193224-24-7Relevant articles and documents
Phenylpropanoid amides of serotonin accumulate in witches' broom diseased bamboo
Tanaka, Eiji,Tanaka, Chihiro,Mori, Naoki,Kuwahara, Yasumasa,Tsuda, Mitsuya
, p. 965 - 969 (2003)
Aciculosporium take (Ascomycota; Clavicipitaceae), causes the witches' broom disease in bamboo, particularly Phyllostachys bambusoides. Since it was observed that endogenous indole-3-acetic acid is reduced in the twigs of the diseased bamboo, the symptoms
Synthesis, biological activities and bioavailability of moschamine, a safflomide-type phenylpropenoic acid amide found in Centaurea cyanus
Park, Jae B.
, p. 1465 - 1472 (2012)
Moschamine is a phenylpropenoic acid amide found in plants. In this article, the synthesis and two biological activities (serotoninergic and cyclooxygenase (COX) inhibitory activities) and bioavailability of moschamine were described. Moschamine was synthesised and confirmed using NMR spectroscopic methods. Using the moschamine synthesised, serotoninergic and COX inhibitory activities were investigated. At the concentration of 10μmolL1, moschamine was able to inhibit forskolin-stimulated cAMP formation by 25% (pa very potent compound that is able to inhibit COX-I by 58% (p1. The oral bioavailability of moschamine was also determined in mice.
Serotonin derivatives, major safflower (Carthamus tinctorius L.) seed antioxidants, inhibit Low-Density Lipoprotein (LDL) oxidation and atherosclerosis in apolipoprotein E-deficient mice
Koyama, Naoto,Kuribayashi, Kanna,Seki, Tetsuya,Kobayashi, Katsunori,Furuhata, Yasufumi,Suzuki, Katsuya,Arisaka, Harumi,Nakano, Takashi,Amino, Yusuke,Ishii, Koichi
, p. 4970 - 4976 (2006)
The effects of defatted safflower seed extract and its phenolic constituents, serotonin derivatives, on atherosclerosis were studied. Ethanol-ethyl acetate extract of safflower seeds (SSE) inhibited low-density lipoprotein (LDL) oxidation induced in vitro
Synthesis of amide and ester derivatives of cinnamic acid and its analogs: Evaluation of their free radical scavenging and monoamine oxidase and cholinesterase inhibitory activities
Takao, Koichi,Toda, Kazuhiro,Saito, Takayuki,Sugita, Yoshiaki
, p. 1020 - 1027 (2017/11/17)
A series of cinnamic acid derivatives, amides (1–12) and esters (13–22), were synthesized, and structure–activity relationships for antioxidant activity, and monoamine oxidases (MAO) A and B, acetylcholinesterase, and butyrylcholinesterase (BChE) inhibitory activities were analyzed. Among the synthesized compounds, compounds 1–10, 12–18, and rosmarinic acid (23), which contained catechol, o-methoxyphenol or 5-hydroxy-indole moieties, showed potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity. Compounds 9–11, 15, 17–22 showed potent and selective MAO-B inhibitory activity. Compound 20 was the most potent inhibitor of MAO-B. Compounds 18 and 21 showed moderate BChE inhibitory activity. In addition, compound 18 showed potent antioxidant activity and MAO-B inhibitory activity. In a comparison of the cinnamic acid amides and esters, the amides exhibited more potent DPPH free radical scavenging activity, while the esters showed stronger inhibitory activities against MAO-B and BChE. These results suggested that cinnamic acid derivatives such as compound 18, p-coumaric acid 3,4-dihydroxyphenethyl ester, and compound 20, p-coumaric acid phenethyl ester, may serve as lead compounds for the development of novel MAO-B inhibitors and candidate lead compounds for the prevention or treatment of Alzheimer’s disease.
