acacetin and linarin

Since enhanced bone resorption due to osteoclast differentiation and activation cause skeletal diseases, there is a growing need in therapeutics for combating bone-resorbing osteoclasts. Botanical antioxidants are being increasingly investigated for their health-promoting effects on bone. Edible Cirsium setidens contains various polyphenols of linarin, pectolinarin, and apigenin with antioxidant and hepatoprotective effects.. This study aimed to determine whether linarin present in Cirsium setidens water extracts (CSE) and its aglycone acacetin inhibited osteoclastogenesis of RANKL-exposed RAW 264.7 murine macrophages for 5 days.. This study assessed the osteoprotective effects of CSE, linarin and acacetin on RANKL-induced differentiation and activation of osteoclasts by using MTT assay, TRAP staining, Western blot analysis, bone resorption assay actin ring staining, adhesion assay and immunocytochemical assay. This study explored the underlying mechanisms of their osteoprotection, and identified major components present in CSE by HPLC analysis.. Linarin and pectolinarin were identified as major components of CSE. Nontoxic linarin and acacetin as well as CSE, but not pectolinarin attenuated the RANKL-induced macrophage differentiation into multinucleated osteoclasts, and curtailed osteoclastic bone resorption through reducing lacunar acidification and bone matrix degradation in the osteoclast-bone interface. Linarin and acacetin in CSE reduced the transmigration and focal contact of osteoclasts to bone matrix-mimicking RGD peptide. Such reduction was accomplished by inhibiting the induction of integrins, integrin-associated proteins of paxillin and gelsolin, cdc42 and CD44 involved in the formation of actin rings. The inhibition of integrin-mediated actin ring formation by linarin and acacetin entailed the disruption of TRAF6-c-Src-PI3K signaling of bone-resorbing osteoclasts. The functional inhibition of c-Src was involved in the loss of F-actin-enriched podosome core protein cortactin-mediated actin assembly due to linarin and acacetin.. These observations demonstrate that CSE, linarin and acacetin were effective in retarding osteoclast function of focal adhesion to bone matrix and active bone resorption via inhibition of diffuse cloud-associated αvβ3 integrin and core-linked CD44.

Topics: Actins; Animals; Bone Matrix; Bone Resorption; Cirsium; Flavones; Focal Adhesions; Glycosides; Hyaluronan Receptors; Integrin alphaVbeta3; Mice; Osteoclasts; Osteogenesis; Phosphatidylinositol 3-Kinases; Plant Extracts; RAW 264.7 Cells

Linarin, a flavone glycoside, is considered to be a promising natural product due to its diverse pharmacological activities, including analgesic, antipyretic, anti-inflammatory and hepatoprotective activities. In this research, the metabolites of linarin in rat intestinal flora and biosamples were characterized using ultra-high-performance liquid chromatography/quadrupole time-of-flight mass spectrometry (UPLC/Q-TOF-MS/MS). Three ring cleavage metabolites (4-hydroxybenzoic acid, 4-hydroxy benzaldehyde and phloroglucinol) were detected after linarin was incubated with rat intestinal flora. A total of 17 metabolites, including one ring cleavage metabolite (phloroglucinol), were identified in rat biosamples after oral administration of linarin. These results indicate that linarin was able to undergo ring fission metabolism in intestinal flora and that hydrolysis, demethylation, glucuronidation, sulfation, glycosylation, methylation and ring cleavage were the major metabolic pathways. This study provides scientific support for the understanding of the metabolism of linarin and contributes to the further development of linarin as a drug candidate.

Topics: Animals; Apigenin; Chromatography, High Pressure Liquid; Flavones; Gastrointestinal Microbiome; Glycosides; Metabolic Networks and Pathways; Methylation; Rats; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; Tandem Mass Spectrometry

To study the flavonoids in the fruits of Buddleja lindleyana.. The compounds were separated by repeated silica gel, RP-18 and Sephadex LH-20. Their structures were elucidated on the basis of chemical evidence and spectral data.. Five flavonoids were isolated and identified as luteolin (1), tricin (2), acacetin (3), acacetin-7-O-β-D-glucopyranoside (4) and linarin(5).. Compounds 3,4 and 5 are isolated from fruits of Buddleja lindleyana for the first time. Compound 2 is isolated from fruits of Buddleja lindleyana for the first time.

