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Sirintorn Yibchokanun - One of the best experts on this subject based on the ideXlab platform.

  • Cinnamic Acid and its derivatives inhibit fructose mediated protein glycation
    2012
    Co-Authors: Sirichai Adisakwattana, Weerachat Sompong, Sathaporn Ngamukote, Aramsri Meeprom, Sirintorn Yibchokanun
    Abstract:

    Cinnamic Acid and its derivatives have shown a variety of pharmacologic properties. However, little is known about the antiglycation properties of Cinnamic Acid and its derivatives. The present study sought to characterize the protein glycation inhibitory activity of Cinnamic Acid and its derivatives in a bovine serum albumin (BSA)/fructose system. The results demonstrated that Cinnamic Acid and its derivatives significantly inhibited the formation of advanced glycation end products (AGEs) by approximately 11.96-63.36% at a concentration of 1 mM. The strongest inhibitory activity against the formation of AGEs was shown by Cinnamic Acid. Furthermore, Cinnamic Acid and its derivatives reduced the level of fructosamine, the formation of N(ɛ)-(carboxymethyl) lysine (CML), and the level of amyloid cross β-structure. Cinnamic Acid and its derivatives also prevented oxidative protein damages, including effects on protein carbonyl formation and thiol oxidation of BSA. Our findings may lead to the possibility of using Cinnamic Acid and its derivatives for preventing AGE-mediated diabetic complications.

  • a series of Cinnamic Acid derivatives and their inhibitory activity on intestinal alpha glucosidase
    2009
    Co-Authors: Sirichai Adisakwattana, Praew Chantarasinlapin, Haruthai Thammarat, Sirintorn Yibchokanun
    Abstract:

    Inhibition of alpha-glucosidase and alpha-amylase delays the digestion of starch and disaccharides to absorbable monosaccharides, resulting in a reduction of postprandial hyperglycemia. Finding effective mammalian alpha-glucosidase inhibitors from natural sources can be beneficial in the prevention and treatment of diabetes mellitus. We investigated the inhibitory activity of Cinnamic Acid derivatives against rat intestinal alpha-glucosidase and porcine pancreatic alpha-amylase in vitro. Among 11 Cinnamic Acid derivatives, caffeic Acid, ferulic Acid, and isoferulic Acid were the most potent inhibitors against intestinal maltase with IC(50) values of 0.74 +/- 0.01, 0.79 +/- 0.04, and 0.76 +/- 0.03 mM, respectively, whereas ferulic Acid (IC(50) = 0.45 +/- 0.01 mM) and isoferulic Acid (IC(50) = 0.45 +/- 0.01 mM) were effective intestinal sucrase inhibitors. However, all Cinnamic Acid derivatives were found to be inactive in pancreatic alpha-amylase inhibition. Kinetic analysis revealed that intestinal maltase was inhibited by caffeic Acid, ferulic Acid, and isoferulic Acid in a mixed-inhibition manner. In addition, ferulic Acid and isoferulic Acid inhibited intestinal sucrase in a mixed type manner, whereas caffeic Acid was a non-competitive inhibitor. The combination of isoferulic Acid and acarbose showed an additive inhibition on intestinal sucrase. This study could provide a new insight into naturally occurring intestinal alpha-glucosidase inhibitors that could be useful for treatment of diabetes and its complications.

  • insulin releasing properties of a series of Cinnamic Acid derivatives in vitro and in vivo
    2008
    Co-Authors: Sirichai Adisakwattana, Preecha Moonsan, Sirintorn Yibchokanun
    Abstract:

    Cinnamic Acid derivatives are naturally occurring substances found in fruits, vegetables, and flowers and are consumed as dietary phenolic compounds. In the present study, Cinnamic Acid and its derivatives were evaluated for insulin secreting activity in perfused rat pancreas and pancreatic β-cells (INS-1) as well as an increase in [Ca2+]i in vitro. The presence of m-hydroxy or p-methoxy residues on Cinnamic Acid was a significantly important substituent as an effective insulin releasing agent. The introduction of p-hydroxy and m-methoxy-substituted groups in Cinnamic Acid structure (ferulic Acid) displayed the most potent insulin secreting agent among those of Cinnamic Acid derivatives. In particular, the stimulatory insulin secreting activities of test compounds were associated with a rise of [Ca2+]i in INS-1. In perfused rat pancreas, m-hydroxyCinnamic Acid, p-methoxyCinnamic Acid, and ferulic Acid (100 μM) significantly stimulated insulin secretion during 10 min of administration. The onset time of in...

