Cytotoxic Properties of Leaf Essential Oil and Components from

Chapter 23

Cytotoxic Properties of Leaf Essential Oil and Components from Indigenous Cinnamon (Cinnamomum osmophloeum Kaneh) 1

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Tzou-Chi Huang , Chi-Tang H o , Hui-Yin F u , and Min-Hsiung P a n 4

Downloaded by COLUMBIA UNIV on July 6, 2012 | http://pubs.acs.org Publication Date: January 12, 2006 | doi: 10.1021/bk-2006-0925.ch023

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Department of Food Science, National Pingtung University, 912 Pingtung, Taiwan Department of Food Science, Rutgers, The State University of New Jersey, 65 Dudley Road, New Brunswick, NJ 08901-8520 Department of Food Science and Technology, Tajen Institute of Technology, 907, Pingtung, Taiwan Department of Food Science, National Kao Hsiung Marine University, Kao Hsiung, Taiwan

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The essential oils from leaves of three Cinnamomum osmophloeum clones (A, Β and C) and their major chemical constituents were investigated. G C and G C - M S analyses showed that Cinnamomum osmophloeum clones A , Β and C contain fram-cinnamaldehyde (90.6%), eugenol (91.3%) and linalool (83.7%), respectively, as the major component. The inhibitory effects of the essential oils on the growth of human leukemia cell lines U937 and K562 Hep-1, in vitro were investigated. A strong cell proliferation inhibition activity for Cinnamomum osmophloeum clone A was observed for cell lines K562, whereas Cinnamomum osmophloeum clone Β and Cinnamomum osmophloeum clone C gave comparatively low inhibition. This trend paralleled the cytotoxic properties of authentic trans-cinnamaldehyde, eugenol and linalool, respectively.

© 2006 American Chemical Society

In Herbs: Challenges in Chemistry and Biology; Wang, M., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2006.

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Volatile Composition of Cinnamon Essential Oil Cinnamon, also known as Canela and Sees (Ceylon cinnamon), is native to Sri Lanka and India, and has also been cultivated in Brazil, Mauritius and Jamaica. Cinnamon is used primarily in the flavor and fragrance industries to impart a cinnamon flavor and/or fragrance to various types of foods, beverages, medical products, and perfumes (/). Cinnamomum osmophloeum Kaneh, also known as pseudocinnamomum, belongs to the Angiospermae subphylum, the Dicotyledoneae class, the Archichlamydeae subclass, the Laurceae family and the Cinnamomum genus. Indigenous cinnamon Cinnamomum osmophloeum Kaneh is an endemic tree that grows in Taiwan's natural hardwood forest at elevations between 400 and 1500 m (2). Both bark and leaves of Cinnamomum osmophloeum Kaneh from the primary forests o f central Taiwan were found to contain high levels of cinnamaldehyde (5). H u et al (4) analyzed the composition of the essential oil of C. osmophloeum leaves collected from 21 provenances in central, southern, and eastern Taiwan. On the basis o f the chemical composition of different leaf essential oils, C osmophloeum was classified into nine types: cassia, cinnamaldehyde, coumarin, linalool, eugenol, camphor, 4-terpineol, linalool-terpineol and mixed types. Similar to C. cassia bark oil, C. osmophloeum is a major source of /rajw-cinnamaldehyde which is recognized as a bioactive substance with potential health effects (5). Cinnamaldehyde has been reported to have anti-platelet aggregating and vasodilatory action, inhibiting collagen-induced platelet aggregation in a dose dependent manner, and antiproliferative activity against human solid tumor cells (6). The oils obtained from leaves of three types, namely, eugenol (clone A ) , linalool (clone B), and cinnamaldehyde (clone C) cultivated by farmers in Taiwan were examined by G C and G C / M S . At least 13 compounds were characterized, as shown in Table I. Clones A , Β and C contain transcinnamaldehyde (90.6%), eugenol (91.3%) and linalool (83.7%), respectively as the major component characterized in this experiment. The oils obtained from leaf, stembark and rootbark of Cinnamomum pauciflorum Nees (Lauraceae), growing wild in northeast India, were examined by G C (7). Cinnamaldehyde was the main component of the oil, with the highest percentage found in the leaf oil (94%), followed by the rootbark oil (92.4%) and stembark oils (85.1%). The oils of four species of Cinnamomum from Madagascar were studied. C zeylanicum contained predominantly (£)-cinnamaldehyde together with camphor (15%). C. camphora was of the 1,8-cineole type (58-63%). Cfragrans contained a- and β-


301 pinenes (8% and 10%), 1,8-cineole (28%) and β-caryophyllene (13%). C angustifolium contained mostly α-phellandrene, rho-cymene, a-caryophyllene, 1,8-cineole and a-pinene (#). The leaf and stem bark oils of Cinnamomum sulphuratum Nees, growing wild in northeast India, were investigated by G C and G C / M S . Geranial (27.8%) geraniol (23.2%) and neral (17.6%) were the major constituents of the leaf oil. The bark oil was rich in (£)-cinnamaldehyde (65.6%) (9).

