Browse
Submit Data
Databases
API
Help

Dataset Information

10 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

The characterization and properties of castaprenol-11, -12 and -13 from the leaves of Aesculus hippocastanum (horse chestnut).

ABSTRACT: The isolation and purification of a mixture of cis-trans-polyprenols from the leaves of Aesculus hippocastanum (horse chestnut) are described. Results of studies involving mass spectrometry, nuclear magnetic resonance, infrared spectroscopy, micro-hydrogenation and ozonolytic degradation show the mixture to be made up of undecaprenol, dodecaprenol and tridecaprenol with dodecaprenol predominating. Each of the prenols contains three trans internal isoprene residues and a cis ;OH-terminal' isoprene residue. They differ from each other only in the number of cis internal isoprene residues. The trivial names castaprenol-11, castaprenol-12 and castaprenol-13 are proposed to describe these compounds. Gas-liquid-chromatographic and reversed-phase partition thin-layer chromatographic evidence suggest the presence in the mixture of small quantities of castaprenol-10 also.

SUBMITTER: Wellburn AR

PROVIDER: S-EPMC1270242 | biostudies-other | 1967 Jan

REPOSITORIES: biostudies-other

ACCESS DATA

Json Xml

Similar Datasets

Antiviral escin derivatives from the seeds of Aesculus turbinata Blume (Japanese horse chestnut).

Project description:Porcine epidemic diarrhea virus (PEDV) causes severe diarrhea and high fatality of piglets, influencing the swine industry. Japanese horse chestnut (seed of Aesculus turbinata) contains many saponin mixtures, called escins, and has been used for a long time as a traditional medicinal plant. Structure-activity relationship (SAR) studies on escins have revealed that acylations at C-21 and C-22 with angeloyl or tigloyl groups were important for their cytotoxic effects. However, the strong cytotoxicity of escins makes them hard to utilize for other diseases and to develop as nutraceuticals. In this research, we investigated whether escin derivatives 1-7 (including new compounds 2, 3, 5 and 6), without the angeloyl or tigloyl groups and with modified glycosidic linkages by hydrolysis, have PEDV inhibitory effects with less cytotoxicity. Compounds 1-7 had no cytotoxicity at 20?M on VERO cells, while compounds 8-10 showed strong cytotoxicity at similar concentrations on PEDV. Our results suggest that escin derivatives showed strong inhibitory activities on PEDV replication with lowered cytotoxicity. These studies propose a method to utilize Japanese horse chestnut for treating PEDV and to increase the diversity of its bioactive compounds.

| S-EPMC7127610 | biostudies-literature

Influence of leaf damage by the horse chestnut leafminer (Cameraria ohridella Deschka & Dimic) on mycorrhiza of Aesculus hippocastanum L.

Project description:In many parts of Europe, the white horse chestnut (Aesculus hippocastanum L.) has been attacked by the horse chestnut leafminer (Cameraria ohridella Deschka & Dimi?), which causes premature leaf dieback. A. hippocastanum L. establishes mutualistic symbiosis with arbuscular mycorrhizal (AM) fungi. This study involved a comparison of mature A. hippocastanum individuals susceptible to C. ohridella and individuals resistant to this insect after a one-time treatment with a chemical preparation injected into the tree trunks 7 years before the investigation began. Concentration of macronutrients in soil and the activity of soil nonspecific dehydrogenase did not differ between soils under canopies of the treated and untreated trees. Concentrations of C and N were significantly higher in leaves of the treated than those of the untreated trees. The infestation by C. ohridella and defoliation of leaves of the untreated trees did not significantly influence the frequency and intensity of AM colonization compared to the chemically treated trees, although a tendency towards higher average AM colonization of roots of the untreated trees, infested by the herbivores, than roots of the non-infested trees was observed. The results also indicated a tendency for higher biomass of fine roots per soil volume under the trees treated against C. ohridella than under the trees invaded by the insect.

| S-EPMC6311180 | biostudies-literature

The characterization of ficaprenol-10, -11 and 12 from the leaves of Ficus elastica (decorative rubber plant).

Project description:Evidence from mass, nuclear-magnetic-resonance and infrared spectrometry and from gas-liquid and thin-layer chromatography is presented in favour of the presence of cis-trans-decaprenol, -undecaprenol and -dodecaprenol in the mixture of polyprenols (2.6mg./g.) isolated from leaf tissue of Ficus elastica. The trivial names ficaprenol-10, -11 and -12 are proposed. Nuclear-magnetic-resonance studies showed that each of these prenols contains three trans internal isoprene residues and a cis ;OH-terminal' isoprene residue. Ficaprenol-11 is the major component of the mixture. Chromatographic evidence suggests the presence also of small amounts of ficaprenol-9 and -13. The precise position of the three trans internal isoprene residues was not determined but it is suggested that these are adjacent to the omega-terminal isoprene residue and that the ficaprenols are formed from all-trans-geranylgeranyl pyrophosphate. It is also suggested that ficaprenol-10, -11, -12 and -13 are probably the same compounds as castaprenol-10, -11, -12 and -13.

| S-EPMC1270243 | biostudies-other

5?-Hy-droxy-eudesm-4(15),11(13)-dien-8?,12-olide.

Project description:The title compound, C(15)H(20)O(3), a sesquiterpene lactone, was isolated from the aerial parts of Carpesium minus Hemsl. (Compositae). The mol-ecule is composed of three rings, with the two cyclo-hexane rings in chair conformations and the cyclo-pentane ring adopting a twist conformation. The A/B ring junction is trans-fused. The absolute configuration shown has been arbitrarily assigned. In the crystal, mol-ecules are linked into [100] chains by O-H?O hydrogen bonds.

| S-EPMC3344144 | biostudies-literature

Robust, universal, and persistent bud secretion adhesion in horse-chestnut trees.

