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Cytotoxic and Free Radical Scavenging Activities of Zingiberaceous Rhizomes

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Cytotoxic and Free Radical Scavenging Activities of Zingiberaceous Rhizomes ORIGINAL ARTICLE Cytotoxic and free radical scavenging activities of Zingiberaceous rhizomes Sariga Zaeoung1, Anuchit Plubrukarn2 and Niwat Keawpradub3 Abstract Zaeoung, S., Plubrukarn, A. and Keawpradub, N. Cytotoxic and free radical scavenging activities of Zingiberaceous rhizomes Songklanakarin J. Sci. Technol., 2005, 27(4) : 799-812 Methanol extracts, water extracts and volatile oils of the fresh rhizomes of Alpinia galanga, Boesenbergia pandurata, Curcuma longa, Kaempferia galanga and Zingiber officinale have been assessed for free radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and cytotoxic activity against MCF7 (breast adenocarcinoma) and LS174T (colon adenocarcinoma) cell lines. Methanol extract of C. µ longa exhibited the most pronounced radical scavenging activity with an EC50 value of 9.7 g/ml, whereas the water extracts and volatile oils showed weak activity. All volatile oils and the methanol extract of C. µ longa showed strong activity against MCF7 and LS174T with IC50 less than 50 g/ml. The oils of A. galanga (AGV), B. pandurata (BPV), C. longa (CLV), K. galanga (KGV) and Z. officinale (ZOV) were analyzed by GC/MS. Trans-3-acetoxy-1,8-cineole, camphor, ar-turmerone, ethyl cinnamate and geranial (E-citral) were detected as main compounds in AGV, BPV, CLV, KGV and ZOV, respectively. The novel compound, p- coumaryl-9-methyl ether, was isolated from methanol extract of A. galanga. ar-Turmerone, curcumin, demethoxycurcumin and bisdemethoxycurcumin were isolated from the methanol extract of C. longa while 6-shogaol, 6-dehydrogingerdione (or 1-dehydrogingerdione) and 6-gingerol were isolated from the methanol 1M.Pharm. Student in Pharmaceutical Sciences, 2Ph.D.(Chemistry), Asst. Prof., 3Ph.D.(Pharmacognosy), Asst. Prof., Department of Pharmacognosy and Pharmaceutical Botony, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat Yai, Songkhla 90112 Thailand. Corresponding e-mail: [email protected] Received, 27 August 2004 Accepted, 14 November 2004 Cytotoxic and free radical scavenging activities of Songklanakarin J. Sci. Technol. Zingiberaceous rhizomes Vol.27 No.4 Jul. - Aug. 2005 800 Zaeoung, S., et al. extract of Z. officinale. Curcumin was the most potent compound for free radical scavenging activity with µ an EC50 value of 2.0 g/ml. Demethoxycurcumin was found to be the most active compound against LS174T µ with an IC50 value of 0.8 g/ml and 6-shogaol was the most potent compound against MCF7 with an IC50 value of 1.7 µg/ml. Key words : p-coumaryl-9-methyl ether, ar-turmerone, curcuminoids, gingerols, volatile oil, Zingiberaceae, Alpinia galanga, Boesenbergia pandurata, Curcuma longa, Kaempferia galanga, Zingiber officinale, cytotoxic, tumour cells, free radical ∫∑§—¥¬àÕ “√‘°“ ·´àÕ÷Èß Õπÿ™‘µ æ≈—∫√Ÿâ°“√ ·≈– π‘«—µ‘ ·°â«ª√–¥—∫ ƒ∑∏‘ϵâ“π‡´≈≈å¡–‡√Áß·≈–µâ“πÕπÿ¡Ÿ≈Õ‘ √–¢Õ߇Àßâ“æ◊™«ß»å¢‘ß «. ߢ≈“π§√‘π∑√å «∑∑. 