Next Article in Journal
Cocoa Shell as a Step Forward to Functional Chocolates—Bioactive Components in Chocolates with Different Composition
Next Article in Special Issue
Subacute Assessment of the Toxicity and Antidepressant-Like Effects of Origanum Majorana L. Polyphenols in Swiss Albino Mice
Previous Article in Journal
Comparative Study of the Chemical Compositions and Antioxidant Activities of Fresh Juices from Romanian Cucurbitaceae Varieties
Previous Article in Special Issue
Anti-Microbial, Anti-Oxidant, and α-Amylase Inhibitory Activity of Traditionally-Used Medicinal Herbs: A Comparative Analyses of Pharmacology, and Phytoconstituents of Regional Halophytic Plants’ Diaspora
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Molecules
Volume 25
Issue 22
10.3390/molecules25225469
molecules-logo
Submit to this Journal Review for this Journal Propose a Special Issue
► Article Menu

Article Menu

share Share announcement Help format_quote Cite question_answer Discuss in SciProfiles thumb_up
...
Endorse textsms
...
Comment
first_page
settings
Order Article Reprints
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Article

Anacyclus pyrethrum (L): Chemical Composition, Analgesic, Anti-Inflammatory, and Wound Healing Properties

by
Fatima Zahra Jawhari
1,*,
Abdelfattah El Moussaoui
1,
Mohammed Bourhia
2,*,
Hamada Imtara
3,
Hamza Mechchate
1,
Imane Es-Safi
1,
Riaz Ullah
4,
Essam Ezzeldin
5,
Gamal A. Mostafa
5,
Andriy Grafov
6,
Samir Ibenmoussa
2,
Dalila Bousta
1 and
Amina Bari
1
1
Laboratory of Biotechnology, Environment, Agri-Food, and Health (LBEAS), Faculty of Sciences, University Sidi Mohamed Ben Abdellah (USMBA) Fez, Fes 30050, Morocco
2
Laboratory of Chemistry-Biochemistry, Environment, Nutrition, and Health, Faculty of Medicine and Pharmacy, University of Casablanca, B.P 5696, Casablanca 20250, Morocco
3
Faculty of Arts and Sciences, Arab American University Palestine, P.O. Box 240, Jenin, Palestine
4
Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
5
Department of Pharmaceutical Chemistry, College of Pharmacy King Saud University, Riyadh 11451, Saudi Arabia
6
Department of Chemistry, University of Helsinki, P.O. Box 55, FI-00014 Helsinki, Finland
*
Authors to whom correspondence should be addressed.
Molecules 2020, 25(22), 5469; https://doi.org/10.3390/molecules25225469
Submission received: 28 October 2020 / Revised: 18 November 2020 / Accepted: 18 November 2020 / Published: 23 November 2020
(This article belongs to the Special Issue Plant Extracts: Biological and Pharmacological Activity—the Second Edition)
Browse Figure
Versions Notes

Abstract

:
Background: Anacyclus pyrethrum (A. pyrethrum) is a wild species belonging to the family Asteraceae, which is used in traditional medicines. Aim of the study: This work was undertaken to study the chemical composition, analgesic, anti-inflammatory, and wound healing properties of hydroalcoholic extracts of different parts (roots, seeds, leaves, and capitula) of A. pyrethrum. Material and Methods: The phytochemical analysis of the studied extracts was conducted by GC-MS. The analgesic activity was evaluated in mice using acetic acid and formaldehyde methods. The anti-inflammatory activity was tested using the inhibitory method of edema induced in rats. The healing activity of the hydroethanolic extracts was explored by excision and incision wound healing models in rats. Results: The phytochemical analysis of the studied plant extracts affirmed the presence of interesting compounds, including some newly detected elements, such as sarcosine, N-(trifluoroacetyl)-butyl ester, levulinic acid, malonic acid, palmitic acid, morphinan-6-One, 4,5.alpha.-epoxy-3-hydroxy-17-methyl, 2,4-undecadiene-8,10-diyne-N-tyramide, and isovaleric acid. The extracts of different parts (roots, seeds, leaves, and capitula) exhibited promising anti-inflammatory, analgesic, and wound healing effects, with percentages of inhibition up to 98%, 94%, and 100%, respectively. Conclusion: This study might contribute towards the well-being of society as it provides evidence on the potential analgesic, anti-inflammatory, and wound healing properties of A. pyrethrum.