Project description:Buds of horse-chestnut trees are covered with a viscous fluid, which remains sticky after long-term exposure to heat, frost, radiation, precipitation, deposition of aerosols and particles, attacks by microbes and arthropods. The present study demonstrates that the secretion does not dry out under arid conditions, not melt at 50 °C, and not change significantly under UV radiation or frost at a microscopic level. It is slightly swellable under wet conditions; and, it universally wets and adheres to substrates having different polarities. Measured pull-off forces do not differ between hydrophilic and lipophilic surfaces, ranging between 58 and 186 mN, and resulting in an adhesive strength up to 204 kPa. The mechanical and chemical properties of secretion resemble those of pressure-sensitive adhesives. The Raman, infrared, and nuclear magnetic resonance spectra show the clear presence of saturated aliphatic hydrocarbons, esters, free carboxylic acids, as well as minor amounts of amides and aromatic compounds. We suggest a multi-component material (aliphatic hydrocarbon resin), including alkanes, fatty acids, amides, and tackifying terpenoids embedded in a fluid matrix (fatty acids) comprising nonpolar and polar portions serving the universal and robust adhesive properties. These characteristics matter for ecological-evolutionary aspects and can inspire innovative designs of multifunctional, biomimetic pressure-sensitive adhesives and varnishes.

| S-EPMC7642395 | biostudies-literature

Complete Genome Sequences of Four Phages of the Horse Chestnut Phyllosphere

Project description:ABSTRACT Bacteriophages play important roles in determining bacterial communities, including plant microbiota. Here, we describe four lytic phages, three Siphoviridae and one Podoviridae, isolated from four different bacterial species found on the leaves of horse chestnut trees. Their double-stranded DNA (dsDNA) genomes range from 39,095 to 46,062 bp and contain 51 to 70 genes.

| S-EPMC8567786 | biostudies-literature

The characterization of Mediator 12 and 13 as conditional positive gene regulators in Arabidopsis.

Project description:Mediator 12 (MED12) and MED13 are components of the Mediator multi-protein complex, that facilitates the initial steps of gene transcription. Here, in an Arabidopsis mutant screen, we identify MED12 and MED13 as positive gene regulators, both of which contribute broadly to morc1 de-repressed gene expression. Both MED12 and MED13 are preferentially required for the expression of genes depleted in active chromatin marks, a chromatin signature shared with morc1 re-activated loci. We further discover that MED12 tends to interact with genes that are responsive to environmental stimuli, including light and radiation. We demonstrate that light-induced transient gene expression depends on MED12, and is accompanied by a concomitant increase in MED12 enrichment during induction. In contrast, the steady-state expression level of these genes show little dependence on MED12, suggesting that MED12 is primarily required to aid the expression of genes in transition from less-active to more active states.

| S-EPMC7271234 | biostudies-literature

The subcellular distribution and biosynthesis of castaprenols and plastoquinone in the leaves of Aesculus hippocastanum.

Project description:Intact chloroplasts and cell walls were prepared from horse-chestnut leaves that had previously metabolized [2-(14)C]mevalonate. The bulk of the castaprenols and plastoquinone-9 was found within the chloroplasts. The remaining portion of the castaprenols was associated with the cell-wall preparation whereas that of the plastoquinone-9 was probably localized in the soluble fraction of the plant cell. The (14)C content of these compounds of different cell fractions indicated the presence of polyisoprenoid-synthesizing activity both inside and outside the chloroplasts. This was confirmed by the relative incorporation of (14)C when ultrasonically treated and intact chloroplasts were incubated with [2-(14)C]mevalonate. As the leaves aged (on the tree) an increase in extraplastidic castaprenols and plastoquinone-9, together with associated synthesizing activities, was observed.

| S-EPMC1270558 | biostudies-other

11?,13-Dihydro-lactucin-8-O-acetate hemihydrate.

Project description:THE TITLE STRUCTURE (SYSTEMATIC NAME: 9-hydroxy-methyl-3,6-di-methyl-3-methyl-ene-2,7-dioxo-3,3a,4,5,9a,9b-hexa-hydro-azu-leno[4,5-b]furan-4-yl acetate hemihydrate), C(17)H(20)O(6)·0.5H(2)O, from Lactuca floridana, has two independent sesquiterpene lactone mol-ecules in the asymmetric unit. Both have their seven-membered rings in the chair conformation. In the crystal, the OH groups and the water mol-ecule form classical O-H?O hydrogen bonds with O?O distances in the range 2.6750?(17)-2.8160?(18)?Å.

| S-EPMC2970292 | biostudies-literature

Tetra-ethyl-ammonium 12-phenyl-ethynylcarba-closo-dodeca-borate, [Et(4)N][12-PhCC-closo-CB(11)H(11)].

Project description:The asymmetric unit of the title compound, C(8)H(20)N(+)·C(9)H(16)B(11) (-) or [Et(4)N][12-PhCC-closo-CB(11)H(11)], consists of one cation and one anion. The [12-PhCC-closo-CB(11)H(11)](-) anion is close to possessing a non-crystallographic plane of mirror symmetry with a nearly linear B-C C-C group, with B-C C and C C-C angles of 177.15?(16) and 176.64?(17)°, respectively.

| S-EPMC2977730 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data