80394-88-3Relevant academic research and scientific papers
Development of bioactive functions in Hydrangeae Dulcis Folium. V. On the antiallergic and antimicrobial principles of Hydrangeae Dulcis Folium. (2). Thunberginols C, D, and E, thunberginol G 3'-O-glucoside, (-)- hydrangenol 4'-O-glucoside, and (+)-hydrangenol 4'-O-glucoside
Yoshikawa, Masayuki,Matsuda, Hisashi,Shimoda, Hiroshi,Shimada, Hiromi,Harada, Emiko,Naitoh, Yoshikazu,Miki, Akiko,Yamahara, Johji,Murakami, Nobutoshi
, p. 1440 - 1447 (1996)
Following the characterization of thunberginols A, B, and F, six bioactive principles, thunberginols C, D, and E, thunberginol G 3'-O- glucoside, (-)-hydrangenol 4'-O-glucoside, and (+)-hydrangenol 4'-O- glucoside, were isolated from Hydrangeae Dulcis Folium, the processed leaves of Hydrangea macrophylla SERINGE var. thunbergii MAKINO, together with four kaempferol and quercetin oligoglycosides. Their chemical structures have been determined on the basis of chemical and physicochemical evidence. Thunberginols C, D, E, and G and (-)-hydrangenol 4'-O-glucoside showed antiallergic activity in the in vitro bioassay using the Schultz-Dale reaction. These components also exhibited inhibitory activities on the histamine release from rat mast cells and on the histamine-induced contraction in isolated guinea pig tracheal chain. In addition, thunberginols C, D, E, and G showed antimicrobial activities against oral bacteria.
Copper-Catalyzed Oxidative Cyclization of Carboxylic Acids
Sathyamoorthi, Shyam,Du Bois
supporting information, p. 6308 - 6311 (2016/12/23)
A method for converting C-H to C-O bonds through oxidative cyclization of carboxylic acids to generate lactone products is described. The reaction employs catalytic amounts of Cu(OAc)2 and potassium persulfate as the terminal oxidant and is performed open to air in an aqueous acetic acid solvent system. Preliminary mechanistic studies suggest that substrate oxidation likely proceeds by sulfate radical anion and that the Cu catalyst has no influence on the product-determining step. These conclusions differ from related investigations that propose the intermediacy of a carboxylate radical.
Synthesis of 3-arylisocoumarins by using acyl anion chemistry and synthesis of thunberginol A and cajanolactone A
Sudarshan, Kasireddy,Manna, Manash Kumar,Aidhen, Indrapal Singh
, p. 1797 - 1803 (2015/05/27)
A new strategy for the synthesis of 3-arylisocoumarins and 8-hydroxy-3-arylisocoumarins was investigated by using acyl anion chemistry for the initial C-C bond formation. The obtained keto esters and keto lactones as intermediates underwent based-promoted intramolecular cyclization to afford 3-arylisocoumarins in good yields. The developed methodology was applied for the synthesis of the important natural products thunberginol A and cajanolactone A.
Titanocene(III) chloride mediated radical-induced synthesis of 3,4-dihydroisocoumarins: synthesis of (±)-hydrangenol, (±)-phyllodulcin, (±)-macrophyllol and (±)-thunberginol G
Mandal, Samir Kumar,Roy, Subhas Chandra
experimental part, p. 11050 - 11057 (2009/04/11)
A radical-promoted synthesis of 3,4-dihydroisocoumarins has been achieved in moderate to good yields using titanocene(III) chloride (Cp2TiCl) as the radical initiator. The total synthesis of four naturally occurring dihydrocoumarins hydrangenol, phyllodulcin, macrophyllol and thunberginol G has been accomplished using the radical technology. Cp2TiCl was prepared in situ from commercially available titanocene dichloride (Cp2TiCl2) and Zn-dust in THF under argon.
Metabolic fate of orally administered phyllodulcin in rats
Yasuda, Takaaki,Kayaba, Saiko,Takahashi, Kana,Nakazawa, Takahiro,Ohsawa, Keisuke
, p. 1604 - 1607 (2007/10/03)
Naturally occurring phyllodulcin (1) was orally administered to rats to investigate its metabolic fate. Urinary metabolites were analyzed by three-dimensional HPLC. Phyllodulcin-3′-O-sulfate (2), phyllodulcin-3′-O-β-glucuronide (3), 2-[2-(3,4-dihydroxyphe
Chemical transformation from dihydroisocoumarin into benzylidene-phthalide by use of regiospecific oxidative lactonization mediated by copper chloride (H) - Syntheses of thunberginol F and hydramacrophyllol A and B
Yoshikawa,Harada,Yagi,Okuno,Muraoka,Koyama,Murakami
, p. 721 - 723 (2007/10/02)
Oxidative lactonization of 2-carboxystilbene mediated by CuCl2 proceeded regiospecifically to give the five-membered lactone. By utilizing this lactonization as a key reaction, chemical transformation from dihydroisocoumarine into benzylideneph