  • structure activity relationships of trans Cinnamic Acid derivatives on α glucosidase inhibition
    2004
    Co-Authors: Sirichai Adisakwattana, Kasem Sookkongwaree, Sophon Roengsumran, Amorn Petsom, Nattaya Ngamrojnavanich, Warinthorn Chavasiri, Sujitra Deesamer, Sirintorn Yibchokanun
    Abstract:

    trans-Cinnamic Acid and its derivatives were investigated for the alpha-glucosidase inhibitory activity. 4-Methoxy-trans-Cinnamic Acid and 4-methoxy-trans-Cinnamic Acid ethyl ester showed the highest potent inhibitory activity among those of trans-Cinnamic Acid derivatives. The presence of substituents at 4-position in trans-Cinnamic Acid altered the alpha-glucosidase inhibitory activity. Increasing of bulkiness and the chain length of 4-alkoxy substituents as well as the increasing of the electron withdrawing group have been shown to decrease the inhibitory activity. 4-Methoxy-trans-Cinnamic Acid was a noncompetitive inhibitor for alpha-glucosidase, whereas, 4-methoxy-trans-Cinnamic Acid ethyl ester was a competitive inhibitor. These results indicated that trans-Cinnamic Acid derivatives could be classified as a new group of alpha-glucosidase inhibitors.

Ross Barnard - One of the best experts on this subject based on the ideXlab platform.

  • hydroxyl substituted benzoic Acid Cinnamic Acid derivatives tyrosinase inhibitory kinetics anti melanogenic activity and molecular docking studies
    2020
    Co-Authors: Yasir Nazir, Aamer Saeed, Muhammad Rafiq, Samina Afzal, Anser Ali, Muhammad Latif, Johannes Zuegg, Waleed M Hussein, Christian Fercher, Ross Barnard
    Abstract:

    Abstract The inhibition of tyrosinase is an established strategy for treating hyperpigmentation. Our previous findings demonstrated that Cinnamic Acid and benzoic Acid scaffolds can be effective tyrosinase inhibitors with low toxicity. The hydroxyl substituted benzoic and Cinnamic Acid moieties of these precursors were incorporated into new chemotypes that displayed in vitro inhibitory effect against mushroom tyrosinase. The most active compound, (2-(3-methoxyphenoxy)-2-oxoethyl (E)-3-(4-hydroxyphenyl) acrylate) 6c, inhibited tyrosinase with an IC50 of 5.7 µM, while (2-(3-methoxyphenoxy)-2-oxoethyl 2, 4-dihydroxybenzoate) 4d had an IC50 of 23.8 µM. In comparison, the positive control, kojic Acid showed tyrosinase inhibition with an IC50 = 16.7 µM. Analysis of enzyme kinetics revealed that 6c and 4d displayed noncompetitive reversible inhibition of the second tyrosinase enzymatic reaction with Ki values of 11 µM and 130 µM respectively. In silico docking studies with mushroom tyrosinase (PDB ID 2Y9X) predicted possible binding modes in the catalytic site for these active compounds. The phenolic para-hydroxy group of the most active compound 6c is predicted to interact with the catalytic site Cu++ ion. The methoxy part of this compound is predicted to form a hydrogen bond with Arg 268. Compound 6c had no observable toxic effects on cell morphology or cell viability at the highest tested concentration of 91.4 µM. When dosed at 91.4 µM onto B16F10 melanoma cells in vitro 6c showed anti-melanogenic effects equivalent to kojic Acid at 880 µM. 6c displayed no PAINS (pan-assay interference compounds) alerts. Our results show that compound 6c is a more potent tyrosinase inhibitor than kojic Acid and is a candidate for further development. Our exposition of the details of the interactions between 6c and the catalytic pocket of tyrosinase provides a basis for rational design of additional potent inhibitors of tyrosinase, built on the Cinnamic Acid scaffold.

Sirichai Adisakwattana - One of the best experts on this subject based on the ideXlab platform.

  • Cinnamic Acid and its derivatives mechanisms for prevention and management of diabetes and its complications
    2017
    Co-Authors: Sirichai Adisakwattana
    Abstract:

    With recent insight into the development of dietary supplements and functional foods, search of effective phytochemical compounds and their mechanisms involved in prevention and management of diabetes and its complications are now being assessed. Cinnamic Acid and its derivatives occur naturally in high levels of plant-based foods. Among various biological activities, Cinnamic Acid and its derivatives are associated with a beneficial influence on diabetes and its complications. The aim of the review is to summarize the potential mechanisms of these compounds for prevention and management of diabetes and its complications. Based on several in vitro studies and animal models, Cinnamic Acid and its derivatives act on different mechanism of actions, including stimulation of insulin secretion, improvement of pancreatic β-cell functionality, inhibition of hepatic gluconeogenesis, enhanced glucose uptake, increased insulin signaling pathway, delay of carbohydrate digestion and glucose absorption, and inhibition of protein glycation and insulin fibrillation. However, due to the limited intestinal absorption being a result of low bioavailability of Cinnamic Acid and its derivatives, current improvement efforts with entrapping into solid and liquid particles are highlighted. Further human clinical studies are needed to clarify the effects of Cinnamic Acid and its derivatives in diabetic patients.

