Properties and Usage of “Liquidambar orientalis”

Aspects of Product Quality in Plant Production

15.12.2016

AYTEN GİZEM ÖZBEK

CONTENTS

INTRODUCTION ................................................................................................................................... 1

1. PHENOLICS ............................................................................................................................... 1

2. PHENOLIC EXTRACTION ....................................................................................................... 2

3. FEATURES OF LIQUIDAMBAR ORIENTALIS ........................................................................ 2

3.1. Distrubition of Liquidamdar species ................................................................................... 2

3.2. Origin and History of Liquidamdar orientalis .................................................................... 3

3.3. Chemical composition of Liquidamdar orientalis ............................................................... 4

3.4. Industrial Usage of Liquidamdar orientalis ........................................................................ 5

3.5. New Aspects and Researches for Liquidamdar orientalis .................................................. 6

4. LIQUIDAMBAR ORIENTALIS AS A FOOD INGREDIENT .................................................... 6

MATERIAL METHOD .......................................................................................................................... 7

RESULTS AND DISCUSSION ............................................................................................................. 8

CONCLUSION ....................................................................................................................................... 8

REFERENCES ........................................................................................................................................ 9

1

INTRODUCTION

1. PHENOLICS

Antioxidants are described as the compounds that can create defence mechanism against free radicals,

though their concentrations are low (Mathew and Abraham, 2006). Antioxidants have ability to capture

reactive oxygen species (ROS) (Lone at al.,2013). Antioxidants are found in plant materials and supplies

from plant materials (Zheng and Wang, 2001) and most of the antioxidant resources rely on plant

phenolics (Atoui et al., 2005). Plant phenolics are synthesized during normal growth of plants as

secondary metabolites (Atoui et al., 2005). Some naturally occurring phenolic compounds can be seen

in Figure 1.

Phenolics have antioxidant, anticarcinogenic, antimutogenic and antimicrobial effects through their

chemical structure. This feature opens wide range of usage area to the plants with high phenolic

compound levels. There are a lot of researches that a diet with rich antioxidant content may provide

various of chronical diseases (Griel and Kris-Etherton, 2006). Oxidative damage of DNA, proteins and

lipids can trigger cardiovascular diseases, cancer and many other problems (Halliwell, 1996). Therefore,

it is considered that diatery antioxidants may provide protection against oxidative diseases (Suzek et al.,

2015).

Figure 1. Some of the naturally synthesized phenolic compounds (Anonymous, 2016a)

2

2. PHENOLIC EXTRACTION

Various number of plant species has been used for ages with a great number of purposes. In a wide range

of plant parts as leaves, flowers, hearthwood and so on were used for phenolic extraction through years.

Diversity of total phenolic compound studies obtain a huge variety of plant species: Dandelion

(Taraxacum officinale), English Lavender (Lavandula angustifolia), Mexican Orageno (Poliomintha

longiflora), society garlic (Tulbaghia violacea) and so on (Zheng and Wang, 2001). One of these

precious plant is Liquidamdar orientalis (L. orientalis), in another name, Anatolian Sweet Gum tree.

Some of these researches belongs to this endemic plant species’ leaves, balsam and hearthwood that

shows high phenolic content. Distribution of L. orientalis can be found in United States of America,

Turkey and China. In our study, our aim was developing a high yield phenolic extraction method in

order to use the extract, which is suitable for consumption, in future processes.

3. FEATURES OF LIQUIDAMBAR ORIENTALIS

3.1. Distrubition of Liquidamdar species

Phenolic-rich plant L. orientalis is usually known as Sığla, günlük or amber ağacı (amber tree) (Li and

Bogle, 1997) in Turkey and it is belong to order of Hamamelidales, family Hamamelidaceae. Name of

L. orientalis, comes from Latin and Arabic origin. It is a compose of liquidius (in Latin) and amber (in

Arabic) which refers to “odoriferous liquid“ (Önal and Özer, 1985).

Length of L. orientalis trees can be classified as medium to

tall. The tallest Liquidambar tree was recorded in Sütçüler,

Turkey, with 35 m. L. orientalis is monoecious (Yaltırık and

Efe, 2010) and their fruit can be seen in Figure 3. Fruit do not

always leave the tree. It can stay for one year from it’s

production (Efe, 1987) (Figure 2).

Liquidambar species are distributed only in North America,

Southern West part of Turkey and East Asia.

The endemic L. oritantalis species are only found in southern

west of Turkey, in Marmaris, Köyceğiz, Çine, Bucak and

Antalya (Figure 3) (Sağdıç et al., 2005). L. orientalis and

philogenetically close other species Liquidambar styraciflua

(North America) and Liquidambar formosana (East China and

Formosa Island) which have enormous economic and ecologic

Figure 2. Fruit and leaves of a Liquidambar Orientalis Tree (Anonymous, 2016b;

Anonymous, 2016c)

3

impact (Günal, 1994). Only four

Liquidambar species could survive and

show distribution today worldwide:

Liquidambar orientalis L. (L.

orientalis), Liquidambar formosana (L.

formosana), Liquidambar styraciflua L.

