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Toshiyuki Furutani et al.
The Journal of organic chemistry, 67(13), 4599-4601 (2002-06-22)
A practical synthesis of methyl (2R,3S)-3-(4-methoxyphenyl)glycidate (-)-2, a key intermediate for diltiazem (1), was developed. Treatment of methyl (E)-4-methoxycinnamate 3 with chiral dioxirane, generated from chiral ketone 4, provided (-)-2 in 77% ee and 89% yield. The crude mixture of
Jinbing Liu et al.
Bioorganic & medicinal chemistry, 16(3), 1096-1102 (2008-03-08)
A series of 1-(1-arylethylidene)thiosemicarbazide compounds and their analogues were synthesized and characterized by 1H NMR, MS. Their tyrosinase inhibitory activities were investigated by an assay based on the catalyzing ability of tyrosinase for the oxidation of L-DOPA, comparing with 4-methoxycinnamic
Yoshio Nakagawa et al.
Biochemical pharmacology, 66(1), 63-73 (2003-06-24)
The metabolism and action of trans-anethole (anethole) and the estrogen-like activity of the compound and its metabolites were studied in freshly isolated rat hepatocytes and cultured MCF-7 human breast cancer cells, respectively. The incubation of hepatocytes with anethole (0.25-2.0mM) caused
M A Lea et al.
Anticancer research, 19(3A), 1971-1976 (1999-09-02)
The objective of this investigation was to study the relationship between histone acetylation and growth inhibition by 4-phenylbutyrate and structural analogs. Inhibition of growth of DS19 mouse erythroleukemia cells and K562 human leukemic cells by 4-phenylbutyrate did not appear to
H V Meyers et al.
Carbohydrate research, 197, 15-32 (1990-03-25)
This study completes the spectroscopic basis for a novel oligosaccharide microanalytical method, wherein a derivatization sequence provides monosaccharide subunits bearing two types of exciton-coupling chromophore groups ("bichromophoric") for circular dichroic spectroscopy, namely 4-bromobenzoate (lambda max 245 nm) and 4-methoxycinnamate (lambda
Natasha Cook et al.
The Australasian journal of dermatology, 43(2), 133-135 (2002-05-02)
We report a case of photoallergic contact dermatitis to two sunscreen agents, methoxycinnamate and oxybenzone, occurring in a 6-year-old Asian boy.
Sirintorn Yibchok-anun et al.
Basic & clinical pharmacology & toxicology, 102(5), 476-482 (2008-03-19)
This study investigated the effect of p-methoxycinnamic acid (p-MCA) on plasma glucose and insulin concentrations in normal and streptozotocin-induced diabetic rats. In both fasting and glucose-loading conditions, an oral administration of p-MCA (40-100 mg/kg) significantly decreased plasma glucose and also
Gia-Sheu Lee et al.
Biotechnology letters, 28(8), 581-585 (2006-04-15)
Using Novozym 435 as catalyst, the syntheses of ethyl ferulate (EF) from ferulic acid (4-hydroxy 3-methoxy cinnamic acid) and ethanol, and octyl methoxycinnamate (OMC) from p-methoxycinnamic acid and 2-ethyl hexanol were successfully carried out in this study. A conversion of
Hisashi Matsuda et al.
Bioorganic & medicinal chemistry letters, 15(7), 1949-1953 (2005-03-23)
1'S-1'-Acetoxychavicol acetate from the rhizomes of Alpinia galanga inhibited nitric oxide (NO) production in lipopolysaccharide-activated mouse peritoneal macrophages with an IC(50) value of 2.3 microM. To clarify the structure-activity relationship of 1'S-1'-acetoxychavicol acetate, various natural and synthetic phenylpropanoids and synthetic
Jinbing Liu et al.
European journal of medicinal chemistry, 44(4), 1773-1778 (2008-06-06)
A series of alkylidenethiosemicarbazide compounds were synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. The results showed that most of the synthesized compounds exhibited significant inhibitory activities. Especially, compound 1f was found to be
Wai Mun Loke et al.
The Journal of nutrition, 139(12), 2309-2314 (2009-10-09)
Flavonoids are phytochemicals that are widespread in the human diet. Despite limitations in their bioavailability, experimental and epidemiological data suggest health benefits of flavonoid consumption. Valid biomarkers of flavonoid intake may be useful for estimating exposure in a range of
S Adisakwattana et al.
Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme, 43(11), 766-773 (2011-10-20)
p-Methoxycinnamic acid (p-MCA) is a cinnamic acid derivative that shows various pharmacologic actions such as hepatoprotective and antihyperglycemic activities. The present study was to elucidate the mechanisms by which p-MCA increases [Ca²⁺]i and insulin secretion in INS-1 cells. p-MCA (100
Wiesława Bylka
Acta poloniae pharmaceutica, 61(4), 307-308 (2004-12-04)
Two isomers E- and Z-p-methoxycinnamic acid were isolated from the leaves with stems of A. vulgaris L. and their structures were determined by 1HMR and 13C NMR spectral data.
Qin Yan et al.
European journal of medicinal chemistry, 44(10), 4235-4243 (2009-06-26)
A series of novel 5-benzylidene barbiturate and thiobarbiturate derivatives were synthesized and evaluated as tyrosinase inhibitors and antibacterial agents. The results demonstrated that some compounds had more potent inhibitory activities than the parent compound 4-hydroxybenzaldehyde (IC(50)=1.22 mM). Particularly, compounds 1a
Victor S Sobolev et al.
Journal of agricultural and food chemistry, 54(10), 3505-3511 (2006-05-17)
The peanut plant (Arachis hypogaea) is known to produce stilbene phytoalexins as a defensive response to fungal invasion; however, the distribution of phytoalexins among different organs of the peanut plant at early stages of growth under axenic conditions has not
Gunasekaran Sivagami et al.
