The isolation of bioactive compounds from Warburgia ugandensis bark: A report of albicanyl acetate, caseamemin and β-sitosterol from Warburgia species

Abstract

Warburgia ugandensis, which is one of the indigenous species of Ethiopia, is known for its wide range of biological activities. A series of drimane sesquiterpenoids have been isolated from the stem bark of the plant. However, there is no report on the herbicidal potential of the plant against invasive weeds like Parthenium hysterophorus. In this study, the herbicidal potential of W. ugandensis against the P. hysterophorus weed was investigated. Following the bioassay protocol, muzigadial as powerful phytotoxic compound together with other eight compounds were isolated from the EtOAc soluble portion of the ethanol extract of the bark of the plant. These compounds were identified using different physical and spectroscopic methods. The isolated compounds are albicanyl acetate (35), caseamemin (36), β-sitosterol (37), muzigadial (38), cinnamolide-3β-acetate (39), ugandensidial (40), 11α-hydroxy muzigadiolide (41), polygodial (42) and 9-deoxymuzigadial (43). The first three compounds are new to the species W. ugandensis. Furthermore, two other compounds namely heptacosanol (44) and hentriacontane (45) were also isolated from this species. In summary, the purpose of this study, to the best of my knowledge, is to provide the three initially identified compounds from the plant material and provide information on the plant's potential utility in agricultural applications.

Keywords

• Warburgia ugandensis
• Albicanyl acetate
• Caseamemin
• Isolation
• Phytotoxic activity

Supporting Institution

The author would to acknowledge Addis Ababa University for providing all necessary material and chemicals for this research work.

Thanks

I would like to thank Dr. Yadessa Melaku for his guidance, supervision throughout this work and editing of the manuscript.

References

1. Arot Manguro, L.O., Ugi, I., Hermann, R., & Lemmen, P. (2003). Flavonol and drimane-type sesquiterpene glycosides of Warburgia stuhlmannii leaves. Phytochemistry, 63(4), 497–502.
2. Arot Manguro, L.O., Ugi, I., Lemmen, P., & Hermann, R. (2003). Flavonol glycosides of Warburgia ugandensis leaves. Phytochemistry, 64(4), 891–896.
3. Babu, S., & Jayaraman, S. (2020). An update on β-sitosterol: A potential herbal nutraceutical for diabetic management. Biomedicine and Pharmacotherapy, 131, 110702.
4. Barrero, A.F., Manzaneda, E.A., Altarejos, J., Salido, S., Ramos, J.M., Simmonds, M.S., & Blaney, W.M. (1995). Synthesis of biologically active drimanes and homodrimanes from (-)-sclareol. Tetrahedron, 51(27), 7435–7450.
5. Brooks, C.J.W., & Draffan, G.H. (1969). Sesquiterpenoids of wazwurgza species-i warburgin and warburgiadione. Tetrahedron, 25, 2865–2885.
6. Chang, K.C., Duh, C.Y., Chen, I.S., & Tsai, I.L. (2003). A cytotoxic butenolide, two new dolabellane diterpenoids, a chroman and a benzoquinol derivative formosan Casearia membranacea. Planta Medica, 69(7), 667–672.
7. Chaturvedula, V.S.P., & Prakash, I. (2012). Isolation of Stigmasterol and ?-Sitosterol from the dichloromethane extract of Rubus suavissimus. International Current Pharmaceutical Journal, 1(9), 239–242.
8. Dumdei, E.J., Kubanek, J., Coleman, J.E., Pika, J., Andersen, R.J., Steiner, O.R., Clardy, J. (1997). New Terpenoid Metabolites from the Skin Extracts, an Egg Mass, and Dietary Sponges of the Northeastern Pacific Dorid Nudibranch Cadlina luteomarginata. Canadian Journal of Chemistry, 75(6), 773–789.

9. Gizachew, Z. (2019). Plant derived compounds against the widespread weed: Parthenium hysterophorus [Unpublished doctoral dissertation]. Addis Ababa University.
10. Gonfa, T., Fisseha, A., & Thangamani, A. (2020). Isolation, characterization and drug-likeness analysis of bioactive compounds from stem bark of Warburgia ugandensis Sprague. Chemical Data Collections, 29, 1-15.
11. Kairu, A., Gichuki, N., Kanya, J., & Kindt, R. (2013). Disappearing medicinal plants in mt . kenya forests , kenya : a case study of east african green heart (Warburgia ugandensis sprague ). Top Class Journal of Herbal Medicine, 2(7), 159–165.
12. Kipkore, W., Wanjohi, B., Rono, H., & Kigen, G. (2014). A study of the medicinal plants used by the Marakwet Community in Kenya. Journal of Ethnobiology and Ethnomedicine, 10(1), 1-22.
13. Maroyi, A. (2014). The genus Warburgia: A review of its traditional uses and pharmacology. Pharmaceutical Biology, 52(3), 378–391.
14. Ngure, P.K., Tonui, W.K., Ingonga, J., Mutai, C., Kigondu, E., Ng’ang’a, Z., Rukunga, G., & Kimutai, A. (2009). In vitro antileishmanial activity of extracts of Warburgia ugandensis (Canellaceae), a Kenyan medicinal plant. Journal of Medicinal Plants Research, 3(2), 061–066.
15. Okello, D., & Kang, Y. (2021). Ethnopharmacological Potentials of Warburgia ugandensis on Antimicrobial Activities. Chinese Journal of Integrative Medicine, 27(8), 633–640.
16. Opiyo, S.A. (2021). Insecticidal Drimane Sesquiterpenes from Warburgia ugandensis against Maize Pests. American Journal of Chemistry, 11(4), 59–65.
17. Rabe, T., & Staden, J. van. (2000). Isolation of an antibacterial sesquiterpenoid from Warburgia salutaris. Journal of Ethnopharmacology, 73, 171–174.
18. Wube, A.A., Bucar, F., Gibbons, S., & Asres, K. (2005). Sesquiterpenes from Warburgia ugandensis and their antimycobacterial activity. Phytochemistry, 66(19), 2309–2315.