Antioxidant and anti-tumour evaluation of compounds identified from fruit of Amomum tsaoko Crevost et Lemaire
Tian-Tian Zhang a, Chuan-Li Lu a,b, Jian-Guo Jiang a,* a College of Food and Bioengineering, South China University of Technology, Guangzhou 510640, China b Nutritional Immunology & Functional Foods, Key Laboratory of Tropical Plant Resources and Sustainable Use,
Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Menglun, Mengla, Yunnan 666303,
A R T I C L E I N F O
Received 26 May 2015
Received in revised form 21 July 2015
Accepted 12 August 2015
A B S T R A C T
This research was aimed to isolate the active compounds with antioxidant and antitumour properties from Amomum tsaoko Crevost et Lemaire, a traditional health food in China.
Ethanol (95%) extract and ethyl acetate fraction was found to have significant DPPH radical scavenging activities and cytotoxicities against cervical cancer cell Hela, hepatoma cells HepG-2 and SMMC-7721, and lung cancer cell A549. Four compounds were isolated from ethyl acetate fraction, and compounds III and IV are identified as new compounds. Compounds III and
IV showed high DPPH radical scavenging activities. Compound II, III and IV exhibited good anti-tumour activity against HepG-2, SMMC-7721, Hela and A549 cell lines. Compound I showed a strong anti-tumour activity only against Hela cell lines. Compounds III and IV were concluded to be the active compositions responsible for potent antioxidant and anti-tumour properties of A. tsaoko, whose molecular mechanism and pathways of inhibiting tumour cell need to be further studied. © 2015 Elsevier Ltd. All rights reserved.
Amomum tsaoko Crevost et Lemaire
Identification 1. Introduction
Amomum tsaoko Crevost et Lemaire, belonging to family
Zingiberaceae, is widely distributed in south-west China. Its dried fruit is a well-known and commercially important spice in south-east Asia (Zhang, Lu, & Jiang, 2014). Water extract of
A. tsaoko has a strong anti-hepatitis B virus effect. A. tsaoko intake displayed hypoglycaemic effect and could lower the triacylglycerol concentrations of plasma and liver in mice (Yu et al., 2010). Recently, a series of studies have described the isolation and identification of the chemical composition from the dried fruit of A. tsaoko using hydrodistillation, microwave assisted extraction, and supersonic solvent extraction (Feng,
Jiang, Wang, & Li, 2010; Li, Wang, Masami, & Lu, 2011). The essential oil from A. tsaoko could serve as a new medicinal source * Corresponding author. College of Food and Bioengineering, South China University of Technology, Guangzhou, 510640, China. Tel.: +86 20 87113849; fax: +86 20 87113843.
E-mail address: firstname.lastname@example.org (J.-G. Jiang).
Abbreviations: DPPH, 2,2-diphenyl-1-picryl-hydrazil radical; MTT, 3-(4,5-dimethylthiazol-z-yl)-2,5-diphenyl tetrazolium bromide; VC, ascorbic acid; HPLC, high-performance liquid chromatography; ESI-MS, electrospray ionization ion trap multiple mass spectrometry; FBS, foetal bovine serum; PBS, phosphate buffer solution; DEPT, distortionless enhancement by polarization transfer; 1H-1H COSY, H-H correlation spectroscopy; HSQC, heteronuclear single-quantum coherence; HMBC, heteronuclear multiple-bond correlation; TMS, tetramethylsilane;
TLC, thin-layer chromatography; PE, petroleum ether fraction; EA, ethyl acetate fraction; W, water fraction; OD, optical density http://dx.doi.org/10.1016/j.jff.2015.08.005 1756-4646/© 2015 Elsevier Ltd. All rights reserved.
J o u rna l o f Func t i ona l F ood s 1 8 ( 2 0 1 5 ) 4 2 3 – 4 3 1
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ScienceDirect for antibacterial and as an antifungal agent (Li et al., 2011; Li,
Zou, Zha, Zheng, & Huang, 1999; Qiu, Shou, Chen, Dai, & Liu, 1999). The volatile oil of A. tsaoko could improve the function of stomach and increase the percutaneous permeation rate of rutondine that has sedative, analgesic and hypnotic effects (Ma & Bai, 2006). However, all these studies on A. tsaoko have not been subjected to detailed chemical constitution analysis, and bioactivity studies were restricted to its crude extracts.
In the present research, the antioxidant activity and antitumour activity of crude extracts of A. tsaoko on cervical cancer cell Hela, hepatoma cells HepG-2 and SMMC-7721, and lung cancer cell A549 were investigated in order to isolate and identify the active compounds responsible for these biological activities. 2. Materials and methods 2.1. Plant material
The dried A. tsaoko, derived from Yunnan province (China), was purchased from Qingping market of Chinese medicinal material in Guangzhou, China. A voucher specimen was deposited in the department of Natural Products Studies, school of Light
Chemistry and Food Science, South China University of Technology. Samples were pulverized to a powder and the dried materials were stored at room temperature until use. 2.2. Chemicals 2,2-Diphenyl-1-picryl-hydrazyl (DPPH) radical, 3-(4,5-dimethyl2-thiazolyl)-2, 5-diphenyl-2-H-tetrazolium bromide (MTT), 5-fluorouracil, ascorbic acid (VC) and high-performance liquid chromatography (HPLC)-grade MeOH were purchased from
Sigma Chemical Co. (St. Louis, MO, USA). Acetone and MeOH employed for the electrospray ionization (ESI)-MS analyses were of HPLC supergradient quality. Foetal bovine serum (FBS) was purchased from Biochrome Co. (Germany). Cell culture DMEM media, trypsin-EDTA (ethylenediaminetetraacetic acid), penicillin, streptomycin and phosphate buffer solution (PBS, pH 7.4) were bought from Thermo Fisher Scientific Inc. (Waltham, MA,
USA). All the other chemicals were of analytical grade. 2.3. General experimental procedure
A Bruker DRX-400 NMR spectrometer (Bruker Biospin Co.,
Karlsruhe, Germany), operating at 400 MHz for 1H and at 101 MHz for 13C, using the UXNMR software package, was used for NMR analysis. Distortionless enhancement by polarization transfer (DEPT), 13C, H-H correlation spectroscopy (1H-1H