.A.; Department of Pharmacology, Karolinska Institute, Stockholm, SwedenT Bíró Affiliation: National Cancer Institute, Bethesda, Maryland, U.S.A.T Szabó Affiliation: National Cancer Institute, Bethesda, Maryland, U.S.A.S Modarres Affiliation: National Cancer Institute, Bethesda, Maryland, U.S.A.M Petersen Affiliation: Department of Physiology, Julius-Maximilians-University Würzburg, Würzburg, GermanyAll authors
Edition/Format: Article Article : English
Publication:British Journal of Pharmacology, v126 n6 (March 1999): 1351-1358
Other Databases: WorldCatWorldCatWorldCat
Summary:
British Journal of Pharmacology (1999) 126, 1351-1358; doi:
A [³H]-resiniferatoxin (RTX) binding assay utilizing rat spinal cord membranes was employed to identify novel vanilloids in a collection of natural products of fungal origin. Of the five active compounds found (scutigeral, acetyl-scutigeral, ovinal, neogrifolin, and methyl-neogrifolin), scutigeral (Ki=19 μM), isolated from the edible mushroom Albatrellus ovinus, was selected for further characterization.
Scutigeral induced a dose-dependent 45Ca uptake by rat dorsal root ganglion neurons with an EC50 of 1.6 μM, which was fully inhibited by the competitive vanilloid receptor antagonist capsazepine (IC50=5.2 μM).
[³H]-RTX binding isotherms were shifted by scutigeral (10-80 μM) in a competitive manner. The Schild plot of the data had a slope of 0.8 and gave an apparent Kd estimate for scutigeral of 32 μM.
Although in the above assays scutigeral mimicked capsaicin, it was not pungent on the human tongue up to a dose of 100 nmol per tongue, nor did it provoke protective wiping movements in the rat (up to 100 μM) upon intraocular instillation.
In accord with being non-pungent, scutigeral (5 μM) did not elicit a measurable inward current in isolated rat dorsal root ganglion neurons under voltage-clamp conditions. It did, however, reduce the proportion of neurons (from 61 to 15%) that responded to a subsequent capsaicin (1 μM) challenge. In these neurons, scutigeral both delayed (from 27 to 72 s) and diminished (from 5.0 to 1.9 nA) the maximal current evoked by capsaicin.
In conclusion, scutigeral and its congeners form a new chemical class of vanilloids, the triprenyl phenols. Scutigeral promises to be a novel chemical lead for the development of orally active, non-pungent vanilloids.  Read more...
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Document Type: Article
All Authors / Contributors: A Szallasi Affiliation: Department of Anatomy and Neurobiology, Washington University School of Medicine, St. Louis, Missouri, U.S.A.; Department of Pharmacology, Karolinska Institute, Stockholm, Sweden; T Bíró Affiliation: National Cancer Institute, Bethesda, Maryland, U.S.A.; T Szabó Affiliation: National Cancer Institute, Bethesda, Maryland, U.S.A.; S Modarres Affiliation: National Cancer Institute, Bethesda, Maryland, U.S.A.; M Petersen Affiliation: Department of Physiology, Julius-Maximilians-University Würzburg, Würzburg, Germany; A Klusch Affiliation: Department of Physiology, Julius-Maximilians-University Würzburg, Würzburg, Germany; P M Blumberg Affiliation: National Cancer Institute, Bethesda, Maryland, U.S.A.; J E Krause Affiliation: Department of Anatomy and Neurobiology, Washington University School of Medicine, St. Louis, Missouri, U.S.A.; O Sterner Affiliation: Department of Organic Chemistry 2, Lund University, Lund, Sweden
ISSN:0007-1188
Language Note: English
Unique Identifier: 5156967416
Notes: A. Szallasi, National Cancer Institute, Bldg. 37, Rm. 3A13, 37 Convent Drive MSC 4255, Bethesda, MD 20892-4255, U.S.A; E-mail: szallasi@exchange.nih.gov
(Received October 1, 1998, Revised December 10, 1998, Accepted December 23, 1998)
Number of Figures: 6
Number of Tables: 1
Number of References: 51
Awards:
Other Titles: Triprenyl phenols function as non-pungent vanilloids

