НАУЧНИ ТРУДОВЕ ТОМ LX “ХРАНИТЕЛНА НАУКА, ТЕХНИКА И ТЕХНОЛОГИИ – 2013“ 18-19 октомври 2013, Пловдив

SCIENTIFIC WORKS VOLUME LX „FOOD SCIENCE, ENGINEERING AND TECHNOLOGIES – 2013“ 18-19 October 2013, Plovdiv

CHEMICAL COMPOSITION AND ANTIFUNGAL ACTIVITY OF VIETNAMESE TURMERIC AROMATIC PRODUCTS OBTAINED FROM CURCUMA LONGA (ZINGIBERACEAE) BY DIFFERENT METHODS Nguyen Thi Mai Huong1, Nguyen Thi Kim Cuc2, Tran Kim Dung2, Tran Lien Ha3, Pham Viet Cuong2 1. Faculty of Food Technology, University of Economic and Technical Industries 2. Institute of Marine Biochemistry, Vietnam Academy of Science and Technology 3. School of biotechnology and food technology, Ha Noi University of Science and Technology ХИМИЧЕН СЪСТАВ И АНТИМИКРОБНА АКТИВНОСТ НА АРОМАТИЧНИ ПРОДУКТИ ОТ ВИЕТНАМСКА КУРКУМА (CURCUMA LONGA (ZINGIBERACEAE)), ПОЛУЧЕНИ ЧРЕЗ РАЗЛИЧНИ МЕТОДИ Abstract: The chemical compositions of Vietnamese turmeric aromatic products obtained by different methods (extraction with different solvents such as chloroform and n-hexane and steam distillation) were determined by GC/MS method. The in vitro test of antifungal activity showed that the turmeric oil in concentration 10% has highest activity against investigated fungi, with inhibition zones around 1.0-1.5 cm. The results aromatic products showed no remarkable difference in antifungal activity. The yeast isolates were more resistant to our turmeric oils than fungal isolates. The essential oil was demonstrated its fungicidal activity against Valsa sp. on King mandarin (Ha Giang province). The obtained results indicate potential application of turmeric essential oil in controlling post harvest fruit decay.

Key words: turmeric essential oil and extract, chemical composition, antifungal activity.

INTRODUCTION Curcumas perhaps originated from India, it was grown in many places and then became wild. Curcuma belongs to the Zingiberaceae family and composed of about 70 species of rhizomateous herbs distributed worldwide [7]. In Vietnam, at least 16 species in the genus Curcuma and many of them have been used in the Vietnamese folk medicine such as Curcuma domestica Val.; C. aeruginosa Roxb.; C. zeoaria (Berg.) Rosc.; C. aromatica Salisb.; C. xanthorrhiza Roxb.; and C. pierreana Gagnep [18]. The usage of Rhizoma Curcumae was first recorded in Yao Xing Lun in 627–649 B.C., the described functions were to remove blood stasis and to alleviate pain [7]. Turmeric and it's isolated compounds have demonstrated various beneficial pharmacological activites such as antioxydant, antiarthritic, antimutagenic, antitumor, antithrombotic, antimicrobial, nematocidal, choleretic and antihepatotoxic [3, 11, 14, 13, 15]. Turmeric is used in medicine as carminative, anthelmintic, laxative, cure for liver ailment; in food as condiment and as insect repellent [14]. It is known that turmeric contains essential oil components, but up to now, great attentions have been paid to the chemical and pharmacological

research of curcumin, demethoxycurcumin and bisdemethoxycurcumin, and most physiological effects refer to the effects of the curcuminoids, in particular curcumin [9]. Most of turmeric essential oil components are bisabolane type sesquiterpenoids and they showed antifungal, antibacterial, antioxidant, antivenom by neutralizing the hemorrhagic effect of the venom in mice, and antitumor effects [24]. The inhibitory effect of turmeric essential oil against microorganisms has been reported by many authors [3, 14, 13, 15]. In this report, the antifungal activity of Vietnamese turmeric oil obtained by extraction with solvents and steam distillation was tested against fungal isolates causing fruit spoilage.

