Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Six New Phragmalin Limonoids from the Stems of Chukrasia tabularis A. Juss.

ABSTRACT: Six new phragmalin limonoids, named moluccensin Z1 (1), moluccensin Z2 (2), carapanolide Y (3), tabulalin N (4), chukvelutilide A1 (5), and velutinasin J (6), as well as two known compounds, chukvelutilide A (7) and velutinasin D (8) were isolated from the stems of Chukrasia tabularis A. Juss. The structures of the new compounds 1?6 were confirmed by spectroscopic methods, including IR and HRESIMS, as well as 1D and 2D NMR, and by comparisons with the data of known analogues. All compounds were tested for ?-glucosidase and acetylcholinesterase inhibitory activities. However, none of the compounds was active against ?-glucosidase and acetylcholinesterase in vitro.

SUBMITTER: Wang YC

PROVIDER: S-EPMC6278448 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Six New Phragmalin Limonoids from the Stems of Chukrasia tabularis A. Juss.

Wang Yan-Cui YC Kong Fan-Dong FD Wang Hao H Mei Wen-Li WL Liu Shou-Bai SB Zhao You-Xing YX Dai Hao-Fu HF

Molecules (Basel, Switzerland) 20181120 11

Six new phragmalin limonoids, named moluccensin Z1 (1), moluccensin Z2 (2), carapanolide Y (3), tabulalin N (4), chukvelutilide A1 (5), and velutinasin J (6), as well as two known compounds, chukvelutilide A (7) and velutinasin D (8) were isolated from the stems of Chukrasia tabularis A. Juss. The structures of the new compounds 1⁻6 were confirmed by spectroscopic methods, including IR and HRESIMS, as well as 1D and 2D ...[more]

PMID: 30463280

Similar Datasets

Limonoids from seeds of Azadirachta indica A. Juss. and their cytotoxic activity.

Project description:Four new limonoid-type nortriterpenoids, 1-detigloyl-1-O-methacryloylsalannin (1), 28-deoxo-2,3-dihydronimbolide (2), 12-acetoxy-3-O-acetyl-7-O-tigloylvilasinin (3) and 12-acetoxy-3-O-acetyl-7-O-methacryloylvilasinin (4), along with five known ones, were isolated from seeds of Azadirachta indica A. Juss. Their structures were elucidated by various spectroscopic methods, including UV, IR, MS, NMR, X-ray crystallography, quantum chemical calculation, as well as by comparison of their spectroscopic data with those reported. In the in vitro cytotoxic assay, 2 showed inhibitory activity against human breast cancer MDA-MB-231 cell line with IC50 value of 7.68±1.74 ?mol/L, and 5 inhibited growth of human cervical cancer Hela cell line, melanoma A375 cell line and promyelocytic leukemia HL-60 cell line, with IC50 12.00±2.08, 17.44±2.11, and 13.95±5.74 ?mol/L, respectively.

| S-EPMC6090013 | biostudies-literature

Trypanocidal and leishmanicidal activity of six limonoids.

Project description:Six limonoids [kotschyienone A and B (1, 2), 7-deacetylgedunin (3), 7-deacetyl-7-oxogedunin (4), andirobin (5) and methyl angolensate (6)] were investigated for their trypanocidal and leishmanicidal activities using bloodstream forms of Trypanosoma brucei and promastigotes of Leishmania major. Whereas all compounds showed anti-trypanosomal activity, only compounds 1-4 displayed anti-leishmanial activity. The 50% growth inhibition (GI50) values for the trypanocidal and leishmanicidal activity of the compounds ranged between 2.5 and 14.9 ?M. Kotschyienone A (1) was found to be the most active compound with a minimal inhibition concentration (MIC) value of 10 ?M and GI50 values between 2.5 and 2.9 ?M. Only compounds 1 and 3 showed moderate cytotoxicity against HL-60 cells with MIC and GI50 values of 100 ?M and 31.5-46.2 ?M, respectively. Compound 1 was also found to show activity against intracellular amastigotes of L. major with a GI50 value of 1.5 ?M. The results suggest that limonoids have potential as drug candidates for the development of new treatments against trypanosomiasis and leishmaniasis.

