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Chemotaxonomical study of the genera Brunnera (Schenk) Jonston,Choriantha
H.Rirdel., Cynoglossum Mill., Solenanthus Ledeb. & Symphytum (Boiss.) L. (Boraginaceae) in
Kurdistan region of Iraq by using High Performance Liquid Chromatography (HPLC) .
Adel Mohan Adai
88
Vol: 13 No: , July 2017
DOI : http://dx.doi.org/10.24237/djps.1303.215A
P-ISSN: 2222-8373
E-ISSN: 2518-9255
Chemotaxonomical study of the genera Brunnera (Schenk)
Jonston,Choriantha H.Rirdel., Cynoglossum Mill., Solenanthus Ledeb. &
Symphytum (Boiss.) L. (Boraginaceae) in Kurdistan region of Iraq by using
High Performance Liquid Chromatography (HPLC).
Adel Mohan Adai
Field Crops Department - Agricultural Technical College - Sulaimani Polytechnic
University
adel.adday@spu,edu.iq
Received: 16 June 2016 Accepted: 19 October 2016
Abstract
In the present study, seven of the phenolic compounds, in seven plant species within five
genera of the Boraginaceae family have been identified which were (Brunnera orientalis
(Schenk) Jonston., Choriantha popoviana H., Cynoglossum creticum Mill, Solenanthus
circinnatus Ledeb, Solenanthus stamineus Defed, Symphytum kurdicum Boiss and Symphytum
tuberosum L.). were studied in order to important the phenolic profile. The chemical
composition of these species were examined for the content of the following phenolic
compounds:Caffeic acid , Estragole,2-6Dimethyl phenol, Coumaric acid, Eugenol,Salicylic
acid, and P-Cresol, by using high performance liquid chromatography (HPLC).The results
showed that the most abundant phenolic acids were: Coumaric acid and Salicylic acid which
were found in all the studied taxa, followed by Caffeic acid was absentfrom Brunnera
orientalis and Solenanthus circinnatus while Eugenol was absentjust from Symphytum
kurdicum Boiss and Symphytum tuberosum L. , also 2-6Dimethyl phenol was absent from
Choriantha popoviana and Cynoglossum creticum, whereas the less prevalent phenolic
compounds were Estragole(4- Allyl anisole) and P-Cresol which found in just two of the
Chemotaxonomical study of the genera Brunnera (Schenk) Jonston,Choriantha
H.Rirdel., Cynoglossum Mill., Solenanthus Ledeb. & Symphytum (Boiss.) L. (Boraginaceae) in
Kurdistan region of Iraq by using High Performance Liquid Chromatography (HPLC) .
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Vol: 13 No: , July 2017
DOI : http://dx.doi.org/10.24237/djps.1303.215A
P-ISSN: 2222-8373
E-ISSN: 2518-9255
studied taxa (the first found in Solenanthus stamineus and Symphytum tuberosum L while the
second one found in Choriantha popoviana H. and Symphytum kurdicum Boiss ). The
different distribution for the presence of phenolic compounds in different species was of
benefit taxonomic value and can be used to enhance taxonomic studies to isolate and identify
plant and do not less important as other taxonomic studies the present study regards as the
first study of these Boraginaceae family genera in Iraq..
Key words: Chemotaxonomical study, Boraginaceae, High performance liquid
chromatography (HPLC), Kurdistan region of Iraq.
Brunnera (Schenk) Jonston,Choriantha H.Rirdel.,
Cynoglossum Mill., Solenanthus Ledeb. & Symphytum (Boiss.) L.
(Boraginaceae) HPLC
Boraginaceae Brunnera orientalis (Schenk) Jonston. Choriantha popoviana H. Rirdel
Cynoglossum creticum Mill Solenanthus circinnatus Ledeb Solenanthus stamineus Defed
Symphytum kurdicum Boiss Symphytum tuberosum L.
