Ent-kaurane glycosides and sesquiterpene lactones of the hirsutinolide type from Vernonia triflosculosa

Kos, Olha; Castro, Vı́ctor; Murillo, R.; Poveda, Luis; Merfort, Irmgard

doi:10.1016/j.phytochem.2005.07.006

Cited by 19 publications

(15 citation statements)

References 21 publications

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“…Both cases inhibited the interaction of NF-B with DNA (Valério et al, 2003), thereby resulting in a reduction in the synthesis of inflammatory mediators, such as chemotatic cytokines. Certain hirsutinolides isolated from Vernonia triflosculosa inhibited IL-8 production in in vitro studies (Kos et al, 2006). Given that IL-8 exerts a potent chemotatic action, the effect of EEVS on neutrophil infiltration might involve the inhibition of this cytokine synthesis as consequence of the presence of sesquiterpene lactone.…”

Section: Discussionmentioning

confidence: 99%

Effectiveness of Vernonia scorpioides ethanolic extract against skin inflammatory processes

Rauh

Horinouchi

Loddi

et al. 2011

Journal of Ethnopharmacology

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Section: Discussionmentioning

confidence: 99%

Effectiveness of Vernonia scorpioides ethanolic extract against skin inflammatory processes

Rauh

Horinouchi

Loddi

et al. 2011

Journal of Ethnopharmacology

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“…Sesquiterpene lactones are commonly found amongst plants of the Asteraceae family (Merfort, 2011). At least 34 sesquiterpene lactones from the Vernonia genus have been reported to possess anticancer and other biological activities including antimalarial, antibiotic, antileishmania, antioxidant, anti-inflammatory, anti-platelet and insecticidal activities (Ganjian et al, 1983; Laekeman et al, 1985; Koshimizu et al, 1994; Kos et al, 2006; Buskuhl et al, 2010; Farombi and Owoeye, 2011; Pratheeshkumar and Kuttan, 2011a; Toyang and Verpoorte, in press). Notable amongst the sesquiterpene lactones from the Vernonia genus with anticancer activity is Vernolide A (Kuo et al, 2003; Pratheeshkumar and Kuttan, 2011b, 2012).…”

Section: Discussionmentioning

confidence: 99%

Cytotoxic sesquiterpene lactones from the leaves of Vernonia guineensis Benth. (Asteraceae)

Toyang

Wabo

Ateh

et al. 2013

Journal of Ethnopharmacology

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Ethnopharmacological relevance Vernonia guineensis Benth. (Asteraceae) preparations are used in folk medicine in Cameroon to treat a number of ailments, including prostate cancer and malaria, and is used as an anthelmintic, adaptogen and antidote. The aim of this study was to continue the validation of the activity of Vernonia guineensis Benth. extracts and isolated molecules against cancer cell lines following the previous isolation of an anti-prostate cancer sugar ester from the root extract. Materials and methods Acetone extracts of Vernonia guineensis Benth. leaves were tested for activity against 10 cancer cell lines (Breast—MDA-MB-231, Breast—MCF-7, Colon—HCT-116, Leukemia—HL-60, Lung—A549, Melanoma—A375, Ovarian—OVCAR3, Pancreas—Mia-paca, Prostate—PC-3 and Prostate—DU-145). The acetone extract was subjected to bioactivity guided fractionation. Anti-proliferation and clonogenic activity of the isolated compounds were tested. The WST-1 assay was used for the anti-proliferation activity, while the standard clonogenic test was used to determine the clonogenic activity. Results The acetone extract of Vernonia guineensis Benth. demonstrated in vitro activity ranging from IC50 4–26 mg/mL against the 10 cell lines. Activity guided fractionation of this extract yielded two sesquiterpene lactones, isolated for the first time from the genus Vernonia. The compounds were characterized using spectroscopic experiments, including a combination of 1D and 2D NMR data. Vernopicrin (1) and Vernomelitensin (2) demonstrated in vitro activity against human cancer cell lines with IC50 ranging from 0.35–2.04 μM (P < 0.05) and 0.13–1.5 μM (P < 0.05), respectively, between the most and least sensitive cell lines for each compound. Vernopicrin was most active against the human melanoma (A375) cell line and least active against the lung cancer (A549) cell line, while Vernomelitensin was also most active against the human melanoma (A375) cell line and least active against the breast cancer (MCF-7) cell line. Both compounds also demonstrated anticlonogenic activity. Conclusion The cytotoxicity demonstrated by the crude extract and isolated sesquiterpenes against cancer cell lines highlights the medicinal potential of V. guineensis. The selective anti-proliferation and dose dependent anticlonogenic activities suggest that the identified sesquiterpenes could be potential antitumor agents..

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“…Kaurane diterpenes are mostly found in different plant species belonging to several families such as Asteraceae [9][10][11][12][13][14][15][16][17] (Wedelia spp., Mikania spp., Oyedaea spp., Baccharis spp., Solidago spp., Vernonia spp., Xanthium spp., Eupatorium spp., Espeletia spp. ), Annonnaceae [18][19][20] (Annonna spp., Xylopia spp., Mitrephora spp.…”

Section: Taxanes Tiglianesmentioning

confidence: 99%

“…As several species of the genus Vernonia (Asteraceae) are used in popular medicine for the treatment of some illnesses, Kos and collaborators [14] investigated the aerial parts of V. triflosculosa Kunth, and they isolated, from its ether-methanol extract, three sesquiterpene lactones and three diterpenes, two of them being the new glycosides 126 and 127. This work described, for the first time, the isolation of kaurane diterpenes in species of the genus Vernonia.…”

Section: Figure 22mentioning

confidence: 99%

Occurrence, Biological Activities and Synthesis of Kaurane Diterpenes and their Glycosides

2007

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This paper presents a review on kaurane diterpenes and their glycoside derivatives, covering aspects of their occurrence, biological activities and the synthesis of these natural products and their analogues. First, it shows and classifies diterpenes, in accordance with the already established structural criteria in the literature. Then, kaurane diterpenes are presented, focusing on their chemical structures, occurrence in the plant kingdom and their main, recently described, biological activities. Moreover, the most significant works, published between 1964 and November 2006, which describe the total synthesis or structural transformations of some kaurane diterpenes, including either semisynthetic and/or microbiological methodologies, are consisely reviewed. At this point, some general considerations on glycosides are introduced, and kaurane glycosides are presented and discussed on the basis of their toxic importance and occurrence in the plant kingdom, having focused on related aspects of their biological activities and the relationships between these activities and the structural factors of their molecules. Finally, the principal methods of glycosidation by enzymatic and chemical processes are both presented, and a few papers on the synthesis of kaurane glycosides are succinctly discussed. Molecules 2007, 12 456

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Ent-kaurane glycosides and sesquiterpene lactones of the hirsutinolide type from Vernonia triflosculosa

Cited by 19 publications

References 21 publications

Effectiveness of Vernonia scorpioides ethanolic extract against skin inflammatory processes

Effectiveness of Vernonia scorpioides ethanolic extract against skin inflammatory processes

Cytotoxic sesquiterpene lactones from the leaves of Vernonia guineensis Benth. (Asteraceae)

Occurrence, Biological Activities and Synthesis of Kaurane Diterpenes and their Glycosides

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