| S-EPMC7253382 | biostudies-literature

Five new mexicanolide type limonoids from Heynea trijuga

Project description:Five new mexicanolide-type limonoids, heytrijunolides A–E (1–5) were isolated from the branches and leaves of Heynea trijuga. The structures of these new compounds were elucidated on the basis of extensive spectroscopic analysis. Compound 3 showed weak cytotoxicity against HL-60, SMMC-7721 and A-549 human tumor cell lines with the IC50 values of 21.88, 20.66 and 12.70 µM, respectively. Electronic Supplementary Material Supplementary material is available for this article at 10.1007/s13659-012-0040-1 and is accessible for authorized users.

| S-EPMC4131624 | biostudies-literature

Trichilones A-E: New Limonoids from Trichilia adolfi.

Project description:In addition to the trichilianones A-D recently reported from Trichilia adolfi, a continuing investigation of the chemical constituents of the ethanol extract of the bark of this medicinal plant yielded the five new limonoids 1-5. They are characterized by having four fused rings and are new examples of prieurianin-type limonoids, having a ε-lactone which in 4 and 5 is α, β- unsaturated. The structures of the isolated metabolites were determined by high field NMR spectroscopy and HR mass spectrometry. The new metabolites were shown to have the ε-lactone fused with a tetrahydrofuran ring which is connected to an oxidized hexane ring joined with a cyclo-pentanone having a 3-furanyl substituent. As the crude extract possesses antileishmanial activity, the compounds were assayed for cytotoxic and antiparasitic activities in vitro in murine macrophage cells (raw 264.7 cells) and in Leishmania amazoniensis as well as L. braziliensis promastigotes. Metabolites 1-3 and 5 showed moderate cytotoxicity (between 30-94 µg/mL) but are not responsible for the antileishmanial effect of the extract.

| S-EPMC8196563 | biostudies-literature

Five New Limonoids from Peels of Satsuma Orange (Citrus reticulata).

Project description:Five new: 21,23-dihydro-21-hydroxy-23-oxonomilin (1), 21,23-dihydro-23-methoxy-21-oxonomilin (2), 21,23-dihydro-21-hydroxy-23-oxonomilinic acid methyl ester (3), 21,23-dihydro-23-methoxy-21-oxolimonin (4), and 21,23-dihydro-21-oxolimonin (5), and seven known limonoids were isolated from peels of satsuma orange (Citrus reticulata). The isolated compounds were evaluated for their inhibitory effects on macrophage activation by an inhibitory assay of nitric oxide (NO) production. Among them, compound (2) exhibited NO inhibitory activity without cytotoxicity.

| S-EPMC6152666 | biostudies-literature

New Phragmalin-Type Limonoids from Chukrasia tabularis and Their ?-Glucosidase Inhibitory Activity.

Project description:Phytochemical investigation on the stems of C. tabularis led to the isolation of five new phragmalin-type limonoids and six known ones. The structures of the new compounds 1-5, named chukbularisins A-E, were elucidated by spectroscopic techniques (IR, HRESIMS, 1D and 2D NMR) and comparisons with published data. All the compounds were evaluated for in vitro ?-glucosidase inhibitory activity. Compounds 2, 3, 4, 5, and 8 exhibited inhibitory activity against ?-glucosidase with IC50 values of 0.06 ± 0.008, 0.04 ± 0.002, 0.52 ± 0.039, 1.09 ± 0.040, and 0.20 ± 0.057 mM, respectively (using acarbose as positive control, IC50 0.95 ± 0.092 mM).

| S-EPMC6274087 | biostudies-other

Twenty-Nine New Limonoids with Skeletal Diversity from the Mangrove Plant, Xylocarpus moluccensis.