Caffeic acid ,
Estragole,2-6Dimethyl phenol, Coumaric acid, Eugenol,Salicylic acid and P-Cresol
high performance Liquid chromatography. (HPLC)
Coumaric acid Salicylic acid
Caffeic acid Brunnera orientalis
Solenanthus circinnatus Eugenol Symphytum 2-
Chemotaxonomical study of the genera Brunnera (Schenk) Jonston,Choriantha
H.Rirdel., Cynoglossum Mill., Solenanthus Ledeb. & Symphytum (Boiss.) L. (Boraginaceae) in
Kurdistan region of Iraq by using High Performance Liquid Chromatography (HPLC) .
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6Dimethyl phenol popoviana Choriantha Cynoglossum
creticum ) Allyl anisole -Estragole(4Cresol-P
Solenanthus stamineus , Symphytum tuberosum
Choriantha popoviana , Symphytum kurdicum
BoraginaceaeChemotaxonomical studyHPLC.
Introduction
Since the early 1960s, phytochemical characters started to attract the attention of plant
taxonomists and rapidly expanding areas of plant taxonomy and how to use the chemical
information to improve the classification of the plant. In fact chemotaxonomy has various
ancient origins, perhaps foremost come the search by herbalists and pharmacologists, for
drugs, that have involved the accumulation of information on the chemical content of a very
wide range of plants, second major ancient origin of chemotaxonomy were the field of
morphology and anatomy, for example, color, crystals and starch which differ in morphology
and chemical composition, (Stace ,1980), also based on (Stace ,1980).The phenolic
compounds which dissolved in the water are the first groups of chemical compounds used in
chemical classification, (Smith, 1976). It is known that the taste and smell of plants or both
play an important role in distinguishing some overlapping taxa, including species and
varieties, regardless of any other description (Al-Musawi,1987;Al-Mashhadany,1992). The
phenolic compounds are used by a large number of researchers to solve taxonomic problems (
BateSmith, 1948,1958; Harborne, 1964,1967a, 1967b; Ribereau, 1972; Cutler,
1969,1972;Rezende & Gottlieb, 1973; Blatt et al., 1994 and Sandor, 1994). Boraginaceae
including about 100 genera with 2000 species in all over the world is divided into four
subfamilies: Boraginoideae, Heliotropioideae, Cordioideae and Ehretioideae (Gottschling et
Chemotaxonomical study of the genera Brunnera (Schenk) Jonston,Choriantha
H.Rirdel., Cynoglossum Mill., Solenanthus Ledeb. & Symphytum (Boiss.) L. (Boraginaceae) in
Kurdistan region of Iraq by using High Performance Liquid Chromatography (HPLC) .
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al., 2001).ButStevens (2001) indicated that the Boraginaceae comprises about 2740 species
distributed in 148 genera. Alkaloids, naphthoquinones, polyphenols, phytosterols, terpenoids
and fatty acids were the main secondary metabolites of the Boraginaceae(Zhou & Duan,
2005; Iqbal et al., 2005). Polyphenols including phenolic acids and flavonoids distributed in
the Boraginaceae have diverse pharmaceutical activities such as antioxidant, anti-inflam-
matory, anti-viral, anti-bacterial and hepato- faprotecting activity (Wu, 1990; Zeng & Zeng,
1994; Iqbal et al., 2005). One of the chemical compound groups used in chemotaxonomy is
water soluble phenolic compounds of plant samples (Smith, 1976). Phenolic compounds were
used by (Bate-Smith,1948 ; Bate-Smith et al. 1967; Harborne, 1964, ; Harborne, 1967b;
Ribereau-Gayon, 1972; Cutler, 1969; 1972; Rezende & Gottlieb , 1973; Blatt et al., 1994 and
Sandor , 1994) to solve taxonomical problems. Phenolic compounds consist of simple
phenols, benzoic and cinnamic acid, coumarins, tannins, lignins, lignans and flavonoids (
Khoddami et al.2013). The use of the distribution patterns of natural plant product-
alkaloids,terpens,phenolics,glucosinolites,terpenoids and carbohydrates is well- established
as amajor tool for investigating population structures,speices,taxonomical problems and
phyletic relationships of genera.Taxonomically ,the most important phenolics are the
flavonoids, which have relatively common nucleus with great variety of types and patterns of
side-groups that characterize the individual compounds.There is usually a considerable
diversity of flavonoids in species (Nakipoklu,2002). The present study aimed to study the
phenolic compounds in some genera within Boraginaceae family that have not been studied
before. The species within the studied genera were Brunnera orientali , Choriantha
popoviana , Cynoglossum creticum , Solenanthus circinnatus , Solenanthus stamineus ,
Symphytum kurdicum and Symphytum tuberosum that some of them found at high altitudes
reaches to 2700 m.The identification process of the phenolic compound has been done by
using high performance Liquid chromatography (HPLC).