COSMETIC COMPOSITION FOR STIMULATING THE CELLULAR ANTI-AGING FUNCTIONS OF THE SKIN
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Paragraph 0051 - 0054; 0084 - 0094, (2015/02/19)
The use of a compound of general formula (I), where: R1, R2, R3, R4, R5 are identical or different and each represent a hydrogen atom, a halogen atom, a hydroxyl group or an —OR′ radical in which R′ i
Total synthesis of (+)- and (-)-decursivine and (±)-serotobenine through a cascade witkop photocyclization/elimination/addition sequence: Scope and mechanistic insights
Hu, Weimin,Qin, Hua,Cui, Yuxin,Jia, Yanxing
supporting information, p. 3139 - 3147 (2013/03/28)
In this article, the total syntheses of antimalarial compound decursivine and its biologically inactive sibling serotobenine are presented. The biomimetic synthesis of (±)-serotobenine was investigated first, but failed. During the subsequent investigatio
Synthesis and structure-activity relationships of serotonin derivatives effect on α-glucosidase inhibition
Takahashi, Toshiyuki,Miyazawa, Mitsuo
, p. 1762 - 1770 (2012/11/14)
The α-glucosidase inhibitory activities of serotonin derivatives were evaluated. Two serotonin derivatives, N-p-coumaroyl serotonin (2) and N-caffeoyl serotonin (4) exhibited most potent inhibition on α-glucosidase, whereas, cinnamic acid derivatives were
Synthesis and structure-activity relationships of phenylpropanoid amides of serotonin on tyrosinase inhibition
Takahashi, Toshiyuki,Miyazawa, Mitsuo
supporting information; experimental part, p. 1983 - 1986 (2011/04/24)
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 activity strongly, the serotonin moiety, the amide linkage and the cinnamic acid moiety affect tyrosinase inhibitory activity. Among tested compounds, compound 4 which contains cathechol moiety exhibited the most antioxidant activity (EC50 = 19.4 ± 2.0 μM), and compound 6 exhibited significant tyrosinase inhibitory activity (IC50 = 5.4 ± 3.6 μM). Our data suggests that a useful clue for the design and development of new tyrosinase inhibitors.
Serotonin derivatives as inhibitors of β-secretase (BACE 1)
Takahashi,Miyazawa, Mitsuo
experimental part, p. 301 - 305 (2012/01/02)
All serotonin derivatives described here (1-9) inhibited BACE 1 in a dose dependent manner. The 50% Inhibition Concentration (IC50) of N-cinnamoyl serotonin (1) was 86.7 ± 4.0 μM. The peptide conjugation of serotonin derivatives influenced the BACE 1 inhibitory activity. Among serotonin derivatives (1-8), introduction of substituents, such as hydroxyl and methoxy groups at the 4′-position decreased the inhibitory activity (N-p-coumaroyl serotonin (2), N-p-methoxy cinnamoyl serotonin (3)). With a hydroxylgroup at the 4′-position, and the meta-hydroxy function being substituted by a hydroxyl group or methoxy group (Ncaffeoyl serotonin (4), N-feruloyl serotonin (5)), inhibitory activity was weakened, (IC50 > 400 μM). BACE 1 inhibitory activity was effected by the substituents of the cinnamic acid moiety. This is the first report on Structure-Activity- Relationships (SAR) for the BACE 1-inhibiting activity of serotonin derivatives. These serotonin derivatives, which have anti-oxidative effects as well are expected to be useful in the study of the mechanisms of Alzheimer's disease.
N-[(Dihydroxyphenyl)acyl]serotonins as potent inhibitors of tyrosinase from mouse and human melanoma cells
Yamazaki, Yoshimitsu,Kawano, Yasuhiro,Yamanaka, Akiko,Maruyama, Susumu
body text, p. 4178 - 4182 (2010/04/26)
A series of N-acyl derivatives of tyramine, tryptamine, and serotonin were synthesized and tested on anti-melanogenic activity. The serotonin derivatives such as N-caffeoylserotonin (3) and N-protocatechuoylserotonin (9) were inhibitory to tyrosinase from
