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Molecules 2018, 23(2), 506; https://doi.org/10.3390/molecules23020506

Triterpene Acids from Frankincense and Semi-Synthetic Derivatives That Inhibit 5-Lipoxygenase and Cathepsin G

1
Department of Pharmaceutical/Medicinal Chemistry, Institute of Pharmacy, Friedrich-Schiller-University, Philosophenweg 14, D-07743 Jena, Germany
2
Department of Pharmaceutical Analytics, Pharmaceutical Institute, Eberhard Karls University, Auf der Morgenstelle 8, D-72076 Tuebingen, Germany
3
Institute of Pharmaceutical Chemistry, University of Frankfurt, Max-von-Laue-Str. 9, D-60438 Frankfurt, Germany
4
Department of Pharmaceutical Technology, Institute of Pharmacy, Friedrich-Schiller-University, Otto-Schott-Strasse 41, D-07745 Jena, Germany
5
Organic Chemistry II, Saarland University, Campus C4.2, D-66123 Saarbruecken, Germany
*
Author to whom correspondence should be addressed.
Received: 2 February 2018 / Revised: 21 February 2018 / Accepted: 21 February 2018 / Published: 24 February 2018
(This article belongs to the Special Issue Plant Derived Natural Products and Age Related Diseases)
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Abstract

Age-related diseases, such as osteoarthritis, Alzheimer’s disease, diabetes, and cardiovascular disease, are often associated with chronic unresolved inflammation. Neutrophils play central roles in this process by releasing tissue-degenerative proteases, such as cathepsin G, as well as pro-inflammatory leukotrienes produced by the 5-lipoxygenase (5-LO) pathway. Boswellic acids (BAs) are pentacyclic triterpene acids contained in the gum resin of the anti-inflammatory remedy frankincense that target cathepsin G and 5-LO in neutrophils, and might thus represent suitable leads for intervention with age-associated diseases that have a chronic inflammatory component. Here, we investigated whether, in addition to BAs, other triterpene acids from frankincense interfere with 5-LO and cathepsin G. We provide a comprehensive analysis of 17 natural tetra- or pentacyclic triterpene acids for suppression of 5-LO product synthesis in human neutrophils. These triterpene acids were also investigated for their direct interference with 5-LO and cathepsin G in cell-free assays. Furthermore, our studies were expanded to 10 semi-synthetic BA derivatives. Our data reveal that besides BAs, several tetra- and pentacyclic triterpene acids are effective or even superior inhibitors of 5-LO product formation in human neutrophils, and in parallel, inhibit cathepsin G. Their beneficial target profile may qualify triterpene acids as anti-inflammatory natural products and pharmacological leads for intervention with diseases related to aging. View Full-Text
Keywords: triterpene acid; 5-lipoxygenase; cathepsin; frankincense; boswellic acid; microsomal prostaglandin E2 synthase triterpene acid; 5-lipoxygenase; cathepsin; frankincense; boswellic acid; microsomal prostaglandin E2 synthase
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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).
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Koeberle, A.; Henkel, A.; Verhoff, M.; Tausch, L.; König, S.; Fischer, D.; Kather, N.; Seitz, S.; Paul, M.; Jauch, J.; Werz, O. Triterpene Acids from Frankincense and Semi-Synthetic Derivatives That Inhibit 5-Lipoxygenase and Cathepsin G. Molecules 2018, 23, 506.

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