Acacetin 7-O-β-d-galactopyranoside from Chrysanthemum indicum
TL;DR: From the yellow flowers of Chrysanthemum indicum, a new flavone glycoside, acacetin 7-O-β- d -galactopyranoside was isolated and its structure established from spectral evidence and synthesis.
About: This article is published in Phytochemistry.The article was published on 1981-01-01. It has received 28 citations till now. The article focuses on the topics: Chrysanthemum indicum & Acacetin.
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TL;DR: Luteolin-7-O-glucoside is primarily hydrolyzed to luteolin in the gastrointestinal tract and then absorbed into the systemic circulation and the pharmacokinetic data demonstrate that the areas under the concentration curves (AUCs) of lutenolin were 261 ± 33 and 611 ± 89 after luteol administration.
Abstract: Luteolin and luteolin-7-O-glucoside were isolated from the ethanolic extract of Dendranthema morifolium Ramat Tzvel. The structures of these analytes were identified by nuclear magnetic resonance ((1)H and (13)C NMR) and mass spectrometry. Ethanolic and water extracts contained luteolin-7-O-glucoside at 4.19 and 6.56%, respectively. However, the level of luteolin was only 0.19% in the ethanolic extract, and luteolin was not detected in the water extract. To examine the pharmacokinetics and bioavailability of luteolin and luteolin-7-O-glucoside in rats, parallel studies of luteolin (10 mg/kg, iv; and 100 mg/kg, po) and luteolin-7-O-glucoside (10 mg/kg, iv; and 1 g/kg, po) were conducted. The analytes were detected by high-performance liquid chromatography coupled with a photodiode array detector. A phenyl-hexyl (150 × 4.6 mm iv; 5.0 μm) column was used to separate the analytes from the biological samples. The pharmacokinetic data demonstrate that the areas under the concentration curves (AUCs) of luteolin were 261 ± 33 and 611 ± 89 (min μg/mL) after luteolin administration (10 mg/kg, iv; and 100 mg/kg, po, respectively). The oral bioavailability of luteolin was 26 ± 6%. The AUCs of luteolin-7-O-glucoside were 229 ± 15 and 2109 ± 350 (min μg/mL) after administration of luteolin-7-O-glucoside (10 mg/kg, iv; and 1 g/kg, po, respectively). The oral bioavailability of luteolin-7-O-glucoside was approximately 10 ± 2%. In the group that received luteolin-7-O-glucoside orally, a biotransformed luteolin product was detected, but this product was not detected in the group that received luteolin-7-O-glucoside intravenously. The biotransformation ratio of luteolin to luteolin-7-O-glucoside (the AUC ratio of metabolite/parent compound) was approximately 48.78 ± 0.12%. These results demonstrate that luteolin-7-O-glucoside is primarily hydrolyzed to luteolin in the gastrointestinal tract and then absorbed into the systemic circulation.
151 citations
TL;DR: Flavonoid p -coumaroylglucosides are valuable markers for chemotaxonomic studies and are universally present in the subgenus Marrubiastrum of Sideritis and in section Betonica of genus Stachys, while 8-hydroxyflavone 7-allosylglucOSides accumulate in the other Siderococcus species.
72 citations
TL;DR: Acacetin is a potent molecule reported for its strong anti-inflammatory and anti-cancer activity, however further scientific evidence is essential to validate its potency in disease models associated with inflammation and cancer.
71 citations
TL;DR: It is suggested that acacetin can protect DA neurons against the neurotoxicity involved in PD via its anti-inflammatory action.
Abstract: Acacetin (5,7-dihydroxy-4′-methoxyflavone), a constituent of flavone naturally present in plants, has anti-cancer and anti-inflammatory activities. Neuroinflammation is thought to be one of the major pathological mechanisms responsible for Parkinson’s disease (PD), and has been a primary target in the development of treatment for PD. In the present study, we evaluated the neuroprotective effect of acacetin in PD induced by 1-methyl-4-phenylpyridine (MPP+)/or 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and examined the related pathways in vitro and in vivo. In primary mesencephalic culture, acacetin protected dopaminergic (DA) cells and inhibited production of inflammatory factors such as nitric oxide, prostaglandin E2, and tumor necrosis factor-α against MPP+-induced toxicity in a dose-dependent manner. Then, we confirmed the effect of acacetin (10 mg/kg/d for 3 d, per os (p.o.)) in a mouse model of PD induced by MPTP (30 mg/kg/d for 5 d, intraperitoneally (i.p.)). In the behavioral test (pole test), the acacetin-treated mice showed decreased time of turning and locomotor activity, which were longer in MPTP-only treated mice. In addition, the acacetin-treated group inhibited degeneration of DA neurons and depletion of dopamine level induced by MPTP toxicity in the substantia nigra and striatum of the brain. Moreover, the acacetin-treated group inhibited microglia activation, accompanied by production of inducible nitric oxide synthases and cyclooxygenase-2. These results suggest that acacetin can protect DA neurons against the neurotoxicity involved in PD via its anti-inflammatory action.
