Leishmanicidal activity of onopordopicrin isolated from the leaves of Brachylaena discolor doi.org/10.26538/tjnpr/v2i7.5

Article Sidebar

PDF DOI
Published: Jul 1, 2018
Keywords:
Asteraceae,, Brachylaena discolor,, Onopordopicrin,, Germanocronolides,, Antileishmanial activity.

Main Article Content

Julião A. Monjane
Chemistry Department, Eduardo Mondlane University, P.O. Box 257, Maputo, Mozambique
Diandra Capusiri
Instituto de Investigaciones Fármaco Bioquímicos, San Andrés University, La Paz, Bolivia.
Alberto Giménez
Instituto de Investigaciones Fármaco Bioquímicos, San Andrés University, La Paz, Bolivia.
Olov Sterner
Centre for Analysis and Synthesis, Lund University, P.O. Box 22100, Lund, Sweden.

Abstract

Brachylaena discolor (Asteraceae) is a medicinal plant used in Mozambique to treat stomachache, tuberculosis, and diabetes. To discover new lead compounds with leishmanicidal activity, a methanolic extract of the leaves of this plant was investigated. Through fractionation, employing several chromatographic methods, two sesquiterpene lactones onopordopicrin (1) and its
germacronolide epoxide derivative (2), together with other ten know phenolic compounds derivatives (3-12) were isolated. The structures of the isolated compounds were determined by spectroscopic methods, mainly 1D and 2D NMR experiments, as well as by comparing their spectroscopic data as reported in the literature. Compounds 1 and 2 were evaluated for their leishmanicidal activity using the Colorimetric method-XXT. Compound 1 showed a significant leishmanicidal activity against Leishmania amazonensis and L. braziliensis (IC50 values 39.6 and 27.9 μM, respectively) as compared to miltefosine (12.5 and 12.0 μM, respectively), a currently
used agent to treat leishmaniosis. While compound 2 was inactive against both stains tested with IC50 values >50μM compared with the same agent. Compounds 3-12 were not assayed for leishmanicidal activity. This is the first study reporting the above-mentioned activity of onopordopicrin (1). The results could suggest that compound 1 is a promising lead structure to treat leishmaniosis.

Downloads

Download data is not yet available.

Article Details

How to Cite
A. Monjane, J., Capusiri, D., Giménez, A., & Sterner, O. (2018). Leishmanicidal activity of onopordopicrin isolated from the leaves of Brachylaena discolor: doi.org/10.26538/tjnpr/v2i7.5. Tropical Journal of Natural Product Research (TJNPR), 2(7), 328-331. https://tjnpr.org/index.php/home/article/view/709
Issue
Vol. 2 No. 7 (2018): Tropical Journal of Natural Product Research
Section
Articles
Creative Commons License

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

How to Cite

A. Monjane, J., Capusiri, D., Giménez, A., & Sterner, O. (2018). Leishmanicidal activity of onopordopicrin isolated from the leaves of Brachylaena discolor: doi.org/10.26538/tjnpr/v2i7.5. Tropical Journal of Natural Product Research (TJNPR), 2(7), 328-331. https://tjnpr.org/index.php/home/article/view/709

References

Bandeira SO, Gaspar F, Pagula FP. Ethnobotany and healthcare in Mozambique. Pharm Biol. 2001; 39(1):70–73.

Bruschi P, Morganti M, Mancini M, Signorini MA. Traditional Healers and Laypeople: A qualitative and quantitative approach to local knowledge on medicinal plants in Muda (Mozambique). J Ethnopharmacol. 2011; 138(2):543–563.

Hostettmann, K; Marston, A; Ndjoko, K; Wolfender, JL. The potential of African plants as a source of drugs. Curr Org Chem. 2000; 4(10):973–1010.

Maroyi A. Traditional use of medicinal plants in SouthCentral Zimbabwe: Review and perspectives. J Ethnobiol Ethnomed. 2013; 9(1):31–48.

Bohlmann F and Zdero C. Sesqueterpene lactones from Brachylaena species. Phytochemistry 1982; 21(3):647–651.

Zdero, C; Bohlmann, F. Sesqueterpene lactones from the genus Brachylaena. Phytochemistry 1987, 26 (9), 2597–2601.

Zdero, C; Bohlmann, F; Wasshausen, DC. Guaianolides from Brachylaena species. Phytochemistry 1991, 30 (11), 3810–3811.

Chaturvedula, VSP; Schilling, JK; Miller, JS; Andriantsiferana, R; Rasamison, VE; Kingston, DGI. Two new triterpene esters from the twigs of Brachylaena ramiflora from the Madagascar rainforest. J. Nat. Prod. 2002, 65 (8), 1222–1224.

Vieira, PC; Himejima, M; Kubo, I. Sesquiterpenoids from Brachylaena hutchisii. J. Nat. Prod. 1991, 45 (2), 416–420.

Beentje, HT. The genus Brachylaena (Compositae: Mutisieae). Kew Bull. 2000, 55 (1), 1–41.

Deutschländer, MS; Lall, N; van de Venter, M. Plant species used in the treatment of diabetes by South African traditional healers: An Inventory. Pharm. Biol. 2009, 47 (4), 348–365.

Jansen, PCM; Mendes, O. Plantas medicinais - Seu uso tradicional em Moçambique, T4 ed.; Partido, I. do, Ed.; Ministério da Saúde Gabinete de estudos de Medicina Tradicional: Maputo, Mozambique, 1991.

Mellem, J. Effect of the methanolic extract of Brachylaena discolor in streptozotocin-induced diabetic rat model. African J. Pharm. Pharmacol. 2013, 7 (12), 636–642.

