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Chemical Constituents of the Essential oil of Sanguisorba minor Scop. Leaves, from Iran

Authors:
  • North Tehran Branch, Islamic Azad University, Tehran, Iran
  • Roudehen Branch, Islamic Azad University

Abstract and Figures

Background: The family Rosaceae, include some large genus, eg; the genus Rose includes 200 species and 18000 cultivars. Objective: Aim of this study is to determine the chemical composition of the hydrodistilled oil of the leaves of Sanguisorba minor scop, of Iranian origin for the first time. Methods: The essential oil obtained by hydrodistillation of Sanguisorba minor was analyzed by GC and GC/MS. Results: The major constituents appeared to be (E, E) farnesyl acetate (13.4%), nonadecane (11.2%) and docosane (11.0%). Conclusion: In Sanguisorba minor we identified 17 components representing 93.2%. It’s rich in regard to aliphatic hydrocarbons (40.6%), five sesquiterpenes (36.8%), one oxygenated monoterpene (7.3%) and one aliphatic aldehyde (8.3%).
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Volume 9, No. 35, Summer 2010
Journal of Medicinal Plants
Chemical Constituents of the Essential oil of Sanguisorba minor Scop.
Leaves, from Iran
Esmaeili A (Ph.D.)1, Masoudi Sh (Ph.D.)2, Masnabadi N (M.Sc.)3, Rustaiyan AH (Ph.D.)4*
1- Department of Chemical Engineering, North Tehran Branch, Islamic Azad University,
Tehran, Iran
2- Department of Chemistry, Central Tehran Branch, Islamic Azad University, Tehran,
Iran
3- Department of Chemistry, Roudhen Branch, Islamic Azad University, Roudhen, Iran
4- Department of Chemistry, Science & Research Campus, Islamic Azad University,
Tehran, Iran
*Corresponding author: Department of Chemistry, Science & Research Campus,
Islamic Azad University, P.O.Box: 14515-775, Tehran, Iran
Tel: +98-21- 22436370, Fax: +98-21- 22436370
E -mail: rustaiyan@excite.com
Receive: 22 May 2010 Acceptance: 24 Aug. 2010
Abstract
Background: The family Rosaceae, include some large genus, eg; the genus Rose includes 200
species and 18000 cultivars.
Objective: Aim of this study is to determine the chemical composition of the hydrodistilled oil of
the leaves of Sanguisorba minor scop, of Iranian origin for the first time.
Methods: The essential oil obtained by hydrodistillation of Sanguisorba minor was analyzed by
GC and GC/MS.
Results: The major constituents appeared to be (E, E) farnesyl acetate (13.4%), nonadecane
(11.2%) and docosane (11.0%).
Conclusion: In Sanguisorba minor we identified 17 components representing 93.2%. It’s rich in
regard to aliphatic hydrocarbons (40.6%), five sesquiterpenes (36.8%), one oxygenated
monoterpene (7.3%) and one aliphatic aldehyde (8.3%).
Keywords: Sanguisorba minor, Rosaceae, Essential oil composition, (E, E) Farnesyl acetate,
Nonadecane, Docosane
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Journal of Medicinal Plants, Volume 9,
No. 35, Summer 2010
Chemical Constituents…
Introduction
The family Rosaceae, include some large
genus, eg; the genus Rose includes 200 species
and 18000 cultivars [1]. Rosa damascena Mill
uses in traditional medicine, eg; analgestic,
antidepressant, anti-inflammatory, diuretic and
cosmetic [2-6]. The essential oil of the plant is
one of the most valuable and important base
material in the flavor and fragrance industry [7].
Also the oil of Rosa damascena petals was
evaluated for its antibacterial effects against
three strains of Xanthomonas axonopodis spp.
vesicatoria. The essential oil may be apotential
control agent in the management of the disease
caused by X. a. vesicatoria in tomato and
pepper plants [8].
The other genus of this family is Sanguisorba
which is represented in the flora of Iran by two
species, S. minor scop and S. officinalis L. [9, 10].
