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Results for “Flavanones”

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At least 145 records · Page 8Linked to original sources
PubMed1999

A new flavanone isolated from rhizoma smilacis glabrae and the structural requirements of its derivatives for preventing immunological hepatocyte damage.

From the rhizome of Smilax glabra Roxb., a new flavanone was isolated and named as smitilbin (1), together with 6 known compounds, engeletin (2), astilbin (3), dihydroquercetin (4), eurryphin (5), resveratrol (6), and 5-O-caffeoylshikimic acid (7). These compounds were applied to the assay of liver nonparenchymal cells (NPC) against hepatocytes (HC) isolated from mice with an immunological liver injury. Against the NPC-caused elevation of ALT (alanine transminase) in culture supernatant from HC, the pretreatment of NPC with flavanoids (1-3) dose-dependently blocked the ALT release while 4, the aglycone of 3, did not. The chromone 5 showed a much stronger inhibition. Compound 6 also showed the activity. However, 1-7 did not show any suppression of NPC or CCl4-induced ALT release when they were used to pretreat HC. These results suggest that compounds 1-3, 5, and 6 could protect the hepatocyte damage from NPC through selectively producing the dysfunction of NPC with an essential requirement of rhamnose, and the chromone part in their structures may be critical for exhibiting the activity rather than through protecting the hepatocyte membranes.

Animals↗
PubMed2001

Flavanone glycosides from Citrus junos and their anti-influenza virus activity.

By bioactivity-guided fractionation, a new flavanone triglycoside, naringenin 7-O-(2",6"-di-O-alpha-rhamnopyranosyl)-beta-glucopyranoside (1), as well as hesperetin 7-O-(2", 6"-di-O-alpha-rhamnopyranosyl)-beta-glucopyranoside (2), hesperidin (3) and narirutin (4) have been isolated from the fruits of Citrus junos Tanaka (Rutaceae). In addition, hesperetin 7-O-(2",6"-di-O-alpha-rhamnopyranosyl)-beta-glucopyranoside (2) is reported for the first time from this plant and inhibits the influenza A virus.

Antiviral Agents↗
PubMed2004

Anti-inflammatory activities of two flavanones, sigmoidin A and sigmoidin B, from Erythrina sigmoidea.

Two prenylated flavanones isolated from Erythrina sigmoidea Hua (sigmoidin A and sigmoidin B) were studied for their ability to inhibit the stable 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical and arachidonic acid metabolism. In addition, the compounds were studied in two experimental models of inflammation induced in mouse ears by 12- O-tetradecanoylphorbol 13-acetate (TPA) and the phospholipase A (2)-induced mouse paw oedema. Both sigmoidins A and B proved to be potent scavengers of the DPPH radical, while the study of the inhibition of arachidonic acid metabolism demonstrated that these same compounds were selective inhibitors of 5-lipoxygenase, with no effect on cyclooxygenase-1 activity. Dose-response inhibitor potency was established for sigmoidin A (IC (50) = 31 microM). In the assay of phospholipase A (2)-induced mouse paw oedema, only the sigmoidin B derivative inhibited oedema formation at 60 min, showing a percentage of inhibition below that obtained with cyproheptadine (59 % vs. 74 %). In the TPA test, sigmoidins A and B decreased the induced oedema by 89 % and 83 %, respectively. This is the first time that the anti-inflammatory activity and antioxidant properties of these prenylflavanones have been reported. The results indicate that the compounds have different mechanisms of action depending on whether one or two prenyl groups are present in ring B.

Animals↗
PubMed2005

New flavanone and chalcone glucosides from Bidens bipinnata Linn.

A new flavanone glucoside, bidenoside F, and a new chalcone glucoside, bidenoside G, along with the known compound iso-okanin 7-O-(4'',6''-diacetyl)-beta-D-glucopyranoside have been isolated from the aerial parts of Bidens bipinnata L. The structures were determined on the basis of spectroscopic methods.

Bidens↗
PubMedDate not supplied

A new geranyl flavanone from Macaranga triloba.

A new geranyl flavanone, 2'-hydroxy-macarangaflavnone A (1), and a known 4',7-dihydroxy-8-methylflavan were isolated from the leaves of Macaranga triloba (Euphorbiceae). The structure of 1 was elucidated based on spectroscopic methods, including 1D and 2D NMR analysis.

Euphorbiaceae↗
PubMed2006

(+)-Apollineanin: a new flavanone from Tephrosia apollinea.

Chemical investigation of the leaves of Tephrosia apollinea has yielded a new flavanone named (+)-apollineanin, together with two known flavones: (-)-semiglabrin and (-)-semiglabrinol. The structure of the new compound was determined on the basis of mass, 1D and 2D NMR spectroscopies including NOE difference spectroscopy. The absolute stereochemistry of (+)-apollineanin was determined by Mosher ester methodology and from CD data.