MATERIALS AND METHODS Materials Rhizomes of Curcuma longa L from Hung Yen province of Viet Nam were collected, cut into pieces and pulverised, average particle size approximately 4 mm. The moisture (about 90%) was determined by drying of the material to constant value at 100oC. Essential oil 1 kg of material was put into Clevenger apparatus, adding water to 1.5 liter and some pumice 539

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stone, and the distillation process was carried out for 8 hours. Extracts Turmeric extracts were obtained by soaking dry powdered rhizome in the solvent with ratio 1:3 (w/v), shaking 200 rpm in 24 hours. The solvent was concentrated under vacuum at 40–50 oC using a rotary flash evaporator (Heidolph, Germany). Oleoresin, a by-product of curcumin production process was kindly given by Enteron Company (Vietnam) also investigated for it’s antibacterial activity. Chemical composition The chemical composition was determined using model GC-System HP6890 MSD 5973 Aglilent on a 30.0 m 9250lm HP-5MS-coated fused silica capillary column with 0.25 lm film thickness. One micro liter of essential oil sample was injected into the GC-MS system using split mode (50:1). The purge flow was 1.0 ml/min. The injector temperature was 2500C. The column temperature was programmed as follows: initial temperature 650C for 2 min, 50C/min to 900C, 900C for 3 min; 200C/min to 1030C; 1030C for 3 min; 80C/min to 1500C; 1500C for 15 min; 200C/min to 2800C. Mass conditions were as follows: electron impact (EI) ionization, electron energy 70.1 eV; interface temperature, 2800C; ion source 0 temperature, 230 C; detector voltage, 1435 V; solvent delay, 3 min. Helium was used as the carrier gas at a flow rate of 1.0 ml/min. All data were obtained by collecting the full-scan mass spectra within a scan range of 45–550 m/z. The identity of the components was assigned by comparing their GC retention time and the mass spectra with those of authentic reference compounds in mass spectra library (≥ 90%). Fungal isolates Fungi and yeasts were isolated from spoiled fruits such as blue dragon (Hylocereus undatus (Haworth) Britton & Rose), mango (Mangifera indica L.), orange (Citrus sinensis, L.), avocado (Persea americana Mill.) and custard apple (Annona squamosa L.). The isolates were tested for their ability causing spoilage of the fruits by inverse infection and selected isolates were identified to genus or species. Determination of antifungal activity The antifungal activity of turmeric aromatic products in vitro was carried out by disc diffusion assay. Young cultures of fungi or yeasts were spreaded on appropriate medium (Czapek-Dox and Hansen). Sterile filter papers (5mm diameter) were impregnated with 20µl oil diluted in Ethylene glycol (100mg/ml). Negative controls were prepared using

SCIENTIFIC WORKS VOLUME LX „FOOD SCIENCE, ENGINEERING AND TECHNOLOGIES – 2013“ 18-19 October 2013, Plovdiv

the same solvent for product dilution. The plates were incubated at 30oC for 2 days. The halo around of the paper discs was measured and expressed as inhibition activity against test microorganisms. All tests were performed in triplicate and mean diameter of the inhibition zone was recorded. Yeast growth inhibition assay To flasks containing 20 ml melted Hansen agar the SD oil in ethylene glycol were added to desired concentration. Control flasks were added equivalent amount of ethylene glycol. One hundred micro liters (about 103 CFU/ml) of each yeast isolate was inoculated into the flasks under aseptic conditions. The media then poured into sterilized Petri plates in triplicates and incubated at 30oC for 24 hours. The colonies developed after incubation were counted and the inhibition effect was calculated using formula: % inhibition = (1-T/C) x100 where T is CFU /ml of test sample and C is CFU/ml of control. The growth inhibition test for fungi was carried out by plate spreading method. The minimum inhibition concentration was reported as the lowest concentration of the oil capable of inhibiting the complete growth of the tested isolate. Bioassay King mandarins (Citrus reticulata × maxima L.) of Ha Giang were harvested at commercial maturity, disinfected with 1% H2O2 and rinsed with distilled water. Air dried fruits were immersed in conidia suspension (approximately 1.2x 105 spores. ml-1) of Fusarium oxysporum for 5 min, air dried. Then the fruits were dipped in turmeric oil 1% and incubated at room temperature (27 ± 2ºC). Experiment was carried out with 5 replicates, and fruits infected with fungi were used as control. Statistical analysi The data were statistically analysed using software SPSS for analysis of variance (ANOVA). A least significant difference (LDS 0.05) was used to test effect of essential oil through a general linear model. Means were compared and separated by Scheffe test at the p= 0.05.

