Teerapich Kasemsuk - Academia.edu (original) (raw)

Papers by Teerapich Kasemsuk

Trends in Sciences

Thai wisdom knows the benefits of mangrove palm fruits to be boiled in water and drink as herbal ... more Thai wisdom knows the benefits of mangrove palm fruits to be boiled in water and drink as herbal medicines for healing gout. However, there is no scientific paper to confirm the relief of gout symptoms by mangrove palm, this is the first report. The mangrove palm: exocarp/mesocarp, endocarp, endosperm, and the whole of fruit in the ripe stage were extracted with water and ethanol. The crude extracts were studied for the phytochemical and inhibitory activity of xanthine oxidase, one of the causes of gout. Most of the crude extracts showed similar phytochemicals as, phenolic compounds, flavonoids, terpenoids, and steroids, but there was no alkaloid, anthraquinone, and iridoid glycoside. The endocarp extracted with ethanol showed the highest phenolic content (102.85±5.73 mg GAE/g), flavonoid content (531.02±10.46 mg QUE/g), and strongest antioxidant activity (26.79±0.57 mg VCE/g). The ethanolic and water extract (heating at 60 °C) of endocarp showed the strongly inhibited xanthine oxid...

วารสารวิชาการและวิจัย มทร.พระนคร, 13(2) : 106-118The Thai wisdom knows the benefits of Carissa ca... more วารสารวิชาการและวิจัย มทร.พระนคร, 13(2) : 106-118The Thai wisdom knows the benefits of Carissa carandas L. to be used as a traditional herbal medicine. However, there was no scientific evidence to show that Carissa carandas L. of Thailand can treat gout or not. In this research, the Carissa carandas L. fruit extract in semi-ripening and ripe stage were studied for the phytochemical and inhibitory activity of xanthine oxidase, one of the causes of gout. The result of hytochemical indicated that the crude extract from semi-ripening stage fruit contained many substances; phenolic compounds, alkaloids, flavonoids, terpenoids, saponins and deoxy sugars. While the ripe stage fruit contained the similar substances excepted saponins. The extract solution of Carissa carandas L. showed the xanthine oxidase inhibitory activity, as the ethanolic extract solution gave the higher activity than water extract solution. The crude extracts of semi-ripening stage fruit presented the higher activity th...

