Prasan Tangyuenyongwatana

A study on artifacts formation in the Thai traditional medicine Prasaplai.

The artificial formation of three fatty acid esters, ( E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl linoleate ( 1), ( E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl oleate ( 2) and ( E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl palmitate ( 3) originating during storage by the interaction of components in Prasaplai preparation was investigated. The artifacts were not formed when 0.1 mL of water or more was added to 1.0 g of the mixture (1 : 1) of Zingiber cassumunar and Nigella sativa even when stored for 20 days. This result showed that water was able to stop the esterification reaction. The formation of the artifacts by chemical reaction under water-free conditions was evaluated. ( E)-4-(3,4-dimethoxyphenyl)but-3-en-1-ol was mixed with linoleic acid in the presence of anhydrous Na (2)SO (4) and stored in a dessicator for 7 days. The artifact ( 1) was formed in 6.0 % yield. It was concluded that a water-free environment is necessary for the direct chemical formation of the artificial esters.

Cellular transport of anti-inflammatory pro-drugs originated from a herbal formulation of Zingiber cassumunar and Nigella sativa

BackgroundThe rhizome of Zingiber cassumunar and the seed of Nigella sativa are two ingredients in Thai traditional medicine to relieve dysmenorrhea and adjust the menstrual cycle. Mixture of these two herbs produces three esters, namely (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl linoleate (1), (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl oleate (2) and (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl palmitate (3). The aim of this study is to examine in vitro absorption of these esters and evaluate their transport across the membrane.MethodsIn vitro transport of these three esters was observed in Caco-2 cell monolayers. The ester compounds 1, 2 and 3 at a concentration of 10 μM were hydrolyzed by porcine liver esterase.ResultsAll esters transported across the Caco-2 cell without enzymatic hydrolysis. The apparent permeability coefficients Papp of compound 1 at 53 μM and 106 μM were 13.94 (0.60) × 10-6 and 14.33 (0.17) × 10-6cm/s respectively, while those of compound 2 were 9.45 (0.29) × 10-6 and 10.08 (0.32) × 10-6cm/s, respectively. Papp values of compound 3 were 7.48 (0.31) × 10-6cm/s at 53 μM and 8.60 (0.55) × 10-6cm/s at 106 μM. Papp values of the parent compound (compound D), i.e. (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-ol were 8.53 (0.83) × 10-6cm/s at 53 μM and 16.38 (0.61) × 10-6cm/s at 106 μM. The ester hydrolysis of compounds 1, 2 and 3 by porcine liver esterase was monitored by HPLC and the hydrolysis reactions were completed within 10 minutes.ConclusionUsing the Caco-2 cell monolayer model, the present study finds that compounds (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl linoleate (1), (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl oleate (2) and (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl palmitate (3) originated from Prasaplai preparation (a Thai herbal formula) may be transported through a facilitated mechanism and serve as pro-drugs to increase the compound D level in the blood.

Biological evaluations of fatty acid esters originated during storage of Prasaplai, a Thai traditional medicine

Three fatty acid esters, (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl linoleate (1), (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl oleate (2), and (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl palmitate (3), originated during storage by the interaction of components in Prasaplai, were synthesized. These three artificial esters were subjected to four biological evaluations. All three compounds were active against Mycobacterium tuberculosis H37Ra for which compounds 1 and 3 had inhibitory concentration at 200 µg mL−1 while compound 2 inhibited at 100 µg mL−1. When all these compounds were subjected to anti-HSV-1 test, compound 2 showed positive activity at 42.6 µg mL−1 without any cytotoxic activity against human vero cell line while compound 3 had the cytotoxicity to vero cell at IC50 38 µg mL−1. Compound 1 was inactive for this test.

Quantitative analysis and toxicity determination of artifacts originated in a Thai traditional medicine Prasaplai.

Prasaplai is a Thai traditional medicine for relieving dysmenorrhea and adjusting the menstrual cycle. Three fatty acid esters, (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl linoleate (1), (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl oleate (2) and (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl palmitate (3) are formed during storage from the reaction of chemical components in two herbs, i.e., fatty acids in Nigella sativa (L.) (Ranunculaceae) and (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-ol (compound D) in Zingiber cassumunar (Roxb.) (Zingiberaceae). The formations of these artifacts were monitored for 1 year and their amounts were analyzed by HPLC at certain periods of time. The results showed that artifact formation was saturated after 73 days of storage. The amount of each artifact in the saturation period ranged from 3.93 ± 0.06 to 4.30 ± 0.18% w/w for compound 1, 1.69 ± 0.08 to 1.9 ± 0.13% w/w for compound 2 and 0.09 ± 0.003 to 0.1 ± 0.005% w/w for compound 3. Cytotoxicity of the artifacts was evaluated using NCI-H187, KB, and BC cancer cell lines and found that the IC50 of all artifacts in all tests were higher than 20 μg/mL. For acute toxicity in mice, the LD50 of each artifact was more than 300 mg/kg.

Development of piperic acid derivatives from Piper nigrum as UV protection agents

Abstract Context: There is a need for the discovery of novel natural and semi-synthetic sunscreen that is safe and effective. Piperine has a UV absorption band of 230–400 nm with high molar absorptivity. This compound has a high potential to be developed to sunscreen. Objective: This study develops new UV protection compounds from piperine by using chemical synthesis. Materials and methods: Piperine was isolated from Piper nigrum L. (Piperaceae) fruits, converted to piperic acid by alkaline hydrolysis, and prepared as ester derivatives by chemical synthesis. The piperate derivatives were prepared as 5% o/w emulsion, and the SPF values were evaluated. The best compound was submitted to cytotoxicity test using MTT assay. Results: Piperic acid was prepared in 86.96% yield. Next, piperic acid was reacted with alcohols using Steglich reaction to obtain methyl piperate, ethyl piperate, propyl piperate, isopropyl piperate, and isobutyl piperate in 62.39–92.79% yield. All compounds were prepared as 5% oil in water emulsion and measured its SPF and UVA/UVB values using an SPF-290S analyzer. The SPF values (n = 6) of the piperate derivatives were 2.68 ± 0.17, 8.89 ± 0.46, 6.86 ± 0.91, 16.37 ± 1.8, and 9.68 ± 1.71. The UVA/UVB ratios of all compounds ranged from 0.860 to 0.967. Cytotoxicity of isopropyl piperate was evaluated using human skin fibroblast cells and the IC50 was equal to 120.2 μM. Discussion and conclusion: From the results, isopropyl piperate is an outstanding compound that can be developed into a UV protection agent.

Standardization of Prasaplai, a Thai traditional preparation for antidysmenorrhea

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