Browse
Submit Data
Databases
API
Help

Dataset Information

5 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Walsogynes H-O from Walsura chrysogyne.

ABSTRACT: Eight new limonoids, walsogynes H-O (1-8) were isolated from the barks of Walsura chrysogyne, and their structures were determined on the basis of the 1D and 2D NMR data. Walsogynes H-M (1-6) and O (8) were concluded to be 11,12-seco limonoids with a dodecahydro-1H-naphtho[1,8-bc:3,4-c']difuran skeleton, and walsogyne N (7) to be 11,12-seco limonoid sharing a unique dodecahydronaphtho[1,8-bc:5,4-b'c']difuran skeleton. Walsogynes H-O (1-8) exhibited potent antimalarial activity against Plasmodium falciparum 3D7 strain with IC₅₀ value of 2.5, 2.6, 1.6, 2.5, 1.5, 2.6, 2.1, and 1.1 µM, respectively.

SUBMITTER: Nugroho AE

PROVIDER: S-EPMC8341256 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Five new limonoids isolated from Walsura robusta.

Project description:Five new toosendanin limonoids with highly oxidative furan ring walsurobustones A-D (1-4), and one new furan ring degraded limonoid walsurobustone E (5) together with one known compound toonapubesic acid B (6) were isolated from the leaves of Walsura robusta. Their structures were elucidated by NMR and MS data. Especially, the absolute configuration of toonapubesic acid B (6) was confirmed by X-ray diffraction study. Compounds 1-6 exhibited good cytotoxicity against the cancer cell lines HL-60, SMMC-7721, A-549, MCF-7, and SW480.

| S-EPMC9947198 | biostudies-literature

Pinnatane A from the bark of Walsura pinnata Hassk.

Project description:In the mol-ecule of pinnatane A, C(30)H(48)O(3), isolated from the bark of Walsura pinnata Hassk, the four cyclo-hexane rings adopt chair conformations; the carboxyl and hydr-oxy substituents occupy axial positions. The cyclo-hexene ring is envelope-shaped. Adjacent mol-ecules are linked by O-H?O hydrogen bonds into a chain running along the c axis.

| S-EPMC2969541 | biostudies-literature

Bioactive A-ring rearranged limonoids from the root barks of Walsura robusta.

Project description:Screening active natural products, rapid identification, and accurate isolation are of great important for modern natural lead compounds discovery1. We hereby reported the isolation of seven new neotecleanin-type limonoids (1-7), seven new limonoids with 5-oxatricyclo[5.4.0.11., 4.]hendecane ring system (8-14), and two new precursors (15-16) together with four known limonoids (17-20) from the root barks of Walsura robusta. Their structures, including their absolute configurations, were elucidated based on analyses of HR-ESI-MS, 1D/2D NMR, ECD spectrum calculations and single-crystal X-ray diffraction techniques. Compounds 2, 8, 9, 11, 13, 14, 18 showed significant anti-inflammatory activities in LPS-induced RAW 264.7 cell line, BV2 microglial cells, and Propionibacterium acnes-stimulated THP-1 human monocytic cells. Walrobsin M (11) exhibited anti-inflammatory activity with IC50 value of 7.96±0.36 ?mol/L, and down-regulated phosphorylation levels of ERK and p38 in a dose-dependent manner.

| S-EPMC6543057 | biostudies-literature

Cytotoxic Effects of Pinnatane A Extracted from Walsura pinnata (Meliaceae) on Human Liver Cancer Cells.

