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In Vitro Activity of 2-Methoxy-1, 4-Naphthoquinone and Stigmasta-7

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In Vitro Activity of 2-Methoxy-1, 4-Naphthoquinone and Stigmasta-7 Hindawi Publishing Corporation Evidence-Based Complementary and Alternative Medicine Volume 2011, Article ID 704721, 8 pages doi:10.1093/ecam/nep147 Original Article In Vitro Activity of 2-methoxy-1,4-naphthoquinone and Stigmasta-7,22-diene-3β-ol from Impatiens balsamina L. against Multiple Antibiotic-Resistant Helicobacter pylori Yuan-Chuen Wang,1 Wan-Yu Li,1 Deng-Chyang Wu,2, 3 Jeh-Jeng Wang,4 Cheng-Hsun Wu,1 Jyun-Ji Liao,1 and Cheng-Kun Lin5 1 Department of Food Science and Biotechnology, National Chung Hsing University, Taichung, Taiwan 2 Division of Gastroenterology, Department of Internal Medicine, Kaoshing Medical University, Kaohsiung, Taiwan 3 Graduate Institute of Healthcare Administration, College of Health Sciences, Kaoshing Medical University, Kaohsiung, Taiwan 4 Faculty of Medicinal and Applied Chemistry, Kaoshing Medical University, Kaohsiung, Taiwan 5 Department of Chemistry, National Chung Hsing University, Taichung, Taiwan Correspondence should be addressed to Yuan-Chuen Wang, [email protected] Received 22 April 2009; Accepted 30 August 2009 Copyright © 2011 Yuan-Chuen Wang et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Infection with Helicobacter pylori is strongly associated with gastric cancer and gastric adenocarcinoma. WHO classified H. pylori as a group 1 carcinogen in 1994. Impatiens balsamina L. has been used as indigenous medicine in Asia for the treatment of rheumatism, fractures and fingernail inflammation. In this study, we isolated anti-H. pylori compounds from this plant and investigated their anti- and bactericidal activity. Compounds of 2-methoxy-1,4-naphthoquinone (MeONQ) and stigmasta-7,22- diene-3β-ol (spinasterol) were isolated from the pods and roots/stems/leaves of I. balsamina L., respectively. The minimum inhibitory concentrations (MICs) and minimum bactericidal concentrations (MBCs) for MeONQ were in the ranges of 0.156– 0.625 and 0.313–0.625 μgmL−1, respectively, and in the ranges of 20–80 μgmL−1 both of MICs and MBCs for spinasterol against antibiotic (clarithromycin, metronidazole and levofloxacin) resistant H. pylori.Notably,theactivityofMeONQwasequivalentto that of amoxicillin (AMX). The bactericidal H. pylori action of MeONQ was dose-dependent. Furthermore, the activity of MeONQ was not influenced by the environmental pH values (4–8) and demonstrated good thermal (121◦C for 15 min) stability. MeONQ abounds in the I. balsamina L. pod at the level of 4.39% (w/w db). In conclusion, MeONQ exhibits strong potential to be developed as a candidate agent for the eradication of H. pylori infection. 1. Introduction Impatiens balsamina L. (Balsaminaceae) is an annual herb which originated in Asia. The whole plant has been Infection with Helicobacter pylori is strongly associated used as indigenous medicine in Taiwan for the treatment of with gastric cancer and gastric adenocarcinoma [1]. WHO rheumatism, swelling and fingernail inflammation. Modern classified H. pylori as a group 1 carcinogen in 1994. Antibi- pharmacological studies have reported this plant demon- otics combined with proton-pump inhibitors, H2-blockers strating antifungal, antibacterial, antitumor, antipruritic and and bismuth salts are the suggested standard treatment antianaphylactic activities [5, 6].Theactivecompounds modalities to eradicate H. pylori [2]. However, H. pylori isolated from this plant include peptides (Ib-AMP1-4) from resistance to antibiotics is thought to be the most impor- seeds, quinones[1, 4-naphthoquinone, lawsone, 2-methoxy- tant factor in eradication failure. Resistance rates are the 1,4-naphthoquinone (MeONQ), balsaquinone, impatienol, highest for metronidazole (MTZ) (19.9–39.2%), followed naphthalene-1,4-dione] from petals, pericarp and aerial by clarithromycin (CLR) (1.7–27.7%), and the lowest for parts, and flavonoids (kaempferol, quercetin, rutin, astra- amoxicillin (AMX), tetracycline and trovafloxacin (0–4.7%) galin, nicotiflorin, naringenin and their derivatives) from [3, 4]. petals and leaves [5–8]. 2 Evidence-Based Complementary and Alternative Medicine MeONQ (Figure 1) was isolated from the genus of Impa- band was developed in the column and was collected. tiens including I. balsamina L., I. bicolor and I. glandulifera The collected fraction was subjected to the third silica gel Royl [7–10]. The plant Swertia calycina (Gentianaceae) was column chromatography orderly eluted with n-hexane-ethyl also found to contain this compound [11]. Some bioactivities acetate(10:0,9:1,8:2).Fromthe8:2 elution,oneband were demonstrated in MeONQ including antipruritic [12], was developed in the column and was collected to yield antiinflammatory, antiallergic [13] and anticancer [14]activ- compound (1) (2.61 g). ities. Furthermore, reducing oral lesion recurrence in human Samples (100 g) of roots/stems/leaves were extracted