Absolute Configuration of Two Eudesmane Derivatives from Verbesina turbacensis H.B.K.

Bruno-Colmenárez, Julia; Amaro-Luis, Juan M.; Ramírez, Irama; Delgado-Méndez, Paulino; Delgado, Graciela Díaz de

doi:10.1007/s10870-009-9610-4

Cited by 2 publications

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“…The absolute configuration of the remaining compounds was assigned tentatively based on biogenetic considerations and on the assumption that they possess the same absolute configuration at C-10. This was also in agreement with the reported absolute configuration of 2 , which had been established by X-ray single-crystal analysis …”

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confidence: 92%

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Eudesmane Sesquiterpenes from Verbesina lanata with Inhibitory Activity against Grapevine Downy Mildew

et al. 2017

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An in-house library of more than 3000 extracts of plant and fungal origin was screened against some major plant pathogens. As one of the hits, an ethyl acetate extract from inflorescences of Verbesina lanata showed significant inhibitory activity in vitro against grapevine downy mildew (Plasmopara viticola), with a MIC value of 35 μg/mL. An emulsifiable concentrate formulation with 50 mg/g of the extract was developed for in vivo evaluation. A suspension of the formulation containing 1 mg/mL of extract lowered leaf surface infection of grapevine seedling by 82% compared to the nontreated control. With the aid of HPLC-based activity profiling, the antifungal activity was correlated with a series of lipophilic compounds. Preparative isolation by a combination of chromatographic techniques afforded 16 eudesmane sesquiterpenes including eight new congeners. Nine compounds were obtained in sufficient quantities to be tested in vitro and were found to inhibit the zoospore activity of P. viticola with MIC values ranging from 4 to 50 μg/mL. The two major compounds, 6β-cinnamoyloxy-4β,9β,15-trihydroxyeudesmane (9) and 6β-cinnamoyloxy-1β,15-dihydroxyeudesm-4-en-3-one (13), showed MIC values of 5 and 31 μg/mL, respectively.

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Section: Resultssupporting

confidence: 92%

“…This was also in agreement with the reported absolute configuration of 2, which had been established by X-ray single-crystal analysis. 29 Antifungal Activity. The crude plant extract showed a minimal inhibitory concentration (MIC 100 ) against P. viticola of 35.4 μg/mL, as determined in two independent experiments (Table 3).…”

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Eudesmane Sesquiterpenes from Verbesina lanata with Inhibitory Activity against Grapevine Downy Mildew

et al. 2017

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Phytochemical Investigation of Verbesina Turbacensis Kunth: Trypanosome Cysteine Protease Inhibition by (–)-Bornyl Esters

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Natural Product Communications

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The bark and leaf essential oils of Verbesina turbacensis were obtained by hydrodistillation and analyzed by GC-MS. The bark oil of the plant was composed mainly of monoterpene hydrocarbons (83.5-90.4%), predominately α-pinene, while the leaf oil was composed mainly of sesquiterpene hydrocarbons, dominated by germacrene-D (29.1-36.9%), and δ-elemene (21.7-22.1%). Three bornyl hydroxycinnamic esters isolated from the acetone bark extract were found to inhibit the cysteine protease, rhodesain. Molecular docking analysis to probe the inhibitory interactions of the esters was also carried out.

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Absolute Configuration of Two Eudesmane Derivatives from Verbesina turbacensis H.B.K.

Cited by 2 publications

References 6 publications

Eudesmane Sesquiterpenes from Verbesina lanata with Inhibitory Activity against Grapevine Downy Mildew

Eudesmane Sesquiterpenes from Verbesina lanata with Inhibitory Activity against Grapevine Downy Mildew

Phytochemical Investigation of Verbesina Turbacensis Kunth: Trypanosome Cysteine Protease Inhibition by (–)-Bornyl Esters

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