480-44-4Relevant articles and documents
Structure determination and quantification of a new flavone glycoside with anti-acetylcholinesterase activity from the herbs of Elsholtzia ciliata
Nugroho, Agung,Park, Jong-Hyuk,Choi, Jae Sue,Park, Kyoung-Sik,Hong, Joon-Pyo,Park, Hee-Juhn
, p. 1 - 8 (2017)
Three acacetin triglycosides (compounds 1, 2 and 3) were isolated from the herbs of Elsholtzia ciliata (Labiatae). The structure were identified as 7-O-β-D-glucopyranosyl-(1?→?2)[α-L-rhamnopyranosyl-(1?→?6)]-β-D-glucopyranoside (compound 1), 7-O-(6-O-acetyl)-β-D-glucopyranosyl-(1?→?2)[α-L-rhamnopyranosyl-(1?→?6)]-β-D-glucopyranoside (compound 2) and 7-O-(6-O-acetyl)-β-D-glucopyranosyl-(1?→?2)[(4-O-acetyl)-α-L-rhamnopyranosyl-(1?→?6)]-β-D-glucopyranoside (compound 3) of acacetin. The structures of these compounds were determined on the basis of 2D-NMR spectroscopic data. Compound 3 has not been isolated from a natural source. In addition, the three compounds were quantitatively analysed by HPLC. Acetylcholinesterase (AChE) inhibition activity was assayed to find anti-Alzheimer’s activity, since this enzyme increases the concentration of acetylcholine (ACh), a neurotransmitter, responsible for brain’s memory. Acacetin, the aglycone of the three compounds, exhibited a potent anti-cholinesterase activity (IC50, 50.33?±?0.87), though its glycosides (1, 2 and 3) were less active. HPLC analysis demonstrated that the three compounds were contained in the MeOH extract in the order of compounds 2 (12.63?mg/g extract) > 3 (3.10?mg/g) > 1 (2.92?mg/g).
Anti-inflammatory activity of flavonoids from Chrozophora tinctoria
Abdallah, Hossam M.,Almowallad, Fahad M.,Esmat, Ahmed,Shehata, Ibrahim A.,Abdel-Sattar, Essam A.
, p. 74 - 80 (2015)
Abstract Chemical investigation of Chrozophora tinctoria (L.) A. Juss. growing in Saudi Arabia revealed the isolation of two new acylated flavonoids identified as acacetin-7-O-β-d-[α-l-rhamnosyl(1 → 6)]3″-E-p-coumaroyl glucopyranoside (4) and apigenin-7-O-(6″-Z-p-coumaroyl)-β-d-glucopyranoside (5), in addition to amentoflavone (1), apigenin-7-O-β-d-glucopyranoside (2), apigenin-7-O-6″-E-p-coumaroyl-β-d-glucopyranoside (3) and rutin (6). The structures of isolated compounds were established by 1D, 2D NMR and HRESIMS spectral data, in addition to comparison with literature data. The anti-inflammatory activities of isolated compounds were assessed by measuring the levels of IL-1β, IL-6, TNF-α and PGE2 in the supernatant media of human peripheral blood mononuclear cells (PBMCs) stimulated by phytohaemagglutinin (PHA). At a concentration of 100 μM, compounds 1, 2, 4 and 6 significantly decreased Il-1β, Il-6 and PGE2 to nearly normal values. All tested compounds caused a dose-dependent decrease in TNF-α level but failed to reach that of the control values.
New C,O-Glycosylflavones from the Genus Silene
Olennikov,Kashchenko
, p. 1026 - 1034 (2020/11/05)
Chromatographic separation of extracts from the aerial parts of three Silene species (Caryophyllaceae) isolated 26 flavonoids including the four new C,O-glycosylflavones acacetin-6-C-(2″-O-β-D-glucopyranosyl)-β-D-glucopyranoside-7-O-β-D-glucopyranoside (s
Preparation method of acacetin
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Page/Page column 7-11, (2019/04/26)
The invention provides a preparation method of acacetin, and solves the problems that a reagent for a conventional chemical synthesis is complex, high in toxicity, unfriendly to environment, severe inreaction condition, and unsuitable for large-scaled industrial production. The preparation method comprises the steps of selecting dihydro myricitrin as an initial raw material, and hydrolyzing the dihydro myricitrin under alkaline environment to obtain a hydroxyacetophenone intermediate; performing a catalyzing cyclization reaction on the hydroxyacetophenone and p-anisaldehyde to obtain a flavonol intermediate; and reducing the flavonol intermediate to obtain an acacetin crude product, and finally, performing refining to obtain acacetin quality products in which the content of a liquid phaseis 98% or above. The technology is low in cost, high in yield, simple in reaction condition, simple and safe to operate, economical and practical, environmental-friendly and pollution-free, the product quality meets market requirements, and the reagent is suitable for large-scale industrial production.
Site-selective synthesis of acacetin and genkwanin through lipase-catalyzed deacetylation of apigenin 5,7-diacetate and subsequent methylation
Fujita, Rie,Hanaya, Kengo,Higashibayashi, Shuhei,Mandal, Susanta,Shoji, Mitsuru,Sugai, Takeshi
, p. 638 - 648 (2019/07/31)
Candida antarctica lipase B-catalyzed deacetylation proceeded with high site-selectivity on the C-4′ acetyl group in apigenin triacetate to give apigenin 5,7-diacetate. Methylation of the liberated hydroxy group with the combination of trimethyloxonium tetrafluoroborate (Meerwein reagent) and 1,8-bis(dimethylamino)naphthalene (proton sponge) in CH2Cl2 proceeded in a quantitative manner to give the product methylated at the C-4′ hydroxy group (acacetin 5,7-diacetate). Even with the same precursor, a different methylation product at the C-7 hydroxy group (genkwanin 4′,5-diacetate) was obtained in 86% yield by applying iodomethane and Cs2CO3 in dimethyl sulfoxide (DMSO). The methylated products were deprotected to form acacetin and genkwanin. We inferred that the latter unexpected methylation was ascribable to the intermolecular migration of an acetyl group from C-7 to C-4′. DFT calculations indicated that the C-7 phenoxide ion was 12.6 kJ/mol more stable than the initially formed C-4′ phenoxide ion.
