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3?-Acet-oxy-8?,10?-dihy-droxy-6?-meth-oxy-eremophil-7(11)-en-8,12-olide.

ABSTRACT: The title compound, C(18)H(26)O(7), is an eremophilenolide which has been isolated from the plant Ligularia duciformis for the first time. The present study confirms the atomic connectivity assigned on the basis of (1)H and (13)C NMR spectroscopy. The mol-ecule contains three fused rings, two six-membered rings in chair confomations and a five-membered ring in a flattened envelope conformation. Two hy-droxy groups are involved in formation of intra- and inter-molecular O-H?O hydrogen bonds. The latter ones link mol-ecules into chains propagating in [010].

SUBMITTER: Wu HB

PROVIDER: S-EPMC3007320 | biostudies-literature | 2010 Jul

REPOSITORIES: biostudies-literature

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3β-Acet-oxy-8β,10β-dihy-droxy-6β-meth-oxy-eremophil-7(11)-en-8,12-olide.

Wu Hai-Bo HB Li Hua H Lan Xiao-Cong XC Wang Wen-Shu WS

Acta crystallographica. Section E, Structure reports online 20100731 Pt 8

The title compound, C(18)H(26)O(7), is an eremophilenolide which has been isolated from the plant Ligularia duciformis for the first time. The present study confirms the atomic connectivity assigned on the basis of (1)H and (13)C NMR spectroscopy. The mol-ecule contains three fused rings, two six-membered rings in chair confomations and a five-membered ring in a flattened envelope conformation. Two hy-droxy groups are involved in formation of intra- and inter-molecular O-H⋯O hydrogen bonds. The ...[more]

PMID: 21588445

Similar Datasets

Crystal structure of 4α-hy-droxy-5α,8β(H)-eudesm-7(11)-en-8,12-olide monohydrate.

Project description:The title compound, C15H22O3·H2O, is a natural producr isolated from Chloranthus japonicus, which is a eudesmane sesquiterpenoid. The two trans-fused six-membered rings have chair confomations. In the crystal, O-H⋯O hydrogen bonds link the components into corrugated layers parallel to the bc plane. There are C-H⋯O inter-actions present within and between the layers.

| S-EPMC4518932 | biostudies-literature

6?,8?-Dihy-droxy-eremophil-7(11)-en-8?,12-olide.

Project description:The title compound, C(15)H(22)O(4), an eremophilane sesquiternoid, was isolated from the roots of Ligularia virgaurea. Both six-membered rings (A and B) adopt chair conformations and the five-membered ring is almost planar (r.m.s. deviation = 0.016?Å). The two methyl and two hy-droxy groups adopt a syn conformation and the A/B ring junction is cis-fused. An intra-molecular O-H?O hydrogen bond generates an S(6) ring. In the crystal, O-H?O hydrogen bonds link the mol-ecules into [100] chains.

| S-EPMC3247365 | biostudies-other

3β,6α-Diacet-oxy-5,9α-dihy-droxy-5α-cholest-7-en-11-one.

Project description:The title compound, C31H48O7, a polyoxygenated steroid, was obtained by chemical oxidation of 7-de-hydro-cholesteryl acetate. The mol-ecular geometry features trans A/B and C/D junctions at the steroid core with the acetyl groups in the equatorial position and a fully extended conformation for the alkyl side chain. A chair conformation is observed for rings A and C while ring B adopts a half-chair conformation. The five-membered ring D has an envelope conformation, with the C atom bearing the methyl group at the flap. The terminal isopropyl group and one acetyl group are disordered over two sets of sites with 0.774 (8):0.226 (8) and 0.843 (7):0.157 (7) ratios, respectively. An intra-molecular S(6) O-H⋯O hydrogen-bonding motif involving a hy-droxy donor and acceptor is observed. In the crystal, chains of mol-ecules running along the b axis are formed via O-H⋯O hydrogen bonds between hy-droxy donors and carbonyl acceptors of the ordered acetyl group, giving rise to a C(14) motif. The chains are wrapped around the 21 screw axes.

| S-EPMC3770383 | biostudies-literature

6?-Hy-droxy-eremophil-7(11)-en-8?,12-olide.

Project description:The title eremophilenolide, C(15)H(22)O(3), is a natural compound isolated from Senecio laetus Edgew. The two cis-fused six-membered rings have chair confomations and the five-membered ring has a planar envelope conformation [maximum deviation = 0.010?(1)?Å]. The ?-hy-droxy group participates in inter-molecular O-H?O hydrogen bonding, forming mol-ecular chains along the a axis.

| S-EPMC3120521 | biostudies-literature

5,6-Dihy-droxy-7,8-di-meth-oxy-flavone.

