Phenolic compounds from the roots of Ochna schweinfurthiana and their antioxidant and antiplasmodial activities

[en] An investigation of compounds extracted from Ochna schweinfurthiana roots with ethyl acetate led to the isolation of three new compounds 4‴-methoxylophirone A (1), 4,4′,4‴–trimethoxylophirone A (2) and (4E;7Z)-3,8-dicarboxy-1-(O-β-D-glucopyranosyl-(1 → 6)-O-β-D-glucopyranosyl-2,9-dihydroxyhexeicosa-4,7-diene (3). Six known compounds were also identified, including Calodenone (4), Calodenine B (5), Lophirone A (6), Gerontoisoflavone A(7), 16α,17-dihydroxy-ent-kauran-19-oic acid (8) and 3β-O-D-glucopyranosyl-β-sitosterol (9). This report describes the first time that compounds 4-8 have been isolated from this plant, while 8 has never been identified in the genus Ochna. Some of the isolated compounds were evaluated for their antiplasmodial activity against the chloroquine-sensitive Plasmodium falciparum strain 3D7 and antioxidant activity using DPPH radical scavenging and Ferric reducing-antioxidant power (FRAP) assays. Compound 5 exhibited prominent radical scavenging and FRAP activities, while 7 had weak activity. Compound 1 showed good in vitro anti-plasmodial activity. The structures of the isolated compounds were elucidated by spectroscopic methods and comparisons with prior data in the literature. © 2016 Phytochemical Society of Europe

Disciplines :

Pharmacy, pharmacology & toxicology

Author, co-author :

Messi, A. N.; Department of Organic Chemistry, Faculty of Science, University of Yaoundé 1, P.O. Box 812, Yaoundé, Cameroon

Ngo Mbing, J.; Department of Organic Chemistry, Faculty of Science, University of Yaoundé 1, P.O. Box 812, Yaoundé, Cameroon, Centre de Recherche en Plantes Médicinales et Médecine Traditionnelle (CRPMT), I.M.P.M, Yaoundé, Cameroon

Ndongo, J. T.; Department of Chemistry, Higher Teacher Training College, University of Yaoundé 1, P. O. Box 47, Yaoundé, Cameroon

Nyegue, M. A.; Laboratory of Microbiology, Faculty of science, University of Yaoundé 1, P.O. Box 812, Yaoundé, Cameroon

Tchinda, A. T.; Centre de Recherche en Plantes Médicinales et Médecine Traditionnelle (CRPMT), I.M.P.M, Yaoundé, Cameroon

Yemeda, F. L.; Laboratory of Microbiology, Faculty of science, University of Yaoundé 1, P.O. Box 812, Yaoundé, Cameroon

Frederich, Michel ; Université de Liège > Département de pharmacie > Pharmacognosie

Pegnyemb, D. E.; Department of Organic Chemistry, Faculty of Science, University of Yaoundé 1, P.O. Box 812, Yaoundé, Cameroon

Language :

English

Title :

Phenolic compounds from the roots of Ochna schweinfurthiana and their antioxidant and antiplasmodial activities

Publication date :

2016

Journal title :

Phytochemistry Letters

ISSN :

1874-3900

eISSN :

1876-7486

Publisher :

Elsevier, Amsterdam, Netherlands

Volume :

Pages :

119-125

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 04 November 2016

Statistics

Number of views

89 (2 by ULiège)

Number of downloads

1 (1 by ULiège)

