Galloylated proanthocyanidins from shea (Vitellaria paradoxa) meal have potent anthelmintic activity against Ascaris suum

A Ramsay; A R Williams; S M Thamsborg; I Mueller-Harvey

doi:10.1016/j.phytochem.2015.12.005

Galloylated proanthocyanidins from shea (Vitellaria paradoxa) meal have potent anthelmintic activity against Ascaris suum

Phytochemistry. 2016 Feb:122:146-153. doi: 10.1016/j.phytochem.2015.12.005. Epub 2015 Dec 18.

Authors

A Ramsay¹, A R Williams², S M Thamsborg², I Mueller-Harvey³

Affiliations

¹ Chemistry and Biochemistry Laboratory, School of Agriculture, Policy and Development, University of Reading, 1 Earley Gate, PO Box 236, Reading RG6 6AT, UK. Electronic address: aina.ramsay@reading.ac.uk.
² Department of Veterinary Disease Biology, Faculty of Health and Medical Sciences, University of Copenhagen, Frederiksberg, Denmark.
³ Chemistry and Biochemistry Laboratory, School of Agriculture, Policy and Development, University of Reading, 1 Earley Gate, PO Box 236, Reading RG6 6AT, UK.

PMID: 26708339
DOI: 10.1016/j.phytochem.2015.12.005

Abstract

Proanthocyanidins (PA) from shea (Vitellaria paradoxa) meal were investigated by thiolytic degradation with benzyl mercaptan and the reaction products were analysed by high performance liquid chromatography-mass spectrometry. These PA were galloylated (≈40%), contained only B-type linkages and had a high proportion of prodelphinidins (>70%). The mean degree of polymerisation was 8 (i.e. average molecular size was 2384Da) and epigallocatechin gallate (EGCg) was the major flavan-3-ol subunit in PA. Shea meal also proved to be a potentially valuable source for extracting free flavan-3-ol-O-gallates, especially EGCg (575mg/kg meal), which is known for its health and anti-parasitic benefits. Proanthocyanidins were isolated and tested for bioactivity against Ascaris suum, which is an important parasite of pigs. Migration and motility tests revealed that these PA have potent activity against this parasitic nematode.

Keywords: Anthelmintic; Ascaris suum; Galloylated; LC–MS; Proanthocyanidins; Shea meal; Thiolysis; Vitellaria paradoxa (Sapotaceae).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Anthelmintics / chemistry
Anthelmintics / isolation & purification*
Anthelmintics / pharmacology*
Ascaris suum / drug effects*
Catechin / analogs & derivatives
Chromatography, High Pressure Liquid
Ericaceae / chemistry*
Flavonoids / chemistry
Gallic Acid / analogs & derivatives*
Gallic Acid / chemistry
Gallic Acid / isolation & purification
Gallic Acid / pharmacology*
Molecular Structure
Proanthocyanidins / chemistry
Proanthocyanidins / isolation & purification*
Proanthocyanidins / pharmacology*
Seeds / chemistry
Swine

Substances

Anthelmintics
Flavonoids
Proanthocyanidins
flavan-3-ol
Gallic Acid
Catechin
epigallocatechin gallate