Project description:Pinnatane A from the bark of Walsura pinnata was investigated for its anti-cancer properties by analyzing the cytotoxic activities and cell cycle arrest mechanism induced in two different liver cancer cell lines. A 3-(4,5-Dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay was used to analyze the pinnatane A selectivity in inducing cell death in cancer and normal cells. Various biological assays were carried out to analyze the anti-cancer properties of pinnatane A, such as a live/dead assay for cell death microscopic visualization, cell cycle analysis using propidium iodide (PI) to identify the cell cycle arrest phase, annexin V-fluorescein isothiocyanate (annexin V-FITC)/PI flow cytometry assay to measure percentage of cell populations at different stages of apoptosis and necrosis, and DNA fragmentation assay to verify the late stage of apoptosis. The MTT assay identified pinnatane A prominent dose- and time-dependent cytotoxicity effects in Hep3B and HepG2 cells, with minimal effect on normal cells. The live/dead assay showed significant cell death, while cell cycle analysis showed arrest at the G₀/G₁ phase in both cell lines. Annexin V-FITC/PI flow cytometry and DNA fragmentation assays identified apoptotic cell death in Hep3B and necrotic cell death in HepG2 cell lines. Pinnatane A has the potential for further development as a chemotherapeutic agent prominently against human liver cells.

| S-EPMC6278294 | biostudies-literature

3-Oxoolean-1-en-28-oic acid-n-hexa-ne-water (4/1/1) from the bark of Walsura pinnata Hassk.

Project description:3-Oxoolean-1-en-28-oic acid, isolated from the bark of Walsura pinnata Hassk, crystallized from n-hexane as an n-hexane 0.25-solvent 0.25-hydrate, C(30)H(46)O(3)·0.25C(6)H(14)·0.25H(2)O. There are two independent mol-ecules in the asymmetric unit of the title compound. The three six-membered cyclo-hexane rings in each mol-ecule adopt chair conformations and the carboxyl substituent occupies an axial/equatorial position. The two independent mol-ecules are linked by a pair of O-H(carbox-yl)⋯O hydrogen bonds into a dimer. The n-hexane mol-ecule is disordered about a twofold rotation axis and the water mol-ecule lies on a twofold rotation axis. In addition, the cyclo-hexone carbonyl group of one of the independent mol-ecules is disordered over two sites with occupancies of 0.75 and 0.25.

| S-EPMC2977831 | biostudies-literature

(20S*,24S*)-25-Hy-droxy-20,24-ep-oxy-A-homo-4-oxadammaran-3-one (Chrysura) isolated from the leaves of Walsura chrysogyne.

Project description:The title dammarane triterpenoid, C(30)H(50)O(4), assigned the name chrysura, was isolated from an ethyl acetate extract of Walsura chrysogyne leaves (Meliaceae). It has 20S*,24S* relative stereochemistry and an oxepanone ring with two methyl groups at position 4. The two cyclo-hexane rings adopt chair conformations. The cyclo-pentane and tetra-hydro-furan rings have envelope conformations; their mean planes make a dihedral angle of 13.1 (3)°, indicating that the rings are only slightly tilted with respect to each other. There is an intra-molecular C-H⋯O hydrogen bond in the mol-ecule, which forms S(6) and S(7) ring motifs. In the crystal, mol-ecules are linked via O-H⋯O and C-H⋯O hydrogen bonds, forming chains propagating along [001] which stack along the b-axis direction.

| S-EPMC3238949 | biostudies-literature

LINCS Pilot Phase Joint Project: Sensitivity measures of six breast cancer cell lines to a library of small molecule kinase inhibitors (single drug treatments). Dataset 8 of 15: Cell count and normalized growth rate inhibition values within biological replicate 1.

Project description:-

2017-03-14 | LDS-1250 | LINCS

MGH (CMT) Growth Inhibition Assay Protocol (9 compound doses: 16 uM to 0.0625 uM) -- DNA Staining

Project description: Not available

2014-05-30 | EDS-1011 | LINCS

Breast Cancer Cell Density: Imaging assay of the density- and context-dependence of small molecule perturbagen response in breast cancer cell lines. Dataset 1 of 3: Cell count and normalized growth rate inhibition values.

Project description:-

2017-03-14 | LDS-1261 | LINCS

MGH (CMT) Growth Inhibition Assay Protocol (9 compound doses: 0.512 uM to 0.002 uM) -- DNA Staining

Project description: Not available