Chemico-biological interactions, 196(1-2), 11-22 (2012-02-14)
We investigated the chemopreventive effect of p-methoxycinnamic acid (p-MCA), an active phenolic acid of rice bran, turmeric, and Kaemperfia galanga against 1,2-dimethylhydrazine-induced rat colon carcinogenesis. Male albino Wistar rats were randomly divided into six groups. Group 1 consisted of control
Jinbing Liu et al.
Bioorganic & medicinal chemistry letters, 21(8), 2376-2379 (2011-03-18)
A series of dihydropyrimidin-(2H)-one analogues and rhodanine derivatives were synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. The results showed that some of the synthesized compounds exhibited significant inhibitory activities. Especially, compound 15 bearing
Wei Yi et al.
European journal of medicinal chemistry, 45(2), 639-646 (2009-11-26)
A series of novel 4-hydroxybenzaldehyde derivatives were synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were investigated. Most of target compounds had more potent inhibitory activities than the parent compound 4-hydroxybenzaldehyde (IC(50)=1.22 mM). Interestingly, compound 3c
So Ra Kim et al.
Brain research. Cognitive brain research, 17(2), 454-461 (2003-07-26)
We previously reported that phenylpropanoids isolated from the roots of Scrophularia buergeriana Miquel (Scrophulariaceae) protected cultured cortical neurons against glutamate-induced neurotoxicity [Kim and Kim, Phytochemistry, 54 (2000) 503-509; Kim et al., Br. J. Pharmacol. 135 (2002) 1281-1291]. In the present
H W Lim et al.
Archives of dermatology, 126(3), 317-323 (1990-03-01)
Twelve patients with photodermatitis for longer than 3 months' duration were identified: 1 patient with chronic photocontact dermatitis, 1 with persistent photosensitivity following exposure to a systemic medication, 6 with persistent light reactivity, and 4 with actinic reticuloid. There were
J P D van Veldhoven et al.
Bioorganic & medicinal chemistry letters, 21(9), 2736-2739 (2010-12-21)
Nicotinic acid (niacin) has been used for decades as an antidyslipidemic drug in man. Its main target is the hydroxy-carboxylic acid receptor HCA2 (GPR109A), a G protein-coupled receptor. Other acids and esters such as methyl fumarate also interact with the
Eun Ju Lee et al.
Planta medica, 68(5), 407-411 (2002-06-12)
Phenylpropanoids isolated from the roots of Scrophularia buergeriana MIQ. (Scrophulariaceae) protected primary cultures of rat hepatocytes from toxicity induced by carbon tetrachloride (CCl(4) ). In this report, we show that two of these phenylpropanoids, 4-O-E- p-methoxycinnamoyl-alpha-L-rhamnopyranoside ester ( 1) and
Dan Xu et al.
Journal of medical microbiology, 60(Pt 11), 1626-1632 (2011-07-02)
This study focused on identifying possible new options derived from natural sources for the treatment of bacterial infections. Several natural products were investigated for their potential in modulating Shigella-host-cell interactions. The proliferation of Shigella sonnei was effectively inhibited inside HEp-2
Wei Yi et al.
Bioorganic & medicinal chemistry letters, 18(24), 6490-6493 (2008-11-11)
A series of helicid analogues were synthesized and evaluated as tyrosinase inhibitors. The results demonstrated that some compounds had more potent inhibitory activities than arbutin (IC(50) 7.3 mM). In particular, compound 1c bearing 4,6-O-benzylidene substituent on the sugar moiety was
Toshiyuki Takahashi et al.
Bioorganic & medicinal chemistry letters, 21(7), 1983-1986 (2011-03-08)
In this manuscript, we synthesized a series of phenylpropanoid amide of serotonin 1-9, analyzed their structural importance for two biologic activities (antioxidant activity and tyrosinase inhibitory activity). While the serotonin moiety and the amide linkage of serotonin derivatives affect antioxidant
Sirichai Adisakwattana et al.
Life sciences, 78(4), 406-412 (2005-09-06)
We investigated the antihyperglycemic effect of p-methoxycinnamic acid (p-MCA), a cinnamic acid derivative, on plasma glucose and insulin concentrations, activities of hepatic glucose-regulating enzymes and hepatic glycogen content in normal and streptozotocin (STZ)-induced diabetic rats. p-MCA (10-100 mg/kg, PO) dose-dependently
N Ikemoto et al.
Carbohydrate research, 239, 11-33 (1993-02-01)
The microscale analytical method that is being developed in this group for the structure determination of oligosaccharides yields monosaccharide derivatives bearing two types of chromophores suitable for exciton-coupling, namely, 4-bromobenzoate (lambda max 245 nm) and 4-methoxycinnamate (lambda max 311 nm).
H M Chawla et al.
Journal of photochemistry and photobiology. B, Biology, 105(1), 25-33 (2011-08-02)
A series of novel calix[4]arene enones (5-7) and cinnamates (12-14) have been synthesized and evaluated for ensuring protection from ultraviolet radiation (UVR). Spectroscopic analyses has revealed that compound 6 absorbs ultraviolet radiations between 280 and 350 nm with an absorption
So Ra Kim et al.
British journal of pharmacology, 135(5), 1281-1291 (2002-03-06)
1. We previously reported that four new phenylpropanoid glycosides and six known cinnamate derivatives isolated from roots of Scrophularia buergeriana Miquel (Scrophulariaceae) protected cultured cortical neurons from neurotoxicity induced by glutamate. Here, we have investigated the structure-activity relationships in the
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