62 citations
TL;DR: In this paper, two flavones, luteolin 7- O -β-glucuronide and diosmetin 7-O -β -glucuride, were isolated and identified from Chrysanthemum morifolium L. v. Ramat leaves.
54 citations
References
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TL;DR: In this paper, the preparation of (2R)-Glycerol-o-D-β-galactopyranoside and radioactively labeled RGG is discussed.
Abstract: Publisher Summary This chapter discusses the preparation of (2R)-Glycerol-o-D-β-galactopyranoside and radioactively labeled RGG. (2R)-Glycerol-o-D-β-galactopyranoside (RGG) with its two glyceryl hydroxyl groups acylated by fatty acids occurs in large amounts in the chloroplasts of plants and algae as one type of galactolipid. After the deacylation of the two fatty acids of the galactolipid, RGG is a carbon source for enteric bacteria, such as Escherichia coli, endowed with lac operon-encoded proteins. By comparing the utilization by E. coli of lactose and RGG, it is proposed that RGG is the natural substrate of the lac operon-encoded metabolic functions of enteric bacteria. The isolation of RGG is accomplished by extracting galactolipids from chloroplasts, deacylating by alkaline hydrolysis, and chromatographic separation of glycerol mono- and digalactosides followed by the crystallization of RGG. The initial crystallization of RGG occur faster if the syrup containing RGG is passed over a BioGel P-2 column after dissolving in 50 ml of water and elution in water.
20 citations
TL;DR: In this article, ein and zweiwertigen Pheeol (Brenzcatechin) wurde sowohl die Einfuhrung eines als auch zweier Zuckerreste vorgenommen.
Abstract: Es wurde gefunden, das durch Zusatz vonBorfluorid zu benzolischen Losungen von β-Pentaacetylglucose und ein- und zweiwertigen Phenolen eine schon bei Zimmertemperatur in guter Ausbeute vor sich gehende Bildung von Phenol-β-pentaglucosidacetaten eingeleitet wird. Im gegensatz zu den anderen Verfahren, bei welchen stets einUberschus der Phenolkomponente verwendet werden mus, liesen sich bei Verwendung von Borfluorid auch bei Einsatz aquimolekularer Mengen der beiden Reaktionspartner in einfacher Weise die gewunschten Glucosidacetate isolieren. An einem. zweiwertigen Pheeol (Brenzcatechin) wurde sowohl die Einfuhrung eines als auch zweier Zuckerreste vorgenommen. Wie bei den anderen sauren Kondensationsmitteln durften auch bei der Borfluoridmethode die Ausbeuten am gewunschten Reaktionsprodukt durch das Isomerisierungsvermogen des Kondensationsmittels auf Penta-acetylglucose bzw. gebildetes Glucosid begrenzt sein.
11 citations
TL;DR: The structure of Moldavoside was assigned the structure acacetin-7-β-D-galactopyranoside by Litvinenko et al..
Abstract: Einem aus Dracocephalum moldavica (Turkische Melisse) isolierten Glykosid, Moldavosid, wurde von Litvinenko und Mitarbb die Struktur eines Acacetin-7-β-D-galaktopyranosids gegeben Durch Kupplung von Isosakuranetin und α-Acetobromgalaktose sowie Dehydrierung des entstandenen Flavanonglykosids synthetisierten wir Acacetin-7- β-D-galaktopyranosid, das mit Moldavosid jedoch nicht identisch war Dagegen zeigte das Moldavosid Ubereinstimmung mit Tilianin (Acacetin-7-β-D-glucopyranosid) Der Name Moldavosid ist daher aus der Literatur zu streichen
On the Structure of Moldavoside — Synthesis of Acacetin-7-β-D-galactopyranoside
The glycoside moldavoside, isolated from Dracocephalum moldavica, was assigned the structure acacetin-7-β-D-galactopyranoside by Litvinenko et al Coupling of isosakuranetin and α - acetobromogalactose followed by dehydrogenation of the resulting flavanone glycoside yielded acacetin-7-β-D-galactopyranoside The synthetic glycoside was not identical with moldavoside Moldavoside however showed identity with tilanine (acacetin-7-β-D-glucopyranoside) Therefore the name moldavoside is to be deleted from the literature
3 citations