(L. styraciflua), and Liquidambar

acalycina (L. acalycina) (Lingbeck et al.,

2015).

3.2. Origin and History of Liquidamdar orientalis

Ancestors of Liquidambar species has been identified by paleonthology and distribution of this species

on earlier geological times (including Cretaceous, Eocene, Oligocene, Miocene, Pliocene and

Pleistocene) were in North America and Euroasia. After Glacial period, distribution showed similar

properties with today (Yaltırık and Efe, 2000).

L. orientalis has always been there for human health. This plant has been used for treatment of skin

diseases like fungi, scabies; gastric problems; asthma and bronchitis. Local people has understood the

importance of this tree to more than 700 years (Eikani et al., 1999), before it has been used as medicine

and cosmetic industry (Hafızoğlu,1982). Moreover, Oil of Liquidambar species dates back to Aztec

Empire (ca. 10,000-7000 BC). Aztecs used it as dermatolical medicine for skin infections (Yaltırık and

Efe, 2000).

Figure 4. Distribution of Liquidambar spicies in the Earth ( Günal, 1994) and in Turkey (Öztürk et al., 2008)

Figure 3. The tallest sığla tree in the earth (Fakir, 2005)

4

3.3. Chemical composition of Liquidamdar orientalis

One of the properties of Sığla tree gives a rise to a new area as functional food: phenolic components.

Protocatechuic acid, (−)-epicatechin and gallic acid were determined as the major phenolics in sığla

leaves (Saraç and Şen, 2014). Other phenolic compunds and their concentrations that obtained by

ethanolic extract can be found in Table1. By usage of these natural phenolic compounds, it can be

effective to produce novel antioxidant food products with aromatic odour.

Table 1. Compounds of phenolics in the ethanolic extract of the leaves of L. orientalis var. orientalis.(Saraç and Şen, 2014)

Phenolic compound Concentrations

(mg/g extract)

Gallic acid 3.258 ± 0.035a

Protocatechuic acid 12.232 ± 0.118

(+)-Catechin 1.622 ± 0.007

Chlorogenic acid 0.429 ± 0.017

Caffeic acid 1.265 ± 0.027

(−)-Epicatechin 7.954 ± 0.493

p-Coumaric acid 0.295 ± 0.003

Ferulic acid 0.811 ± 0.031

trans-Cinnamic acid 0.071 ± 0.003

Quercetin 0.17 ± 0.005

Kaempferol 0.031 ± 0.0003

Apigenin 0.006 ± 0.0009

Essential oil (Sığla Oil) and eight othe species were determined for their antioxidant properties by Topal

et al. (Topal et al., 2008). In the study, they characterized 66 components from Sığla oil. The major

components were menthol, 17b-dihydroxy-5b-androstan-3one and octyl alcohol acetate. As shown in

Figure 5, Sığla oil had the most valuable results in both screening methods (Topal et al. 2008).

5

Figure 5. Free radical-scavenging activity percentages of nine essential oils evaluated by DPPH assay and comparison with

the BHT-positive control (Topal et al. 2008).

Sığla oil contains a huge number of cinnamic acid which has a great impact as antimicrobial and

antioxidant properties. Thus, antimicrobial properties of these tree can be obtained (Lingbeck et al.,

2015).

In addition to oil, the leaves of the Liquidambar trees have antimicrobial properties. Terpinen-4-ol, α-

terpineol, α-pinene, and sabinene from leaf oil have the most important chemicals for providing

antibacterial feature (Lingbeck et al., 2015).

3.4. Industrial Usage of Liquidamdar orientalis

Medical and cosmetic properties of this plant has been known for a long time and it is mostly used in

southern west part of Turkey (Saraç and Şen, 2014). Usage of Sığla oil of known as fixative in soaps

and perfumery. Medical properties are based on Sığla oil (as known as storax or styrax) and essential

oils from extract of leaves (Yaltırık and Efe, 2000).

Swine influenza virus H1N1 is susceptible to antiviral drug Tamiflu® which has an ingredient

“oseltamivir phosphate”. Oseltamivir phosphate synthesis from shikimic acid and Chinese star anise

plant was the initial source for shikimic acid before Escherichia coli’s production. Still some of the plant

species are used for shikimic acid production. Liquidambar species, spesifically L. styraciflua, contains

shikimic acid in their leaves, bark, and young seeds. Therefore, Liquidambar species are valuable

resources for that effectively inhibit the H1N1 virus. (Lingbeck et al., 2015).

