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3α-Hy-droxy-tirucalla-8,24-dien-21-oic acid.

ABSTRACT: The title compound, C(30)H(48)O(3), a triterpene isolated from the resin of canarium schweinfurthiiand, is an isomer of the previously reported triterpene 3α-hy-droxy-tirucalla-7,24-dien-21-oic acid [Mora et al. (2001 ▶). Acta Cryst. C57, 638-640], which crystallizes in the same trigonal space group. The title mol-ecule consists of four fused rings having chair, half-chair, half-chair and envelope conformations for rings A, B, C and D, respectively (steroid labelling). An intra-molecular C-H⋯O hydrogen bond generates an S(7) ring. In the crystal, mol-ecules are linked by O-H⋯O and C-H⋯O inter-actions, forming (001) sheets.

SUBMITTER: Yousuf S

PROVIDER: S-EPMC3099970 | biostudies-literature |

REPOSITORIES: biostudies-literature

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A cocrystal of 3α-hy-droxy-tirucalla-8,24-dien-21-oic acid and 3β-fluoro-tirucalla-7,24-dien-21-oic acid (0.897:0.103).

Project description:The title compound, 0.897C(30)H(48)O(3).0.103C(30)H(47)O(2)F is a co-crystal of two triterpenes isolated from the resin of Canarium schweinfurthiiand Engl. Both triterpenes consists of four trans-fused rings having chair/half-chair/half-chair and envelope conformations. The mol-ecular conformations are stabilized by intra-molecular C-H⋯O hydrogen bonds, forming rings of S(7) graph-set motif. In the crystal, mol-ecules are linked by inter-molecular O-H⋯O and C-H⋯O inter-actions, forming sheets parallel to (001). All atoms. excepting the axially-oriented hydroxyl group in the major component and the equatorially-oriented fluorine atom in the minor component, are overlapping.

| S-EPMC3099936 | biostudies-literature

11,20-Dihy-droxy-3-oxopregna-1,4-dien-21-oic acid monohydrate.

Project description:The title compound, C(21)H(28)O(5)·H(2)O, is the hydrate of a steroid derivative and was obtained by degradation of solid prednisolone sodium phosphate. The six C atoms in ring A are nearly co-planar with a mean deviation of 0.015?Å. Rings B and C are both in chair conformations, while ring D has an envelope form. In the crystal, inter-molecular O-H?O hydrogen-bonding inter-actions occur between the hy-droxy groups, carbonyl O atoms and solvent water mol-ecules, resulting in an overall three-dimensional structure.

| S-EPMC3120479 | biostudies-literature

(3R,4S,5S,8S,10R,13R)-3-Hy-droxy-kaura-9(11),16-dien-18-oic acid.

Project description:The title compound, C(20)H(28)O(3), was isolated during our investigation into the chemical composition and pharmacological activity of Centipeda cunninghamii (DC.) A. Braun & Asch. (Asteraceae). The enanti-opure compound, a diterpene with a carbon skeleton, is composed of three six- and one five-membered rings in chair, twist-boat, half-chair and envelope conformations, respectively. Each mol-ecule makes one intra- and one inter-molecular O-H?O hydrogen bond in the crystal lattice, forming hydrogen-bonded chains along [010]. The absolute configuration of the compound was assigned on the basis of optical rotation measurements.

| S-EPMC3275267 | biostudies-literature

17?-Hy-droxy-17?-methyl-androsta-1,4-dien-3-one.

Project description:The title compound, C20H28O2, is a steroid with strong anabolic properties. The present solvent-free form crystallizes with two mol-ecules per asymmetric unit. In the crystal, both mol-ecules are involved in the formation of O-H?O hydrogen-bonded chains which extend along the b-axis direction.

| S-EPMC3588272 | biostudies-literature

Propargylaminyl 3α-hy-droxy-11-oxo-18β-olean-12-en-29-oate.

