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. Author manuscript; available in PMC: 2019 Mar 27.
Published in final edited form as: Nat Prod Res. 2018 Feb 19;33(2):287–291. doi: 10.1080/14786419.2018.1440225

Chemical and biological studies on Bridelia ferruginea grown in Nigeria

Michael Afolayan a,b,c, Radhakrishnan Srivedavyasasri a, Olayinka T Asekun b, Oluwole B Familoni b, Samir A Ross a,d
PMCID: PMC6098982  NIHMSID: NIHMS957797  PMID: 29457749

Abstract

Phytochemical investigation of the methanolic extract of dried leaves of Bridelia ferruginea led to the isolation and identification of fourteen compounds (1–14): compound 1 [mixture of palmitic, stearic and oleic acids], stearyl monoester of 2-O-β-ᴅ-glucosylglycerol (2), 6β-hydroxy-(20R)-24-ethylcholest-4-en-3-one (3a), 6β-hydroxy-(20R)-24-ethylcholest-4,22-dien-3-one (3b), lutein (4), vomifoliol (5), corilagin (6), kaempferide-3-O-β-ᴅ-glucoside (7), myricetin (8), isomericitrin (9), isoquercetin (10), myricitrin (11), quercitrin (12), rutin (13), and β-sitosterol glucoside (14). The total extract exhibited moderate activity towards CB2 receptor and 90% inhibition against leishmanial pathogen Trypanosoma brucei. Compound 4 exhibited 73% displacement in CB2 receptor with IC50 56.47 μM, and 93% inhibition towards T. brucei with IC50 4.16 μM. Compound 11 showed 99% inhibition towards Escherichia coli with IC50 1.123 μM.

Keywords: Bridelia ferruginea, flavonoids, cannabinoid receptor, antileishmanial, antibacterial

Graphical abstract

graphic file with name nihms957797u1.jpg

1. Introduction

Bridelia ferruginea (Euphorbiaceae) commonly found in Savannah regions, is usually a gnarled shrub which sometimes reaches the size of a tree. This plant in Southern Nigeria is considered as sacred and is featured in certain rituals and ceremonies. It is used as ethnomedicine for treatment of various ailments in many parts of Africa. The bark, roots, fruits and leaves decoctions are used mainly as purgative and a vermifuge (Cimanga et al. 1999; Okwu and Ukanwa 2010; Mbah et al. 2012). Previous biological studies showed that crude extracts of this plant has capability to lower the fasting blood sugar levels of rats and humans, also used to cure piles, diarrhea, female sterility, rheumatic pains (Mostafa et al. 2006; Pettit et al. 2016), intestinal and bladder disorders, skin diseases, dysentery, and elephantiasis of the scrotum (Bruyne et al. 1997). Other reported activities of the bark extract include antineuroinflammatory (Olajide et al. 2012), typanocidal (Ekanem et al. 2008), antioxidant (Oloyede and Babalola 2012), antimicrobial (Adeoye et al. 1988), antimolluscidal, anti-inflammatory (Olajide et al. 1999), analgesic and antipyretic properties (Akuodor et al. 2011). B. ferruginea plant is reported to contain tannins and flavonoids (Oliver-Bever 1986; Addae-Mensah and Munenge 1989; Bruyne et al. 1997; Cimanga et al. 1999, 2001; Rashid et al. 2000; Okwu and Ukanwa 2010). Based on traditional medicinal uses, previous reported activities and our crude extract showed moderate activity towards CB2 receptor and potent against leishmanial pathogen encouraged to study the cannabinoid, opioid receptors and antileishmanial activities for the compounds isolated from B. ferruginea.

2. Results and discussion

Phytochemical investigation of the methanolic extract of dried leaves of B. ferruginea led to the isolation of fourteen compounds (1–14, Figure 1). The isolated compounds were identified by their NMR, MS and GC-MS spectral data analyses. Compound 1 (oily mass), further analysis by GC MS was identified to be a mixture of three fatty acids [palmitic (53.5%), stearic (16.2%) and oleic (14.3%)]. A fatty acid monoester of 2-O-β-ᴅ-glucosylglycerol (2) (Colombo et al. 1996), the fatty acid was identified by using GC-MS to be stearic acid. Compound 3 was found to be a mixture of 6β-hydroxy-(20R)-24-ethylcholest-4-en-3-one, (3a), as major and 6β-hydroxy-(20R)-24-ethylcholest-4,22-dien-3-one (3b) as minor (Kontiza et al. 2006), lutein (4) (Moss 1976), vomifoliol (5) (Hammami et al. 2004), corilagin (6) (Moreira et al. 2013), kaempferide-3-O-β-ᴅ-glucoside (7) (Lee et al. 2008), myricetin (8) (Zhang et al. 2011), isomyricetin (9), isoquercetin (10) (Ren et al. 2012), myricitrin (11) (Aderogba et al. 2013), quercitrin (12), rutin (13) (Zhang et al. 2014), β-sitosterol glucoside (14).

Figure 1.

Figure 1

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Compounds isolated from B. ferruginea.

The total extract exhibited moderate activity towards CB2 receptor (48% displacement) and 90% inhibition towards Trypanosoma brucei with IC50 8.48 μM. Lutein (4) exhibited 73% displacement in CB2 receptor with IC50 56.47 μM (Figure 2) and moderate activity in Delta and Mu opioid receptors (65% and 49% displacement, respectively). Also 4 showed 93% activity against T. brucei (IC50 4.16 μM) and moderate activity towards Leishmania donovani (48%, IC50 9.3 μM). Myricitrin (11) showed 99% inhibition towards Escherichia coli Pinh with IC50 1.123 μM.

Figure 2.

Figure 2

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Binding summary of Lutein (4) towards CB2 receptor.

3. Conclusion

The methanolic extract of dried leaves of B. ferruginea showed 90% activity towards T. brucei and moderate activity (48% displacement) towards CB2 receptor. Bioassay guided fractionation and purification yielded fourteen compounds (1–14). Compounds 2–7, 9, and 12 were reported for the first time from this plant. Lutein (4) exhibited strong activity towards CB2 receptor and leishmanial pathogen T. brucei. Myricitrin (11) exhibited potent activity towards E. coli Pinh.

Supplementary Material

SI

Acknowledgments

The project was supported by Sheda Science and Technology Complex, Nigeria and National Center for Natural Product Research, USA. We acknowledge Award number P20GM104932 from the National Institute of General Medical Sciences for bioassay results.

Funding

This work was supported by the National Institute of General Medical Sciences [grant number P20GM104932].

Footnotes

Disclosure statement

No potential conflict of interest was reported by the authors.

ORCID

Radhakrishnan SrivedavyasasriiDhttp://orcid.org/0000-0001-9495-7169

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Supplementary Materials

SI
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