The invention relates to a raw material to synthesize the tin setose thistle glucoside naringin method (by machine translation)
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, (2018/11/22)
The invention discloses a to naringin as raw material synthetic tin setose thistle glucoside method, comprises the following steps: S1, synthesis of wild lacquer tree glucoside; S2, compound 5, 7 - dihydroxy - 2 - (4 - methoxyphenyl) - 4 H - chromen - 4 - one synthesis; acetoxy methyl) - 6 - ((5 - hydroxy - 2 - (4 - methoxyphenyl) - 4 - oxo - 4 H - chromen - 7 - yl) oxy) tetrahydro - 2 H - pyran - 3, 4, 5 - [...] acetate synthesis; S4, compound 5 - hydroxy - 2 - (4 - methoxyphenyl) - 7 - (( (2 S, 3 R, 4 S, 5 S, 6 R) - 3, 4, 5 - trihydroxy - 6 - (hydroxymethyl) tetrahydro - 2 H - pyran - 2 - Kiki) oxy) - 4 H - benzopyran - 4 - one synthesis. The invention to naringin as raw materials, by oxidation, methylation, hydrolysis reaction to synthesize tian jigan. (by machine translation)
Encoding matter with regiospecific 12C/13C isotopic labels
La Clair, James J.
supporting information, p. 2611 - 2614 (2018/03/21)
Society suffers due to an inability to regulate matter. This study presents a practical tool for the encryption of materials by adjusting the levels of 13C at regiospecific atoms within a molecule to generate a stable-isotopically encoded signature. This system is demonstrated by securing a document by adapting natural product chemistry as an encryption device. This approach delivers a complex signal that would be difficult to intercept due to the need for access to extraction protocols, sophisticated NMR instrumentation and a vital level of prior knowledge. Overall, this discovery offers an important tool to monitor and track valuable entities on our planet.
Structure-activity relationship of the inhibitory effects of flavonoids on nitric oxide production in RAW264.7 cells
Jiang, Wen-Jun,Daikonya, Akihiro,Ohkawara, Mitsuyoshi,Nemoto, Takashi,Noritake, Ryusuke,Takamiya, Tomoko,Kitanaka, Susumu,Iijima, Hiroshi
, p. 1 - 5 (2016/12/30)
We isolated flavonoids from herbal specimens from the Tibetan region (Sophora yunnanensis and Rhodiola sacra) that suppress nitric oxide (NO) production in macrophages stimulated by lipopolysaccharide and interferon-γ. The isolated flavonoids carry symmetric substitutions in the B ring (R3′= R5′). We analyzed the quantitative structure-activity relationship of the inhibitory activity by comparative molecular field analysis (CoMFA) using this series of flavonoids. Use of flavonoids with symmetrical substitutions in the B ring made it simpler to align molecules because it was not necessary to consider a huge number of combinations due to the B-ring conformation. The CoMFA model, whose cross-validated q2value was 0.705, suggested the existence of a hydroxy group at the 5-position, the choice of the A/C-ring scaffold (chromane or chromene) and electrostatic field around the B ring are important for NO inhibitory activity. Flavonoids synthesized based on the CoMFA model exhibited significant inhibitory potential against NO production, validating the predictive capability of the CoMFA model.
Lysionotin preparation method
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, (2017/09/05)
The invention provides a lysionotin preparation method. The lysionotin preparation method is characterized by including preparation steps: step one, adopting phloroglucinol and acetic anhydride as reaction materials, and performing Friedel-Crafts reaction under catalysis of boron trifluoride diethyl etherate to obtain 2,4,6-trihydroxyacetophone; step two, subjecting 2,4,6-trihydroxyacetophone obtained at the step one to annulation reaction with p-anisoyl chloride under catalysis of potassium carbonate to obtain 5,7-dyhydroxy-4'-methoxyflavone; step three, subjecting 5,7-dyhydroxy-4'-methoxyflavone to free radical reaction under catalysis of NBS to obtain 5,7-dyhydroxy-6,8-dibromo-4'-methoxyflavone; step four, subjecting 5,7-dyhydroxy-6,8-dibromo-4'-methoxyflavone obtained at the step three to methoxylation reaction with sodium methylate under catalysis of cuprous bromide to obtain lysionotin.
Synthesis of acacetin and resveratrol 3,5-di-O-β-glucopyranoside using lipase-catalyzed regioselective deacetylation of polyphenol glycoside peracetates as the key step
Hanamura, Shun,Hanaya, Kengo,Shoji, Mitsuru,Sugai, Takeshi
, p. 19 - 26 (2016/03/30)
Acacetin and resveratrol 3,5-di-O-β-glucopyranoside were synthesized from naturally abundant naringin and piceid in 65% and 62% overall yield, respectively. The key steps were the regioselective deacetylation of the peracetates of the glycosylated forms with Candida antarctica lipase B (Novozym 435) and Burkholderia cepacia lipase (Amano PS-IM). Deacetylation occurred exclusively at the least hindered position of the aromatic moieties and all acetyl groups in the sugar side chain remained intact. This excellent selectivity enabled regiospecific transformation of the liberated phenolic hydroxy groups, resulting in efficient synthesis of the target molecules.
