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Cyclo-art-24-ene-3?,26-diol from the leaves of Aglaia exima.

ABSTRACT: Cyclo-art-24-ene-3?,26-diol, C(30)H(50)O(2), isolated from the leaves of Aglaia exima, has three six-membered rings fused together that adopt chair conformations. There are two independent mol-ecules in the asymmetric unit. O-H?O hydrogen bond inter-actions between the hydroxyl groups in the 3? and 26 positions lead to the formation of a layer structure parallel to (10).

SUBMITTER: Awang K

PROVIDER: S-EPMC3007388 | biostudies-literature | 2010 Jul

REPOSITORIES: biostudies-literature

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Cyclo-art-24-ene-3β,26-diol from the leaves of Aglaia exima.

Awang Khalijah K Loong Xe Min XM Mohamad Khalit K Chong Soon Lim SL Ng Seik Weng SW

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

Cyclo-art-24-ene-3β,26-diol, C(30)H(50)O(2), isolated from the leaves of Aglaia exima, has three six-membered rings fused together that adopt chair conformations. There are two independent mol-ecules in the asymmetric unit. O-H⋯O hydrogen bond inter-actions between the hydroxyl groups in the 3β and 26 positions lead to the formation of a layer structure parallel to (10). ...[more]

PMID: 21588429

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(20S)-Dammar-24-ene-3?,20-diol monohydrate from the bark of Aglaia exima (Meliaceae).

Project description:In the title compound {systematic name: (1R,2R,5R,7R,10R,11R,14S,15R)-14-[(2S)-2-hy-droxy-6-methyl-hept-5-en-2-yl]-2,6,6,10,11-penta-methyl-tetra-cyclo-[8.7.0.0(2,7).0(11,15)]hepta-decan-5-ol monohydrate}, C(30)H(52)O(2)·H(2)O, the three fused cyclo-hexane rings adopt chair conformations and the hy-droxy substituent of one of these occupies an axial position. The fused cyclo-pentane ring adopts an envelope conformation (with the flap atom being the C atom bearing the methyl group) and the 3-methyl-but-2-enyl portion of its substituent is disordered over three sets of sites in a 0.413?(7):0.250?(7):0.337?(7) ratio. The O atoms of both water mol-ecules occupy special positions of 2 site symmetry. In the crystal, O(s)-H?O(w) and O(w)-H?O(s) (s = steroid and w = water) hydrogen bonds link hy-droxy groups and water mol-ecules, forming a three-dimensional network. The crystal studied was found to be a non-merohedral twin with a 0.518?(1):0.482?(1) component ratio.

| S-EPMC3435729 | biostudies-literature

Cycloart-24-ene-26-ol-3-one, a New Cycloartane Isolated from Leaves of Aglaia exima Triggers Tumour Necrosis Factor-Receptor 1-Mediated Caspase-Dependent Apoptosis in Colon Cancer Cell Line.

Project description:Plants in the Meliaceae family are known to possess interesting biological activities, such as antimalaral, antihypertensive and antitumour activities. Previously, our group reported the plant-derived compound cycloart-24-ene-26-ol-3-one isolated from the hexane extracts of Aglaia exima leaves, which shows cytotoxicity towards various cancer cell lines, in particular, colon cancer cell lines. In this report, we further demonstrate that cycloart-24-ene-26-ol-3-one, from here forth known as cycloartane, reduces the viability of the colon cancer cell lines HT-29 and CaCO-2 in a dose- and time-dependent manner. Further elucidation of the compound's mechanism showed that it binds to tumour necrosis factor-receptor 1 (TNF-R1) leading to the initiation of caspase-8 and, through the activation of Bid, in the activation of caspase-9. This activity causes a reduction in mitochondrial membrane potential (MMP) and the release of cytochrome-C. The activation of caspase-8 and -9 both act to commit the cancer cells to apoptosis through downstream caspase-3/7 activation, PARP cleavage and the lack of NFkB translocation into the nucleus. A molecular docking study showed that the cycloartane binds to the receptor through a hydrophobic interaction with cysteine-96 and hydrogen bonds with lysine-75 and -132. The results show that further development of the cycloartane as an anti-cancer drug is worthwhile.

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(E)-(25S)-23-Acetyl-5?-furost-22-ene-3?,26-diol.

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1,2,3,4-Tetra-methyl-cyclo-pent-2-ene-1,4-diol.

Project description:The title compound, C(9)H(16)O(2), crystallizes with two mol-ecules in the asymmetric unit. The structure displays inter-molecular O-H?O hydrogen bonding.

| S-EPMC2959352 | biostudies-other

2,9,16,19,22,25-Hexaoxatetra-cyclo-[24.4.0.2.0]dotriaconta-1(26),4,6,10(15),11,13,27,29,31-nona-ene.