Project description:The title compound, C(33)H(49)NO(3), is the propargyl-amide of 18β-glycyrrhetinic acid, a penta-cyclic triterpenoid of inter-est as a therapeutic agent. The five six-membered rings of the glycyrrhetinic acid moiety show normal geometries, with four rings in chair conformations and the unsaturated ring C in a half-chair conformation. In the crystal, the terminal N-propargylcarboxamide group has remarkable structural effects on weak hydrogen-bond-like inter-actions. Particularly noteworthy are an inter-molecular O-H⋯π inter-action accepted side-on by the terminal alkyne group [O⋯C = 3.097 (2) and 3.356 (2) Å] and a short inter-molecular C-H⋯O inter-action [C⋯O = 3.115 (2) Å] donated by the alkyne C-H group. An N-H⋯O [N⋯O = 3.251 (2) Å] and a C(alkyl)-H⋯O [C⋯O = 3.254 (2) Å] interaction complement the crystal structure.

| S-EPMC3247445 | biostudies-literature

21-Hy-droxy-pregna-1,4-diene-3,20-dione.

Project description:The title compound, C(21)H(28)O(3), is a fungal transformed metabolite of decoxycorticosterone acetate, consisting of four fused rings A, B, C and D. Ring A is nearly planar, with a maximum deviation of 0.010?(3)?Å from the least-squares plane, while the trans-fused rings B and C adopt chair conformations. The five-membered ring D is in an envelope conformation. The orientation of the side chain is stabilized by an intramolecular O-H?O hydrogen bond. In the crystal, adjecent mol-ecules are linked by C-H?O hydrogen bonds into extended zigzag chains along the a axis.

| S-EPMC3213563 | biostudies-literature

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

(2Z,4E)-1-(5-Fluoro-2-hy-droxy-phen-yl)-5-(4-fluoro-phen-yl)-3-hy-droxy-penta-2,4-dien-1-one.

Project description:In the title mol-ecule, C17H12F2O3, the dihedral angle between the benzene rings is 8.6?(2)°. In the crystal, two pairs of O-H?O hydrogen bonds connect the mol-ecules into inversion dimers. In addition, weak C-H?F hydrogen bonds link the dimers into a two-dimensional network parallel to (10-4). The carbonyl O atom is an acceptor for two weak intra-molecular hydrogen bonds.

| S-EPMC3914111 | biostudies-literature

Plasma fetal bile acids 7α-hydroxy-3-oxochol-4-en-24-oic acid and 3-oxachola-4,6-dien-24-oic acid indicate severity of liver cirrhosis.

Project description:Two 3-oxo-Δ4 fetal bile acids, 3-oxachola-4,6-dien-24-oic acid (1) and 7α-hydroxy-3-oxochol-4-en-24-oic acid (2), occur normally in the human fetus but remain elevated in neonates and children with severe cholestatic liver disease due to an autosomal recessive inborn error of metabolism affecting Δ4-3-oxo-steroid 5β-reductase (AKR1D1). Relatively little is known about 1 and 2 in adult patients with liver disease. The chemical synthesis of 1 and 2 is therefore described and their quantitation in plasma by ultrarapid chromatography-triple quadrupole mass spectrometry. Plasma concentrations of 1 and 2 were investigated in 25 adult patients with varying degrees of liver cirrhosis with and without hepatocellular carcinoma (HCC). Highly statistically significant correlations (P < 0.0001) were found between severity of liver cirrhosis, determined by the Child-Pugh and MELD scores, with plasma 1 and 2 concentrations, both alone and combined. The presence of HCC did not influence these correlations. Plasma cholic, chenodeoxycholic, deoxycholic, lithocholic or ursodeoxycholic acids, free and as their glycine or taurine conjugates, did not correlate with Child-Pugh or MELD score when corrected for multiple comparisons. These findings demonstrate that plasma levels of fetal bile acids 3-oxachola-4,6-dien-24-oic acid and 7α-hydroxy-3-oxochol-4-en-24-oic acid and likely deteriorating AKR1D1 activity indicate the severity of liver cirrhosis measured by the Child-Pugh and MELD scores.

| S-EPMC8050265 | biostudies-literature

(2E,4E)-1-(2-Hy-droxy-phen-yl)-5-phenyl-penta-2,4-dien-1-one.

Project description:In the structure of the title chalcone, C(17)H(14)O(2), derived from cinnamaldehyde, the olefine group has a trans configuration. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯O hydrogen-bond inter-action with graph-set motif S(6).

| S-EPMC3200610 | biostudies-literature

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