RESULTS AND DISCUSSION Chemical composition of turmeric oil The chemical composition of the aromatic products is shown in Table 1. The main constituent of turmeric oil was arturmerone (30.33%), followed by alpha-turmerone (14.14%). 16 unidentified compounds contributed 540

НАУЧНИ ТРУДОВЕ ТОМ LX “ХРАНИТЕЛНА НАУКА, ТЕХНИКА И ТЕХНОЛОГИИ – 2013“ 18-19 октомври 2013, Пловдив

about 37.19% of the oil. The obtained essential oil composed mainly sesquiterpenes (betacaryophyllene, alpha-humulene, ar-curcumene, αzingiberene, β–bisabolene, β–sesquiphellandrene, zingiberene, ar-tumerone, α–tumerone). Only two compounds were monoterpenes (1,8-cineole, terpinolene). In the chlorophorm and the hexane extracts the major compound was β-turmerone, contributing 63.94 % and 55.99 %, respectively. Monoterpenes could not be detected in these extracts, but 3 others minor compounds were uncovered in hexane extract and amount of unknown spectrum was less than in turmeric essential oil. Nine compounds were detected in the oleoresin, among which ar-turmeron and β–turmerone predominated with more than 41 % and 23 %, respectively. Moreover, caryophyllene is in trans-, not in beta-form as in the method essential oil or extracts with hexane and chloroform. Chemical composition of turmeric essential oil from different parts and from various geographic regions of Curcuma have been reported [18, 24]. The essential oil from Indian rhizomes of Curcuma longa composed 47 constituents, 24 of which could be identified. The major components were ar-turmerone (31.1%), turmerone (10.0%), curlone (10.6%) and ar-curcumene (6.3%) [12]. The essential oil profile from Thai Lan Curcuma longa shows turmerone as the main compound (50%), other major constituents were curlone, α-farnesene and α-zingiberene [16]. The main components of Curcuma kwangsiensis (China) essential oil including β-elemene, curzerenone, curcumol, curdione, germacrone, and β-elemenone [27]. Turmeric oils from rhizomes of Vietnamese Curcuma aff. aeruginosa Roxb. extracted by petroleum ether composed ten sesquiterpene hydrocarbons and eight oxygen containing sesquiterpenoids; and of C.aromatica Salisb. were six oxygenated sesquiterpenes [18, 19]. It was obviously that, there was considerable quantitative variation in the main components depending upon the cultivars from which the oil was produced and the used method. Antifungal activity in vitro The antifungal activity of the obtained oils was assessed qualitatively and quantitatively by determination of inhibition zones and zone diameter (Table 2). The test fungi and yeasts were isolated from spoiling orange (Valsa sp.; F. oxysporum; Hansenulla sp.), blue dragon (C. tenuisimum; Rhodoturola sp.), avocado (Geotrichum candidum), Annona squamosa (Aspergillus awamori), and mango (Aspergillus versicolor; Candida sp. and