The essential oil of Sanguisorba minor has not
been investigated up to now, so we decided to
examin the leaves oil.
Materials and Methods
Plant Materials
The leaves of Sanguisorba minor were
collected from Taleghan regions, North of
Tehran, in Agust 2008. A voucher specimen has
been deposited at the Herbarium of the
Research Institute of Forests and Rangelands
(TARI), Tehran, Iran.
Isolation of the Essential Oil
The leaves of the plants were dried at
room temperature and hydrodistilled for 3h
using a Clevenger- type apparatus. The oil was
dried over anhydrous sodium sulfate and stored
at 2°C in the dark. The yield based on dry
weight was 0.2% (w/w).
Table 1- Percentage composition of the leaf oils of Sanguisorba minor
Compound RIa %
linalool 1098 73.0
nonanal 1099 8.5
dodecane 1199 3.6
tridecane 1299 2.4
(E)-α-damascenone 1380 3.2
tetradecane 1399 3.8
β-caryophyllene 1418 9.7
germacrene D 1480 5.4
caryophyllene oxide 1581 5.1
hexadecane 1600 0.1
heptadecane 1700 1.2
octadecane 1800 2.4
(E,E)-farnesyl acetate 1843 13.4
nonadecane 1900 11.2
eicosane 2000 2.6
henicosane 2100 2.3
docosane 2200 11.0
Total 93.2
aRetention indices as determined on a DB-5 column using the homologous series
of n-alkane
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Esmaeili & Authors
The oil was dried over anhydrous sodium
sulfate and stored at 2°C in the dark. The yield
based on dry weight was 0.2% (w/w).
Gas Chromatography
GC analysis was performed on a Shimadzu
IS A gas chromatograph equipped with a
split/splitless injector (250°C) and a flame
ionization detector (250 °C). N2 was used as
carrier gas (1mL/min) and the capillary used
was DB-5 (50 m × 0.2 mm, film thickness 0.32
µm).
The column temperature was kept at 60 °C
for 3 min and then heated to 220°C with a
5°C/min rate and kept constant at 220 °C for 5
min. Relative percentage amounts were
calculated from peak area using a Shimadzu C-
R4A chromatopac without the use of
correction factors.
Gas Chromatography-Mass Spectrometry
GC/MS analysis was performed using a
Hewlett-Packard 5973 with a HP-5MS column
(30m x 0.25 mm, film thickness 0.25 µm). The
column temperature was kept at 60 °C for 3 min
and programmed to 220 °C at a rate of
5 °C /min and kept constant at 220 °C for 5 min.
The flow rate of helium as carrier gas with
(1 mL/min). MS were taken at 70 eV.
Identification of the constituents of the oil was
made by comparison of their mass spectra and
relative retention indices (RRI) with those
given in the literature and those authentic
samples [11, 12].
Results
The chemical composition of the oil of
Sanguisorba minor is given in Table I. As it is
shown, about 93.2% (17 component) of the oil
were identified. The oil of S. minor consisted
mainly often aliphatic hydrocarbons (40.6%),
five sesquiterpenes (36.8%), one oxygenated
monoterpene (7.3%) and one aliphatic
aldehyde (8.3%). (E, E) Farnesyl acetate
(13.4%), nonadecane (11.2%) and docosane
(11.0%) were the major components in this
oil, followed by β-caryophyllene (9.7%),
nonanal (8.5%) and linalool (7.3%).
Discussion
There are a few reports on the essential
oils of Rutaceae family, eg. the composition of
the essential oil from the underground parts of
Geum reptans L. was analysed by GC and
GC/MS.
The main classed of the compounds
present are monoterpenoids (20.5%) and fatty
acids (52.0%) with linolenic acid as the
predominant constituents (18.3%) [13]. In
other study the essential oil composition of
three strawberry genotypes, Fragaria ananassa
Duch. Were examined by GC/MS. The major
components were linalool (16.1-18.8%) and
nonanal (5.9-16.6%). Many of the other
constituents were aliphatic in nature [14].
