Polyoxygenated Stigmastane-Type Steroids from Vernonia kotschyana Sch. Bip. ex Walp. and Their Chemophenetic Significance

Author:

Tseme Wandji Nadine123,Bitchagno Gabin Thierry M.34ORCID,Mawabo Kamga Isabelle5,Tchamgoue Joseph12ORCID,Nkenfou Celine Nguefeu56ORCID,Lenta Bruno Ndjakou1,Sewald Norbert3ORCID,Kouam Simeon Fogue1ORCID

Affiliation:

1. Department of Chemistry, Higher Teacher Training College, University of Yaounde I, Yaounde P.O. Box 47, Cameroon

2. Department of Organic Chemistry, Faculty of Science, University of Yaounde I, Yaounde P.O. Box 812, Cameroon

3. Organic and Bioorganic Chemistry, Faculty of Chemistry, Bielefeld University, D-33501 Bielefeld, Germany

4. Department of Chemistry, University of Dschang, Dschang P.O. Box 67, Cameroon

5. Department of Biology, Higher Teacher Training College, University of Yaounde I, Yaounde P.O. Box 47, Cameroon

6. Molecular Biology Center, Yaounde P.O. Box 14495, Cameroon

Abstract

Four polyoxygenated stigmastanes (1–4) alongside known analogues (7–8) and flavonoids (5–6) were isolated from a dichloromethane/methanol (1:1, v/v) extract of the whole plant of Vernonia kotschyana Sch. Bip. ex Walp. (Asteraceae). Their structures were determined by means of spectroscopic and spectrometric analysis. The relative stereochemistry of the new compounds was established and confirmed via biosynthesis evidence and cyclization of 1 under acidic conditions. A plausible biosynthetic pathway to the new compounds and the chemophenetic significance of the isolated constituents were also discussed. The crude extract, fractions, and compounds (1–3) were assessed for their antibacterial activity against five highly prevalent bacterial strains. The fractions and compounds showed low to moderate activity with minimal inhibitory concentrations (MICs) > 125 µg/mL.

Funder

German Academic Exchange Service

Alexander von Humboldt Foundation

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

Reference33 articles.

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3. Stigmastane derivatives from the roots of Vernonia guineensis and their antimicrobial activity;Donfack;Phytochem. Lett.,2012

4. Bitter principle and a related steroid glucoside from V. amygdalina, a possible medicinal plant for wild chimpanzees;Ohigashi;Chem. Biol. Technol. Agric.,1991

5. Antischistosomal activities of sesquiterpene lactones and steroid glucosides from Vernonia amygdalina, possibly used by wild chimpanzees against parasite-related diseases;Jisaka;Biosci. Biotechnol. Biochem.,1992

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