Neue furanoeremophilane und andere sesquiterpene aus vertretern der gattung Euryops

Bohlmann, Ferdinand; Zdero, Christa

doi:10.1016/s0031-9422(00)94305-x

Cited by 117 publications

(46 citation statements)

References 18 publications

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“…From sample 9 (type 3), furanoeremophilane (12) H-NMR data of 15 were identical with those of 6b-acetoxy-1,10-epoxyfuranoeremophilane reported by Bohlmann et al [28] and by Burgueno-Tapia et al [29]. Bohlmann and co-workers initially assigned the configuration of the epoxide to be 1a,10a, but they later revised the configuration to be 1b,10b [30]. The 1 H-NMR data of 15 were clearly different from those of 6b-acetoxy1a,10a-epoxyfuranoeremophilane (20) reported by Kitagawa et al [32].…”

supporting

confidence: 69%

High Diversity of Ligularia dictyoneura in Chemical Composition and DNA Sequence

Nagano

Iwazaki

Matsushima

et al. 2007

Chemistry & Biodiversity

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The chemical composition of root extracts of the title species collected at 20 different places in the Hengduan Mountains of China was examined. From these samples, a total of 17 eremophilane derivatives were isolated, three of which were new franoeremophilane derivatives: 3beta-acetoxy-6beta-(angeloyloxy)furanoeremophilan-10beta-ol, 1alpha-acetoxyfuranoeremophilan-15,6alpha-olide, and 6beta-[2-(hydroxymethyl)prop-2-enoyloxy]furanoeremophil-1(10)-ene. Based on the chemical composition, the samples could be classified into as many as seven types: one type containing non-furanoeremophilane derivatives and the other six containing furanoeremophilane derivatives with different oxidation levels. Results of DNA sequencing of the atpB-rbcL region and the internal transcribed spacers of the ribosomal RNA gene also indicated a high diversity in the species.

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supporting

confidence: 69%

High Diversity of Ligularia dictyoneura in Chemical Composition and DNA Sequence

Nagano

Iwazaki

Matsushima

et al. 2007

Chemistry & Biodiversity

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“…Therefore the absolute configuration of compounds 2 and 3 should be 4S, 6R and 4R, 6R, respectively. epi-cacalone (6), 6 adenostin B (7), 21 cacalol (8), 21 cacalol acetate (9), 22 cacalohastine (10), 23 adenostylide (11), 24 radulifolin C (12), 10 radulifolin D (13), 9 epi-radulifolin F (14), 9 hyperin (15) were determined by comparison of their physical and spectroscopic features with those reported in the literature. The absolute stereochemistry of cacalone (5) and epi-cacalone(6) has been determined 6 but, since their CD data were not available in literature, they were obtained in the present work.…”

Section: Resultsmentioning

confidence: 99%

Modified eremophilanes and anti-inflammatory activity of Psacalium cirsiifolium

Arciniegas¹,

Pérez-Castorena²,

Nieto‐Camacho³

et al. 2013

J. Braz. Chem. Soc.

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Quatro novos eremofilanos modificados, juntamente com dez derivados conhecidos de cacalol, dois cariofilenos, um aromadendreno e um flavonoide foram purificados a partir de Psacalium cirsiifolium. As estruturas destes compostos foram elucidadas por análise espectroscópica. A atividade anti-inflamatória dos extratos e de sete dos compostos isolados foi avaliada no modelo de 12-O-tetradecanoilforbol-13-acetato (TPA) de inflamação aguda induzida. O composto inédito 2a-hidroxiadenostin B (4) mostrou uma atividade dependente da dose (IC 50 0,41 mmol por orelha) e um efeito de inibição de neutrófilos medido pelo teste de mieloperoxidase (MPO) semelhante ao efeito da indometacina, 0,31 e 1,0 mmol por orelha.Four new modified eremophilanes, together with ten known cacalol derivatives, two caryophyllenes, one aromadendrene and one flavonoid were isolated from Psacalium cirsiifolium. The structures of these compounds were elucidated by spectroscopic analysis. The antiinflammatory activity of extracts and of seven of the isolated compounds was evaluated on 12-O-tetradecanoylphorbol-13-acetate (TPA) model of induced acute inflammation. The new compound 2a-hydroxyadenostin B (4) showed a dose dependent activity (IC 50 0.41 mmol per ear) and a neutrophil inhibition effect as measured by the myeloperoxidase (MPO) assay similar to that of indomethacin at 0.31 and 1.0 mmol per ear.

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“…[3] Although we are aware of methyl migrations and carbon skeleton rearrangements in terpene biosynthesis today,h is suggestions were of startling novelty at the time and can be considered amilestone for subsequent investigations of terpene biosynthesis.O ver the years,isolation and characterization of several eremophilane synthases,aswell as investigation of their mechanisms of action, substantiated Robinsonsproposal that the biosynthesis of eremophilanes proceeds via an eudesmane cation ( Figure 1). [5] One example of afurantype eremophilane is microsphaeropsisin B( 1), am ember isolated from co-cultivation of the endophytic fungus Tricho-derma sp.3 07 with the aquatic pathogenic bacterium Acinetobacter johnsonii B2. [5] One example of afurantype eremophilane is microsphaeropsisin B( 1), am ember isolated from co-cultivation of the endophytic fungus Tricho-derma sp.3 07 with the aquatic pathogenic bacterium Acinetobacter johnsonii B2.…”

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confidence: 99%

The Furan Shuffling Hypothesis: A Biogenetic Proposal for Eremophilane Sesquiterpenoids

et al. 2019

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Based on the structural similarities of the recently isolated eremophilane-type sesquiterpenoids microsphaeropsisin Ba nd Ca nd the iso-eremophilane periconianone C, ar evised biogenetic hypothesis for C8-C11-connected isoeremophilanes is presented and corroborated by strong experimental evidence.The first enantioselective total syntheses of microsphaeropsisin Ba nd Cw ere achieved starting from ak nowni ntermediate,w hose synthesis was elaborated previously in the total synthesis of periconianone A, and in atotal of 15 steps starting from g-hydroxy carvone.M ild reaction conditions for the subsequent a-ketol rearrangement not only resulted in the herein proposed conversion of microsphaeropsisin Bi nto periconianone C, but also in the conversion of microsphaeropsisin Ci nto 4-epi-periconianone C.

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Neue furanoeremophilane und andere sesquiterpene aus vertretern der gattung Euryops

Cited by 117 publications

References 18 publications

High Diversity of Ligularia dictyoneura in Chemical Composition and DNA Sequence

High Diversity of Ligularia dictyoneura in Chemical Composition and DNA Sequence

Modified eremophilanes and anti-inflammatory activity of Psacalium cirsiifolium

The Furan Shuffling Hypothesis: A Biogenetic Proposal for Eremophilane Sesquiterpenoids

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