The Journal of King Mongkut's University of Technology North Bangkok, 2021

พืชสกุลสละ เป็นหนึ่งในพืชที่มีความสำคัญทางเศรษฐกิจของประเทศไทย ซึ่งกระบวนการแปรรูปพืชสกุลนี้ทำให้... more พืชสกุลสละ เป็นหนึ่งในพืชที่มีความสำคัญทางเศรษฐกิจของประเทศไทย ซึ่งกระบวนการแปรรูปพืชสกุลนี้ทำให้เกิดเปลือกและเมล็ดสละเป็นของเหลือใช้ทางการเกษตรจำนวนมาก งานวิจัยนี้จึงมีวัตถุประสงค์เพื่อศึกษาการใช้ประโยชน์จากเปลือกและเมล็ดของสละด้วยการทดสอบฤทธิ์ต้านอนุมูลอิสระของเปลือกและเมล็ดของพืชสกุลสละและพัฒนาเป็นผลิตภัณฑ์สบู่ก้อนที่มีฤทธิ์ต้านอนุมูลอิสระ โดยได้คัดกรองฤทธิ์ต้านอนุมูลอิสระ DPPH ของพืชสกุลสละ 5 ชนิด คือ ระกำ สละกำ สละหม้อ สละเนินวง และสละสุมาลี ผลการวิจัยพบว่าสารสกัดเอทานอลของเปลือกพืชสกุลสละมีฤทธิ์ต้านอนุมูลอิสระสูงกว่าเมล็ดอย่างมีนัยสำคัญทางสถิติ (P≤0.05) และเปลือกสละสุมาลีมีฤทธิ์ต้านอนุมูลอิสระสูงสุด โดยพบว่าเปลือกสละสุมาลีมีฤทธิ์ต้านอนุมูลอิสระสูงใกล้เคียงวิตามินซี (IC50 1.03+-0.04 ไมโครกรัมต่อมิลลิลิตร) และสูงกว่าเมล็ดและเนื้อสละ โดยมีค่า IC50 เท่ากับ 7.93+-0.04 99.22+-0.51 และ 353.98+-1.70 ไมโครกรัมต่อมิลลิลิตร ตามลำดับ นอกจากนี้สารสกัดเอทานอลของเปลือกสละสุมาลียังแสดงฤทธิ์ยับยั้งเอนไซม์ไทโรซิเนสสูงกว่าเมล็ดและเนื้อสละ โดยมีค่า IC50 เท่ากับ 419.80+-3.22 1821.62+-6.69 และมากกว่า 1000 ไมโครกรัมต่อมิลลิลิตร ตามลำดับ แต่ต่ำกว่าสารมาตรฐานโคจิก (IC50 1.18+-0.24 ไมโครกรัมต่อมิลลิลิตร) เมื่อนำสารสกัดเอทานอลของเปลือกสละสุมาลีมาผสมในสบู่กลีเซอรีนแบบก้อนใสและก้อนขุ่นพบว่าสบู่ทั้งสองชนิดมีฤทธิ์ต้านอนุมูลอิสระแต่น้อยกว่าสารสกัดเอทานอลก่อนการผสม โดยมีค่า IC50 เมื่อใช้เอทานอลเป็นตัวทำละลายสบู่เท่ากับ 351.13+-24.74 และ 347.56+-18.71 ไมโครกรัมต่อมิลลิลิตร ตามลำดับSalacca is one of the important economic plant of Thailand of which the fruit processing causes an abundance of peels and seeds as agricultural waste. Therefore, to increase the value of salak peels and seeds, antioxidant activity screening and antioxidant soap product developed from these agricultural wastes were studied in this research. Five cultivars of Salacca genus; Rakam, Salakam, Salamoa, Noenwong, and Sumalee, were determined for an antioxidant activity using DPPH assay. The result revealed that ethanolic extracts by maceration of salak peels showed significantly higher than those from salak seeds (p≤0.05). Sumalee peels’ ethanolic extracts exhibited the highest antioxidant activity which was close to the activity of vitamin C (IC50 1.03 ± 0.04 μg/mL) and higher than those of the seed and plump extracts with the IC50 of 7.93 ± 0.04, 99.22 ± 0.51, and 353.98 ± 1.70 μg/mL, respectively. Moreover, tyrosinase inhibitory activity of Sumalee peel extracts also presented higher activity than the seed and plump extracts with the IC50 of 419.80 ± 3.22, 1821.62 ± 6.69, and >1000 μg/mL, respectively but lower than Kojic acid standard (IC50 1.18 ± 0.24 μg /mL). After Sumalee peels’ ethanolic extracts were mixed in the clear and opaque glycerin soap, the antioxidant of both soap types was detected but less than the ethanol extract before mixing with the IC50 at 351.13 ± 24.74 and 347.56 ± 18.71 μg/mL, respectively

Asian Pacific Journal of Cancer Prevention : APJCP, 2017

Gastric cancer is the most common cancer in Eastern Asia. Increasing chemoresistance and general ... more Gastric cancer is the most common cancer in Eastern Asia. Increasing chemoresistance and general systemic toxicities have complicated the current chemotherapy leading to an urgent need of more effective agents. The present study reported a potent DNA topoisomerase IIα inhibitory activity of an andrographolide analogue (19-triisopropyl andrographolide, analogue-6) in gastric cancer cells; MKN-45, and AGS cells. The analogue was potently cytotoxic to both gastric cancer cell lines with the half maximal inhibitory concentration (IC50 values) of 6.3±0.7 μM, and 1.7±0.05 μM at 48 h for MKN-45, and AGS cells, respectively. It was more potent than the parent andrographolide and the clinically used, etoposide with the IC50 values of >50 μM in MKN-45 and 11.3±2.9 μM in AGS cells for andrographolide and 28.5±4.4 μM in MKN-45 and 4.08±0.5 μM in AGS cells for etoposide. Analogue-6 at 2 μM significantly inhibited DNA topoisomerase IIα enzyme in AGS cells, induced DNA damage, activated cleaved...

The Thai wisdom knows the benefits of Carissa carandas L. to be used as a traditional herbal medi... more The Thai wisdom knows the benefits of Carissa carandas L. to be used as a traditional herbal medicine. However, there was no scientific evidence to show that Carissa carandas L. of Thailand can treat gout or not. In this research, the Carissa carandas L. fruit extract in semiripening and ripe stage were studied for the phytochemical and inhibitory activity of xanthine oxidase, one of the causes of gout. The result of phytochemical indicated that the crude extract from semi-ripening stage fruit contained many substances; phenolic compounds, alkaloids, flavonoids, terpenoids, saponins and deoxy sugars. While the ripe stage fruit contained the similar substances excepted saponins. The extract solution of Carissa carandas L. showed the xanthine oxidase inhibitory activity, as the ethanolic extract solution gave the higher activity than water extract solution. The crude extracts of semi-ripening stage fruit presented the higher activity than the ripe stage one with the IC 50 values of 2....

