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Molecules 2016, 21(9), 1234; doi:10.3390/molecules21091234

HSCCC Separation of the Two Iridoid Glycosides and Three Phenolic Compounds from Veronica ciliata and Their in Vitro Antioxidant and Anti-Hepatocarcinoma Activities

1,2,†
,
1,2,†
,
1,2
,
1,2
,
1,2
,
1,2
and
1,2,*
1
Key Laboratory of Bio-Resources and Eco-Environment of Ministry of Education, College of Life Sciences, Sichuan University, Chengdu 610065, Sichuan, China
2
National and Local Joint Engineering Laboratory for Energy Plant Bio-Oil Production and Application, Chengdu 610065, Sichuan, China
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 27 August 2016 / Revised: 7 September 2016 / Accepted: 12 September 2016 / Published: 15 September 2016
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Abstract

Five main compounds, including two iridoid glycosides (catalposide, verproside) and three phenolic compounds (luteolin, 4-hydroxy benzoic acid, 3,4-dihydroxy benzoic acid), were separated and prepared from the crude extract of Veronica ciliata by high-speed countercurrent chromatography. n-Hexane/n-butanol/water (1.5:5:5, v/v/v) was used for the separation of catalposide and verproside. n-Hexane/n-butanol/water (3:2:5, v/v/v) was used for the separation of luteolin, 4-hydroxy benzoic acid and 3,4-dihydroxy benzoic acid. The head-to-tail elution mode was used with a flow rate of 5.0 mL/min and a rotary speed of 800 rpm. Finally, a total of 1.28 mg luteolin, 6 mg 4-hydroxy benzoic acid, 2 mg 3,4-dihydroxy benzoic acid, 2 mg verproside and 10 mg catalposide with purities of 98%, 99.1%, 99.5%, 99.8% and 99%, respectively, were obtained from 200 mg of crude extract. In addition, their structure was identified using MS, 1H-NMR and 13C-NMR. To the best of our knowledge, this is the first report of the separation and purification of iridoid glycosides and phenolic compounds from V. ciliata by high-speed countercurrent chromatography (HSCCC). Among these compounds, luteolin, 4-hydroxy benzoic acid and 3,4-dihydroxy benzoic acid were separated from V. ciliata Fisch. for the first time. The results of the antioxidant activity show that protocatechuic acid and luteolin have strong antioxidant activity compared to 2,6-di-tert-butyl-4-methylphenol (BHT) and vitamin C (Vc). Five compounds also exhibited strong anti-hepatocarcinoma activities. View Full-Text
Keywords: separation; iridoid glycosides; phenolic compounds; Veronica ciliata; high-speed countercurrent chromatography; antioxidant; anti-hepatocarcinoma separation; iridoid glycosides; phenolic compounds; Veronica ciliata; high-speed countercurrent chromatography; antioxidant; anti-hepatocarcinoma
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MDPI and ACS Style

Lu, Q.; Sun, Y.; Shu, Y.; Tan, S.; Yin, L.; Guo, Y.; Tang, L. HSCCC Separation of the Two Iridoid Glycosides and Three Phenolic Compounds from Veronica ciliata and Their in Vitro Antioxidant and Anti-Hepatocarcinoma Activities. Molecules 2016, 21, 1234.

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