Flavanones↗
PubMed1997

Evidence for antiradical and antioxidant properties of four biologically active N,N-diethylaminoethyl ethers of flavanone oximes: a comparison with natural polyphenolic flavonoid (rutin) action.

The antiradical and antioxidant activities of four biologically active N,N-diethyloaminoethyl ethers of flavanone oximes (N,N-DEAEFo) were investigated in vitro and compared with these of polyphenolic flavonoid (rutin). Four experimental models were used: iron- and ascorbate driven Fenton systems, gamma-radiolysis, xanthine/xanthine oxidase system and diphenylpicrylhydrazyl (DPPH) radical scavenging. The results clearly indicate that N,N-DEAEFo are acting as promising antioxidants and radioprotectors comparable to rutin activities: they should prove to be useful under acute oxidative stress conditions for which both properties were required.

Antioxidants↗
PubMed2006

Antileukemia activity of MSFTZ-a novel flavanone analog.

A newly synthesized flavanone derivative, (+/-)-(3aRS,4SR)-2-(2-chloro-4-methyl- sulfonylphenyl)-4'-chloro-3a,4-diethoxy-flavane[4,3-d]-Delta-1,2,3-thiadiazoline (MSFTZ), was investigated for its antileukemia activity and molecular mechanisms. Cytotoxicity assay confirmed the high antiproliferative efficiency of MSFTZ in six leukemia cell lines (including two drug-resistant cell lines), with 50% inhibition of cell viability values ranging from 1.0 to 9.2 micromol/l. The results of flow cytometry assay showed that the percentage of apoptotic HL-60 cells was 68.3% after 48 h treatment with MSFTZ, suggesting that the activation of the apoptosis pathway was an anticancer property of MSFTZ. Furthermore, the protein changes related to apoptosis were investigated. Exposure of HL-60 cells to MSFTZ induced pro-caspase-9 and pro-caspase-3 cleavage, X-linked inhibitor of apoptosis protein and Bcl-X(L) downregulation, and poly(ADP-ribose) polymerase degradation. Treatment of cells with MSFTZ resulted in a time-dependent reduction in phosphorylation (activation) of extracellular signal-regulated kinase 1/2 and an increase in phosphorylation (activation) of Jun N-terminal kinase. Taken together, our results demonstrated that activation of mitogen-activated protein kinase and apoptotic cascade is involved in MSFTZ-induced antileukemia activity. All data suggest that MSFTZ is a promising chemotherapy drug.

Antineoplastic Agents↗
PubMed1994

Flavanones with potent antibacterial activity against methicillin-resistant Staphylococcus aureus.

With the therapeutic concept of using the defensive ability of plants against microbial infections, phytoalexin, an antimicrobial phytochemical was studied for its ability to inhibit the growth of methicillin-resistant Staphylococcus aureus (MRSA). Extracts from Sophora exigua (Leguminosae) were fractionated by serial chromatography and the anti-MRSA activity of each fraction was determined by the agar-plate method. Among the active isolates, 5,7,2',6'-tetrahydroxy-6-isoprenyl-8-lavandulyl-4'-methox yflavanone (exiguaflavanone D) completely inhibited the growth of all the MRSA strains examined at the concentration of 1.56-6.25 micrograms mL-1, and 5, 2',6'-trihydroxy-8-lavandulyl-7-methoxy-flavanone (exiguaflavanone B) inhibited at a concentration of 50 micrograms mL-1. This former compound is expected to be a phytotherapeutic agent for MRSA infections as an alternative to conventional antibiotics with unwanted side-effects or the appearance of antibiotic-resistant bacteria.

Anti-Bacterial Agents↗
PubMed1987

Induction of the nodA promoter of Rhizobium leguminosarum Sym plasmid pRL1JI by plant flavanones and flavones.

An expression vector containing the Rhizobium leguminosarum nodA promoter cloned in front of the Escherichia coli lacZ gene was used to characterize the properties of the R. leguminosarum nodA gene-inducing compound(s) present in sterile root exudate of the host plant Vicia sativa L. subsp. nigra (L.). The major inducing compound was flavonoid in nature, most likely a flavanone. The commercially available flavonoids naringenin (5,7,4'-trihydroxyflavanone), eriodictyol (5,7,3'4'-tetrahydroxyflavanone), apigenin (5,7,4'-trihydroxyflavone), and luteolin (5,7,3',4'-tetrahydroxyflavone) induced the nodA promoter to the same level as the root exudate. On the basis of chromatographic properties, it was concluded that none of these compounds is identical to the inducer that is present in root exudate. The induction of the nodA promoter by root exudate and by the most effective inducer naringenin was very similar, as judged from the genetic requirements and the kinetics of induction.