  • Cinnamic Acid and its derivatives inhibit fructose mediated protein glycation
    2012
    Co-Authors: Sirichai Adisakwattana, Weerachat Sompong, Sathaporn Ngamukote, Aramsri Meeprom, Sirintorn Yibchokanun
    Abstract:

    Cinnamic Acid and its derivatives have shown a variety of pharmacologic properties. However, little is known about the antiglycation properties of Cinnamic Acid and its derivatives. The present study sought to characterize the protein glycation inhibitory activity of Cinnamic Acid and its derivatives in a bovine serum albumin (BSA)/fructose system. The results demonstrated that Cinnamic Acid and its derivatives significantly inhibited the formation of advanced glycation end products (AGEs) by approximately 11.96-63.36% at a concentration of 1 mM. The strongest inhibitory activity against the formation of AGEs was shown by Cinnamic Acid. Furthermore, Cinnamic Acid and its derivatives reduced the level of fructosamine, the formation of N(ɛ)-(carboxymethyl) lysine (CML), and the level of amyloid cross β-structure. Cinnamic Acid and its derivatives also prevented oxidative protein damages, including effects on protein carbonyl formation and thiol oxidation of BSA. Our findings may lead to the possibility of using Cinnamic Acid and its derivatives for preventing AGE-mediated diabetic complications.

  • a series of Cinnamic Acid derivatives and their inhibitory activity on intestinal alpha glucosidase
    2009
    Co-Authors: Sirichai Adisakwattana, Praew Chantarasinlapin, Haruthai Thammarat, Sirintorn Yibchokanun
    Abstract:

    Inhibition of alpha-glucosidase and alpha-amylase delays the digestion of starch and disaccharides to absorbable monosaccharides, resulting in a reduction of postprandial hyperglycemia. Finding effective mammalian alpha-glucosidase inhibitors from natural sources can be beneficial in the prevention and treatment of diabetes mellitus. We investigated the inhibitory activity of Cinnamic Acid derivatives against rat intestinal alpha-glucosidase and porcine pancreatic alpha-amylase in vitro. Among 11 Cinnamic Acid derivatives, caffeic Acid, ferulic Acid, and isoferulic Acid were the most potent inhibitors against intestinal maltase with IC(50) values of 0.74 +/- 0.01, 0.79 +/- 0.04, and 0.76 +/- 0.03 mM, respectively, whereas ferulic Acid (IC(50) = 0.45 +/- 0.01 mM) and isoferulic Acid (IC(50) = 0.45 +/- 0.01 mM) were effective intestinal sucrase inhibitors. However, all Cinnamic Acid derivatives were found to be inactive in pancreatic alpha-amylase inhibition. Kinetic analysis revealed that intestinal maltase was inhibited by caffeic Acid, ferulic Acid, and isoferulic Acid in a mixed-inhibition manner. In addition, ferulic Acid and isoferulic Acid inhibited intestinal sucrase in a mixed type manner, whereas caffeic Acid was a non-competitive inhibitor. The combination of isoferulic Acid and acarbose showed an additive inhibition on intestinal sucrase. This study could provide a new insight into naturally occurring intestinal alpha-glucosidase inhibitors that could be useful for treatment of diabetes and its complications.

  • insulin releasing properties of a series of Cinnamic Acid derivatives in vitro and in vivo
    2008
    Co-Authors: Sirichai Adisakwattana, Preecha Moonsan, Sirintorn Yibchokanun
    Abstract:

    Cinnamic Acid derivatives are naturally occurring substances found in fruits, vegetables, and flowers and are consumed as dietary phenolic compounds. In the present study, Cinnamic Acid and its derivatives were evaluated for insulin secreting activity in perfused rat pancreas and pancreatic β-cells (INS-1) as well as an increase in [Ca2+]i in vitro. The presence of m-hydroxy or p-methoxy residues on Cinnamic Acid was a significantly important substituent as an effective insulin releasing agent. The introduction of p-hydroxy and m-methoxy-substituted groups in Cinnamic Acid structure (ferulic Acid) displayed the most potent insulin secreting agent among those of Cinnamic Acid derivatives. In particular, the stimulatory insulin secreting activities of test compounds were associated with a rise of [Ca2+]i in INS-1. In perfused rat pancreas, m-hydroxyCinnamic Acid, p-methoxyCinnamic Acid, and ferulic Acid (100 μM) significantly stimulated insulin secretion during 10 min of administration. The onset time of in...