2548 27(4) : 799-812 ‡¡◊ËÕπ” “√ °—¥‡¡∏“πÕ≈ “√ °—¥πÈ” ·≈–πÈ”¡—πÀÕ¡√–‡À¬®“°‡Àßâ“ ¥¢Õßæ◊™«ß»å¢‘ß∑’Ë„™â‡ªìπ‡§√◊ËÕ߇∑» 5 ™π‘¥§◊Õ ¢à“ (Alpinia galanga) °√–™“¬ (Boesenbergia pandurata) ¢¡‘Èπ™—π (Curcuma longa) ‡ª√“–ÀÕ¡ (Kaempferia galanga) ·≈–¢‘ß (Zingiber officinale) ¡“∑¥ Õ∫ƒ∑∏‘ϵâ“πÕπÿ¡Ÿ≈Õ‘ √–¥â«¬«‘∏’ DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging assay ·≈–ƒ∑∏‘ϵâ“π‡´≈≈å¡–‡√Á߇µâ“π¡ MCF7 ·≈–¡–‡√Áß≈”‰ â LS174T æ∫«à“ “√ °—¥‡¡∏“πÕ≈ ®“°‡Àßâ“¢¡‘Èπ™—π¡’ƒ∑∏‘ϵâ“πÕπÿ¡Ÿ≈Õ‘ √–¥’∑’Ë ÿ¥‚¥¬¡’§à“§«“¡‡¢â¡¢âπ∑’Ë°”®—¥Õπÿ¡Ÿ≈Õ‘ √–‰¥â 50% (EC ) ‡ªìπ 9.7 50 ‰¡‚§√°√—¡/¡≈. „π¢≥–∑’Ë “√ °—¥πÈ”·≈–πÈ”¡—πÀÕ¡√–‡À¬¡’ƒ∑∏‘ϵâ“πÕπÿ¡Ÿ≈Õ‘ √–µË”¡“° à«π°“√∑¥ Õ∫ƒ∑∏‘ϵâ“π ‡´≈≈å¡–‡√Áß æ∫«à“πÈ”¡—πÀÕ¡√–‡À¬®“°‡Àßâ“æ◊™∑—Èß 5 ™π‘¥ ·≈– “√ °—¥‡¡∏“πÕ≈®“°‡Àßâ“¢¡‘Èπ™—π¡’ƒ∑∏‘Ï¥’ ‚¥¬¡’ §à“§«“¡‡¢â¡¢âπ∑’ˬ—∫¬—Èß°“√‡æ‘Ë¡®”π«π¢Õ߇´≈≈å¡–‡√Áß 50% (IC ) πâÕ¬°«à“ 50 ‰¡‚§√°√—¡/¡≈. ®“°°“√«‘‡§√“–Àå 50 Õߧåª√–°Õ∫∑“߇§¡’¥â«¬ GC/MS æ∫«à“ “√ ”§—≠∑’Ë¡’ª√‘¡“≥¡“°∑’Ë ÿ¥„ππÈ”¡—πÀÕ¡√–‡À¬®“°‡Àßâ“¢à“ °√–™“¬ ¢¡‘È𠙗𠇪√“–ÀÕ¡ ·≈–¢‘ß §◊Õ trans-3-acetoxy-1,8-cineole, camphor, ar-turmerone, ethyl cinnamate ·≈– geranial (E-citral) µ“¡≈”¥—∫ ·≈–·¬°‰¥â “√„À¡à 1 ™π‘¥§◊Õ p-coumaryl-9-methyl ether ®“° “√ °—¥‡¡∏“πÕ≈¢Õ߇Àßâ“¢à“ à«π “√ °—¥‡¡∏“πÕ≈¢Õ߇Àßâ“¢¡‘Èπ™—π·¬° “√‰¥â 4 ™π‘¥§◊Õ ar-turmerone, curcumin, demethoxycurcumin ·≈– bisdemethoxycurcumin ·≈–®“° “√ °—¥‡¡∏“πÕ≈¢Õ߇Àßâ“¢‘ß·¬° “√‰¥â 3 ™π‘¥§◊Õ 6-shogaol, 6-dehydroginger- dione (À√◊Õ 1-dehydrogingerdione) ·≈– 6-gingerol ®“°°“√∑¥ Õ∫æ∫«à“ curcumin ¡’ƒ∑∏‘ϵâ“πÕπÿ¡Ÿ≈Õ‘ √–¥’∑’Ë ÿ¥ ‚¥¬¡’§à“ EC ‡ªìπ 2.0 ‰¡‚§√°√—¡/¡≈. à«π demethoxycurcumin ¡’ƒ∑∏‘ϵâ“π‡´≈≈å¡–‡√Áß≈”‰ â LS174T ¥’∑’Ë ÿ¥ 50 ‚¥¬¡’§à“ IC ‡∑à“°—∫ 0.8 ‰¡‚§√°√—¡/¡≈. „π¢≥–∑’Ë 6-shogaol ¡’ƒ∑∏‘ϵâ“π‡´≈≈å¡–‡√Á߇µâ“π¡ MCF7 ¥’∑’Ë ÿ¥‚¥¬¡’§à“ 50 IC ‡∑à“°—∫ 1.7 ‰¡‚§√°√—¡/¡≈. 50 ¿“§«‘™“‡¿ —™‡«∑·≈–‡¿ —™æƒ°…»“ µ√å §≥–‡¿ —™»“ µ√å ¡À“«‘∑¬“≈—¬ ߢ≈“π§√‘π∑√å Õ”‡¿ÕÀ“¥„À≠à ®—ßÀ«—¥ ߢ≈“ 90112 Cancer is perhaps the most progressive and are known to decrease the risk of many chronic devastating disease posing a threat of mortality to diseases such as cancer and cardiovascular dis- the entire world despite significant advances in orders. The antioxidant activity may be a result of medical technology for its diagnosis and treatment. one of the following: specific scavenging of reactive All cells are exposed to oxidative stress, and thus free radicals, scavenging of oxygen-containing oxidation, and free radicals may be important in compounds such as hydrogen peroxide, or chelation carcinogenesis at multiple tumour sites (Sies, to metals (Priyadarsini, 1997). The Zingiberaceae 1997). Phytochemical and dietary antioxidants is a well-known plant family in Southeast Asia Cytotoxic and free radical scavenging activities of Songklanakarin J. Sci. Technol. Zingiberaceous rhizomes Vol.27 No.4 Jul. - Aug. 2005 801 Zaeoung, S., et al. and many of its species are being used in tradi- Genesys 5 UV spectrometer was used for measur- tional medicine, which is found to be effective ing the absorbance in DPPH assay. The Power in the treatment of several diseases. The five Wave X plate reader (Bio-TEK Instruments Inc.) Zingiberaceous plants, Alpinia galanga (Greater was used for measuring absorbance (OD) in galanga), Boesenbergia pandurata (Fingerroot), cytotoxic assay. IR spectra were recorded on a Curcuma longa (Turmeric), Kaempferia galanga Jasco IR-810 spectrometer (KBr). UV spectra were (Proh hom) and Zingiber officinale (Ginger), were obtained from a Hewlett Packard 8452A diode investigated as they are perennial herbs widely array spectrometer (scanning mode). 