Project description:The title compound (systematic name5,6-dihy-droxy-7,8-dimeth-oxy-2-phenyl-chromen-4-one), C17H14O6, is a flavone that was isolated from the petroleum ether-soluble fraction of the rare traditional Chinese medicinal herb Saussurea involucrata. The flavone mol-ecule is almost planar, with a dihedral angle between the planes of the benzo-pyran-4-one group and the attached phenyl group of 1.89 (6)°. The 5-hy-droxy group forms a strong intra-molecular hydrogen bond with the carbonyl group, resulting in a six-membered hydrogen-bonded ring. The 6-hy-droxy group also forms an intra-molecular O-H⋯O contact. In the crystal, the molecules are linked by O-H⋯O and C-H⋯O hydrogen bonds and π-π inter-actions [3.37 (2)-3.39 (2) Å], which build up a three-dimensional network.

| S-EPMC3770373 | biostudies-literature

8?-Acet-oxy-14?-benzo-yloxy-N-methyl-13?,15?-dihy-droxy-1?,6?,16?-trimeth-oxy-4?-(meth-oxy-meth-yl)aconitane: hypaconitine isolated from 'fuzi'.

Project description:The title compound, C(33)H(45)NO(10), has an aconitine carbon skeleton with four six-membered rings and two five-membered rings. The five-membered rings adopt envelope configurations and the six-membered N-containing heterocyclic ring displays a chair conformation. Two intra-molecular O-H?O hydrogen bonds occur.

| S-EPMC3009068 | biostudies-literature

4',5-Dihy-droxy-7-meth-oxy-flavanone dihydrate.

Project description:The title compound, C(16)H(14)O(5)·2H(2)O [systematic name: 5-hy-droxy-2-(4-hy-droxy-phen-yl)-7-meth-oxy-chroman-4-one dihydrate], is a natural phytoalexin flavone isolated from the native chilean species Heliotropium taltalense and crystallizes with an organic mol-ecule and two water mol-ecules in the asymmetric unit. The 5-hy-droxy group forms a strong intra-molecular hydrogen bond with the carbonyl group, resulting in a six-membered ring. In the crystal, the components are linked by O-H?O hydrogen bonds, forming a three-dimensional network. The 4-hy-droxy-phenyl benzene ring is bonded equatorially to the pyrone ring, which adopts a slightly distorted sofa conformation. The title compound is the hydrated form of a previously reported structure [Shoja (1990 ?). Acta Cryst. C46, 1969-1971]. There are only slight variations in the mol-ecular geometry between the two compounds.

| S-EPMC3254395 | biostudies-literature

3β,6β-Diacet-oxy-5,9α-dihy-droxy-5α-cholest-7-en-11-one acetic acid 0.04-solvate.

Project description:The title compound, C31H48O7·0.04CH3COOH, is a polyoxy-genated steroid obtained by selective chemical oxidation of 7-de-hydro-cholesteryl acetate. The asymmetric unit comprises three mol-ecules of the steroid (Z' = 3) and a mol-ecule of acetic acid which has occupancy factor 0.131 (5). The geometric parameters of the independent mol-ecules do not reveal significant differences. In one mol-ecule, the terminal isopropyl group is disordered over two sets of sites with occupancy ratio 0.869 (5):0.131 (5). The three mol-ecules reveal different hydrogen-bonding patterns. Each of them is involved in an intra-molecular S(6) hydrogen-bonding motif, involving hy-droxy groups as donor and acceptor. In the crystal, two independent mol-ecules form dimers through hydrogen bonding between an OH donor and an acetate carbonyl acceptor, giving rise to R 2 (2)(16) ring patterns. A single hydrogen bond between the OH group and a ketone carbonyl group is observed between two symmetry-independent mol-ecules.

| S-EPMC3685037 | biostudies-literature

(+)-Methyl 3β-acet-oxy-13-carb-oxy-19-hy-droxy-11-oxo-C-norolean-18-en-30-oate γ-lactone.

Project description:The title compound, C(33)H(46)O(7), is an unusual oxydation product of the therapeutic agent glycyrrhetinic acid that has, in comparison to the latter, a distinctly altered triterpene structure with one five- and four six-membered carbocycles complemented by a γ-lactone ring with a spiro-junction and a ring double bond. The junction between the five-membered ring C, a cyclo-penta-none ring, and the six-membered ring D, previously in question, was found to be cis, confirming earlier structure assignments based solely on chemical transformations. In the solid state, the compound exhibits five intra- and four inter-molecular C-H⋯O inter-actions with H⋯O distances less than or equal to 2.70 Å and C-H⋯O greater than 100°.

| S-EPMC2983216 | biostudies-literature

N'-(3,4-Dihy-droxy-benzyl-idene)-2-meth-oxy-benzohydrazide.

Project description:The title compound, C(15)H(14)N(2)O(4), was prepared from 3,4-dihy-droxy-benzaldehyde and 2-meth-oxy-benzhydrazide in absolute methanol. An intra-molecular N-H?O hydrogen bond makes an S(6) ring motif and the dihedral angle between the aromatic rings is 3.2?(3)°. The meta-O atom is disordered over two positions in a 0.809?(6):0.191?(6) ratio. The crystal structure features O-H?N and O-H?O hydrogen bonds.

| S-EPMC3393303 | biostudies-literature

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