Acknowledgements
We are grateful to Dr. V. Mozaffarian
(Research Institute of Forests and Rangelands,
Tehran) for helpful assistance in collecting plant
material and for botanical identification.
References
1. Gudin S. genetics and breeding, Plant
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2. Wells FV, Billet M. Perfumery
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Journal of Medicinal Plants, Volume 9,
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Chemical Constituents…
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4. Furia TE. Bellanca N. Fenaroli's hand
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Rechinger and I.C.Hedge, Akademische Druck
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Names, Farhang Moaser, Tehran, 1996, pp:481.
11. Eight Peak index of mass spectra, Unwin
Brothers LTD, Surry, 2001, pp: 400 - 20.
12. Adams RP. Identification Essential Oils
Components by Gas Chromatography/Mass
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Stream IL, USA, 2001, pp: 40 - 100.
13. Schultze W. Mit dir, Lili Marleen. Die
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Essent. Oil Res. 1993; 5: 109 - 11.
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... 12 A similar efficiency of the distillation process of essential oil from the herb Epilobium angustifolium L. (0.035%) was obtained by Nowak et al. (2021). In the research of Esmaeili et al. (2010) concerning the extraction of essential oil from S. minor they achieved a yield based on dry weight of 0.2% (w/w) (Esmaeili et al., 2010). No analysis of the composition of the essential oil of great burnet has been found in the literature, but analyses of the S. minor essential oil are available. ...
... 12 A similar efficiency of the distillation process of essential oil from the herb Epilobium angustifolium L. (0.035%) was obtained by Nowak et al. (2021). In the research of Esmaeili et al. (2010) concerning the extraction of essential oil from S. minor they achieved a yield based on dry weight of 0.2% (w/w) (Esmaeili et al., 2010). No analysis of the composition of the essential oil of great burnet has been found in the literature, but analyses of the S. minor essential oil are available. ...
... They also identified compounds that are classified as fragrances: lavandulol (3.07%), linalool (2.78%), hexahydrofarnesyl acetone (2.35%) (E)-β-Ionone (2.05%), eugenol (1.72%), farnesyl acetone (1.01%), and methyl cinnamate (0.40%) (Wieteska et al., 2013). Esmaeili et al. (2010) identified 17 compounds (93.2%) in the essential oil of S. minor, mainly aliphatic hydrocarbons (40.6%), five sesquiterpenes (36.8%), one oxygenated monoterpene (7.3%), and one aliphatic aldehyde (8.3%). The major components in this oil were (E, E) Farnesyl acetate (13.4%)a terpene compound, nonadecane (11.2%), and docosane (11.0%), followed by β-caryophyllene (9.7%), nonanal (8.5%), and linalool (7.3%) (Esmaeili et al., 2010). ...
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Introduction Sanguisorba officinalis L. is classified as a medicinal plant and used in traditional medicine. The root of this plant is mainly used as a medicinal raw material, but the above-ground parts are also a valuable source of health-promoting biologically active compounds. Method The study aimed to evaluate the antioxidant activity and total polyphenol content (TPC) of extracts prepared in 70% and 40% aqueous ethanol solution (dry extract content 50–500 g/L) from the aerial parts of S. officinalis. The essential oil was isolated from the tested raw material, and its composition was determined using GC-MS. Ethanolic extracts and essential oil have been tested for antibacterial activity. The extract in 70% v/v ethanol (dry extract content: 500 g/L) was subjected to HPLC analysis for the content of selected phenolic acids and an ex vivo skin permeation study. The ability of these metabolites to permeate and accumulate in the skin was analysed. Results Extracts prepared at both ethanol concentrations showed similar antioxidant activity and TPC. Depending on the method, concentration of solvent, and dry extract content (50–500 g/L), the activity ranged from 1.97 to 84.54 g Trolox/L. TPC range of 