Phytotherapy Research, 2021

Acanthoic acid (AA) is an active substance that is extracted from Croton oblongifolius Roxb., a t... more Acanthoic acid (AA) is an active substance that is extracted from Croton oblongifolius Roxb., a traditional plant in Thailand. The antiinflammatory effect of AA on NF‐κB pathway has been exclusively reported, however, its anticancer effect is still lacking. PEL is a B cell lymphoma that is mostly found in HIV patients. The prognosis and progression of PEL patients are terribly poor with a median survival time less than 6 months, so the new effective treatment is urgently needed. In this study, we found that AA effectively inhibited PEL cell proliferation with IC50s at 120–130 μM in well‐representative cells, while the IC50s of AA in PBMC were higher (>200 μM). AA increased percentages of Annexin V/PI positive cells, whereas adding of caspase inhibitor (Q‐VD‐OPh) prevented AA‐induced cell death. The antiapoptotic protein, c‐FLIP, was downregulated by AA which leading to the activation of caspase‐8 and ‐3. Combination of AA and TRAIL dramatically enhanced apoptotic cell death. In P...

Bioorganic & Medicinal Chemistry, 2021

A novel series of acanthoic acid analogues containing triazole moiety were synthesized through es... more A novel series of acanthoic acid analogues containing triazole moiety were synthesized through esterification and CuAAC reaction. Evaluation of their biological activities against four cell lines of cholangiocarcinoma cells showed that 3d exhibited the strongest activity with an IC50 value of 18 µM against KKU-213 cell line, which was 8 fold more potent than acanthoic acid. Interestingly, the triazole ring and nitro group on benzyl ring play very significant role in cytotoxic activity. The computational studies revealed that 3d occupies the binding energy of -12.7 and -10.8 kcal/mol with CDK-2 and EGFR protein kinases, respectively. This result might provide a beginning for the development of acanthoic acid analogues as an anticancer agent.

Biomedicine & Pharmacotherapy, 2018

Hyperactivation of Wnt/β-catenin signaling implicated in oncogenesis of colorectal cancer (CRC) i... more Hyperactivation of Wnt/β-catenin signaling implicated in oncogenesis of colorectal cancer (CRC) is a potential molecular target for chemotherapy. An andrographolide analogue, 3A.1 (19-tert-butyldiphenylsilyl-8, 17-epoxy andrographolide) has previously been reported to be potently cytotoxic toward cancer cells by unknown molecular mechanisms. The present study explored the anti-cancer activity of analogue 3A.1 on Wnt/β-catenin signaling in colon cancer cells (HT29 cells) which were more sensitive to the others (HCT116 and SW480 cells). Analogue 3A.1 inhibited viability of HT29 cells with IC 50 value of 11.1 ± 1.4 μM at 24 h, which was more potent than that of the parent andrographolide. Analogue 3A.1 also suppressed the proliferation of HT29 cells and induced cell apoptosis in a dose-dependent manner. Its apoptotic activity was accompanied with increased expressions of proteins related to DNA damages; PARP-1 and γ-H2AX. In addition, analogue 3A.1 significantly inhibited T-cell factor and lymphoid enhancer factor (TCF/LEF) promoter activity of Wnt/β-catenin signaling. Accordingly, the expressions of Wnt target genes and β-catenin protein were suppressed. Moreover, analogue 3A.1 increased the activity of GSK-3β kinase, which is a negative regulator responsible for degradation of intracellular β-catenin. This mode of action was further supported by the absence of the effects after treatment with a GSK-3β inhibitor, and over-expression of a mutant β-catenin (S33Y). Our findings reveal, for the first time, an insight into the molecular mechanism of the anti-cancer activity of analogue 3A.1 through the inhibition of Wnt/β-catenin/GSK-3β pathway and provide a therapeutic potential of the andrographolide analogue 3A.1 in CRC treatment.