Chemotaxonomical study of the genera Brunnera (Schenk) Jonston,Choriantha
H.Rirdel., Cynoglossum Mill., Solenanthus Ledeb. & Symphytum (Boiss.) L. (Boraginaceae) in
Kurdistan region of Iraq by using High Performance Liquid Chromatography (HPLC) .
Adel Mohan Adai
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DOI : http://dx.doi.org/10.24237/djps.1303.215A
P-ISSN: 2222-8373
E-ISSN: 2518-9255
Materials and Methods
Sample collection and Preparation:
Samples have been were obtained from deferent locations in Kurdistan region of Iraq in April
to september (2014 and 2015). The Harborne method was followed for extraction of phenolic
compound in vegetative plant parts as follows, ( Harborne1973) .
Leaves and stems of the samples were dried at 25 °C in darkness and analyzed after grinding
in a household blender. All samples were analyzed within 3 months of collection.The
extraction method used for dried samples as follows: 50 ml of%70 methyl alcohol was added
to 5 gm of dried sample, and left at room temperature for 48 hrs. The extraction mixture then
filtered, and then the extraction was concentrated to adequate volume in order to get rid of
alcohol by using air conditioner in as much as volume of Petroleum Ether (80-100 boiling
point) was added to the product, mixture shacked gently, placed in separating funnel and left
for some time to separated clearly into two layer. There by the major part of chlorophyll
dissolved in petroleum ether, and float because of its lesser density than water extraction of
phenolic compounds that dissolve in water and make the lower layer, which drown from
lower of funnel and injected to HPLC .
HPLC Analysis
The analytical HPLC system employed consisted of high performance liquid chromatograph
apparatus in the Sulaimani Polytechnic University, Agricaltural Technical College. The
separation was achieved on Analytical column: Eurospher 100, C18, 5µm, 250 x 4.6 mm at
ambient temperature. The mobile phase consisted of water-acetonitrile water: concentrated
phosphoric acid (400:600: 3± 0.05). The flow rate was 0.8 mL/min and the injection volume
was 20 μL. The monitoring wavelength was 254. The identification of each compound was
based on a combination of retention time and spectral matching.
Results and Discussion
This research was done in pure standards Conditions that used with HPLC method. The
present study included delimitation of a quality of phenolic compounds in the studied species,
Chemotaxonomical study of the genera Brunnera (Schenk) Jonston,Choriantha
H.Rirdel., Cynoglossum Mill., Solenanthus Ledeb. & Symphytum (Boiss.) L. (Boraginaceae) in
Kurdistan region of Iraq by using High Performance Liquid Chromatography (HPLC) .
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depending on some available standard materials. The kinds of phenolic compounds which
detected in the samples are presented in Table (1) with the Retention times of each of them
and the standard curves of them illustrated in (Figure 2) with their structure (figure 1) .
Table (1) Retention time of standard phenolic compounds by (HPLC).
No.