SCIENTIFIC WORKS VOLUME LX „FOOD SCIENCE, ENGINEERING AND TECHNOLOGIES – 2013“ 18-19 October 2013, Plovdiv

Torulopsis sp.) and one laboratory strains S. cerevisiae The obtained results showed that turmeric oil obtained by steam distillation in used concentration has highest activity against investigated fungi, with inhibition zones around 1.0-1.5 cm. The yeast isolates were more resistant to our turmeric oils than fungal isolates. The remained oils showed no remarkable difference in their antifungal activity. Numerous reports concerning antimicrobial activity of turmeric oil from Curcuma sp. [15, 18, 19, 24]. Extract with hexane of C. longa was found effective in growth inhibition of fifteen isolates of dermatophytes (Trichophyton, Epidermophyton and Microsporum) in vitro and in vivo [3]. Rukayadi et al. [22] investigated anticandidal activity of xanthorrhizol, isolated from the methanol extract of Curcuma xanthorrhiza Roxb., using six Candida species. The anti-Fusarium oxysporum f. sp cicer and anti-Alternaria porri effects were evaluated for 75 different essential oils, including Curcuma longa L. (Zingiberaceae) [17]. Antibacterial effect of essential oil obtained by hydrodistillation and extracts with petroleum ether and ethanol from five Zingiberaceae species: ginger (Zingiber officinale Roscoe.), galanga (Alpinia galanga Sw.), turmeric (Curcuma longa L.), kaempferia (Boesenbergia pandurata Holtt.) and bastard cardamom (Amomum xanthioides Wall.) was investigated by Norajit et al. [17]. Dhinga et al. [8] reported that the growth of Aspergillus flavus, A. ruber, A. ochraceus (stored grain and feed deteriorating fungi), Fusarium semitectum, Colletorticum gloeosporioides and A. niger (post-harvest rot of tropical fruits and vegetables) and C. musae (banana fruit anthracnose) at 0.1% rhizome oil of C. longa was reduced 5070%. The response of these fungi to the oil was varried significantly, A. flavus, C. gloeosporioides and C. musae were the most sensitive with growth inhibition above 70%. The growth of the A. niger was inhibited only 36%, while A. ruber and A. ochraceus were moderatly sensitive to turmeric oil (50% and 57% inhibition, respectively). Fathima et al. [10] evaluated anti Phomopsis azadirachtae effect of five essential oils (eucalyptus oil, fennel oil, pepper oil, nutmeg oil, coriander oil) and two oleoresins namely, capsicum oleoresin and turmeric oleoresin. The result showed that nutmeg oil, coriander oil and turmeric oleoresin were very effective against P. azadirachtae. Nutmeg oil, coriander oil and turmeric oleoresin inhibited the growth and the pycnidial formation and sporulation of P. azadirachtae at concentrations of 2000, 3000 and 4000 ppm, respectively. 541

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According to some reports, the main component responsible for antibacterial activity of turmeric oil is ar-turmerone [8]. But our results did not support this opinion, as the antifungal activity of the oleoresin was weaker than the essential oil, although arturmerone in the oleoresin was higher than in the essential oil (42% vs 30%). At the present, it is recognized that the components in essential oil may be synergistic to inhibitory principles against microorganisms [1, 16, 17]. Singh et al. [23] examined antimicrobial activity of Indian turmeric oil with 49.76% turmerones against Staphylococcus aureus, Pseudomonas aerugenosa, Candida albicans and Aspergillus niger responsible for causing eye infection. The oil showed very good inhibition activity against investigated strains at low concentration (1.95-6.7µl/ml). Our results demonstrated that the essential oil presented stronger antifungal activity than the extracts, and the sensitivity degree of the test organisms may be depend on their intrinsic tolerance and the nature and combinations of compounds present in the oils. This result is in corresponding with others [3, 15]. Minimum inhibitory concentrations (MICs) The essential oil exhibited highest inhibition activity was used for MICs assay. The spreading method was used for determination of MICs for fungal isolates. The obtained results showed that, at oil concentration 20 mg/ml, growth of G. candidum and C. tenuisinum was completely inhibited, the same effect for remaining isolates was reached at 30 mg/ml of the oil (Table 3). The growth inhibition effect of the oil against yeast isolates were determined by counting developed colonies at Hansen medium supplemented with essential oil (table 4). The oil was most effective against S. cerevisiae, for other yeast strains a higher concentrations (30 to 60 mg/ml) were required to completely inhibit their growth. The MICs values indicate that fungi isolates were more susceptible to the oil than yeast isolates. In vivo assay The king mandarins were treated with Fusarium oxysporum and turmeric oil as described above. After 7 days of preservation, there were black spots in bottom of controls, meanwhile the fruits treated with the oil remain unchanged. Mycelial growth development was observed within 25 days after inoculation on 100% control fruits, and tested fruits maintain their integrity and color (Fig.1). Plant essential oils are considered non-phytotoxic compounds and are potentially effective as natural pesticides for crop protection. The major components of plant essential oils are mono- and

SCIENTIFIC WORKS VOLUME LX „FOOD SCIENCE, ENGINEERING AND TECHNOLOGIES – 2013“ 18-19 October 2013, Plovdiv

sesquiterpenes, monoand sesquiterpene hydrocarbons, some phenolic compounds have been reported strong potential to inhibit microbial pathogens [2]. There are numerous reports of in vitro antimicrobial activity of plant essential oils, but only some reports on in vivo effect of selective essential oils was investigated. The beneficial effects of using essential oils as postharvest preservative measure on horticultureal product quality were reported for few fresh produce such as pears, citrus, strawberries, tomato, cherries and grapes [2;5;12]. Essential oils from eucalyptus and cinnamon reduced decay in strawberries and tomatoes with no effects on fruit firmness [21]. The received results demonstrated that our turmeric oil can be used as postharvest decay control agent.