1. Introduction

The traditional use of medicinal plants as natural remedies against various pathologies has received full attention from the scientific community. In the last few decades, herbal medicines have been extensively used to fight diseases worldwide due to their efficiency, low costs, and few side effects [1]. Plants contain an immense variety of bioactive molecules for therapeutic, agri-food, and cosmetic uses [2]. For many years, medicinal plants have been considered a promising source of essential raw material for the discovery of natural compounds that are used as subsequent drugs to fight ailments [3].
Anacyclus pyrethrum (L) is commonly known as African pyrethrum, akarkarha, tigendesste, and igendess. It is a species belonging to the family Asteraceae, which is indigenous to Morocco, Algeria, and Spain [4,5]. This species includes the two varieties Anacyclus pyrethrum var. pyrethrum (L) and Anacyclus pyrethrum var. depressus (Ball) Maire [6,7].
In traditional medicine, the roots of A. pyrethrum (L) are recommended for treating toothache, salivary secretion, angina, digestive problems, lethargy, female infertility, and even paralysis of the tongue and limbs. They are used in the form of cream-based animal fats to treat gout and sciatica and keep illness away [8]. Other pharmacological and biological properties of Anacyclus pyrethrum (L) roots have been reported in the literature, such as sialagogue [9], aphrodisiac [10,11,12], immunostimulant [13,14], antidepressant [15,16], antimicrobial [17,18], insecticide [19], anesthetic [20], anti-inflammatory [21,22], anticonvulsant [10,23,24], antioxidant [25], antidiabetic [26,27], and memory enhancer [28] properties.
This work refers to a study that aimed to investigate the chemical profile, analgesic, anti-inflammatory, and healing properties of different parts (roots, seeds, leaves, and capitula) of Anacyclus pyrethrum (L) endemic to Moroccan soil. Even though Manouze et al. (2017) studied the anti-inflammatory effect of Anacyclus pyrethrum, their work was limited to roots only, unlike in the present study, where we made a comparison between areal and root parts and even included samples from a different geographic area.

2. Results

2.1. Analgesic Activity of Samples Demonstrated by the Acetic Acid Method

The extracts of different parts of A. pyrethrum (L) showed a significant analgesic effect against pain caused by acetic acid compared to the control lot, with an inhibition percentage that ranged from 12% to 94% (p < 0.001). Detailed results are presented in Table 1.
The reference product diclofenac showed a pain inhibition percentage of 43%. Based on the analgesic activity evaluated by the acetic acid test (Table 1), we found that the fraction of A. pyrethrum roots (APPR) at a dose of 300 mg/kg was the most active, with an inhibition percentage of 94.10 ± 4.35%. The fraction of A. pyrethrum leaves (APPF) at a dose of 500 mg/kg was the least active when compared to the other samples, with an inhibition percentage of 12.00 ± 5.27%. Concerning the effect of the seed fraction (APPG), the effect increased in a dose-dependent manner, unlike in the root fraction (APPR), where we noticed a decrease in the effects when increasing concentrations. However, the leaves (APPF) and capitula (APPC) fractions used at 300 and 500 mg/kg, respectively, had the best effects compared to other doses, reducing the number of contortions. The contortions observed for these doses were significantly lower than those observed for the control group (p < 0.001).

2.2. Analgesic Activity of Samples Identified by the Formaldehyde Method

After the formaldehyde injection, the intensity of pain was recorded during the first phase (0–5 min) and the second phase (15–30 min) (Table 2).
The extracts of different parts inhibited the pain induced by formaldehyde in the paws of mice. In the first phase (0–5 min), the inhibition ranged from 67% to 94%. However, in the second phase (15–30 min), the inhibitory effect of extracts varied from 76 to 91% compared to the control group. Diclofenac and plant extracts showed similar effects of pain inhibition in the two phases.

