Anti-inflammatory norhopanes from the root bark of Fagaropsis angolensis (Engl.) H.M.Gardner

Justus Mukavi; Leonidah Kerubo Omosa; Vaderament-A Nchiozem-Ngnitedem; Justin Nyaga; Ruth Omole; Gabin Thierry M Bitchagno; Michael Spiteller

doi:10.1016/j.fitote.2020.104690

Anti-inflammatory norhopanes from the root bark of Fagaropsis angolensis (Engl.) H.M.Gardner

Fitoterapia. 2020 Oct:146:104690. doi: 10.1016/j.fitote.2020.104690. Epub 2020 Jul 22.

Authors

Justus Mukavi¹, Leonidah Kerubo Omosa², Vaderament-A Nchiozem-Ngnitedem³, Justin Nyaga⁴, Ruth Omole⁵, Gabin Thierry M Bitchagno⁶, Michael Spiteller⁷

Affiliations

¹ School of Pure and Applied Sciences, University of Embu, P. O. Box 6 - 60100, Embu, Kenya; Department of Chemistry, University of Nairobi, P. O. Box 30197 - 00100, Nairobi, Kenya.
² Department of Chemistry, University of Nairobi, P. O. Box 30197 - 00100, Nairobi, Kenya. Electronic address: leoomosa@gmail.com.
³ Department of Chemistry, University of Nairobi, P. O. Box 30197 - 00100, Nairobi, Kenya; Department of Chemistry, University of Dschang, P. O. Box 67, Dschang, Cameroon; Institute of Environmental Research (INFU), Department of Chemistry and Chemical Biology, Chair of Environmental Chemistry and Analytical Chemistry, TU Dortmund, Otto-Hahn-Straße 6, 44221 Dortmund, Germany.
⁴ School of Pure and Applied Sciences, University of Embu, P. O. Box 6 - 60100, Embu, Kenya.
⁵ School of Chemistry and Material Science, Technical University of Kenya, P. O. Box 52428 - 00200, Nairobi, Kenya.
⁶ Department of Chemistry, University of Dschang, P. O. Box 67, Dschang, Cameroon.
⁷ Institute of Environmental Research (INFU), Department of Chemistry and Chemical Biology, Chair of Environmental Chemistry and Analytical Chemistry, TU Dortmund, Otto-Hahn-Straße 6, 44221 Dortmund, Germany.

PMID: 32707156
DOI: 10.1016/j.fitote.2020.104690

Abstract

Two new norhopane derivatives namely 3β,6β,22-trihydroxy-7β,11α-di[(4-hydroxybenzoyl)oxy]-21αH-24-norhopa-4(23)-ene (1) and 3β,6β,22-trihydroxy-7β-[(4-hydroxybenzoyl)oxy]-21αH-24-norhopa-4(23)-ene (2) together with two previously reported compounds, including a norhopane, 3β,6β,11α-trihydroxy-7β-[(4-hydroxybenzoyl)oxy]-24-norhopa-4(23),17(21)-diene (3) and a norneohopane, (21αH)-24-norneohopa-4(23), 22(29)-diene-3β,6β,7β-triol 7-caffeate (4) were isolated from the root bark of Fagaropsis angolensis. Elucidation of their structures was achieved by spectroscopic (NMR, IR and UV) and spectrometric (HRESIMS) data and by comparison of these data with those of related compounds in the literature. Compounds 1-4 were evaluated for their anti-inflammatory activity by measuring the levels of cytokines, IL-1β, IL-2, GM-CSF and TNF-α in lipopolysaccharide (LPS) stimulated peripheral blood mononuclear cells (PBMC). All tested compounds decreased secretion of IL-1β and TNF-α. Compounds 2 and 4 caused significant decrease of the production of IL-2, GM-CSF and TNF-α compared to the reference drug, ibuprofen. These findings showed that the root barks of F. angolensis are rich source of norhopane derivatives and further provide a scientific rationale of using this plant in Kenyan folk medicine to relieve pain.

Keywords: Anti-inflammatory activity; Fagaropsis angolensis; Norhopanes; Rutaceae; Structure elucidation.

MeSH terms

Adult
Anti-Inflammatory Agents / isolation & purification
Anti-Inflammatory Agents / pharmacology*
Cells, Cultured
Cytokines / analysis
Humans
Kenya
Leukocytes, Mononuclear / drug effects
Male
Molecular Structure
Pentacyclic Triterpenes / isolation & purification
Pentacyclic Triterpenes / pharmacology*
Phytochemicals / isolation & purification
Phytochemicals / pharmacology
Plant Bark / chemistry
Plant Roots / chemistry
Rutaceae / chemistry*

Substances

Anti-Inflammatory Agents
Cytokines
Pentacyclic Triterpenes
Phytochemicals