Figure 1. King mandarins after 30 days of incubation at room temperature. A. Control; B. Treatment with the oil

CONCLUSIONS Turmeric essential oil has been shown a broad spectrum of activity against plant fungi responsible for postharvest diseases. It was considered as safe for human health and was used for centries in Asian traditional medicine. Interest in the using of plant essential oils as antimicrobial agents for fresh commodities has increased in the last few years. This is first work on using turmeric oil in fresh fruit decay control. Unfortunately, the applied concentrations may cause some deteriorations, so correct doses and combination of the essential oil with other components can improve it’s effectiveness. It was obviously that turmeric oil can be used as the potential alternative for postharvest decay control. Acknowledgement: The paper was accomplished with financial support of Ministry of Science and Technology (Vietnam), project 2008T/16.

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Table 1 Chemical composition of Vietnamese turmeric aromatic product obtaining by different methods. Area (%) Compounds Essential oil α-zingiberene

3.44

Extract with chloroform −

Extract with hexan −

Oleoresin

ar-turmeron

30.33

−

−

41.27

Β-turmerone

−*

63.94

55.99

23.75

Β-caryophyllene

3.02

0.79

0.93

0.40

Β-bisabolene

0.72

0.41

0.65

0.48

Β-sesquiphellandrene

4.42

2.26

3.14

3.10

Α-humulene

0.79

0.25

−

−

1,8- cineole

0.45

−

−

−

Terpinolene

1.87

−

−

−

ar-curcumene

3.02

−

5.11

1.57

Zingiberene

0.27

0.33

0.34

0.38

Zingiberene 1,3-cyclohexadie

−

−

−

3.26

4-7-10- cycloundecatriene

−

−

0.37

−

Caryophyllene oxide

−

−

1.54

−

Α-caryophylen

−

−

0.37

−

Italicene * - not detected

−

−

−

0.18

−

Table 2 Antifungal activity of the extracts from the rhizomes of Vietnamese C. Longa. Inhibition zones, cm Fungi Essential oil Extract with Extract with Oleoresin negative chloroform hexane control Valsa sp. 1.1 0.5 0.7 0.5 0 A. awamori 1.0 0.4 0.3 0.7 0 A. versicolor 1.1 0.4 0.3 0.4 0 G. candidum 1.4 0.6 0.6 0.6 0 C. tenuisimum 1.5 0.6 0.6 0.5 0 F. oxysporum 1.2 0.5 0.6 0.5 0 Rhodoturola sp. 0.8 0.3 0.4 0.3 0 Hansenula sp. 0.6 0.4 0.5 0.3 0 Candida sp. 0.7 0.4 0.4 0.4 0 Torulopsis sp. 1.2 0.5 0.6 0.5 0 S. cerevisiae 1.3 0.5 0.9 0.9 0 Table 3. Minimum inhibitory concentration of turmeric oil against different fungi isolates Essential oil, mg/ml

Fungi Valsa sp.

10 + 20 + 30 – (+) Growth; (–) No growth

A. awamori

A. ersicolor

G. andidum

C. tenuisimum

F. oxysporum

+ + –

+ + –

+ – –

+ – –

+ + –

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SCIENTIFIC WORKS VOLUME LX „FOOD SCIENCE, ENGINEERING AND TECHNOLOGIES – 2013“ 18-19 October 2013, Plovdiv

Table 4. MICs of Vietnamese turmeric oil against different yeast isolates. Yeast isolates Essential oil (mg/ml) Yeast number, (CFU/ml) 0 5.2 x 103 S. cerevisiae 5 3.7x103 10 0 0 1.4 x 103 Rhodoturola sp. 20 1.2 x 102 30 0 0 8.6 x 102 20 2.4 x 102 Candida sp. 40 4.0 x 10 50 0 0 1.5 x 103 20 6.6 x 102 Torulopsis sp. 40 1.6 x 102 50 1.2 x 102 60 0 0 2.2 x 103 40 8.5 x 102 Hansenulla sp. 50 4.5 x 102 60 0

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