Project description:The title 22-crown-6 unit, C(26)H(28)O(6), comprising of three benzo groups and triethyl-ene glycol, was prepared by the reaction of ?,?'-dibromo-p-xylene with 1,8-bis-(2-hydroxy-phen-oxy)-3,6-dioxaoctane in the presence of Cs(2)CO(3) with tetra-hydro-furan (THF) and recrystallized from dichloro-methane-hexane (1:20 v/v) at room temperature. In the mol-ecular structure, two O atoms of the central ethyl-ene glycol in the triethyl-ene glycol unit exhibit exo conformations due to intra-molecular C-H?O inter-actions. A number of C-H?O and C-H?? inter-molecular inter-actions contribute to the stabilization of the crystal packing.

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The isolation of cholest-5-ene-3beta,26-diol from human brain.

Project description:Cholest-5-ene-3beta,26-diol, isolated from human brain, was further characterized by oxidation to 3-oxocholest-4-en-26-ol and to 3-oxocholest-4-en-26-oic acid. Identification was achieved by comparison (by t.l.c., g.l.c. and g.l.c.-mass spectrometry) with corresponding reference compounds derived from kryptogenin.

| S-EPMC1166347 | biostudies-other

Cytotoxic Rocaglate Derivatives from Leaves of Aglaia perviridis.

Project description:Rocaglates are a series of structurally complex secondary metabolites with considerable cytotoxicity that have been isolated from plants of the Aglaia genus (Meliaceae). A new rocaglate (aglapervirisin A, 1) and its eight new biosynthetic precursors of rocaglate (aglapervirisins B-J, 2-9) together with five known compounds, were isolated from the leaves of Aglaia perviridis. Their structures were elucidated based on a joint effort of spectroscopic methods [IR, UV, MS, ECD, 1D- and 2D-NMR, HRESIMS], chemical conversion and single-crystal X-ray diffraction. Among these isolates, three (1, 10-11) were silvestrols, a rare subtype rocaglates, exhibiting notable cytotoxicity against four human tumor cell lines, with IC50 values between 8.0 and 15.0 nM. Aglapervirisin A (1) induces cell cycle arrest at the G2/M-phase boundary at concentration 10 nM accompanied by reductions in the expression levels of Cdc2 and Cdc25C in HepG2 cells after 72h co-incubation, and further induces the apoptosis of HepG2 cells at concentrations over 160 nM.

| S-EPMC4730247 | biostudies-literature

cis-Cyclo-heptane-1,2-diol.

Project description:The title compound, C(7)H(14)O(2), is a vicinal diol derived from cyclo-heptane with cis-orientated hydr-oxy groups. The mol-ecules shows no non-crystallographic symmetry. The O-C-C-O torsion angles of both mol-ecules present in the asymmetric unit [-66.4 (2) and -66.9 (2)°] are similar to those in trans-configured cyclo-hexane derivatives (including pyran-oses) as well as rac-trans-cyclo-heptane-1,2-diol, but smaller than those in trans-configured cyclo-pentane derivatives (including furan-oses). In the crystal structure, O-H⋯O hydrogen bonds furnish the formation of sheets parallel to [110].

| S-EPMC2971971 | biostudies-literature

Cabraleahy-droxy-lactone from the leaves of Aglaia exima.

Project description:Cabraleahy-droxy-lactone, C(27)H(44)O(3), isolated from the leaves of Aglaia exima, has three six-membered rings fused together that adopt chair conformations. Its two five-membered rings are enveloped shaped. The hy-droxy group is in an axial position. It is a hydrogen-bond donor to the carbonyl O atom of an adjacent mol-ecule; the O-H⋯O inter-actions lead to the formation of a helical chain that runs along the b axis. There are two independent mol-ecules in the asymmetric unit.

| S-EPMC2983197 | biostudies-literature

(?(4)-Cyclo-octa-tetra-ene)(?(8)-cyclo-octa-tetra-ene)iodido-tantalum(V).

Project description:The title complex, [Ta(?(4)-C8H8)(?(8)-C8H8)I], lies across a crystallographic mirror plane that includes the Ta(V) atom and the iodide ligand. One cyclo-octa-tetra-ene (cot) ring is ?(4)-coordinating and is bis-ected by the mirror plane. The fold angle between the plane of the coordinating butadiene portion and the middle plane of the ring is 27.4?(4)°. An additional minor fold angle of 9.3?(7)° exists between the final plane in the ring and the middle plane. The other cot?ring is ?(8)-coordinating and is also cut by the mirror plane. In this case, the ring is disordered over the mirror plane, and one position is modeled with appropriate restraints and constraints with respect to distances, angles and displacement parameters (the second position is generated by symmetry). This ring is nearly planar, with an r.m.s. deviation of only 0.05?Å when all eight C atoms are included in the calculation. Pairs of inter-molecular ?(8)-cot?rings are parallel stacked and slightly off center, with a centroid-centroid distance of 3.652?Å. No other significant inter-molecular inter-actions are observed. The compound is of inter-est as the first structurally characterized mixed halogen-cot?complex of the group 5 metals and contains the longest terminal Ta-I distance [3.0107?(5)?Å] reported to date.

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