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Simultaneous Determination of Sesquiterpene Lactones in Ixeris Chinensis by HPLC

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Simultaneous Determination of Sesquiterpene Lactones in Ixeris Chinensis by HPLC 872 Journal of Food and Drug Analysis, Vol. 20, No. 4, 2012, Pages 872-878 doi:10.6227/jfda.2012200417 Simultaneous Determination of Sesquiterpene Lactones in Ixeris chinensis by HPLC QINGHU WANG*, WULIJI AO, XIN YING, GENXIAO MENG, XIAOLAN WU AND WENQUAN TAI College of Traditional Mongolian Medicine, Inner Mongolia University for Nationalities, Tongliao 028000, Inner Mongolia, China (Received: February 15, 2012; Accepted: July 18, 2012) ABATRACT A reversed-phase high-performance liquid chromatographic method is described for the simultaneous determination of six sesqui- terpene lactones: 3β-[3-(4-hydroxyphenyl)acetyl-β-D-glucopyranosyloxy]-8β-hydroxy-4(15),10(14)11(13)-guaiatrien-12,6-olide (AR1) 3β-[3-(4-hydroxyphenyl)acetyl-β-D-glucopyranosyloxy]-4(15),10(14)11(13)-guaiatrien-12,6-olide (AR2), 3β-(β-D-glucopyranosyloxy)- 8β-(4-hydroxyphenyl)acetoxy-4(15),10(14)11(13)-guaiatrien-12,6-olide (AR3), 3β-(β-D-glucopyranosyloxy)-8β-(2-hydroxy-3- methylbutanoyloxy)acetoxy-4(15),10(14)11(13)-guaiatrien-12,6-olide (AR4), 3β-(β-D-glucopyranosyloxy)-4(15),10(14)11(13)- guaiatrien-12,6-olide (AR5), and 3β-hydroxy-4(15),10(14)11(13)- guaiatrien-12,6-olide (AR6) in the whole plant of Ixeris chinensis. The separation by gradient elution was performed on Hypersil ODS-2 column (250 mm × 4.6 mm, 5 µm) at 30°C with acetonitrile and water as the mobile phase, and monitored by absorbance at 238 nm. The parameters of linearity, precision, accuracy, and specificity of the method were evaluated. The recovery of the method is 95.85-98.19%, and linearity (r > 0.9993) was obtained for all sesquiterpene lactones. A high degree of specificity as well as repeatability and reproducibility (relative standard deviation values less than 2.0%) were also achieved. This assay was successfully applied to the determination of six sesquiterpene lactones in ten samples. The results indicated that the developed assay method was rapid, accurate, reliable and could be readily utilized as a quantitative analysis method for I. chinensis. Key words: HPLC, simultaneous determination, sesquiterpene lactones, Ixeris chinensis INTRODUCTION 8β-hydroxy-4(15),10(14)11(13)-guaiatrien-12,6-olide (AR1) 3β-[3-(4-hydroxyphenyl)acetyl-β-D-glucopyranosyloxy]- Ixeris chinensis <Thumb.