Scientific Reports, 2018

The Wnt/β-catenin signaling pathway plays a key role in the progression of human colorectal cance... more The Wnt/β-catenin signaling pathway plays a key role in the progression of human colorectal cancers (CRCs) and is one of the leading targets of chemotherapy agents developed for CRC. The present study aimed to investigate the anti-cancer effects and molecular mechanisms of 19-O-triphenylmethyl andrographolide (RS-PP-050), an andrographolide analogue and determine its activity in the Wnt/β-catenin pathway. RS-PP-050 was found to potently inhibit the proliferation and survival of HT-29 CRC cells. It induces cell cycle arrest and promotes apoptotic cell death which was associated with the activation of PARP-1 and p53. Furthermore, RS-PP-050 exerts inhibitory effects on β-catenin transcription by suppressing T-cell factor/lymphocyte enhancer factor (TCF/LEF) activity in cells overexpressing β-catenin and by down-regulating the endogenous expression of Wnt target genes. RS-PP-050 also decreased the protein expression of the active form of β-catenin but functions independently of GSK-3β, ...

The Journal of Organic Chemistry, 2018

A new strategy for the synthesis of bis-indoletriazoles was developed using a sequential one-pot ... more A new strategy for the synthesis of bis-indoletriazoles was developed using a sequential one-pot four-step procedure via I2 and H2SO4-SiO2 catalyzed Friedel-Crafts reactions of indole with aldehyde followed by N-alkylation with propargyl bromide, azidation and copper(I)-catalyzed azide alkyne cycloaddition (CuAAC). The reaction proceeded smoothly at room temperature in a short time and a series of bis-indoletriazoles were obtained in good to excellent yields proving the generality of this one-pot methodology.

Bioorganic & medicinal chemistry letters, Jan 27, 2018

New iridoid glycoside derivatives from durantoside I, the latter from the dried flowers and leave... more New iridoid glycoside derivatives from durantoside I, the latter from the dried flowers and leaves of Citharexylum spinosum, were synthesized by variously modifying a sugar moiety by silylation or acetylation and/or removal of cinnamate group at C-7 position and subsequent screening for comparative cytotoxicity against several cancer cell lines. Addition of alkylsilane to durantoside I and removal of cinnamate group were most effective in improving cytotoxicity.

Medicinal Chemistry Research, 2017

Important anticancer cytotoxicological properties are reported from synthetic analogs of 14-deoxy... more Important anticancer cytotoxicological properties are reported from synthetic analogs of 14-deoxy-12hydroxy-andrographolide, a compound that occurs in Andrographis paniculata, an indigenous Southeast Asia plant. Cytotoxicities of 15 synthesized 14-deoxy-12hydroxy-andrographolide analogs were evaluated against a panel of cancer cell lines with some exhibiting much greater than the parent compound. For example analog 2j was 6-35 times more potent than the parent compound and the anticancer agent, ellipticin, on all cell lines except LU-1 cancer cells. With promising cytotoxicities and simple preparation, this compound has significant potential in the treatment of cancer.

European Journal of Medicinal Chemistry, 2017

An efficient one-pot synthesis of novel andrographolide analogues is reported from a naturally oc... more An efficient one-pot synthesis of novel andrographolide analogues is reported from a naturally occurring and abundant andrographolide isolated from aerial parts of Andrographis paniculata. Reactions in the one-pot proceed through a cascade epoxide ring opening by aniline derivatives/intramolecular ring closing and oxa-conjugate addition-elimination reactions. This methodology produces a new series of 17-amino-8-epi-isoandrographolide analogues in fair to excellent yields with high stereoselectivity using an economic and environmental procedure without base or catalyst at room temperature. Twenty-five analogues were obtained and cytotoxicity of all new analogues were evaluated against six cancer cell lines to search for a new lead compound based on andrographolide structure.

Organic & Biomolecular Chemistry, 2016

A mild, efficient and metal-free method was described for the green synthesis of dipyrromethanes ... more A mild, efficient and metal-free method was described for the green synthesis of dipyrromethanes from aldehydes and unsubstituted pyrrole catalyzed by SO3H-functionalized ionic liquids (SO3H-ILs) in aqueous media at room temperature.

Bioorganic & medicinal chemistry letters, Dec 1, 2017

A series of 14-deoxy-11,12-didehydroandrographolide analogues were synthesized from naturally occ... more A series of 14-deoxy-11,12-didehydroandrographolide analogues were synthesized from naturally occurring andrographolide and their cytotoxicity evaluated against nine cancer cell lines including cholangiocarcinoma. Analogues 5a and 5b exhibited the most potent cytotoxicity with ED50s of 3.37 and 3.08 μM on KKU-M213 cell lines and 2.93 and 3.27 μM on KKU-100 cell lines, respectively. Selective cytotoxicity on cholangiocarcinoma cell lines identified in this study highlight the importance of structural modification in the development of drugs for this cancer.