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Antioxidant Effect of Berberine and its Phenolic Derivatives Against Human Fibrosarcoma Cells
Pongkittiphan, Veerachai,Chavasiri, Warinthorn,Supabphol, Roongtawan Asian Pacific Journal of Cancer Prevention 2015 Asian Pacific journal of cancer prevention Vol.16 No.13
Berberine (B1), isolated from stems of Coscinium fenestratum (Goetgh.) Colebr, was used as a principle structure to synthesize three phenolic derivatives: berberrubine (B2) with a single phenolic group, berberrubine chloride (B3) as a chloride counter ion derivative, and 2,3,9,10-tetra-hydroxyberberine chloride (B4) with four phenolic groups, to investigate their direct and indirect antioxidant activities. For DPPH assay, compounds B4, B3, and B2 showed good direct antioxidant activity ($IC_{50}$ values=$10.7{\pm}1.76$, $55.2{\pm}2.24$, and $87.4{\pm}6.65{\mu}M$, respectively) whereas the $IC_{50}$ value of berberine was higher than $500{\mu}M$. Moreover, compound B4 exhibited a better DPPH scavenging activity than BHT as a standard antioxidant ($IC_{50}=72.7{\pm}7.22{\mu}M$) due to the ortho position of hydroxyl groups and its capacity to undergo intramolecular hydrogen bonding. For cytotoxicity assay against human fibrosarcoma cells (HT1080) using MTT reagent, the sequence of $IC_{50}$ value at 7-day treatment stated that B1 < B4 < B2 ($0.44{\pm}0.03$, $2.88{\pm}0.23$, and $6.05{\pm}0.64{\mu}M$, respectively). Berberine derivatives, B2 and B4, showed approximately the same level of CAT expression and significant up-regulation of SOD expression in a dose-dependent manner compared to berberine treatment for 7-day exposure using reverse transcription-polymerase chain reaction (RT-PCR) assays. Our findings show a better direct-antioxidant activity of the derivatives containing phenolic groups than berberine in a cell-free system. For cell-based system, berberine was able to exert better cytotoxic activity than its derivatives. Berberine derivatives containing a single and four phenolic groups showed improved up-regulation of SOD gene expression. Cytotoxic action might not be the main effect of berberine derivatives. Other pharmacological targets of these derivatives should be further investigated to confirm the medical benefit of phenolic groups introduced into the berberine molecule.
Cl3CCONH2/PPh3: A Versatile Reagent for Synthesis of Esters
Chantarasriwong, Oraphin,Jang, Doo Ok,Chavasiri, Warinthorn Taylor Francis 2008 Synthetic communications Vol.38 No.16
<P> Cl3CCONH2/PPh3 was a versatile reagent to convert carboxylic acids into their corresponding acid chlorides. This intermediate was clearly confirmed by spectroscopic methods (IR, 1H, 13C NMR). This one-pot reaction of in situ acid chloride generated with various alcohols successfully furnished the corresponding esters in moderate to excellent yields.</P>
Chaysripongkul, Skydow,Pluempanupat, Wanchai,Jang, Doo-Ok,Chavasiri, Warinthorn Korean Chemical Society 2009 Bulletin of the Korean Chemical Society Vol.30 No.9
$Cl_3CCONH_2$ coupled with $PPh_3$ was determined to be an effective reagent for the conversion of carboxylic acids to their corresponding acid chlorides. Subsequently, these acid chlorides were successfully trapped with amines in the presence of 4-picoline, yielding amides. This practical and efficient protocol can be utilized for the synthesis of biological amides in excellent yields.
Application of Cl3CCONH2/PPh3 towards the Synthesis of Bioactive Amides
Skydow Chaysripongkul,Wanchai Pluempanupat,장두옥,Warinthorn Chavasiri 대한화학회 2009 Bulletin of the Korean Chemical Society Vol.30 No.9
Cl3CCONH2 coupled with PPh3 was determined to be an effective reagent for the conversion of carboxylic acids to their corresponding acid chlorides. Subsequently, these acid chlorides were successfully trapped with amines in the presence of 4-picoline, yielding amides. This practical and efficient protocol can be utilized for the synthesis of biological amides in excellent yields.
Thanase Ariyawatkul,Witchate Pichaisak,Cholavech Chavasiri,Visit Vamvanij,Sirichai Wilartratsami,Panya Luksanapruksa 대한척추외과학회 2019 Asian Spine Journal Vol.13 No.6
Study Design: Retrospective study. Purpose: This study aimed to investigate the association of surgical intervention with clinical and quality of life (QoL) outcomes in patients who underwent posterior spinal surgery for lumbar spinal stenosis (LSS) with spinal calcium pyrophosphate dihydrate deposition (SCPPD) versus that in those who underwent the surgery for LSS without SCPPD. Overview of Literature: Calcium pyrophosphate (CPP)-associated arthritis is one of the most common types of arthritis. The clinical outcomes are well studied in CPP-associated arthritis of the appendicular joints. However, few studies have investigated SCPPD. Methods: A single-institution database was reviewed. LSS patients were categorized as those who did and did not have SCPPD, based on histologic identification. Clinical presentations and postoperative results were analyzed. Disability and QoL were assessed using the Oswestry Disability Index (ODI) and the 36-item Short-Form Health Survey. Results: Thirty-four patients were enrolled, with 18 patients being allocated to the SCPPD group and 16 being allocated to the non-SCPPD group. Preoperative and postoperative pain scores were not significantly different between the groups (p=0.33 and p=0.48, respectively). The average preoperative ODI score in the SCPPD group was slightly higher than that in the non-SCPPD group (57 vs. 51, p=0.33); however, the postoperative ODI score was significantly lower (15 vs. 43, p=0.01). The postoperative physical function, vitality, and mental health of the SCPPD patients were also significantly improved (p=0.03, p=0.022, and p=0.022, respectively). Conclusions: Surgical intervention resulted in good clinical outcomes in SCPPD patients. As per our findings, total removal of CPP-involved tissue is unnecessary. As such, surgery should be performed as indicated according to clinical presentation without considering the presence of CPPD.
Synthesis of N-phenylphthalimide Derivatives as ${\alpha}-Glucosidase$ Inhibitors
Pluempanupat, Wanchai,Adisakwattana, Sirichai,Yibchok-Anun, Sirintorn,Chavasiri, Warinthorn 대한약학회 2007 Archives of Pharmacal Research Vol.30 No.12
Sixteen N-phenylphthalimide derivatives were synthesized and their ability to inhibit ${\alpha}-glucosidase$ was investigated. N-(2,4-dinitrophenyl)phthalimide was a potent inhibitor of yeast ${\alpha}-glucosidase\;(IC_{50};\;0.158{\pm}0.005mM)\;and\;maltase\;(IC_{50};\;0.051{\pm}0.008mM)$, whereas it did not inhibit sucrase. From a Lineweaver-Burk plot of ${\alpha}-glucosidase$ kinetics, N-(2,4-dichlorophenyl)phthalimide was found to be a competitive inhibitor of yeast ${\alpha}-glucosidase$. These results indicate that N-(2,4-dinitrophenyl)phthalimide could be a representative of a new group of ${\alpha}-glucosidase$ inhibitors.