3.80–37.04 g GA/L. Gallic acid (424 mg/L) and vanillic acid (270 mg/L) had the highest concentrations among the phenolic acids analysed. Vanillic acid (10 μg) permeates the skin at the highest concentration. The highest accumulation in the skin was found for 2,5-dihydroxybenzoic acid (53 μg/g skin), 2,3-dihydroxybenzoic acid (45 μg/g skin), and gallic acid (45 μg/g skin). The tested ethanolic extracts exhibited antibacterial activity. Samples with a dry extract concentration of 500 g/L showed the largest growth inhibition zones. The most sensitive strains to these extracts were P. aeruginosa (24 mm), S. lutea (23 mm), and S. pneumoniae (22 mm). The smallest inhibition zones were observed for B. subtilis (17 mm). The essential oil showed weaker antimicrobial activity (growth inhibition zone 8–10 mm). The GC-MS method identified 22 major components of the essential oil, including aliphatic hydrocarbons, unsaturated terpene alcohols, aliphatic aldehydes, unsaturated and saturated fatty acids, sesquiterpene, phytyl ester of linoleic acid, nitrogen compound, phytosterol, terpene ketone, phenylpropanoids, aliphatic alcohol, diterpenoid, aromatic aldehyde, and aliphatic carboxylic acid. Discussion The conducted research has shown that ethanolic extracts from Sanguisorbae herba are a valuable source of compounds with antibacterial and antioxidant potential, including phenolic acids. The fact that selected phenolic acids contained in the tested extract have the ability to permeate and accumulate in the skin provides the basis for conducting extended research on the use of extracts from this plant raw material in cosmetic and pharmaceutical preparations applied to the skin.
... Phenolic acids, triterpenoids, tannins and flavonoids have been reported as major components from the extracts of S. minor [3]. There is an objective lack of extensive information about the chemical composition of essential oil of S. minor [4]. ...
... Only one paper from Iran has presented the chemical composition of the hydrodistilled oil of the leaves of the species. In that study,17 components (93,2 %) were identified from the essential oil of S. minor leaves [4]. ...
... We could scarcely find the literature data related to the chemical composition of S. minor essential oil. The single available study which could be used for comparison with our results, was a study on essential oil from the leaves of this plant native to Iran [4]. In that research, authors identified much fewer compounds of essential oil than were found in this study (17 components vs. 67). ...
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Methanolic extracts of twenty selected medicinal plant species collected from the Takhte-e-Sartashtak region, that utilize to prevent and cure different kinds of diseases in traditional medicine, have been examined for antimicrobial activity against some pathogenic microorganisms. These twenty plant species belong to eleven families including, Apiaceae, Asteraceae, Berberidaceae, Cupressaceae, Datiscaceae, Euphorbiaceae, Lamiaceae, Papaveraceae, Rhamnaceae, Rosaceae, and Thymelaceae. They were tested against five microorganisms including two gram-positive bacteria, Bacillus cereus and Staphylococcus aureus two gram-negative bacteria, Escherichia coli, and Pseudomonas aeruginosa and one fungus, Candida albicans with the method of disk diffusion and determination of growth inhibition zone were tested. Most of the plants showed antimicrobial activity. Results observed methanolic extracts of all of these plant species (except one) were active against at least one or more microorganisms. Only one plant species (Physospermum cornubiense (L.) DC., (Apiaceae)) was not active against none of the microorganisms. Sanguisorba minor Scop. (Rosaceae) was active against all five microorganisms. Most antimicrobial activities belong to Ferulago angulata (Schltdi.) Boiss. (Apiaceae) against Candida albicans, also Glaucium grandiflorum Boiss. & Huet (Papaveraceae) and Datisca cannabina L. (Datiscaceae) against S. aureus. Only one taxon, Sanguisorba minor Scop. (Rosaceae), was the only active species against Escherchia coli. The MIC, MBC, and MFC of plant extracts were approximately different.