> Nakai (Compositae) is a 4(15),10(14)11(13)-guaiatrien-12,6-olide (AR2), 3β-(β- perennial plant found in various areas in China and used as D-glucopyranosyloxy)-8β-(4-hydroxyphenyl)acetoxy- a folk medicine for the treatment of bronchitis, pneumonia, 4(15),10(14)11(13)-guaiatrien-12,6-olide (AR3), 3β-(β-D- pharyngitis, dysentery, and poisonous indigestion on the glucopyranosyloxy)-8β-(2-hydroxy-3-methylbutanoyloxy) (1) basis of its antifebrile, antidotal, and analgesic effects . The acetoxy-4(15),10(14)11(13)-guaiatrien-12,6-olide (AR4), known constituents of this plant include triterpenes(2), and 3β-(β-D-glucopyranosyloxy)-4(15),10(14)11(13)-guaiatrien- (3) flavonoids . Studies on some other species of this genus 12,6-olide (AR5), and 3β-hydroxy-4(15),10(14)11(13)- revealed the presence of sesquiterpene lactones such as guaiatrien-12,6-olide (AR6) whose structures are shown guaianolides, eudesmanolides, germacranolides, and their in Figure 1. Unfortunately, to date, except the report on glycosides(4-6). Recently a series of sesquiterpene lactones determination of luteolin in I. chinensis by reversed-phase identified from the whole plant of I. chinensis(7-9) and the high-performance liquid chromatography (RP-HPLC)(12), diverse biological activity reported for guaianolides(10,11) there is no literature giving an accurate quality evaluation of prompted us to undertake a further investigation of the I. chinensis because of unavailability of commercial refer- guaianolides in this plant. In our phytochemical investigation, ence standards. several sesquiterpene lactones were isolated including In the present study, a novel HPLC method was devel- 3β-[3-(4-hydroxyphenyl)acetyl-β-D-glucopyranosyloxy]- oped to determine the six sesquiterpene lactones in ten * Author for correspondence. Tel: +86-0475-8314242; samples of I. chinensis simultaneously. The established Fax: +86-0475-8314242; E-mail [email protected] method has the advantage of adequate sensitivity, precision, 873 Journal of Food and Drug Analysis, Vol. 20, No. 4, 2012 14 14 14 14 accuracy and is also suitable for the quality control of I. 10 O 2 1 2 10 chinensis. R2 1 OH 24 5 10 7 HO 5 10 O 1''O 1 R 24 1 7 15 5 2 HO 5 OH O 2''1'' 4 7 15 4 7 6'' 4'' OH 13 13 15 O 11 15 O 11 MATERIALS AND METHODS 2'' OH 13 13 6'' 4'' O12 11 12 HO OR1 O 11 12 O 12 O OR AR6 HO 1 O O AR6 I. Reagents and Samples 5' 4' 2' 1' 5' 4' 3' AR1 :R = R = OH 1 HO 7' 3' CH2' 2CO1' 2 LC-grade acetonitrile was purchased from Merck (Darm- AR :R OH 1 1 = HO 7' CH2CO R2 = stadt, Germany); deionized water was purified by Milli-Q AR : R H 2 1 = HO CH2CO R2 = system (Millipore, Bedford, MA, USA); all other solvents AR : R H 2 1 = HO CH2CO R2 = were of analytical grade from Yuwang Industry Co. Ltd. AR H (Dezhou, China). Ten samples were obtained from different 3 :R1 = R2 = HO CH2CO AR H 3 :R1 = R2 = HO CH2CO habitats in China, and identified by Prof. Bateer (College of 1' 3' CH AR :R H C CH CH 3 Mongolian Medicine and Pharmacy, Inner Mongolia Univer- 4 1 = R2 = 1' 3' CH AR H CH 3 4 :R1 = R2 = OC OHCH CH 3 sity for Nationalities, China). Samples were deposited at the CH AR :R H R H O OH 3 Herbarium of Inner Mongolia University for Nationalities. 