Abstract:

British Journal of Pharmacology (1999) 126, 1351-1358; doi:
A [³H]-resiniferatoxin (RTX) binding assay utilizing rat spinal cord membranes was employed to identify novel vanilloids in a collection of natural products of fungal origin. Of the five active compounds found (scutigeral, acetyl-scutigeral, ovinal, neogrifolin, and methyl-neogrifolin), scutigeral (Ki=19 μM), isolated from the edible mushroom Albatrellus ovinus, was selected for further characterization.
Scutigeral induced a dose-dependent 45Ca uptake by rat dorsal root ganglion neurons with an EC50 of 1.6 μM, which was fully inhibited by the competitive vanilloid receptor antagonist capsazepine (IC50=5.2 μM).
[³H]-RTX binding isotherms were shifted by scutigeral (10-80 μM) in a competitive manner. The Schild plot of the data had a slope of 0.8 and gave an apparent Kd estimate for scutigeral of 32 μM.
Although in the above assays scutigeral mimicked capsaicin, it was not pungent on the human tongue up to a dose of 100 nmol per tongue, nor did it provoke protective wiping movements in the rat (up to 100 μM) upon intraocular instillation.
In accord with being non-pungent, scutigeral (5 μM) did not elicit a measurable inward current in isolated rat dorsal root ganglion neurons under voltage-clamp conditions. It did, however, reduce the proportion of neurons (from 61 to 15%) that responded to a subsequent capsaicin (1 μM) challenge. In these neurons, scutigeral both delayed (from 27 to 72 s) and diminished (from 5.0 to 1.9 nA) the maximal current evoked by capsaicin.
In conclusion, scutigeral and its congeners form a new chemical class of vanilloids, the triprenyl phenols. Scutigeral promises to be a novel chemical lead for the development of orally active, non-pungent vanilloids.

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Primary Entity

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A [³H]-resiniferatoxin (RTX) binding assay utilizing rat spinal cord membranes was employed to identify novel vanilloids in a collection of natural products of fungal origin. Of the five active compounds found (scutigeral, acetyl-scutigeral, ovinal, neogrifolin, and methyl-neogrifolin), scutigeral (Ki=19 μM), isolated from the edible mushroom Albatrellus ovinus, was selected for further characterization.
Scutigeral induced a dose-dependent 45Ca uptake by rat dorsal root ganglion neurons with an EC50 of 1.6 μM, which was fully inhibited by the competitive vanilloid receptor antagonist capsazepine (IC50=5.2 μM).
[³H]-RTX binding isotherms were shifted by scutigeral (10-80 μM) in a competitive manner. The Schild plot of the data had a slope of 0.8 and gave an apparent Kd estimate for scutigeral of 32 μM.
Although in the above assays scutigeral mimicked capsaicin, it was not pungent on the human tongue up to a dose of 100 nmol per tongue, nor did it provoke protective wiping movements in the rat (up to 100 μM) upon intraocular instillation.
In accord with being non-pungent, scutigeral (5 μM) did not elicit a measurable inward current in isolated rat dorsal root ganglion neurons under voltage-clamp conditions. It did, however, reduce the proportion of neurons (from 61 to 15%) that responded to a subsequent capsaicin (1 μM) challenge. In these neurons, scutigeral both delayed (from 27 to 72 s) and diminished (from 5.0 to 1.9 nA) the maximal current evoked by capsaicin.
In conclusion, scutigeral and its congeners form a new chemical class of vanilloids, the triprenyl phenols. Scutigeral promises to be a novel chemical lead for the development of orally active, non-pungent vanilloids.
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