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

• Main Authors: Opanasopit Praneet (Author), Kowapradit Jariya (Author), Tangyuenyongwatana Prasan (Author), Gritsanapan Wandee (Author)
• Format: Book
• Published: BMC, 2009-09-01T00:00:00Z.
• Subjects: article
• Online Access: Connect to this object online.

Summary

<p>Abstract</p> <p>Background</p> <p>The rhizome of <it>Zingiber cassumunar </it>and the seed of <it>Nigella sativa </it>are two ingredients in Thai traditional medicine to relieve dysmenorrhea and adjust the menstrual cycle. Mixture of these two herbs produces three esters, namely (<it>E</it>)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl linoleate (1), (<it>E</it>)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl oleate (2) and (<it>E</it>)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl palmitate (3). The aim of this study is to examine <it>in vitro </it>absorption of these esters and evaluate their transport across the membrane.</p> <p>Methods</p> <p><it>In vitro </it>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.</p> <p>Results</p> <p>All esters transported across the Caco-2 cell without enzymatic hydrolysis. The apparent permeability coefficients <it>P</it>_appof compound 1 at 53 μM and 106 μM were 13.94 (0.60) × 10^-6and 14.33 (0.17) × 10^-6cm/s respectively, while those of compound 2 were 9.45 (0.29) × 10^-6and 10.08 (0.32) × 10^-6cm/s, respectively. <it>P</it>_appvalues 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. <it>P</it>_appvalues of the parent compound (compound D), i.e. (<it>E</it>)-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.</p> <p>Conclusion</p> <p>Using the Caco-2 cell monolayer model, the present study finds that compounds (<it>E</it>)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl linoleate (1), (<it>E</it>)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl oleate (2) and (<it>E</it>)-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.</p>

Item Description

10.1186/1749-8546-4-19
1749-8546