Topics: Buddleja; Flavones; Flavonoids; Fruit; Glycosides; Luteolin; Phytochemicals

To optimize the hydrolysis process of linarin by response surface methodology, and to use the model of aldose reductase to study the acacetin's activity of aldose reductase inhibitory.. The model of acacetin enzyme in vitro was established by the determination of fluorescence absorption of NADPH, the inhibition rate of acacetin aldose reductase was calculated, and then the IC50 of hydrolysis was obtained. The hydrolysis process of linarin hydrolysis condition was optimized by using response surface method.. The results indicated that the IC50 of acacetin (2.74 mg x L(-1)) was less than the IC50 of linarin (3.53 mg x L(-1)). Hydrolyzation time of 7.4 h, sulphuric acid concentration of 0.54 mol x L(-1) and the ratio of material to liquid of 3 : 1 were the optimum conditions.. Hydrolyzate acacetin has preferable inhibitory activity of aldose reductase. The optimized hydrolysis condition of linarin is convenient to use with good predictability.

Topics: Aldehyde Reductase; Animals; Diabetic Retinopathy; Drugs, Chinese Herbal; Enzyme Inhibitors; Flavones; Glycosides; Glycosylation; Humans; Hydrolysis; Male; Rats; Rats, Wistar; Retina

To promote its comprehensive utilization, the involatile constituents of Mentha haplocalyx were studied systematically.. The chemical components were isolated and purified by silca gel column chromatography and recrystallization. The chemical structures were elucidated on the basis of physico-chemical properties and spectral data.. Eight compounds were isolated and identified as: acacetin (I), tilianine (II), linarin (III), n-butyl-beta-D-fructopyranoside (IV), ursolic acid (V), oleanolic acid (VI), beta-sitosterol (VII), daucosterol (VIII).. Compounds I approximately V were obtained from this plant for the first time.

Topics: Flavones; Glycosides; Mentha; Plant Components, Aerial; Plants, Medicinal; Triterpenes; Ursolic Acid

This study was carried out to assess the anticancer efficacy of linarin (LN), linarin acetate (LA) and acacetin (AC), the flavonoid compounds with the same flavone ring structure but different substitution, against human prostate cancer (PCA), LNCaP and DU145 cells. LN was isolated and purified from Chrysanthemum zawadskii; LA was chemically synthesized from LN, and AC obtained commercially. In each case, the cells were treated with these agents at 25-100 microM doses for 24-72 h. LN and LA showed moderate cell growth inhibition with different time kinetics as compared to AC. LN caused up to a 5-fold increase in cell death and LA enhanced cell death by up to 4-fold with the increase in treatment time in both cell lines. AC showed a time- as well as dose-dependent stronger cell growth inhibition (20-70%) accompanied by cell death as compared to LN and LA in both the cell lines. LN or LA did not show any profound effect on cell cycle arrest except for a moderate G1 arrest, whereas, AC showed a stronger G1 and/or G2-M arrest depending on the doses and treatment times. G1 arrest was associated with an increase in Cip1/p21 and a decrease in CDK2, CDK4 and CDK6 protein levels. G2-M arrest was associated with a decrease in Cdc25C, Cdc2/p34 and cyclin B1, which were more prominent in LNCaP compared to DU145 cells. LN, LA and AC induced cell death was associated with significant increase in apoptosis induction (up to 5-6-fold) accompanied by poly-(ADP-ribose) polymerase cleavage. Overall, AC showed more potent anticancer efficacy among these three flavonoids, which was diminished when its flavone ring was modified by disaccharide rhamnose substitution at C7 (LN) or acetylation of this substituted group (LA). These findings, for the first time, revealed the structural determinants in anticancer efficacy and mechanisms of these three flavonoids against human PCA cells.

Topics: Apoptosis; Cell Cycle; Cell Cycle Proteins; Cell Proliferation; Chrysanthemum; Flavones; Glycosides; Humans; Male; Poly(ADP-ribose) Polymerases; Prostatic Neoplasms; Rhamnose; Structure-Activity Relationship; Tumor Cells, Cultured

Semisynthesis of linarin and acacetin from the Citrus flavonoid diosmin was performed via, as first intermediate, the 3'-O-phenyltetrazolyl ether of diosmin. This paper relates also a semisynthetic access to 6-iodoapigenin derivatives, which are key compounds in the synthesis of some biflavonoids such as robustaflavone.

Topics: Biflavonoids; Citrus; Diosmin; Flavones; Flavonoids; Glycosides; Molecular Structure; Plants, Medicinal

To study the chemical constituents in Yinqiaosan Powder that have antiviral action on influenza.. Isolation of the constituents by different kinds of column chromatography and elucidation of their structures by chemical and spectral methods.. Seven flavonoids were obtained, and six of them were identified as linarin, acacetin, hesperidin, isoquiritigenin, isoquiritin and hyperoside respectively.. Linarin and acacetin were isolated from Yinqiaosan Powder for the first time.

Topics: Antiviral Agents; Drug Combinations; Drugs, Chinese Herbal; Flavones; Flavonoids; Glycosides; Hesperidin; Plants, Medicinal; Powders