New Fatty Acid Esters Originate During Storage by the Interaction of Components in Prasaplai, a Thai Traditional Medicine

Abstract

Prasaplai is a Thai traditional preparation composed of twelve ingredients; during storage three newly emerging compounds were detected by HPLC. Their structures were established as the new (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl linoleate, (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl oleate and the known (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl palmitate on the basis of spectral data and chemical evidence. The artificial esters were already observable after one day of storage of the freshly prepared dry mixture, and steadily increased during a storage period of 30 days and more. A systematic search indicated that the three esters arose from the interaction of compounds contained in the rhizomes of Zingiber cassumunar and the seeds of Nigella sativa.

References

• 1 National list of essential drugs A .D.1999. National essential drug list committee. 1999: p 2
• 2 Poomchusri N T. Ayurvedic study. 2nd edn. Bangkok; Promjakkanpimp 1973: p 194
• 3 Wichailuk S, Wichailuk S. Legislation of drug. Bangkok; Nitiwet 1988: p 46
• 4 Masuda T, Jitoe A. Phenyl butanoid monomers from the rhizomes of Zingiber cassumunar .  Phytochemistry. 1995;  39 459-61
• 5 Kuroyanagi M, Fukushima S, Yoshihira K, Natori S, Dechatiwongse T, Mihashi K, Nishi M, Hara S. Further characterization of the constituents of a Thai medicinal plant, Zingiber cassumunar Roxb.  Chem Pharm Bull. 1980;  28 2948-59
• 6 Tuntiwachwuttikul P, Pancharoen O, Jaipetch T, Reutrakul V. Phenylbutanoids from Zingiber cassumunar .  Phytochemistry. 1981;  20 1164-5
• 7 Amatayakul T, Cannon J R, Dampawan P, Dechatiwongse T, Giles R GF, Huntrakul C, Kusamran K, Mokkhasamit M, Raston C L, Reutrakul V, White A H. Chemistry and crystal structure of some constituents of Zingiber cassumunar .  Austr J Chem. 1979;  32 71-88
• 8 Gad A M, El-Dakhakhny M, Hassan M M. Studies on the chemical constituents of Egyptian Nigella sativa oil.  Planta Medica. 1963;  11 134-8
• 9 Schulte V E, Weber K. Schnelle Herstellung der Fettsäuremethylester aus Fetten mit Trimethylsulfoniumhydroxid oder Natriummethylat.  Fat Sci Technol. 1989;  91 181-3
• 10 Dandik L, Aksoy H A. The kinetics of hydrolysis of Nigella sativa (black cumin) seed oil catalyzed by native lipase in ground seed.  J Am Oil Chem Soc. 1992;  69 1239-41
• 11 Jo B. Databank NIST (National Institute of Standards and Technology). Gaithersburg, USA (Version 1.6);