2.3. Anti-Inflammatory Activity

Hydroalcoholic extracts from A. pyrethrum parts significantly prevented the evolution of the rat paw volume in all phases (1, 3, and 5 h) compared to the control group through two methods of treatment (p < 0.001) (Table 3). After the first hour, the inhibition percentage varied from 61% to 71% in the groups treated by oral gavage. While the groups were treated dermally, the inhibition percentage was more important and varied from 60% to 82%. At the fifth hour, the inhibition percentage significantly increased for all samples and reached 94% in the lots treated with APPC and APPG by oral administration, and 96% and 98% in the same lots dermally treated. The reference product of diclofenac significantly and progressively reduced edema by 94% with dermal application and 79% with oral administration.

2.4. Wound Healing Activity

The comparison of the mean wound area of groups treated with extracts and those treated with Madecassol (control group) showed a significant difference, which started becoming very clear after three days of treatment (p < 0.001) (Table 4). As shown in Table 4, which represents the wound healing activity of samples as a function of time, the wounds treated with a pomade prepared from APPC extracts (10% and 5%) healed after twelve and fourteen days of treatment, respectively. The healing for APPR (5%) and APPG (10%) started becoming very important after fourteen days of treatment. On the last day (20 days), complete healing was recorded for all extracts, and a reappearance of hair was noticed in the scars.

2.5. Phytochemical Identification of Plant Extracts

The extracts of different parts (roots, seeds, leaves, and capitula) were analysed by GC/MS. As shown in Table 5 and Figure 1, GC/MS analysis confirmed the presence of twenty compounds in extracts studied, including N-isobutyl-dodeca-2,4,8,10-tetraenamide, N-isobutyl-2,4-octadiene-6-monoynamide, levulinic acid, propanedioic acid, palmitic acid, morphinan-6-One,4,5.Alpha.-epoxy-3-hydroxy-17-methyl, 2,4-undecadiene-8,10-diyne-N-tyramide, and dodeca-2E,4E,nE-trienoic acid 4-hydroxyphenylethylamide.