Table I. Volatile Compounds Identified in the Essential Oil of Cinnamomum


Compound a-pinene camphene benzaldehyde β-pinene linalool benzenepropanal methylchavicol c«-cinnamaldehyde ircww-cinnamaldehyde bornyl acetate eugenol D-limonene cinnamyl acetate

A 0.48 0.26 0.01 0.24 2.56 0.04 0.01 0.02 1.23 0.06 91.15 0.34 3.60

Concentration (%) Β C 0.54 0.07 0.12 0.17 0.08 0.63 0.62 0.58 0.91 87.72 0.45 0.32 0.62 0.43 0.57 0.01 3.02 90.58 0.36 1.01 1.21 2.25 0.01 0.42 4.44 2.86

Stem Bark 0.04 0.27 0.18 0.01 1.06 0.46 0.32 0.60 91.41 0.74 1.47 0.02 3.42

The levels of the total essential oil in cinnamon leaf samples were determined by distillation. The fresh cinnamon leaves harvested in August, 2003 from a local farm (Taiwan Cinnamon Co., Pingtung) were used in this study. The cinnamon leaves were dehydrated to a final moisture content of approximately 5%, moisture-free basis or less, as follows: Low temperature air dryer: drying temperature 30±2 °C, and total drying time 20 h.; Freeze-drying: freezing temperature -30 °C, drying temperature 30 °C, vacuum 0.15-0.20 mm Hg, drying time 12 h.; Solar drying: dried under sun shine at temperatures ranging between 30 °C to 35 ° C ; Hot air shelf-drying: drying temperature 80±2 °C, and total drying time 16 h. Changes in the recovery of the volatile compounds due to


302 drying are shown in Figure 1. The recovery of total essential oil from fresh leaves in air-drying at low temperature (30 °C), freeze-drying, solar drying and hot air-dried (80 °C), was 94%, 93%, 89%, and 75%, respectively. Freeze drying and air-drying at 30 °C produced quite similar results and caused hardly any loss in volatiles as compared to fresh cinnamon leaf, whereas solar drying and hot air-drying at 80 °C brought about substantial losses in cinnamon leaf essential oil.


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Fresh cold air Freeze sun 30 Φ j dried dried

oven dried 80 Φ j

Figure 1. Effect of drying on the essential oil recovery from cinnamon leave.

Principal component analysis (PCA) provides a better understanding of the variation among volatile compositions of samples and has been widely used to evaluate food flavors (10). Each principal component of the axis is a linear combination of the original variable. From the G C analysis of 5 different drying methods, 13 major peaks were used as variable for principle component analysis (PCA). In PCA, it can be observed that the first four principal components had eigenvalues greater than 1.0 and accounted for 87.62% of the total variance. Figure 2 shows a plot of the values for the first two principal components, which together account for 68.60% (43.71% + 24.89%) of the variation in the data. From a chemical compositional point of view, the quality of the air-dried samples (30 °C) is similar to that of freeze dried samples, since both were grouped from fresh cinnamon leave. Considering the operation cost, air-drying (30 °C) rather than freeze drying is recommended as a cost-effective method for farmers to store their cinnamon.


303 solar dryincpven * dried 80

c Φ c

â Ε ο ο Έ 0.4

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air

• dried freezj&S dried

• fresh


Principal component 1 Figure 2. Plot of samples offresh and dried cinnamon leaf on the coordinate grid defined by principal component 1 and 2.

Antimicrobial and Insecticidal Activity of Cinnamaldehyde Cinnamaldehyde, the principal of cinnamon flavor, is a potent antimicrobial compound present in cinnamon essential oils. Cinnamaldehyde exhibits strong antibacterial activity against several human food-borne pathogens (11), intestinal bacteria (12), and meat spoilage organisms (13). Cinnamaldehyde revealed potent inhibition against postharvest disease fiingi (14) and aflatoxin production fungi (15). Insecticidal activity of cinnamaldehyde against oak nut weevil (16), termite (17), and grain storage insects (75) was reported as well. These inhibitory activities were attributed, at least in part, to the inactivation of rat intestinal and nephritic N a 7 K ATPase (19). In vitro studies demonstrated an inhibitory effect on activity of many enzymes, including mushroom tyrosinase (20) and nitric oxide synthase (21). +

Cytotoxic Properties of Leaf Essential Oil Three human leukemia cell lines were obtained from the American Type Culture Collection (ATCC), namely K562, C E M and U937 cell lines. These cell lines were cultured in RPMI 1640 medium with 10% fetal bovine serum (Gibco, B R L ) , supplemented with 5 mm L-glutamine and 50 \ig/mL of antibiotics (Penicillin/Streptomycin, Gibco, B R L ) at 37 °C in a humidified 5% C 0 incubator (22). Cells were seeded in 96-well plates at an initial density of 2.0>

Cytotoxic Properties of Leaf Essential Oil and Components from

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