Next Article in Journal
Evaluation of Antioxidant Capacity, Protective Effect on Human Erythrocytes and Phenolic Compound Identification in Two Varieties of Plum Fruit (Spondias spp.) by UPLC-MS
Next Article in Special Issue
The Investigation of the Antitumor Agent Toxicity and Capsaicin Effect on the Electron Transport Chain Enzymes, Catalase Activities and Lipid Peroxidation Levels in Lung, Heart and Brain Tissues of Rats
Previous Article in Journal
Semisynthesis and Inhibitory Effects of Solidagenone Derivatives on TLR-Mediated Inflammatory Responses
Article Menu

Export Article

Open AccessFeature PaperArticle
Molecules 2018, 23(12), 3198; https://doi.org/10.3390/molecules23123198

Binding Efficacy and Thermogenic Efficiency of Pungent and Nonpungent Analogs of Capsaicin

1
School of Pharmacy, University of Wyoming, Wyoming, Laramie, WY 82071, USA
2
Department of Chemistry, University of Wyoming, Laramie, WY 82071, USA
*
Author to whom correspondence should be addressed.
Academic Editor: Pin Ju Chueh
Received: 10 November 2018 / Revised: 30 November 2018 / Accepted: 3 December 2018 / Published: 4 December 2018
(This article belongs to the Special Issue Capsaicin II)
Full-Text   |   PDF [4752 KB, uploaded 13 December 2018]   |  
  |   Review Reports

Abstract

(1) Background: Capsaicin, a chief ingredient of natural chili peppers, enhances metabolism and energy expenditure and stimulates the browning of white adipose tissue (WAT) and brown fat activation to counter diet-induced obesity. Although capsaicin and its nonpungent analogs are shown to enhance energy expenditure, their efficiency to bind to and activate their receptor—transient receptor potential vanilloid subfamily 1 (TRPV1)—to mediate thermogenic effects remains unclear. (2) Methods: We analyzed the binding efficiency of capsaicin analogs by molecular docking. We fed wild type mice a normal chow or high fat diet (± 0.01% pungent or nonpungent capsaicin analog) and isolated inguinal WAT to analyze the expression of thermogenic genes and proteins. (3) Results: Capsaicin, but not its nonpungent analogs, efficiently binds to TRPV1, prevents high fat diet-induced weight gain, and upregulates thermogenic protein expression in WAT. Molecular docking studies indicate that capsaicin exhibits the highest binding efficacy to TRPV1 because it has a hydrogen bond that anchors it to TRPV1. Capsiate, which lacks the hydrogen bond, and therefore, does not anchor to TRPV1. (4) Conclusions: Long-term activation of TRPV1 is imminent for the anti-obesity effect of capsaicin. Efforts to decrease the pungency of capsaicin will help in advancing it to mitigate obesity and metabolic dysfunction in humans. View Full-Text
Keywords: capsaicin; capsiate; capsaicin-β-d-glucopyranoside; obesity; hydrogen bond; molecular docking; thermogenesis; heat capsaicin; capsiate; capsaicin-β-d-glucopyranoside; obesity; hydrogen bond; molecular docking; thermogenesis; heat
Figures

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

Supplementary material

SciFeed

Share & Cite This Article

MDPI and ACS Style

Baskaran, P.; Covington, K.; Bennis, J.; Mohandass, A.; Lehmann, T.; Thyagarajan, B. Binding Efficacy and Thermogenic Efficiency of Pungent and Nonpungent Analogs of Capsaicin. Molecules 2018, 23, 3198.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top