Structure-Pungency Relationships and TRP Channel Activation of Drimane Sesquiterpenes in Tasmanian Pepper (Tasmannia lanceolata).

التفاصيل البيبلوغرافية
العنوان:	Structure-Pungency Relationships and TRP Channel Activation of Drimane Sesquiterpenes in Tasmanian Pepper (Tasmannia lanceolata).
المؤلفون:	Mathie K; Chair of Food Chemistry and Molecular Sensory Science, Technische Universität München , Lise-Meitner-Straße 34, D-85350 Freising, Germany , and., Lainer J; Chair of Food Chemistry and Molecular Sensory Science, Technische Universität München , Lise-Meitner-Straße 34, D-85350 Freising, Germany , and., Spreng S; Chair of Food Chemistry and Molecular Sensory Science, Technische Universität München , Lise-Meitner-Straße 34, D-85350 Freising, Germany , and., Dawid C; Chair of Food Chemistry and Molecular Sensory Science, Technische Universität München , Lise-Meitner-Straße 34, D-85350 Freising, Germany , and., Andersson DA; Kings's College London , Wolfron Centre for Age-Related Diseases, London SE1 1UL, United Kingdom., Bevan S; Kings's College London , Wolfron Centre for Age-Related Diseases, London SE1 1UL, United Kingdom., Hofmann T; Chair of Food Chemistry and Molecular Sensory Science, Technische Universität München , Lise-Meitner-Straße 34, D-85350 Freising, Germany , and.
المصدر:	Journal of agricultural and food chemistry [J Agric Food Chem] 2017 Jul 19; Vol. 65 (28), pp. 5700-5712. Date of Electronic Publication: 2017 Jul 07.
نوع المنشور:	Journal Article
اللغة:	English
بيانات الدورية:	Publisher: American Chemical Society Country of Publication: United States NLM ID: 0374755 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-5118 (Electronic) Linking ISSN: 00218561 NLM ISO Abbreviation: J Agric Food Chem Subsets: MEDLINE
أسماء مطبوعة:	Original Publication: Washington, American Chemical Society.
مواضيع طبية MeSH:	Taste, Calcium Channels/metabolism , Nerve Tissue Proteins/metabolism , Plant Extracts/chemistry , Sesquiterpenes/chemistry , Transient Receptor Potential Channels/metabolism , Winteraceae/*chemistry, Adult ; Animals ; CHO Cells ; Calcium/metabolism ; Calcium Channels/genetics ; Cricetulus ; Female ; Humans ; Male ; Mice ; Mice, Knockout ; Nerve Tissue Proteins/genetics ; Plant Extracts/metabolism ; Polycyclic Sesquiterpenes ; Sesquiterpenes/metabolism ; TRPA1 Cation Channel ; Transient Receptor Potential Channels/genetics ; Winteraceae/metabolism ; Young Adult
مستخلص:	Sensory-guided fractionation of extracts of Tasmanian pepper berries revealed 20 drimane sesquiterpens, among which polygodial, warburganal, and 1β-acetoxy-9-deoxy-isomuzigadial exhibited the lowest pungency threshold concentrations on the tongue surface (0.6-2.8 nmol/cm ² ) and elicited a dose-dependent calcium influx into mTRPA1 expressing CHO cells with the lowest EC 50 values (4.5 ± 1.0 to 16.7 ± 7.5 μmol/L) and a good correlation to oral pungency thresholds (R ² = 0.986, linear regression). Calcium imaging assays demonstrated these chemosensates to induce a calcium influx into cultured trigeminal neurons prepared from wildtype (TRPA1 ^+/+ ) mice, whereas no calcium influx was observed in neurons from TRPA1 knockout mice (TRPA1 ^-/- ), thus confirming the α,β-unsaturated 1,4-dialdehyde structure to be the required structural motif for a low oral puncency thresholds and activation of the Transient Receptor Potential Channel A1 (TRPA1). Time-resolved NMR experiments confirmed the pungency mediating mechanism for electrophilic drimane sesquiterpene dialdehydes to be different from that found for other electrophilic pungent agents like isothiocyanates, which have been shown to undergo a covalent binding with cysteine residues in TRPA1. Instead, the high-impact chemosensates polygodial, warburganal, and 1β-acetoxy-9-deoxy-isomuzigadial showed immediate reactivity with the ε-amino group of lysine side chains to give pyrrole-type conjugates, thus showing evidence for TRPA1 activation by covalent lysine modification.
فهرسة مساهمة:	Keywords: TRPA1; TRPV1; Tasmanian pepper; Tasmannia lanceolata; drimane; half-tongue test; pungency; taste dilution analysis
المشرفين على المادة:	0 (Calcium Channels) 0 (Nerve Tissue Proteins) 0 (Plant Extracts) 0 (Polycyclic Sesquiterpenes) 0 (Sesquiterpenes) 0 (TRPA1 Cation Channel) 0 (TRPA1 protein, human) 0 (Transient Receptor Potential Channels) 0 (Trpa1 protein, mouse) 0 (drimane) SY7Q814VUP (Calcium)
تواريخ الأحداث:	Date Created: 20170629 Date Completed: 20170728 Latest Revision: 20191210
رمز التحديث:	20240829
DOI:	10.1021/acs.jafc.7b02356
PMID:	28657737
قاعدة البيانات:	MEDLINE

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الوصف
تدمد:	1520-5118
DOI:	10.1021/acs.jafc.7b02356