Lonergan, G; Routsi, E; Georgiardis, T; Agelis, G; Hondrelis, J; Matsoukas, J; Larsen, LK; Caplan, FR. Isolation, NMR studies, and biological activities of onopordopicrin from Centaurea sonchzfola. J. Nat. Prod. 1992, 55 (5), 225–228.

Bach, SM; Fortuna, MA; Attarian, R; Trimarco, JT; Catalán,CAN; Av-Gay, Y; Bach, H. Antibacterial and cytotoxic activities of the sesquiterpene lactones cnicin and onopordopicrin. Nat. Prod. Comm. 2011, 6 (11), 163–166.

Formisano, C; Sanna, C; Ballero, M; Chianese, G; Sirignano, C; Rigano, D; Millán, E; Muñoz, E; Taglialatela-Scafati, O. Anti-inflmmatory sesquiterpene lactones from Onopordum illyricum L . ( Asteraceae ), an Italian Medicinal Plant. Fitoterapia 2017, 116, 61–65.

Onguéné, A; Ntie-Kang, P; Lifongo, F. The potential of antimalarial compounds derived from African medicinal plants, Part I: A pharmacological evaluation of alkaloids and terpenoids. Malar. J. 2013, 12 (1), 4–25.

Novello, CR; Teresinha, I; Schuquel, A; Sakuragui, CM; Luftmann, H; Ueda-Nakamura, T; Nakamura, CV; Mello, JCP. Evaluation of the antiproliferative activity of the leaves from ArctiumlLappa by a bioassay-guided fractionation. Molecules 2012, 17, 1852–1859.

Zimmermann, S; Fouché, G; De Mieri, M; Yoshimoto, Y; Usuki, T; Nthambeleni, R; Parkinson, CJ; Van Der Westhuyzen, C; Kaiser, M; Hamburger, M. Structure-Activity Relationship Study of sesquiterpene lactones and their semisynthetic amino derivatives as potential antitrypanosomal products. Molecules 2014, 19 (3), 3523–3538.

Capusiri, ES; Pinell, GR; Huallpara, JCT; Turba, AG. Colorimetric method - XTT: As a tool for high performance evaluation of substances with leishmanicidal activity. Biofabro 2008, 16, 21–27.

Park, CH; Kim, KH; Lee, IK; Lee, SY; Choi, SU; Lee, JH; Lee, KR. Phenolic onstituents of Acorus gramineus. Arch. Pharm. Res. 2011, 34 (8), 1289–1296.

Lee, Y-M; Kwon, M-J; Kim, J-K; Suh, H; Choi, J-S; Song, YO. Isolation and identification of active principle in Chinese cabage Kimchi responsable for antioxidant effect. Korean J. Food Sci. Technol. 2004, 36 (1), 129–133.

Jin, MR; Xu, H; Duan, CH; Chou, GX. Two new flavones from Salvia plebeia. Nat. Prod. Res. 2015, 29 (14), 1315–1322.

Wollenweber, E; Dörr, M; Roitman, JN; Schilling, E. External flavonoids of three species of Viguiera (Asteraceae). Z. Naturforsch. 1995, 50c, 588–590.

Park, S; Cui, X; Ahn, D; Lee, EB; Cha, DS; Jeon, H; Zee, OP; Kim, Y; Kim, DK. Anti-oxidative activities of 3’-hydroxygenkwanin from the flower buds of Daphne genkwa. Nat. Prod. Sci. 2014, 20 (2), 80–85.

Miyazawa, M; Hisama, M. Antimutagenic activity of flavonoids from Chrysanthemum morifolium. Biosci. Biotechnol. Biochem. 2003, 67 (10), 2091–2099.

Al-Youssef, H; Hassan, WHB. Phytochemical and biological studies of the aerial parts of Carissa edulis growing in Saudi Arabia. Biomed. Pharmacol. J. 2012, 5 (1), 9–18.

Kunert, O; Haslinger, E; Schmid, MG; Reiner, J; Bucar, F; Mulatu, E; Abebe, D; Debella, A. Three saponins, a steroid, and a flavanolglycoside from Achyrantes aspera. Monatshefte für Chemie 2000, 131 (2), 195–204.

Wei, X; Huang, H; Wu, P; Cao, H; Ye, W. Phenolic constituents from Mikania micrantha. Biochem. Syst. Ecol.2004, 32 (11), 1091–1096.

Güvenalp, Z; Demirezer, LO. Flavonol glycosides from Asperula arvensis L. Turk. J. Chem. 2005, 29, 163–169.

Chadwick, M; Trewin, H; Gawthrop, F; Wagstaff, C. Sesquiterpenoids lactones: Benefits to plants and people. Int. J. Mol. Sci. 2013, 14 (6), 12780–12805.

Chan-Bacab, MJ; Peña-rodríguez, LM. Plant natural products with leishmanicidal activity. Nat. Prod. Rep. 2001, 18, 674–688.

Fournet, A; Muñoz, V; Roblot, F; Hocquemiller, R. Antiprotozoal activity of dehydrozaluzanin C, a sesquiterpene lactone isolated from Munnozia maronii (Asteraceae). Phytother. Res. 1993, 7, 111–115.

Sinisi, A; Millán, E; Abay, SM; Habluetzel, A; Appendino, G; Muñoz, E; Taglialatela-Scafati, O. Poly-electrophilic sesquiterpene lactones from Vernonia amygdalina: New members and differences in their mechanism of thiol trapping and in bioactivity. J. Nat. Prod. 2015, 24, 1618–1623.

Majd M, Liu Q, Karimzadeh G, Malboobi MA, Beekwilder J, Cankar K, Vos R, Todorović S, Simonović A, Bouwmeester H. Biosynthesis and localization of parthenolide in glandular trichomes of feverfew (Tanacetum Parthenium L. Schulz

Bip.). Phytochemistry 2011; 72:1739–1750