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3.5. New Aspects and Researches for Liquidamdar orientalis

Antibacterial properties (Sağdıç ve ark., 2005) and antioxidant activity (Topal et al., 2008) of the balsam

of this tree “Sığla yağı” or “Sığla oil” has been identified with in vitro experiments. Antioxidative

activity of Sığla oil in the rat livers, that has been treated with hepatotoxcic and oxidative stress, was

proofed by Suzek and his collegues (Suzek at al., 2015). Results of their experiments represent

antioxidative and protective effect of Sığla oil on rat livers. Besides of this features, nowadays, new

researches shows that oil of L. orientalis has high antibacterial and antioxidant activities (Gan et al.,

2010). Bayazit has shown considerable effect of Sığla oil on healing strock parameters high

concentration of Sığla oil’s facilitator effect on breakdown of fibrin bloot clots and decreased systolic

and diastolic pressure (Bayazit, 2009). In addition to these studies, Sığla Oil has a high antibacterial

feature on mainly B. Cereus and the other bacteries (B. subtilis, C. xerosis, E. aerogenes, E. faecalis,

K. pneumoniae, M. luteus, M. smegmatis, P. vulgaris, P. aeruginosa, P. fluorescens and S. Aureus)

(Sağdıç et al., 2005).

Essential oils from L. orientalis resin has also nematicidal activity against Bursaphelenchus xylophilus

(common pine wood nematode). Major components of this extract was determined as hydrocinnamyl

alcohol (41%) and trans-cinnamyl alcohol (45%) by Kim et al. (Kim et al., 2008).

Preventation from Aedes aegypti (A. aegypti) mosquitoes (causes yellow fever disease) is possible with

Sığla oil. The LC50 value was calculated to be 194.93 ppm by Imam et al. fort his enviromentally friendly

insecticide (Imam et al., 2013).

4. LIQUIDAMBAR ORIENTALIS AS A FOOD INGREDIENT

5.

Plant species always used for developing human health. Herbal threpies and phytotherapy drugs regain

their popularity and consumers demand increases for plant based drugs. Plant based additives or drugs

used for protection from free radical attacks on DNA and diseases caused from this attack. Another

opportunity to use phenolics from plant species can be decrease the speed of aging. (Ghazali et al.,

2011).

Sığla leaves or sığla oil has not been used as a food additive since now. However, high phenolic

concentration of this tree and other medicinal and antibacterial effects of this tree gives us an idea to

clear our minds to see new horizons. Extraction methods used for total extraction of phenolics either not

available for safety food production or has low yield for extraction. In our study, our aim was using new

extraction solvents and parameters to archieve high yield for phenolic extraction. The studies should be

continue for their effects in human safety.

7

MATERIAL METHOD

Leaves of L. orientalis plant were collected from Marmaris, Village of Karacasöğüt in September 2015

from various numbers of plants an dried under room conditions. Homogenization occured by using

blender and leaf samples stored in room temperature and in dried place.

For developing extraction methods, ethanol, distilled water, gyserine, ethyl acetate and their

combinations were selected. Other variables were selected as extraction time, solvent:solid ratio and

process time. A certain method was developed with Response Surface Methodology (RSM). After

extraction, centrifugation 4000 rpm in 5 minutes were occurred and the supernant were separated for

the total phenolic content determination.

Total phenolic content was determined by using Folin-Ciocalteu Method (Blainski at al., 2013) and the

results were given as Gallic acid equvalent.

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RESULTS AND DISCUSSION

Results of the extraction experiments represented 9011 ppm Gallic Acid as the best result in selected

extraction solvents and the parameters were shown below (Table 2). This result is more valuable than

the reseaches in the literature while the ethanol extract from Saraç and Şen had their values around 333

ppm from their ethanolic extract (Saraç and Şen, 2013).

Table 2. Total phenolic contents of designed by RSM.

Std Run Time (Minute) Solvent/Solid Temperature

(ºC)

Gallic Acid

Equvalent

(ppm)

5 9 30 12 20 3327.2727

1 4 30 4 40 3537.0629

3 17 30 20 40 5774.8251

7 5 30 12 60 4766.4336

10 6 135 20 20 4865.3846

9 16 135 4 20 3891.9347

14 1 135 12 40 6832.8671

16 2 135 12 40 7270.2797

13 8 135 12 40 6488.0769

17 12 135 12 40 7270.2797

15 13 135 12 40 6376.5734

11 7 135 4 60 4510.3963

12 10 135 20 60 9011.014

6 11 240 12 20 5789.5804

4 3 240 20 40 7954.5455

2 15 240 4 40 6392.028

8 14 240 12 60 8810.4895

CONCLUSION

During the time, studies focused on extraction processes from Sığla oil. However, this study represents,

leaves of Sığla tree has also great amount of total phenolic compound. The first research for showing

antioxidant, mutagenic, antimutagenic and phenolic compounds of Liquidambar oritantalis was only in

2013 (Saraç and Şen, 2013). It is necessary to research more in that subject. In addition, extraction

processes for total phenolics had been done with some chemicals that can not be used as a food additive.

Therefore, our study has a new perspective to use the extract as a food additive.

Hopefully, usage of extract from Sığla leaves will provide a new healty, functional drink which contains

a various number of phenolic compounds. A novel fragnant product like soda or alcoholic drink will be

available for consuming.

9

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