  • structure activity relationships of trans Cinnamic Acid derivatives on α glucosidase inhibition
    2004
    Co-Authors: Sirichai Adisakwattana, Kasem Sookkongwaree, Sophon Roengsumran, Amorn Petsom, Nattaya Ngamrojnavanich, Warinthorn Chavasiri, Sujitra Deesamer, Sirintorn Yibchokanun
    Abstract:

    trans-Cinnamic Acid and its derivatives were investigated for the alpha-glucosidase inhibitory activity. 4-Methoxy-trans-Cinnamic Acid and 4-methoxy-trans-Cinnamic Acid ethyl ester showed the highest potent inhibitory activity among those of trans-Cinnamic Acid derivatives. The presence of substituents at 4-position in trans-Cinnamic Acid altered the alpha-glucosidase inhibitory activity. Increasing of bulkiness and the chain length of 4-alkoxy substituents as well as the increasing of the electron withdrawing group have been shown to decrease the inhibitory activity. 4-Methoxy-trans-Cinnamic Acid was a noncompetitive inhibitor for alpha-glucosidase, whereas, 4-methoxy-trans-Cinnamic Acid ethyl ester was a competitive inhibitor. These results indicated that trans-Cinnamic Acid derivatives could be classified as a new group of alpha-glucosidase inhibitors.

Yasir Nazir - One of the best experts on this subject based on the ideXlab platform.

  • hydroxyl substituted benzoic Acid Cinnamic Acid derivatives tyrosinase inhibitory kinetics anti melanogenic activity and molecular docking studies
    2020
    Co-Authors: Yasir Nazir, Aamer Saeed, Muhammad Rafiq, Samina Afzal, Anser Ali, Muhammad Latif, Johannes Zuegg, Waleed M Hussein, Christian Fercher, Ross Barnard
    Abstract:

    Abstract The inhibition of tyrosinase is an established strategy for treating hyperpigmentation. Our previous findings demonstrated that Cinnamic Acid and benzoic Acid scaffolds can be effective tyrosinase inhibitors with low toxicity. The hydroxyl substituted benzoic and Cinnamic Acid moieties of these precursors were incorporated into new chemotypes that displayed in vitro inhibitory effect against mushroom tyrosinase. The most active compound, (2-(3-methoxyphenoxy)-2-oxoethyl (E)-3-(4-hydroxyphenyl) acrylate) 6c, inhibited tyrosinase with an IC50 of 5.7 µM, while (2-(3-methoxyphenoxy)-2-oxoethyl 2, 4-dihydroxybenzoate) 4d had an IC50 of 23.8 µM. In comparison, the positive control, kojic Acid showed tyrosinase inhibition with an IC50 = 16.7 µM. Analysis of enzyme kinetics revealed that 6c and 4d displayed noncompetitive reversible inhibition of the second tyrosinase enzymatic reaction with Ki values of 11 µM and 130 µM respectively. In silico docking studies with mushroom tyrosinase (PDB ID 2Y9X) predicted possible binding modes in the catalytic site for these active compounds. The phenolic para-hydroxy group of the most active compound 6c is predicted to interact with the catalytic site Cu++ ion. The methoxy part of this compound is predicted to form a hydrogen bond with Arg 268. Compound 6c had no observable toxic effects on cell morphology or cell viability at the highest tested concentration of 91.4 µM. When dosed at 91.4 µM onto B16F10 melanoma cells in vitro 6c showed anti-melanogenic effects equivalent to kojic Acid at 880 µM. 6c displayed no PAINS (pan-assay interference compounds) alerts. Our results show that compound 6c is a more potent tyrosinase inhibitor than kojic Acid and is a candidate for further development. Our exposition of the details of the interactions between 6c and the catalytic pocket of tyrosinase provides a basis for rational design of additional potent inhibitors of tyrosinase, built on the Cinnamic Acid scaffold.

Baoan Song - One of the best experts on this subject based on the ideXlab platform.