1H- and 13C- cultivated in Thailand and tropical regions of Asia, NMR spectra were recorded at 500/125 MHz on a and have been commonly used as medicinal plants Varian Inova 500 NMR spectrometer. Chemical and spices in Thailand. The rhizomes of these shifts (δ) were reported in ppm scale (J in Hz), five plants possess diverse biological activities, using either TMS or operating solvent as internal for instance, antimicrobial (Yamada et al., 1992; standards. EIMS data were recorded on a Hewlett- Hiserodt et al., 1998), antiulcer (Al-Yahya et al., Packard HP 5890 Series II Plus GC-HP 5972 Mass 1990; Matsuda et al., 2003), antiinflammatory Selective Detector (EI mode with mass range of (Araujo and Leon, 2001), antioxidant (Selvam et 35-700 amu). FABMS data were recorded by a al., 1995), cytotoxic and antitumour (Itokawa et al., MAT 95 XL mass spectrometer (solid probe). 1987; Murakami et al., 1995, 2000; Pal et al., 2001), Analysis of the volatile oils was carried out by vasorelaxant (Othman et al., 2002), antispasmodic GC/MS with a Hewlett-Packard HP5890 Series II (Ammon and Wahl, 1991), antihepatotoxic (Hikino Plus GC-HP 5972 Mass Selective Detector. The et al., 1985) and antidepressant activities (Noro operating conditions were as follows: inlet tem- et al., 1983; Yu et al., 2002). Although there have perature 250ºC, initial temperature 70ºC, detector been many reports concerning chemical consti- temperature 280ºC and final temperature 280ºC tuents and some biological activities of these five (hold for 5 min). It was performed with column species, only a few reports focused on cytotoxic HP-5 (length 30 m, film thickness 0.25 µm and activity against human tumour cells and antio- internal diameter 0.25 mm). Carrier gas was ultra xidative activity against free radicals. Plant high purity helium (UHP He). materials used in the previous studies were mainly crude extracts except for some curcuminoids from Chromatography C. longa and some gingerols from Z. officinale Analytical TLC was performed on precoated (Hikino et al., 1985; Hiserodt et al., 1998; Pal et plates of silica gel 60 F254 (Merck, 0.2 mm thick). al., 2001). Besides, pure compounds responsible The zones were detected under UV at 254 nm and for antioxidant activity have not yet been identified by spraying with anisaldehyde reagent. Preparative from A. galanga, B. pandurata and K. galanga. TLC was performed on silica gel 60 GF254 plates Therefore, further study on antioxidant and (Merck, 0.5 mm thick), activated at 105ºC for 30 cytotoxic activities of the extracts and volatile min before use. Silica gel 60 (Merck, 0.040-0.063 oils, and isolation of the compounds responsible mm) was used for vacuum liquid chromatography for these two activities would provide additional (VLC) and column chromatography (CC). useful data on biological activities of these five Sephadex® LH-20 of Amersham Pharmacia Biotech plants. AB (Sweden) was used for size-exclusion chro- matography, and was suspended in methanol Materials and Methods overnight before use. Instrumentation Assay for free radical scavenging activity Optical rotations were measured on a Polax- The following procedure was modified from L polarimeter (sodium D-line 589 nm). Spectronic those described by Blois (1958) and Yamasaki et Cytotoxic and free radical scavenging activities of Songklanakarin J. Sci. Technol. Zingiberaceous rhizomes Vol.27 No.4 Jul. - Aug. 2005 802 Zaeoung, S., et al. al. (1994). Test samples were dissolved in absolute to inhibit cell growth by 50%) was calculated from ethanol and diluted for at least 5 concentrations dose-response curves plotting between % inhibi- (two-fold dilutions).
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