Protease-inhibiting, molecular modeling and antimicrobial activities of extracts and constituents from Helichrysum foetidum and Helichrysum mechowianum (compositae)

Fanny-Aimée Essombe Malolo; Achille Bissoue Nouga; Antoine Kakam; Katrin Franke; Lidwine Ngah; Otavio Flausino Jr; Emmanuel Mpondo Mpondo; Fidele Ntie-Kang; Jean Claude Ndom; Vanderlan da Silva Bolzani; Ludger Wessjohann

doi:10.1186/s13065-015-0108-1

Protease-inhibiting, molecular modeling and antimicrobial activities of extracts and constituents from Helichrysum foetidum and Helichrysum mechowianum (compositae)

Chem Cent J. 2015 May 30:9:32. doi: 10.1186/s13065-015-0108-1. eCollection 2015.

Affiliations

¹ Department of Pharmacy, University of Douala, Douala, P.O. Box 812, Cameroon.
² Department of Chemistry, University of Douala, Douala, P.O. Box 567 24157, Cameroon.
³ Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120 Halle (Saale), Germany.
⁴ Química, Departamento de Química Orgânica, Núcleo de Bioensaio, Biossíntese e Ecofisiologia de Produtos Naturais-NuBBE, Universidade Estadual Paulista (UNESP) Instituto de Rua Prof. Francisco Degni s/n, Araraquara, São Paulo 14.800-900 Brazil.
⁵ Chemical and Bioactivity Information Centre, Department of Chemistry, University of Buea, P. O. Box 63, Buea, Cameroon.

Abstract

Background: Helichrysum species are used extensively for stress-related ailments and as dressings for wounds normally encountered in circumcision rites, bruises, cuts and sores. It has been reported that Helichysum species are used to relief abdominal pain, heart burn, cough, cold, wounds, female sterility, menstrual pain.

Results: From the extracts of Helichrysum foetidum (L.) Moench, six known compounds were isolated and identified. They were 7, 4'-dihydroxy-5-methoxy-flavanone (1), 6'-methoxy-2',4, 4'-trihydroxychalcone (2), 6'-methoxy-2',4-dihydroxychalcone -4'-O-β-D-glucoside (3), apigenin (4), apigenin-7-O-β-D-glucoside (5), kaur-16-en-18-oic acid (6) while two known compounds 3,5,7-trihydroxy-8-methoxyflavone (12), 4,5-dicaffeoyl quinic acid (13) together with a mixture of phytosterol were isolated from the methanol extract of Helichrysum mechowianum Klatt. All the compounds were characterized by spectroscopic and mass spectrometric methods, and by comparison with literature data. Both extracts and all the isolates were screened for the protease inhibition, antibacterial and antifungal activities. In addition, the phytochemical profiles of both species were investigated by ESI-MS experiments.

Conclusions: These results showed that the protease inhibition assay of H. foetidum could be mainly attributed to the constituents of flavonoids glycosides (3, 5) while the compound (13) from H. mechowianum contributes to the stomach protecting effects. In addition, among the antibacterial and antifungal activities of all the isolates, compound (6) was found to possess a potent inhibitor effect against the tested microorganisms. The heterogeneity of the genus is also reflected in its phytochemical diversity. The differential bioactivities and determined constituents support the traditional use of the species. Molecular modelling was carried out by computing selected descriptors related to drug absorption, distribution, metabolism, excretion and toxicity (ADMET). Graphical abstractCompounds isolated from Helichrysum species (Compositae).

Keywords: Antimicrobial; Compositae; ESI-MS; Helichrysum foetidum; Helichysum mechowianum; Protease inhibition assay.