  • design synthesis anti tmv activity and preliminary mechanism of Cinnamic Acid derivatives containing dithioacetal moiety
    2020
    Co-Authors: Yanju Wang, Yuqin Luo, Baoan Song
    Abstract:

    Abstract A series of Cinnamic Acid derivatives, which contained dithioacetal moiety, were designed and synthesized, and their anti-plant virus activity against Tobacco mosaic virus (TMV) were evaluated. Most target compounds exhibited good anti-plant virus activities. Compound 2y, especially at 500 mg/L concentration, had an excellent activity against TMV, and its curative, protective, and inactivating activities were 62.5%, 61.8%, and 83.5%, respectively. These activity values were significantly superior to those of ribavirin (45.9%, 39.8%, and 70.3%) and xiangcaoliusuobingmi (44.7%, 48.3%, and 71.7%) and comparable to those of ningnanmycin (61.9%, 53.3%, and 85.2%). Compound 2y presented an EC50 value of 50.7 mg/L for inactivating activity against TMV, which was superior to those of ningnanmycin (51.5 mg/L), ribavirin (160.4 mg/L), and xiangcaoliusuobingmi (83.0 mg/L). Through transmission electron microscopy, we found that compound 2y caused a certain degree of damage to TMV particles, which caused them to break and bend. Four conventional hydrogen bonds were formed with amino Acid residues GLN34, THR37, ARG90, and ARG46 of TMV coat protein (CP) through molecular docking. Microscale thermophoresis test results showed that compound 2y with TMV CP had a strong binding force, and the dissociation constant (Kd) was 1.6 μM. In summary, the Cinnamic Acid derivatives containing dithioacetal moiety provide a foundation for further research on antiviral agents.

  • Novel 1,3,4-Oxadiazole Derivatives Containing a Cinnamic Acid Moiety as Potential Bactericide for Rice Bacterial Diseases
    2019
    Co-Authors: Shaobo Wang, Xiuhai Gan, Yanju Wang, Jixiang Chen, Yuyuan Yang, Baoan Song
    Abstract:

    Rice bacterial leaf blight and leaf streak are two important bacterial diseases of rice, which can result in yield loss. Currently, effective antimicrobials for rice bacterial diseases are still lacking. Thus, to develop highly effective and low-risk bactericides, 31 novel 1,3,4-oxadiazole derivatives containing a Cinnamic Acid moiety were designed and synthesized. Bioassay results demonstrated that all compounds exhibited good antibacterial activities in vitro. Significantly, compounds 5r and 5t showed excellent antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo) and X. oryzae pv. oryzicola (Xoc), with the 50% effective concentration (EC50) values of 0.58 and 0.34, and 0.44 and 0.20 μg/mL, respectively. These compounds were much better than thiodiazole copper (123.10 and 161.52 μg/mL) and bismerthiazol (85.66 and 110.96 μg/mL). Moreover, compound 5t had better protective and curative activities against rice bacterial leaf blight and leaf streak than thiodiazole copper and bismerthiazol in vivo. Simultaneously, the in vivo efficacy of the compounds was demonstrated by real-time quantitative PCR to quantify bacterial titers. In addition, a three-dimensional quantitative structure⁻activity relationship model was created and presented good predictive ability. This work provides support for 1,3,4-oxadiazole derivatives containing a Cinnamic Acid moiety as a potential new bactericide for rice bacterial diseases

  • Synthesis, Nematicidal Evaluation, and 3D-QSAR Analysis of Novel 1,3,4-Oxadiazole–Cinnamic Acid Hybrids
    2018
    Co-Authors: Jixiang Chen, Xiuhai Gan, Yongzhong Chen, Baojing Song, Baoan Song
    Abstract:

    A series of novel 1,3,4-oxadiazole–Cinnamic Acid hybrids were synthesized. The bioassays results indicated that compounds 1, 2, 7, and 8 showed excellent nematicidal activities against Tylenchulus semipenetrans with LC50,48h values of 9.7 ± 1.6, 15.6 ± 2.8, 8.0 ± 0.5, and 19.8 ± 2.9 mg/L, respectively, which were higher than those of avermectin (32.6 ± 4.5 mg/L) and fosthiazate (67.8 ± 1.7 mg/L). Low-toxicity compound 26, with excellent nematicidal activity in vitro (LC50,48h = 8.2 ± 1.2 mg/L), was designed on the basis of the predictive CoMFA (q2 = 0.795, r2 = 0.921) and CoMSIA (q2 = 0.762, r2 = 0.912) models. The control effect of compound 26 was 69.8% at an effective dose of 1.0 g per plant in a field experiment, which was superior to that of fosthiazate (67.2%). This work indicated that 1,3,4-oxadiazole–Cinnamic Acid hybrids may be used as potential nematicides