Escherichia coli↗
PubMed2002

Two new acylated flavanone glycosides from the leaves and branches of Phyllanthus emblica.

Two new acylated flavanone glycosides, (S)-eriodictyol 7-O-(6"-O-trans-p-coumaroyl)-beta-D-glucopyranoside (1) and (S)-eriodictyol 7-O-(6"-O-galloyl)-beta-D-glucopyranoside (2) were isolated from the leaves and branches of Phyllanthus emblica together with a new phenolic glycoside, 2-(2-methylbutyryl)phloroglucinol 1-O-(6"-O-beta-D-apiofuranosyl)-beta-D-glucopyranoside (3), as well as 22 known compounds. Their structures were determined by spectral and chemical methods.

Acylation↗
PubMed2003

Three diterpenoids (excoecarins V1-V3) and a flavanone glycoside from the fresh stem of Excoecaria agallocha.

Three new diterpenoids, excoecarins V1-V3 (1-3) and a new flavanone glycoside (7) were isolated from the fresh stem of Excoecaria agallocha L. Their structures were elucidated as: 2alpha,3alpha,18-trihydroxy-3beta,20-epoxybeyer-15-ene (1), ent-2,3-secokaur-16-en-2,3-dioic acid (2), ent-3,4-seco-16alpha-hydroxyatis-4(19)-en-3-oic acid (3), and 3,5,7,3',5'-pentahydroxy-2R,3R-flavanonol 3-O-alpha-L-rhamnopyranoside (7) on the basis of spectroscopic data, chemical evidence, and/or X-ray analysis.

Diterpenes↗
PubMed2006

Synthesis, biological evaluation and in silico metabolic and toxicity prediction of some flavanone derivatives.

Flavones chemically are anthoxanthins, occur either in the free state or as glycosides associated with tannins (flavanoids). Flavanoids (derivatives of flavone) possess various pharmacological activities and due to its xanthine-oxidase enzyme inhibitory effect it also has superoxide-scavenging activities. A series of 2-phenyl-2,3-dihydrochromon-4-one derivatives (flavanone derivatives) were synthesized from chalcones by cyclization method and their activities were evaluated against some gram positive and gram-negative bacteria. IR, NMR and CHN analysis confirmed the structure of the synthesized compounds. The results of the antibacterial studies shows that compounds 2b, 2e, 2f and 2h possess activity against many bacterial strains. Among that the compound (2h) has remarkable activity against all strains viz. 25 microg/ml inhibitory concentration against S. aureus, S. sonnei, E. coli, S. typhimurium and V. cholerae. Compound 2f possess minimum inhibitory concentration of 200 microg/ml against E. coli and S. typhimurium and 25 microg/ml against S. sonnei, S. dysenteriae and V. cholerae. In silico metabolic and toxicity study of the synthesized compounds were performed and the predicted result showed that the compound having hydroxyl functional group undergo sulfate and O-glucuronide conjugation reaction and methoxy derivatives undergo demethylation reaction. The biologically active compounds are free of toxicity in oncogene, teratogen, sensitivity and immunotoxicity.

Anti-Bacterial Agents↗
PubMed2005

A new flavanone, reflexin, from Cuscuta reflexa and its selective sensing of nitric oxide.

A new compound, reflexin, 5-hydroxy-7-methoxy-6-(2,3-epoxy-3-methylbutyl)-flavanone, is isolated from the stems of Cuscuta reflexa along with three other known compounds. This new compound has good potential for application especially in the photoactivity of reflexin. It was found to be sensitive to glutathione, forming a fluorescent product that is utilized for sensing nitric oxide (NO). The lowest detection limit of NO analysis was found to be 0.05 micro/M.

Biosensing Techniques↗
PubMedDate not supplied

Cytotoxic chalcones and flavanones from the tree bark of Cryptocarya costata.

A new flavanone, 7-hydroxy-5,6-dimethoxyflavanone (1), together with three other flavonoids, didymocarpin (2), 2',4'-dihydroxy-5',6'-dimethoxychalcone (3), and isodidymocarpin (4), had been isolated from the methanol extract of the tree bark of Cryptocarya costata. The structures of these compounds were determined based on spectral evidence, including UV, IR, 1-D and 2-D NMR, and mass spectra. Cytotoxic properties of compounds 1-4 were evaluated against murine leukemia P-388 cells. The chalcones 3 and 4 were found to have substantial cytotoxicity with IC50 of 5.7 and 11.1 microM, respectively.

Animals↗