Scandenolide

Assessment of sesquiterpene lactones isolated from Mikania plants species for their potential efficacy against Trypanosoma cruzi and Leishmania sp.[Pubmed:28945741]

PLoS Negl Trop Dis. 2017 Sep 25;11(9):e0005929.

Four sesquiterpene lactones, mikanolide, deoxymikanolide, dihydromikanolide and Scandenolide, were isolated by a bioassay-guided fractionation of Mikania variifolia and Mikania micrantha dichloromethane extracts. Mikanolide and deoxymikanolide were the major compounds in both extracts (2.2% and 0.4% for Mikania variifolia and 21.0% and 6.4% for Mikania micrantha respectively, calculated on extract dry weight). Mikanolide, deoxymikanolide and dihydromikanolide were active against Trypanosoma cruzi epimastigotes (50% inhibitory concentrations of 0.7, 0.08 and 2.5 mug/mL, for each compound respectively). These sesquiterpene lactones were also active against the bloodstream trypomastigotes (50% inhibitory concentrations for each compound were 2.1, 1.5 and 0.3 mug/mL, respectively) and against amastigotes (50% inhibitory concentrations for each compound were 4.5, 6.3 and 8.5 mug/mL, respectively). By contrast, Scandenolide was not active on Trypanosoma cruzi. Besides, mikanolide and deoxymikanolide were also active on Leishmania braziliensis promastigotes (50% inhibitory concentrations of 5.1 and 11.5 mug/mL, respectively). The four sesquiterpene lactones were tested for their cytotoxicity on THP 1 cells. Deoxymikanolide presented the highest selectivity index for trypomastigotes (SI = 54) and amastigotes (SI = 12.5). In an in vivo model of Trypanosoma cruzi infection, deoxymikanolide was able to decrease the parasitemia and the weight loss associated to the acute phase of the parasite infection. More importantly, while 100% of control mice died by day 22 after receiving a lethal T. cruzi infection, 70% of deoxymikanolide-treated mice survived. We also observed that this compound increased TNF-alpha and IL-12 production by macrophages, which could contribute to control T. cruzi infection.

Antimicrobial constituents of the leaves of Mikania micrantha H. B. K.[Pubmed:24098556]

PLoS One. 2013 Oct 2;8(10):e76725.

BACKGROUND: To isolate plant-derived compounds with antimicrobial activity from the leaves of Mikania micrantha, to determine the compounds configuration, and to evaluate their antimicrobial activity against eight plant pathogenic fungi (Exserohilum turcicum, Colletotrichum lagenarium, Pseudoperonispora cubensis, Botrytis cirerea, Rhizoctonia solani, Phytophthora parasitica, Fusarium solani, and Pythium aphanidermatum,) and four plant pathogenic bacteria (gram negative bacteria: Ralstonia dolaanacearum, Xanthomonas oryzae pv. Oryzae, Xanthomonas Campestris pv. Vesicatoria, and Xanthomonas campestris pv. Citri), and four bacteria (gram positive bacteria: Staphyloccocus aureus, Bacillus subtilis, Micrococcus luteus, and Bacillus cereus). METHODS AND RESULTS: Antimicrobial constituents of the leaves of M. micrantha were isolated using bioactivity- guided fractionation. The antifungal activity of the isolated compounds was evaluated by the inhibit hypha growth method and inhibit spore germination method. Characterization of antibacterial activity was carried out using the minimum inhibitory concentrations (MICs) and the minimum bactericidal concentrations (MBCs). MIC and MBC were determined by the broth microdilution method. Six compounds - deoxymikanolide, Scandenolide, dihydroScandenolide, mikanolide, dihydromikanolide, and m - methoxy benzoic acid - have been isolated from leaves of Mikania micrantha H. B. K. Deoxymikanolide, Scandenolide, and dihydroScandenolide were new compounds. The result of bioassay showed that all of isolated compounds were effective against tested strains and deoxymikanolide showed the strongest activity. CONCLUSIONS AND SIGNIFICANCE: The leaves of M. micrantha may be a promising source in the search for new antimicrobial drugs due to its efficacy and the broadest range. Meanwhile, adverse impact of M. micrantha will be eliminated.

Analgesic sesquiterpene dilactone from Mikania cordata.[Pubmed:11731117]

Fitoterapia. 2001 Dec;72(8):919-21.

The crude extract of Mikania cordata (1 and 3 g/kg, p.o.) and deoxymikanolide (1) (10 mg/kg, p.o.) significantly inhibited acetic acid-induced writhing in mice. Three other sesquiterpene dilactones isolated from the same plant, namely mikanolide, dihydromikanolide and Scandenolide, did not show significant analgesic activity.

Inhibition of leukotriene and platelet activating factor synthesis in leukocytes by the sesquiterpene lactone scandenolide.[Pubmed:2168055]

Planta Med. 1990 Jun;56(3):268-70.

The sesquiterpene lactone Scandenolide, isolated from the Philippines medicinal plant Mikania cordata, at a dose of 100 microM completely inhibited whole blood chemiluminescence in response to the activators PMA and zymosan. In isolated inflammatory rat leukocytes this compound inhibited both leukotriene B4 and 5-HETE production with IC50 of 15 microM and 30 microM, respectively. The formation of the cyclooxygenase product thromboxane B2 was not inhibited in the concentration range 10 to 200 microM of Scandenolide. The formation of the potent inflammatory mediator platelet activating factor (PAF) was suppressed by microM concentrations of Scandenolide with an IC50 of less than 20 microM. The presence of a compound in M. cordata which inhibits some of the inflammatory mediators such as leukotrienes and PAF may explain at least in part some of its medicinal properties.