Compound names
Retention time (minute)
1
Caffeic acid
3.431
2
Coumaric acid
3.796
3
Eugenol
4.401
4
Estragole(4- Allyl anisole)
5.751
5
2-6Dimethyl phenol
5.936
6
Salicylic acid
5. 951
7
P-Cresol
7.855
Fig. (1) Chemical structures of standards phenolic compounds. (Dewick, 1997).
Chemotaxonomical study of the genera Brunnera (Schenk) Jonston,Choriantha
H.Rirdel., Cynoglossum Mill., Solenanthus Ledeb. & Symphytum (Boiss.) L. (Boraginaceae) in
Kurdistan region of Iraq by using High Performance Liquid Chromatography (HPLC) .
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DOI : http://dx.doi.org/10.24237/djps.1303.215A
P-ISSN: 2222-8373
E-ISSN: 2518-9255
The results in Table (2)and figure (2(A,B) ,3,4,5,6,7,8,9) shows the kinds of phenolic
compounds which obtained by methanolic extracts of the plant material from the seven
samples. According to available standards compounds the results were as follows (Table1, 2):
1-Coumaric acid and Salicylic acid present in all studied taxa.
2- Caffeic acid was revealed in species Choriantha popoviana, Cynoglossum creticum ,
Solenanthus stamineus , Symphytum kurdicum , Symphytum tuberosum .
3- Eugenol was found in species Brunnera orientalis , Choriantha popoviana , Cynoglossum
creticum , Solenanthus circinnatus and Solenanthus stamineus .
4- 2-6Dimethyl phenol was existing in species Brunnera orientalis , Solenanthus circinnatus
and Solenanthus stamineus .
and Solenanthus stamineus) was identified in two species, Allyl anisole -Estragole(4 -5
Symphytum tuberosum .
6- P-Cresol was found in two species also , Choriantha popoviana and Symphytum kurdicum
. But according to numbers of phenolic compounds, the studied species might divides into
three parts Table (1,2):
a- Species contain six phenolic compounds such as Solenanthus stamineus (1, 2, 3, 4, 5,6).
b-Species contain five phenolic compounds such as Choriantha popoviana (1, 2, 3, 6,
7). C- Species contain four phenolic compounds such as Brunnera orientalis .and
Solenanthus circinnatus (2, 3, 5, 6) , Cynoglossum creticum (1, 2, 3, 6) , Symphytum
kurdicum (1, 2, 6, 7) and Symphytum tuberosum (1, 2, 4, 6).
Chemotaxonomical study of the genera Brunnera (Schenk) Jonston,Choriantha
H.Rirdel., Cynoglossum Mill., Solenanthus Ledeb. & Symphytum (Boiss.) L. (Boraginaceae) in
Kurdistan region of Iraq by using High Performance Liquid Chromatography (HPLC) .
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Table (2) Distribution of phenolic compounds in species.
Species
Phenolic compounds
Caffeic
acid
Coumaric
acid
Eugenol
Estragole(4-
Allyl anisole)
2-6Dimethyl
phenol
Salicylic
acid
P-Cresol
Brunnera
orientalis
X
X
X
X
Choriantha
popoviana
X
X
X
X
X
Cynoglossum
creticum
X
X
X
X
Solenanthus
circinnatus
X
X
X
X
Solenanthus
stamineus
X
X
X
X
X
X
Symphytum
kurdicum
X
X
X
X
Symphytum
tuberosum
X
X
X
X
Number of taxa
5
7
5
2
3
7
2
A
Chemotaxonomical study of the genera Brunnera (Schenk) Jonston,Choriantha
H.Rirdel., Cynoglossum Mill., Solenanthus Ledeb. & Symphytum (Boiss.) L. (Boraginaceae) in
Kurdistan region of Iraq by using High Performance Liquid Chromatography (HPLC) .
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B
Fig. 2( A& B) Diagram of standards phenolic compounds by (HPLC).
Fig. (3) Typical HPLC chromatograph of Brunnera orientalis.