... In order to explore the chemical composition of the essential oil of S. minor leaves from Iran, Esmaeili et al. 2010 observed 17 components, the majority of which were aliphatic hydrocarbons, followed by sesquiterpenes, an oxygenated monoterpene, and an aliphatic aldehyde. Farnesyl acetate, nonadecane, and docosane were the main components, followed by caryophyllene, nonanal, and linalool [64]. Reher et al. (1991) made an interesting observation, pointing out that from a systematic standpoint, Sanguisorba minor's triterpenoid pattern more closely approaches Sarcopoterium spinosum (family Rosaceae) than Sanguisorba officinalis [58]. ...
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Analiza składu olejku eterycznego oraz ekstraktów otrzymanych z ziela krwiściągu mniejszego (Sanguisorba minor Scop.) metodą GC/MS Analysis of the composition of essential oil and extracts obtained from the herb of salad burnet (Sanguisorba minor Scop.) by GC/MS method Streszczenie. Celem badań prowadzonych w 2010 r. na Zachodniopomorskim Uniwersytecie Technologicznym w Szczecinie (północno-zachodnia Polska) było określenie składu olejku ete-rycznego, ekstraktu heksanowego i etanolowego otrzymanych z ziela krwiściągu mniejszego (San-guisorba minor Scop.) metodą GC/MS. Materiał badawczy stanowiło ziele zebrane z roślin dwu-letnich. Głównymi związkami, jakie zidentyfikowano, były: nerol, geraniol i fitol (w olejku ete-rycznym), 13-metylohentriakontan, kwas palmitynowy, fitol, ester metylowy kwasu linolenowego i witamina E (w ekstrakcie etanolowym) oraz 11-metylohentriakontan, 11-decyloheneikozan, tritriakontan, 3-metylotritriakontan i γ-sitosterol (w ekstrakcie heksanowym). Słowa kluczowe: krwiściąg mniejszy (Sanguisorba minor Scop.), analiza GC/MS, olejek eterycz-ny, ekstrakt heksanowy i etanolowy WSTĘP Krwiściąg mniejszy (Sanguisorba minor Scop.) jest to bylina kłączowa występująca w klimacie umiarkowanym [Jadczak i Grzeszczuk 2008], naleŜąca do rodziny róŜowa-tych (Rosaceae) [Karpowiczowa 1973]. Według Dreyer [2008] krwiściąg mniejszy dora-sta do wysokości 70 cm, a organem podziemnym jest kłącze [Jadczak i Grzeszczuk 2008]. McVicar [2006] podaje, Ŝe liście krwiściągu są szarozielone, ząbkowane na brze-gach. Kwiaty są promieniste, barwy róŜowej, zebrane w podłuŜne główkowate kwiato-stany na szczytach rozgałęzionych pędów, kwitną od czerwca do września. Liście mają ciekawy orzechowo-ogórkowy, ostry zapach [Grau i in. 1996, Jadczak i Grzesz-czuk 2008].
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Ethnopharmacological relevance: Many wild and cultivated plants are rich in mineral elements and bioactive compounds and are consumed for health purposes. Studies have demonstrated the curative properties of many of these food plants. In this paper, we discuss the properties of several plants with potential health benefits that have previously received little attention. Aim of the study: This review provides an overview and critical discussion of food plants perceived by informants (emic view) as healthy or used as 'food medicine' in Italy. Pharmacological activity of these plants is explored, based upon published scientific research (etic view). Preparation methods, taste perception, toxicity and various potentialities of some food plants are also discussed. Materials and methods: The present review includes literature available from 1877 to 2012. The information was collected from books, scientific papers, and abstracts that reported any plants used as food medicine in Italy. The perceived health properties were analyzed in the framework of recent international phytochemical and phytopharmacological literature. Results: A total of 67 edible wild plants and 18 cultivated vegetables, distributed into 20 families, were reported by informants (in literature). Several plants were highly cited (e.g., Taraxacum officinale Webb., Crepis vesicaria L., Allium cepa L., Allium sativum L.). The most frequent health properties attributed to edible plants by the informants were: laxative (22 species), diuretic (15), digestive (11), galactagogue (8), antitussive (cough) (8), hypotensive (7), tonic (7), sedative (7), hypoglycemic (6). Conclusions: Some edible plants are promising for their potential health properties, such as Crepis vesicaria L., Sanguisorba minor Scop. and Sonchus oleraceus L. Several wild species were perceived by informants to maintain health but have never been studied from a phytochemical or pharmacological point of view: e.g., Asparagus albus L., Crepis leontodontoides All., Hyoseris radiata L. subsp. radiata, Phyteuma spicatum L.
