499-20-7Relevant articles and documents
New benzoic acid and caffeoyl derivatives with anti-inflammatory activities isolated from leaves of Ilex kaushue
Kakumu, Yuya,Mitsunaga, Tohru,Nguyen, Thi Minh Tu,Yamauchi, Kosei
, (2021/08/16)
A new benzoic acid, 3-[2-(2-hydroxyphenyl)acetoxy]benzoic acid (1), and two new caffeoyl derivatives, methyl (3E,5Z)-di-O-caffeoylquinate (2) and dhurrin 6′-O-caffeate (3), along with 20 known compounds were isolated from the leaves of Ilex kaushue collected in Vietnam. Their structures were elucidated on the basis of 1 D and 2 D NMR spectroscopy, and high-resolution MS spectrometry. The absolute configuration of 2 and 3 was unambiguously established by comparison of experimental and calculated ECD spectra and/or chemical reactivity. In addition, new compounds were evaluated for inhibitory effects of their tumor necrosis factor-α (TNF-α) production and cell cytotoxicity on lipopolysaccharide-induced RAW264 macrophage cells. All of those moderately suppressed TNF-α production in ratios of approximately 50% or higher at 25–100 μM, without cell cytotoxicity.
General and Stereocontrolled Approach to the Chemical Synthesis of Naturally Occurring Cyanogenic Glucosides
Moller, Birger L.,Olsen, Carl E.,Motawia, Mohammed S.
supporting information, p. 1198 - 1202 (2016/05/24)
An effective method for the chemical synthesis of cyanogenic glucosides has been developed as demonstrated by the synthesis of dhurrin, taxiphyllin, prunasin, sambunigrin, heterodendrin, and epiheterodendrin. O-Trimethylsilylated cyanohydrins were prepared and subjected directly to glucosylation using a fully acetylated glucopyranosyl fluoride donor with boron trifluoride-diethyl etherate as promoter to afford a chromatographically separable epimeric mixture of the corresponding acetylated cyanogenic glucosides. The isolated epimers were deprotected using a triflic acid/MeOH/ion-exchange resin system without any epimerization of the cyanohydrin function. The method is stereocontrolled and provides an efficient approach to chemical synthesis of other naturally occurring cyanogenic glucosides including those with a more complex aglycone structure.
Taxiphyllin 6′-O-gallate, actinidioionoside 6′-O-gallate and myricetrin 2′-O-sulfate from the leaves of Syzygium samarangense and their biological activities
Mamdouh, Nabil Samy,Sugimoto, Sachiko,Matsunami, Katsuyoshi,Otsuka, Hideaki,Kamel, Mohamed Salah
, p. 1013 - 1018 (2015/02/19)
Three new compounds were isolated from a MeOH extract of the leaves of Syzygium samarangense, one new cyanogenic glucoside, taxiphyllin 6′-O-gallate (1), one new megastigmane glucoside, actinidioionoside 6′-O-gallate (2), and one new sulfated flavonoid rhamnoside, myricetrin 2″-O-sulfate (3), together with 14 known compounds, lupeol (4), demethoxymatteucinol (5), cryptostrobin (6), betulinic acid (7), β-sitosterol glucoside (8), 2R-prunasin (9), myrciaphenone A (10), 1-feruloyl-β-D-glucopyranoside (11), (3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxymegastigman-7-ene (12), guaijaverin (13), myricetin 4′-methyl ether 3-O-α-L-rhamno-pyranoside (14), myricetrin (15), gallic acid (16) and actinidioionoside (17). The structures of the new compounds were determined through a combination of spectroscopic, HPLC and chemical analyses.
Catalytic degradation of amygdalin by extracellular enzymes from Aspergillus niger
Chang, Jun,Zhang, Yan
experimental part, p. 195 - 200 (2012/06/16)
Amygdalin is a controversial anti-tumor natural product that has been used as an alternative cancer drug for many years. The anti-tumor mechanism and metabolism of amygdalin have been the focus of many studies. However, previous studies by our group demonstrated that amygdalin itself has no anti-tumor activity, but rather the active ingredients were determined to be amygdalin degradation products. To screen novel drugs with anti-tumor activity, the extracellular enzymes from Aspergillus niger were used to degrade amygdalin. Within 4 h of the catalytic reaction at 37°, amygdalin was rapidly degraded into four products. The products were then extracted and purified by column chromatography. By comparing the HPLC chromatograms, 1H NMR, 13C NMR and MS data, the products were identified as mandelonitrile, prunasin, benzaldehyde and phenyl-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2- yloxy)-acetonitrile (PTMT), a novel hydroxyl derivative of prunasin. Furthermore, pharmacology studies of these compounds demonstrated that 10 mg/kg of PTMT significantly suppressed the growth of S-18 tumor cells within 11 days in a concentration-dependent manner.
