Dataset Information

Tenulin 0.25-hydrate, a sesquiterpene lactone isolated from Helenium amarum.

ABSTRACT: The asymmetric unit of the title compound, C17H22O5·0.25H2O [systematic name: 2-hy-droxy-2,2a,6,9a-tetra-methyl-2a,4a,5,6,6a,9a,9b,9c-octa-hydro-2H-1,4-dioxadi-cyclo-pent[cd,f]azulene-3,9-dione 0.25-hydrate], a natural product isolated from Helenium amarum, contains two independent tenulin mol-ecules and half a water mol-ecule of crystallization situated on a twofold rotation axis. The hy-droxy group of the hemiketal moiety is in a ?-position. In the crystal, each water mol-ecule inter-acts with four tenulin mol-ecules via O-H?O hydrogen bonds. The two independent tenulin mol-ecules (A and B) differ only in the character of their participation in hydrogen bonding. Specifically, while A is an acceptor of Owater-H?O A and a donor of O A -H?O B hydrogen bonds, mol-ecule B is an acceptor of the latter hydrogen bond and the donor of an O B -H?Owater hydrogen bond. In the crystal, these O-H?O hydrogen bonds link the tenulin and water mol-ecules into layers parallel to the ac plane.

SUBMITTER: Knight KS

PROVIDER: S-EPMC3793741 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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Tenulin 0.25-hydrate, a sesquiterpene lactone isolated from Helenium amarum.

Knight Kyle S KS Smith Cole T CT Waddell Thomas G TG Noll Bruce B

Acta crystallographica. Section E, Structure reports online 20130710 Pt 8

The asymmetric unit of the title compound, C17H22O5·0.25H2O [systematic name: 2-hy-droxy-2,2a,6,9a-tetra-methyl-2a,4a,5,6,6a,9a,9b,9c-octa-hydro-2H-1,4-dioxadi-cyclo-pent[cd,f]azulene-3,9-dione 0.25-hydrate], a natural product isolated from Helenium amarum, contains two independent tenulin mol-ecules and half a water mol-ecule of crystallization situated on a twofold rotation axis. The hy-droxy group of the hemiketal moiety is in a β-position. In the crystal, each water mol-ecule inter-acts with ...[more]

PMID: 24109328

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Project description:New regimens are constantly being pursued in cancer treatment, especially in the context of treatment-resistant cancer stem cells (CSCs) that are assumed to be involved in cancer recurrence. Here, we investigated the anti-cancer activity of sesquiterpene lactones (SLs) isolated from Ambrosia arborescens and of synthetic derivatives in breast cancer cell lines, with a specific focus on activity against CSCs. The breast cancer cell lines MCF-7, JIMT-1, and HCC1937 and the normal-like breast epithelial cell line MCF-10A were treated with the SLs damsin and coronopilin, isolated from A. arborescens, and with ambrosin and dindol-01, synthesized using damsin. Inhibitory concentration 50 (IC50) values were obtained from dose-response curves. Based on IC50 values, doses in the ?M range were used for investigating effects on cell proliferation, cell cycle phase distribution, cell death, micronuclei formation, and cell migration. Western blot analysis was used to investigate proteins involved in cell cycle regulation as well as in the NF-?B pathway since SLs have been shown to inhibit this transcription factor. Specific CSC effects were investigated using three CSC assays. All compounds inhibited cell proliferation; however, damsin and ambrosin were toxic at single-digit micromolar ranges, while higher concentrations were required for coronopilin and dindol-01. Of the four cell lines, the compounds had the least effect on the normal-like MCF-10A cells. The inhibition of cell proliferation can partly be explained by downregulation of cyclin-dependent kinase 2. All compounds inhibited tumour necrosis factor-?-induced translocation of NF-?B from the cytoplasm to the nucleus. Damsin and ambrosin treatment increased the number of micronuclei; moreover, another sign of DNA damage was the increased level of p53. Treatment with damsin and ambrosin decreased the CSC subpopulation and inhibited cell migration. Our results suggest that these compounds should be further investigated to find efficient CSC-inhibiting compounds.

Dataset Information

Tenulin 0.25-hydrate, a sesquiterpene lactone isolated from Helenium amarum.

Publications

Tenulin 0.25-hydrate, a sesquiterpene lactone isolated from Helenium amarum.

Similar Datasets

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