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The essential oil composition of three strawberry genotypes, Fragaria x ananassa Duch. were examined by GC/MS. Thirty-seven compounds were detected of which sixteen were identified. The major components were linalool (16.08–18.80%) and nonanal (5.89–16.63%). Many of the other constituents were aliphatic in nature. Differences in oil composition among the three cultivars were observed.
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Terpenes are present in the essential oils obtained from herbs and spices. They are produced by these plant species as a chemical defense mechanism against phytopathogenic microorganisms. Therefore, terpenes have attracted great attention in the food industry, e.g., they have been used in foods such as cheese as natural preservatives to prevent fungal growth. Herein, we describe the microbial transformation of onopordopicrin (1) by Aspergillus niger. Four product 11α H-dihydroonopordopicrin (2), 11β H-dihydroonopordopicrin (3), 3β-hydroxy-11β H-dihydroonopordopicrin (4), and 14-hydroxy-11β H-dihydroonopordopicrin (5) were obtained. Their structures were identified on the basis of chemical and spectroscopic data. All the four compounds were novel.
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Leaves of three strawberry cultivars (Bounty', `Honeoye', and `Kent') were collected at random from plants growing in an experimental trial at the Agriculture Canada, Research Station farm at Lavaltrie, Quebec. Steam-distillation was carried out on 300g of leaves in 3L of distilled water in a 5L flask. The essential oils were analyscd with a Varian 6000 gas chromatogmph. Thirty-seven compounds were detected of which sixteen were identified. The major components were linalool and nonanal. Many of the other constituents were aliphatic in nature. Differences in oil composition among the three cultivars were observed. Essential oil composition might therefore be used as a selection criteria for insect or disease resistance. Their effect upon mites will be assayed in future studies by testing them as sex, food, or oviposition lures.
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The essential oil of Rosa damascena Mill. is one of the most valuable and important base material in the flavor and fragrance industry. The aim of this study was to determine the effects of harvest date, fermentation duration and Tween 20 treatment on the essential oil content and composition of the rose petals. The essential oil content and composition were significantly different in the petals harvested at various dates (May 24, June 1, 8, and 15, 2002). The highest oil content was found on May 24 harvest (0.040%), and then a gradual decrease was observed up to last harvest date (0.032%). The highest percentages of geraniol, nerol, and phenylethyl alcohol were obtained from the petals harvested on May 24. However, the highest percentages of citronellol and linalool were found from the petals harvested on June 8. The petals collected freshly were fermented for various duration (0, 12, 24, and 36 h) at 25 °C in sacks. The highest essential oil content was found in the non-fermented petals. As fermentation duration increased, essential oil content gradually decreased. The most significant changes during the fermentation were observed in citronellol and geraniol contents. Citronellol/geraniol (C/G) ratio increased from 0.57 to 10.31 throughout the fermentation. In the other experiment, Tween 20 was added into the distillation water at various concentrations (0, 1000, 2500, and 5000 ppm). Although Tween 20 generally raised the contents of essential oil, it did not significantly influence the oil composition. The highest oil content (0.045%) was obtained from the distillation treated with 2500 ppm of Tween 20. Oil content had high positive correlations with geraniol and linalool contents (r=0.55 and 0.53, respectively), but high negative correlation with citronellol content (r=−0.48).
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The essential oil of Rosa damascena petals was evaluated for its antibacterial effects against three strains of Xanthomonas axonopodis spp. vesicatoria. The essential oil may be a potential control agent in the management of the disease caused by X.a. vesicatoria in tomato and pepper plants.
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