Project description:Twenty-nine new limonoids-named xylomolins A₁-A₇, B₁-B₂, C₁-C₂, D-F, G₁-G₅, H-I, J₁-J₂, K₁-K₂, L₁-L₂, and M-N, were isolated from the seeds of the mangrove plant, Xylocarpus moluccensis. Compounds 1-13 are mexicanolides with one double bond or two conjugated double bonds, while 14 belongs to a small group of mexicanolides with an oxygen bridge between C1 and C8. Compounds 15-19 are khayanolides containing a Δ8,14 double bond, whereas 20 and 21 are rare khayanolides containing a Δ14,15 double bond and Δ8,9, Δ14,15 conjugated double bonds, respectively. Compounds 22 and 23 are unusual limonoids possessing a (Z)-bicyclo[5.2.1]dec-3-en-8-one motif, while 24 and 25 are 30-ketophragmalins with Δ8,9, Δ14,15 conjugated double bonds. Compounds 26 and 27 are phragmalin 8,9,30-ortho esters, whereas 28 and 29 are azadirone and andirobin derivatives, respectively. The structures of these compounds, including absolute configurations of 15-19, 21-23, and 26, were established by HRESIMS, extensive 1D and 2D NMR investigations, and the comparison of experimental electronic circular dichroism (ECD) spectra. The absolute configuration of 1 was unequivocally established by single-crystal X-ray diffraction analysis, obtained with Cu Kα radiation. The diverse cyclization patterns of 1-29 reveal the strong flexibility of skeletal plasticity in the limonoid biosynthesis of X. moluccensis. Compound 23 exhibited weak antitumor activity against human triple-negative breast MD-MBA-231 cancer cells with an IC50 value of 37.7 μM. Anti-HIV activities of 1, 3, 8, 10, 11, 14, 20, 23-25, and 27 were tested in vitro. However, no compounds showed potent inhibitory activity.

| S-EPMC5793086 | biostudies-literature

Two New Phenolic Constituents from the Stems of Euphorbia griffithii.

Project description:Phytochemical studies on MeOH extract of stems of Euphorbia griffithii led to the isolation of one new hydrolyzable tannin dimer, corilagiffithiin (1) and one new galloyl-glucoside (2), alongside six known ones (3-8). Their structures and absolute configurations were determined by in depth spectroscopic analyses and comparison of their 1D NMR and MS data with literature reported values. Configurations of sugar moieties were determined by acidic hydrolysis and subsequent GC analysis of their corresponding trimethylsilylated L-cysteine adduct. At a concentration of 50 ?M, compounds 1-3 showed no anti-inflammatory activities.

| S-EPMC6872693 | biostudies-literature

New Cadinane Sesquiterpenes from the Stems of Kadsura heteroclita.

Project description:As part of our continual efforts to exploit 'Tujia Ethnomedicine' for their pharmacophoric functionalities, we herein investigated Kadsura heteroclita collected from a deep Wulin mountain area in northern Hunan province. The current study resulted in the isolation of three new sesquiterpenes: 6?,9?,15-trihydroxycadinan-4-en-3-one (1), (+)-3,11,12-trihydroxycalamenene (2), (-)-3,10,11,12-tetrahydroxy-calamenene (3), along with four known sesquiterpenes (4-7), and a cytochalasin H (8). Their chemical structures were elucidated by 1D-, and 2D-NMR spectroscopy, and HRESI-MS, CD spectrometry. The antioxidant, and cytotoxic activities of the compounds were evaluated. Compound 8 exhibited a strong antioxidant effect with an IC50 value of 3.67 µM on isolated human polymorphonuclear cells or neutrophils.

| S-EPMC6539153 | biostudies-literature

Soloist evaluations of six Old Italian and six new violins.

Project description:Many researchers have sought explanations for the purported tonal superiority of Old Italian violins by investigating varnish and wood properties, plate tuning systems, and the spectral balance of the radiated sound. Nevertheless, the fundamental premise of tonal superiority has been investigated scientifically only once very recently, and results showed a general preference for new violins and that players were unable to reliably distinguish new violins from old. The study was, however, relatively small in terms of the number of violins tested (six), the time allotted to each player (an hour), and the size of the test space (a hotel room). In this study, 10 renowned soloists each blind-tested six Old Italian violins (including five by Stradivari) and six new during two 75-min sessions--the first in a rehearsal room, the second in a 300-seat concert hall. When asked to choose a violin to replace their own for a hypothetical concert tour, 6 of the 10 soloists chose a new instrument. A single new violin was easily the most-preferred of the 12. On average, soloists rated their favorite new violins more highly than their favorite old for playability, articulation, and projection, and at least equal to old in terms of timbre. Soloists failed to distinguish new from old at better than chance levels. These results confirm and extend those of the earlier study and present a striking challenge to near-canonical beliefs about Old Italian violins.

| S-EPMC4034184 | biostudies-literature