5 1 = 2 = (4-6) AR :R H H Sesquiterpene lactones (AR , AR , AR , AR , AR , Figure5 1. Chemical1 = structuresR2 = of six sesquiterpene lactones used in the 1 2 3 4 5 study. AR6) were isolated and purified from the I. Chinensis. Their 1 Table 1. H-NMR (600 MHz, J in Hz) spectral data for compounds AR1- AR6 in CD3OD No. AR1 AR2 AR3 AR4 AR5 AR6 1 3.02 (1H, t, 9.6) 2.98 (1H, t, 9.6) 2.95 (1H, t, 9.6) 3.03 (1H, t, 9.6) 2.97 (1H, t, 9.3) 2.98 (1H, t, 9.3) 2 2.28 (1H, m) 2.37 (1H, m) 2.43 (1H, m) 2.41(1H, m) 2.33 (1H, m) 2.37 (1H, m) 1.89 (1H, m) 1.94 (1H, m) 1.98 (1H, m) 2.02 (1H, m) 1.98 (1H, m) 1.91 (1H, m) 3 4.62 (1H, t,7.2) 4.65 (1H, t,7.2) 4.64 (1H, t,7.2) 4.64 (1H, t, 9.6) 4.65 (1H, t,7.0) 4.60 (1H, t,7.0) 5 2.81 (1H, m) 2.80 (1H, m) 2.80 (1H, m) 2.86 (1H, m) 2.82 (1H, t, 9.3) 2.83 (1H, t, 9.3) 6 4.23 (1H, t, 9.6) 4.16 (1H, t, 9.6) 4.46 (1H, t, 9.6) 4.64 (1H, t, 96) 4.18 (1H, t, 9.3) 4.16 (1H, t, 9.3) 7 2.88(1H, m) 2.90 (1H, m) 3.34 (1H, m) 3.34 (1H, m) 2.91 (1H, m) 2.90 (1H, m) 8 3.98 (1H, m) 2.24 (1H, m) 5.49 (1H, m) 5.64 (1H, m) 2.23 (1H, m) 2.27 (1H, m) 1.48 (1H, m) 1.45 (1H, m) 1.49 (1H, m) 9 2.27 (1H, m) 2.20 (1H, m) 2.65 (1H, m) 2.62 (1H, m), 2.25 (1H, m) 2.26 (1H, m) 2.74 (1H, m) 2.52 (1H, m) 2.52 (1H, m) 2.52 (1H, m) 2.58 (1H, m) 2.54 (1H, m) 13 6.01 (1H, d, 3.0) 6.08 (1H, d, 3.0) 6.03 (1H, d, 3.6) 6.21 (1H, d, 3.6) 6.04 (1H, d, 3.3) 6.05 (1H, d, 3.3) 5.04 (1H, d, 3.0) 5.57 (1H, d, 3.0) 5.44 (1H, d, 3.6) 5.61 (1H, d, 3.6) 5.54 (1H, d, 3.3) 5.55 (1H, d, 3.3) 14 5.08 (1H, s) 5.01 (1H, s) 5.06 (1H, s) 5.16 (1H, s) 5.01 (1H, s) 5.06 (1H, s) 4.90 (1H, s) 4.93 (1H, s) 4.77 (1H, s) 4.95 (1H, s) 4.97 (1H, s) 4.79 (1H, s) 15 5.38 (1H, s) 5.42 (1H, s) 5.48 (1H, s) 5.48 (1H, s) 5.46 (1H, s) 5.44 (1H, s) 5.31 (1H, s) 5.34 (1H, s) 5.33 (1H, s) 5.38 (1H, s) 5.33 (1H, s) 5.30 (1H, s) 2′ 3.56 (2H, s) 3.60 (2H, s) 3.46 (2H, s) 3.88 (1H, m) 3′ 1.98 (1H, m) 4′ 7.04 (1H, d, 8.4) 7.08 (1H, d, 8.4) 7.00 (1H, d, 8.4) 0.95 (3H, d, 6.0) 5′ 6.73 (1H, d, 8.4) 6.75 (1H, d, 8.4) 6.70 (1H, d, 8.4) 0.88 (3H, d, 6.0) 6′ 7′ 6.73 (1H, d, 8.4) 6.75 (1H, d, 8.4) 6.70 (1H, d, 8.4) 8′ 7.04 (1H, d, 8.4) 7.08 (1H, d, 8.4) 7.00 (1H, d, 8.4) 1″ 4.54 (1H, d, 7.2) 4.60 (1H, d, 7.2) 4.46 (1H, d, 7.2) 4.46 (1H, d, 7.2) 4.47 (1H, d, 7.5) 2″ 3.35 (1H, m) 3.38 (1H, m) 3.18 (1H, m) 3.18 (1H, m) 3.20 (1H, m) 3″ 4.92 (1H, m) 5.02 (1H, m) 3.42 (1H, m) 3.34 (1H, m) 3.43 (1H, m) 4″ 3.50 (1H, m) 3.52 (1H, m) 3.30 (1H, m) 3.30 (1H, m) 3.32 (1H, m) 874 Journal of Food and Drug Analysis, Vol.
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