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Flavonoids from Stem Bark of Artocarpus altilis (Parkinson ex F.A.Zorn) Fosberg

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Abstract

Purpose

The growing antimicrobial resistance to available chemotherapies has been generating concerns globally. Tropical rain forest of Nigeria is rich in medicinal plants used by traditional healers to combat various human pathologies. This study investigated the stem bark of Artocarpus altilis for antibacterial compounds.

Methods

Hydroalcoholic stem bark extract of A. altilis (Parkinson ex F.A.Zorn) Fosberg was obtained by maceration and subsequently partitioned. The EtOAc fraction was repeatedly fractionated and purified using column chromatography, size exclusion chromatography and recrystallization methods to afford compounds 1–5, which were identified by extensive analysis of 1H, 13C, DEPT, APT, COSY, HSQC, HMBC, and HRESIMS spectra. Broth microdilution assay was used to determine the antibacterial activity of 1–5.

Results

Four flavonoids: An isomer of Artonine E (1) and Artonine E (4), 9-(3,3-dimethylpyranyl)-5,6-dihydro-2,3,4,8 tetrahydroxy-11-(3-methylbut-2-enyl)-5-(1-propen-2-yl) benzo [c] xanthen-7-one (2), 5-hydroxy-8,8-dimethyl-3-(3-methylbut-2-enyl)-2-(3,4,5-trihydroxyphenyl) pyrano [6,7-c]-4H-chromen-4-one (3) and one unprenylated flavonoid: 3,5,7-trihydroxyl-2-(2,4-dihydroxylphenyl)-4H-chromene-4-one (5) are hereby reported. The minimum inhibitory concentration of compounds ranged from 3.91–62.5 µg/mL.

Conclusion

This study provides insights into the antibacterial chemical components of A. altilis stem bark, thereby contributing to the chemistry of the plant. It also justifies the ethnomedicinal use of the plant in the treatment microbial infection in wounds in Nigeria.

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Abbreviations

DCM:

Dichloromethane

EtOAc:

Ethyl acetate

TMPs:

Traditional medical practitioners

r.t.:

Room temperature

NCIB:

National collection of industrial bacteria

DBE:

Double bond equivalence

HRESIMS:

High resolution electrospray ionisation mass spectrometry

MHA:

Mueller Hinton agar

NA:

Nutrient Agar

NB:

Nutrient broth

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Acknowledgements

The authors are grateful to the NMR and MS Units of the Central Analytical Facilities of the Stellenbosch University, South Africa for recording the NMR and HRESIMS spectra.

Funding

This research did not receive any funding or grant from funding agencies in public, private, commercial or not-for-profit sectors.

Author information

Authors and Affiliations

  1. Drug Research and Production Unit, Faculty of Pharmacy, Obafemi Awolowo University, Ile-Ife, 220005, Nigeria

    Seun B. Ogundele, Felix O. Olorunmola & Joseph M. Agbedahunsi

  2. Department of Chemical and Physical Sciences, Faculty of Natural Sciences, Walter Sisulu University, Mthatha, 5117, South Africa

    Ayodeji O. Oriola & Adebola O. Oyedeji

Authors
  1. Seun B. Ogundele
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  2. Ayodeji O. Oriola
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  3. Adebola O. Oyedeji
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  4. Felix O. Olorunmola
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  5. Joseph M. Agbedahunsi
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Contributions

Conceptualisation, Study design, and Administration of Research (JMA), Data curation, Methodology, Investigation of Experimental work, Interpretation and Analysis of Results and Writing the original draft (SBO), Supervision and Resources (AOO & FOO), NMR and MS Instrumentation (AOO). All authors approved the final manuscript draft.

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Correspondence to Seun B. Ogundele.

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Ogundele, S.B., Oriola, A.O., Oyedeji, A.O. et al. Flavonoids from Stem Bark of Artocarpus altilis (Parkinson ex F.A.Zorn) Fosberg. Chemistry Africa 5, 1921–1935 (2022). https://doi.org/10.1007/s42250-022-00489-z

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