immunodeficiency virus patients was also reported for this with 95% ethanol according to the aforementioned method compound [15]. Antimicrobial activity against fungal and and 13.11 g of extract were obtained. This extract was bacterial pathogens were also published [7, 16]. fractionated with water and n-hexane. The n-hexane fraction Spinasterol (Figure 1) was isolated from the plants of I. was collected (1.88 g) and subjected to a silica gel column balsamina, Adenophora tetraphylla, Medicago sativa, Poly- chromatography orderly eluted with n-hexane-ethyl acetate althia cerasoides Bedd and Pueraria mirifica [8, 17–20]. The (10 : 0, 9 : 1 and 8 : 2) to yield two bands in the column from bioactivity reported in spinasterol includes antibacterial the 8 : 2 elution. The lower band was collected (0.638 g) and action against Streptococcus mutans and S. sorbrinus [19]and then subjected to the second silica gel column chromatog- antitumor effect against breast, ovarian and skin cancer cells raphy orderly eluted with n-hexane–ethyl acetate (100 : 0, [20]. 95 : 5, 90 : 10, 85 : 15). From the 85 : 15 elution, two bands In our previous study, we revealed the whole plant of I. were developed in the column. The upper band was collected balsamina L. exhibiting strong bactericidal H. pylori activity, and subjected to the third silica gel column chromatography especially, the acetone and ethyl acetate pod extracts. This eluted with n-hexane–ethyl acetate (75 : 25) to give three activity was higher than any previously reported natural bands in the column. The middle band was collected to yield products [21]. compound (2) (0.089 g). Therefore, in the current study, we isolated anti-H. pylori compounds from I. balsamina L., in which a silica gel chro- 2.3. Instrumentations. UV and IR spectra were recorded on matography was used. Minimum inhibiory concentrations a UV/Visible Hitachi U-2800 (Japan) spectrophotometer (MICs), minimum bactericidal concentrations (MBCs), 1 ff and a Bruker Equinox 55 (USA) FTIR, respectively. H time-kill assay, e ect of environmental pH, and thermal and 13C NMR spectra were recorded at 600 and 150 MHz, stability of the isolated compounds were examined. Multiple respectively, on a Varian Inova 600 (USA) spectrometer. antibiotic-resistant H. pylori strains were used in the tests. Chemical shifts are reported in δ units (ppm) and coupling constants (J)inHZ .CDCl3 (Sigma-Aldrich, St. Louis, MO, 2. Methods USA) was used as the solvent and TMS (Sigma-Aldrich, St. Louis, MO, USA) as the internal standard, in which chemical 2.1. Plant Materials. Impatiens balsamina L. (white flower) shifts for CDCl3 were δH 7.266 and δC 77.335. MS spectra were collected from a local farm in Erhshuei township were measured on a EI-Finnigan/Thermo Quest MAT 95 XL between May 2007 and August 2007, which were identified (Germany) mass spectrometer. Melting point was performed by Professor Yang-Shiun Chang from the Institute of the on the Mel-Temp (USA). Chinese Pharmaceutical Science China Medical University. Voucher specimens (No. 258526) were deposited at the 2.4. Bacterial Strains and Cultivation. Helicobacter pylori Institute of Ecology and Evolutionary Biology, College of Life strains of ATCC 700824, 43504, and 43526 were obtained Science, National Taiwan University. The parts of pods and from American Type Culture Collection (ATCC). Helicobac- mixed roots/stems/leaves were dried by a warm stream of ter pylori strains of KMUH 4917, 4952, and 4967 were air (below 60◦C) and ground (0.25 mm particle size) for the isolated from the stomach of patients from Chung-Ho anti-H. pylori compounds isolation. Memorial Hospital, Kaohsiung Medical University. Of these 2.2. Extraction and Isolation. The I. balsamina L. pod extract H. pylori strains, the three ATCC strains have resistance to was prepared according to Wang and Huang [22]. In brief, MTZ, the three clinical strains are cross-resistance to CLR, a mixture of 100 g of pod sample and 700 mL of acetone MTZ and levofloxacin (LVX); and all the test strains are was stirred at room temperature for 1 h, and then was sensitive to AMX. centrifuged at 13,666 g for 15 min at 4◦C. The residue was Avolumeof0.1mLofH. pylori suspension was added extracted twice more with 700 mL of acetone of each time. in 5 mL tryptic soy broth (TSB, Difco, USA, pH 7.3), with All the supernatants were collected and concentrated in a Columbia agar (bioMerieux,´ France, pH 7.3) slant contain- rotary vacuum evaporator at less than 40◦C, and thus the ing 5% (v/v) defibrinated sheep blood formed at the bottom pod extract (7.28 g) was obtained. This extract was subjected of the test tube. The broth was incubated in a microaerophilic to a silica gel column [Kiesel gel 60 (40–63 μm), Merck, jarsystem(BBL,USA;5%O2 and 10% CO2 in air, an OXOID ◦ Germany; 2.5 cm i.d. × 33 cm] chromatography eluted with BR 056A gas-generating kit was used) at 37 Cfor72hto 7 −1 dichloromethane-methanol (150 : 1, v/v) to develop two produce 0.5–2.0 × 10 cfu mL of the bacterial counts.
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