More statistics

Scopus citations^®

Scopus citations^®
without self-citations

OpenCitations

Bibliography

Abdullahi, M.I., LLiya, L., Haruna, A.K., Sule, M.I., Abdullahi, M.S., Preliminary Phytochemical and Antimicrobial investigations of leaf extracts of Ochna schweinfurthiana (Ochnaceae). Afr. J. Pharm. Pharmacol. 4 (2010), 083–086.
Abdullahi, M.I., Musa, A.M., Haruna, A.K., Sule, M.I., Abdulmalik, I.A., Abdullahi, M.S., Abimiku, A.G., LLiya, L., Anti-microbial flavonoid diglycoside from the leaves of Ochna schweinfurthiana Hoffm (Ochnaceae). Niger. J . Pharm. Sci. 10 (2011), 1–7.
Abdullahi, M.I., Musa, A.M., Haruna, A.K., Pateh, U.U., Sule, M.I., Abdullahi, M.S., Abdulmalik, M., Akinwande, Y., Abimiku, A.G., LLiya, L., Isolation and characterization of an anti-microbial biflavonoid from the chloroform-soluble fraction of methanolic root extract of Ochna schweinfurthiana (Ochnaceae). Afr. J. Pharm. Pharmacol. 8 (2014), 93–99.
Anuradha, V., Srinivas, P.V., Rao, R.R., Manjulatha, K., Purohit, M.G., Rao, J.M., Isolation and synthesis of analgesic and anti-inflammatory compounds from Ochna squarrosa L. Bioorg. Med. Chem. 74 (2006), 6820–6826.
Arbonier, M., 2000. Arbres, arbustes et liane des zones sèche d'Afrique de l'Ouest CIRAD/MNHN, Montpellier, France, p. 541.
Benzie, I.F.F., Strain, J.J., The ferric reducing ability of plasma (FRAP) as a measure of antioxidant power: the FRAP assay. J. Anal. Biochem. 239 (1999), 70–76.
Brand-williams, W., Cuvelier, M.E., Berset, C., Use of a free radical method to evaluate. Food Sci. Technol. 28 (1995), 25–30.
Burkill, H.M., 2nd ed. Families, M.-R., (eds.) The Useful Plants of West Tropical Africa, vol. 4, 1997, Royal Botanical Gardens, Kew p. 275.
Chaurasia, N., Wichtl, M., Sterols and steryl gycosides from Urtica dioica. J. Nat. Prod. 50 (1987), 881–885.
Dhooghe, L., Maregesi, S., Mincheva, I., Ferreira, D., Marais, J.P.J., Lemière, F., Matheeussen, A., Cos, P., Maes, L., Vlietinck, A., Apers, S., Pieters, L., Antiplasmodial activity of (I-3, II-3)-biflavonoids and other constituents from Ormocarpum kirkii. Phytochemistry 71 (2010), 785–791.
Feng, S., Hao, J., Xu, Z., Chen, T., Qiu, S.X.S., Polyprenylated isoflavanone and isoflavonoids from Ormosia henryi and their cytotoxicity and anti-oxidation activity. Fitoterapia 83 (2012), 161–165.
Frédérich, M., De Pauw, M.C., Prosperi, C., Strychnogucines A and B, two new antiplasmodial bisindole alkaloids from Strychnos icaja. J. Nat. Prod. 64 (2001), 12–16.
Gülçin, I., Alici, H.A., Cesur, M., Determination of in vitro antioxidant and radical scavenging activities of propofol. Chem. Pharm. Bull. 53 (2005), 281–285.
Ghogomu, R., Sondengam, B.L., Martin, M.T., Bodo, B., Lophirone A, a biflavonoid with unusual skeleton from Lophira lanceolata. Tetrahedron Lett. 28 (1987), 2967–2968.
Gulsen, T., Mehmet, O., Mehmet, E.D., Aziz, T., Antioxidant and anticholinesterase activities of five wild mushroom species with total bioactive contents. Pharm. Biol. 53 (2015), 824–830.
Hertz, W., Kulanthaivel, P., Ent-pimaranes, ent-kauranes, heliangolides and other constituent of three Helianthus species. Phytochemistry 23 (1984), 1453–1459.
Jonville, M.C., Kodja, H., Humeau, L., Screening of medicinal plants from Reunion Island for antimalarial and cytotoxic activity. J. Ethnopharmacol. 120 (2008), 382–386.
Kumar, M., Ahmad, A., Rawat, P., Khan, M.F., Rasheed, N., Gupta, P., Sathiamoorthy, B., Bhatia, G., Palit, G., Maurya, R., Antioxidant flavonoid glycosides from Evolvulus alsinoides. Fitoterapia 81 (2010), 234–242.
Likhitwitayawuid, K., Kaewamatawong, R., Ruangrungsi, N., Mono- and biflavonoids of Ochna integerrima. Biochem. Syst. Ecol. 33 (2005), 527–536.
Messanga, B.B., Tih, R.G., Kimbu, S.F., Sondengam, B.L., Martin, M.T., Bodo, B., Calodenone, a new isobiflavonoid from Ochna calodendron. J. Nat. Prod. 55 (1992), 245–248.
Messanga, B.B., Kimbu, S.F., Sondengam, B.L., Bodo, B., Two new fatty acid glucosides from the root bark of Ochna calodendron. Fitoterapia 72 (2001), 732–736.
Monks, M.R., Ferraz, A., Bordgnon, S.A., Machado, K.R., Richter, M.F., da Rocha, A.B., In vitro cytotoxicity of extracts from Brazilian Asteraceae. Pharm. Biol. 40 (2002), 494–500.
Ndongo, J.T., Issa, M.E., Messi, A.N., Ngo Mbing, J., Cuendet, M., Pegnyemb, D.E., Bochet, C.G., Cytotoxic flavonoids and other constituents from the stem bark of Ochna schweinfurthiana. Nat. Prod. Res. 17 (2015), 1684–1687.
Pegnyemb, D.E., Tih, R.G., Sondengam, B.L., Blond, A., Bodo, B., Isolation and structure elucidation of a new isoflavonoid from Ochna afzelii. Pharm. Biol. 41 (2003), 218–220.
Rao, K.V., Sreeramulu, K., Venkata, R.C., Gunasekar, D., Martin, M.T., Bodo, B., Two new biflavonoids from Ochna obtusada. J. Nat. Prod. 60 (1997), 632–634.
Soobrattee, M.A., Neergheen, V.S., Luximon-Ramma, A., Aruoma, O.I., Bahoru, T., Phenolics as potential antioxidant therapeutic agents: mechanism and actions. Mutat. Res./Fundam. Mol. Mech. Mutagenesis 579 (2005), 200–213.
Trager, W., Jensen, J.B., Human malaria parasites in continuous culture. Science 193 (1976), 673–675.
Wu, Y.C., Hung, Y.C., Chang, F.R., Cosentino, M., Wang, H.K., Lee, K.H., Identification of ent-16β, 17-dihydroxykauran-19-oic acid as an anti-HIV principle and isolation of the new diterpenoids annosquamosins A and B from Annona squamosa. J. Nat. Prod. 59 (1996), 635–637.