Chemotaxonomical study of the genera Brunnera (Schenk) Jonston,Choriantha
H.Rirdel., Cynoglossum Mill., Solenanthus Ledeb. & Symphytum (Boiss.) L. (Boraginaceae) in
Kurdistan region of Iraq by using High Performance Liquid Chromatography (HPLC) .
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Fig. (4) Typical HPLC chromatograph of Choriantha popoviana.
Fig. (5) Typical HPLC chromatograph of Cynoglossum creticum .
Chemotaxonomical study of the genera Brunnera (Schenk) Jonston,Choriantha
H.Rirdel., Cynoglossum Mill., Solenanthus Ledeb. & Symphytum (Boiss.) L. (Boraginaceae) in
Kurdistan region of Iraq by using High Performance Liquid Chromatography (HPLC) .
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Fig. (6) Typical HPLC chromatograph of Solenanthus circinnatus .
Fig. (7) Typical HPLC chromatograph of Solenanthus stamineus .
Chemotaxonomical study of the genera Brunnera (Schenk) Jonston,Choriantha
H.Rirdel., Cynoglossum Mill., Solenanthus Ledeb. & Symphytum (Boiss.) L. (Boraginaceae) in
Kurdistan region of Iraq by using High Performance Liquid Chromatography (HPLC) .
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Fig. (8) Typical HPLC chromatograph of Symphytum kurdicum .
Fig. (9) Typical HPLC chromatograph of Symphytum tuberosum.
Chemotaxonomical study of the genera Brunnera (Schenk) Jonston,Choriantha
H.Rirdel., Cynoglossum Mill., Solenanthus Ledeb. & Symphytum (Boiss.) L. (Boraginaceae) in
Kurdistan region of Iraq by using High Performance Liquid Chromatography (HPLC) .
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So there were contrasts in the phenolic profile of the contemplated species due to the
reverence in their genomic structure and this is in compatible with (Proestos and Komaitis,
2013) who found that the nearness of polyphenols in any plant is generally affected by
hereditary variables .
Varying interpretation and evaluation of morphological characters very often result in
disagreement regarding classification. In such instances taxonomists as a rule look for
characters other than morphological ones (Erdtman 1952; Wodehous1959 ; Benson1962 ;
Davis & Heywood1963) characters are considered first. Sometimes they produce convincing
evidence and sometimes they fail to do so. In such situations, chemical characters may
become very useful guides to taxonomists. At present, one important task of chemotaxonomy
consists in procuring additional evidence in all cases of obscure relationships of plants.
Therefore the determination of phenolic content in any plant by using HPLC technique is
very important in solving many of the taxonomic problems as well as It extremely reduces
time and efforts compared with other chromatographic method.
Conclusions
To use phenolic compounds more widely as genetic markers, these would have to be not only
universal and abundant but also environmentally stable and convenient for identifying
taxonomic position (Fairbbothers et al.,1975). By reviewing the resources available, it was
clear that the current study is the first to address the genera of races above developing in Iraq
has been the current study dealt with determining the quality of phenolic compounds in taxa
races the above as the method is used high performance Liquid chromatography (HPLC). As
mentioned earlier, and with the help of standard phenoles that we were able to be provided
with the adoption of a seven standard phenoles Figure 1 and Table 1. Expressed taxa races the
above important variations in the content of phenolic compounds and build on the results of
these compounds can adopt taxonomic evidence of no less importance than the other
phenotypic traits, including the anatomical and chromosomal, environmental and pollen.
Chemotaxonomical study of the genera Brunnera (Schenk) Jonston,Choriantha
H.Rirdel., Cynoglossum Mill., Solenanthus Ledeb. & Symphytum (Boiss.) L. (Boraginaceae) in
Kurdistan region of Iraq by using High Performance Liquid Chromatography (HPLC) .
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E-ISSN: 2518-9255
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Chemotaxonomical study of the genera Brunnera (Schenk) Jonston,Choriantha
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Kurdistan region of Iraq by using High Performance Liquid Chromatography (HPLC) .
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