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.
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 ¼ 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 IC 50 was equal to 120.2 mM. Discussion and conclusion: From the results, isopropyl piperate is an outstanding compound that can be developed into a UV protection agent.
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 H(37)Ra for which compounds 1 and 3 had inhibitory concentration at 200 microg mL(-1) while compound 2 inhibited at 100 microg mL(-1). When all these compounds were subjected to anti-HSV-1 test, compound 2 showed positive activity at 42.6 microg mL(-1) without any cytotoxic activity against human vero cell line while compound 3 had the cytotoxicity to vero cell at IC(50) 38 microg mL(-1). Compound 1 was inactive for this test.
Zingiber cassumunar (Zingiberaceae) has been widely used as a traditional medicine in southeast Asia, especially Thailand, for treatment of asthma, inflammation, and joint pain. (E)-4-(3,4-dimethoxyphenyl)butadiene, or DMPBD, a major component in the rhizome, has been reported to be an active anti-inflammatory agent. This research developed a TLC-densitometry method for the simultaneous quantification of DMPBD in the rhizome extracts of four varieties of Z. cassumunar. DMPBD (dimethoxyphenylbutadiene) was found in the range of 0.90 +/- 0.01 to 1.61 +/- 0.05% (w/w). [corrected] The method was validated for linearity, precision, accuracy, robustness, LOD, and LOQ. The linearity was indicated by a good regression coefficient 0.9940 and covered the range of 130 to 703 ng/band. Intraday and interday precision (RSD) were less than 2%. Accuracy of the method was evaluated by a recovery study conducted at three different levels; the average recovery was 103.1%. The LOD and LOQ were 10 and 40 ng, respectively. The proposed TLC-densitometry method was simple, precise, specific, sensitive, and inexpensive. This method can be used for routine QC of raw materials of Z. cassumunar rhizomes, extracts, and its products, especially Prasaplai, a Thai traditional medicine for relieving dysmenorrhea.
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 IC(50) of all artifacts in all tests were higher than 20 microg/mL. For acute toxicity in mice, the LD(50) of each artifact was more than 300 mg/kg.
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