Studies on the syntheses of sesquiterpene lactones. 10. Improved syntheses of (+)-tuberiferin and the related .alpha.-methylene-.gamma.-lactones and their biological activities

Andô, Masataka; Wada, Tetsuo; Kusaka, Haruhiko; Takase, Kahei; Hirata, Naomi; Yanagi, Yoshikazu

doi:10.1021/jo00230a028

Cited by 46 publications

(29 citation statements)

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“…The 13 C-NMR spectrum exhibited downfield-shifted signals at d C 204.7 (8a) and 202.6 (7a), assignable to C(3) and indicating a CO moiety in that position. Signals of the main component (7a) were in perfect agreement with those reported for tuberiferin [12]. 1 H-NMR data of the second component (8a) were similar to those reported for 7a, differing mainly in an additional signal at d H 3.75 (s, 3 H), assignable to a MeO group.…”

supporting

confidence: 85%

Eudesmane Derivatives from Hieracium intybaceum

Grass¹,

Zidorn²,

Ellmerer³

et al. 2004

Chemistry & Biodiversity

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Two new eudesmanolides, 4beta-H,3beta-(beta-D-glucopyranosyloxy)eudesma-1,11(13)-dien-12,6-olide (5a) and 3beta-D-glucopyranosyloxyeudesma-1,4(15),11(13)-trien-12,6-olide (5b), as well as two related, known compounds, tuberiferin (7a) and dehydrobrachylaenolide (7b), were isolated from the CH2Cl2 extract of subaerial parts of Hieracium intybaceum All. Compounds 6a, 6b, 8a, and 8b, the Me esters of the corresponding sesquiterpenic acids related to 5a, 5b, 7a, and 7b, respectively, were obtained as artifacts during the isolation process. Additionally, linoleic acid (1), linolenic acid (2), the lignane syringaresinol 4'-O-beta-D-glucopyranoside (3), and the guaianolide dehydrocostus lactone (4) were also isolated from H. intybaceum. Structure elucidations were based on mass spectrometry and extensive 1D- and 2D-NMR spectroscopy.

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supporting

confidence: 85%

Eudesmane Derivatives from Hieracium intybaceum

Grass¹,

Zidorn²,

Ellmerer³

et al. 2004

Chemistry & Biodiversity

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“…A large number of pseudoguaianolides, 4,5-secopseudoguaianolides, guaianolides, and 4,5-secoguaianolides have been shown to exhibit biological activities, including antitumoral [23], root-growth and germination inhibitory activities [24][25][26][27], as well as preventive or curative activities against phytopatogenic fungi [24,26]. Shimoma et al [28] reported the regio-and stereoselective synthesis of common synthetic intermediates via kinetic resolution with Lipase PS, (Fig.…”

Section: Herbicidesmentioning

confidence: 99%

“…Thus, Pitacco et al [84] explored the possibility of using enzymes for the kinetic resolution of an α-methylene-γ-lactone, ethyl 2-methyl-4-methylene tetrahydro-5-oxo-2-furancarboxylate (27). The resolution was achieved with Porcine pancreatic lipase (PPL) and Candida rugosa lipase (CRL) in the presence of a cosolvent, and afforded both enantiomers of the corresponding acid with high enantiomeric excesses, (Fig (11)).…”

Section: 3) Of Candidamentioning

confidence: 99%

Biocatalysis Applied to the Synthesis of Agrochemicals

Aleu¹,

Bustillo²,

Hernández-Galán³

et al. 2006

COC

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“…1A, were synthesized according to the procedure previously described (16,17). In brief, (11S)-3-oxoeudesmano-13,6␣-lactone derivative, which exists in the form of needles (m.p.…”

mentioning

confidence: 99%

Chemical Modification of Santonin into a Diacetoxy Acetal Form Confers the Ability to Induce Differentiation of Human Promyelocytic Leukemia Cells via the Down-regulation of NF-κB DNA Binding Activity

Kim

Song

Choi

et al. 2006

Journal of Biological Chemistry

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Many sesquiterpene lactone compounds either induce or enhance the cell differentiation of human leukemia cells. However, we reported in a previous study that santonin, a eudesmanolide sesquiterpene lactone, exerts no effects on the differentiation of leukemia cells. In this report, to evaluate the possibility of chemically modifying santonin into its derivatives with differentiation inducing activity, we synthesized a series of santonin derivatives, and determined their effects on cellular differentiation in the human promyelocytic leukemia HL-60 cell system. A diacetoxy acetal derivative of santonin (DAAS) was found to induce significant HL-60 cell differentiation in a dose-dependent manner, whereas santonin in its original form did not. The HL-60 cells were differentiated into a granulocytic lineage when exposed to DAAS. In addition, the observed induction in cell differentiation closely correlated with the levels of NF-B DNA binding activity inhibited by DAAS. Both Western blot analyses and kinase inhibitor studies determined that protein kinase C, ERK, and phosphatidylinositol 3-kinase were upstream components of the DAAS-mediated inhibition of NF-B binding activity in HL-60 leukemia cells. The results of this study indicate that santonin can, indeed, be chemically modified into a derivative with differentiation inducing abilities, and suggest that DAAS might prove useful in the treatment of neoplastic diseases.

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Studies on the syntheses of sesquiterpene lactones. 10. Improved syntheses of (+)-tuberiferin and the related .alpha.-methylene-.gamma.-lactones and their biological activities

Cited by 46 publications

References 0 publications

Eudesmane Derivatives from Hieracium intybaceum

Eudesmane Derivatives from Hieracium intybaceum

Biocatalysis Applied to the Synthesis of Agrochemicals

Chemical Modification of Santonin into a Diacetoxy Acetal Form Confers the Ability to Induce Differentiation of Human Promyelocytic Leukemia Cells via the Down-regulation of NF-κB DNA Binding Activity

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