3. Discussion

The development of therapeutic agent-based natural products has become indispensable for modern medicines, in order to fight or prevent diseases. Medicinal herbs have historically demonstrated their value as an exhaustible source of potentially bioactive compounds, and nowadays, still represent an important reservoir for the identification of novel drug candidates [29].
In the present study, the hydro-ethanoic extracts of different parts of A. pyrethrum (L) had inhibitory effects on abdominal cramps resulting from the injection of acetic acid and the pain induced by the injection of formaldehyde solution. Pain caused by the injection of acetic acid and formaldehyde is due to the release of endogenous mediators that activate the nociceptive neurons, bradykinin, serotonin, cyclooxygenases, and their metabolites (e.g., PGE2 and PGF2a) in the peritoneal fluid. In addition, these solutions might activate peritoneal receptors and stimulate nociceptive nerve terminals [15]. In the present work, the analgesic effects of samples could be explained by the fact that the extracts studied might reduce the liberation of different inflammatory mediators such as serotonin, prostaglandins (PGE2 and PGEα), bradykinin, and histamine [30]. The analgesic effect investigated in this study is in accordance with the findings reported in previous literature [9,15,21,27]. Moreover, Rimbau et al. (1999) explained that the presence of alkamides in A. pyrethrum (L) extracts is responsible for the analgesic effect, inhibiting cyclooxygenase (COX) and 5-lipoxygenase (LOX) enzymes [31].
The injection of carrageenan induces the release of several inflammatory mediators, as follows: Serotonin and histamine within the first hour, and between 1.5 and 3 h, and bradykinin beyond the third hour [30]. Concerning the results of anti-inflammatory activity obtained in this study, the extracts found to reduce edema were significantly induced by carrageenan compared to the untreated groups and, therefore, we may affirm that the samples tested have an antagonistic effect on the liberation of responsible mediators for the inflammatory process. The phytochemicals detected in plant extracts are responsible for their anti-inflammatory effect induced by carrageenan and which may act, individually or in synergy, at different levels of the multifactorial process of inflammation [32]. Moreover, flavonoids have a membrane-stabilizing effect by reducing vasodilatation, which ameliorates the strength and integrity of blood vessel walls, while alkaloids may act through the prevention of neurogenic inflammation [33]. These results agree with those reported in the literature [21,23].
Regarding the wound healing activity, the macroscopic examination of wounds revealed a better evolution, with a substantial diminution in the wound diameter of treated animals with different extracts compared to both positive and negative controls. The healing effects of plant extracts could be attributed to their antibacterial effects, which ensure the protection of damaged tissues and the wound microenvironment from bacteria. Furthermore, the healing effects might also be due to the anti-inflammatory activity of plant extracts that manage immune cell accumulation at the wound site [29,34].
Chromatographic analysis of the studied extracts affirmed the presence of several components in the capitula, leaves, and seeds of A. pyrethrum (L) that may be involved in analgesic, anti-inflammatory, and healing activities. In the present work, twenty compounds were detected by GC-MS, and among them, sarcosine N-(trifluoroacetyl)-butyl ester, levulinic acid, propanedioic acid, palmitic acid, morphinan-6-one, 4,5 alpha-epoxy-3-hydroxy-17-methyl, 2,4-undecadiene-8,10-diyne-N-tyramide, and isovaleric acid compounds were detected for the first time in this work, according to the best of our knowledge. Some of the compounds identified in the studied extracts of A. pyrethrum (L), such as alkylamides ((2,4)-N-isobutyl-2,4-undecadiene-8,10-diynamide, N-isobutyl-dodeca-2,4,8,10-tetraenamide, N-isobutyl-2,4-octadiene-6-monoynamide, N-isobutyl-2,4-heptadiene-6-monoynamide, and N-isobutyl-2,6,8-datrienamide), were previously confirmed to have activities such as immunomodulatory, antithrombotic, antimicrobial, antiviral, antioxidant, anti-inflammatory, analgesic, anticancer, antidiabetic, and antiprotozoal activities [35,36,37,38]. Moreover, levulinic acid was found to have anti-inflammatory, anticonvulsant, and antioxidant activities [39,40,41,42]. Propanedioic acid was found to be an antimycobacterial, antimicrobial, anticancer, anticonvulsant, antiparasitic, antiviral, anti-HIV, anti-diabetic, antihypertensive, anti-hyperlipidemic, and monoamine oxidase inhibitor agent [43]. Cinnamic acid is well-known for its antioxidant, antitumor, antimicrobial, and antimycobacterial properties [44,45,46]. Pellitorin is an insecticidal, antibacterial, anticancer, anticoagulant, and anti-inflammatory agent [47,48,49]. Morphinan-6-One and 4,5.Alpha.-Epoxy-3-Hydroxy-17-Methyl have analgesic activities [50,51]. Isovaleric acid has a therapeutic effect as an antidyslipidemic anticonvulsant [3,52,53]. The richness of the studied extract in different chemical compounds with numerous activities, as reported in the earlier literature, could justify the obtained results in terms of the analgesic, anti-inflammatory, and wound healing properties, as described in the present work.

4. Materials and Methods

4.1. Plant Samples

A. pyrethrum was harvested in July 2018 from the Timahdite region of Morocco. The plant was identified by a botanist and given the voucher number A31/31-5-18/TM. It has been deposited at the herbarium of the Department of Biology, Laboratory of Biotechnology, Environment, Agri-Food, and Health (LBEAS), Faculty of Sciences Dhar el Mahraz, Sidi Mohammed Ben Abdallah Fes University, Morocco. Different parts (roots, seeds, leaves, and capitula) of A. pyrethrum were washed with distilled water, separated, and dried in a shady place in a well-ventilated room for one week, before being sprayed and stored in bags away from light.

4.2. Extract Preparation

A total of 100 g of powder of different parts (roots, seeds, leaves, and capitula) of A. pyrethrum was extracted by maceration with 1000 mL of 70% ethanol at room temperature for 48 h. The mixtures were filtered and evaporated at 40 °C, and the residue obtained was then kept at 4 °C until further use. The extraction yield for roots and seeds was 16% and 10%, respectively, and a value of 14% was noted for both leaves and capitula extracts.

4.3. Preparation and Administration of Test Samples

Regarding oral administration, the crude extracts obtained were dissolved in distilled water and then stirred using a magnetic stirrer for 3 min. Afterward, they were orally administered to mice by using the gavage technique. The volume used for administration was determined according to the following formula [54]:
V = D   ×   P C
where V is the volume of extract selected to be administered (mL), D is the dose (mg/kg), P is the weight of the animal (kg), and C is the concentration of extract selected to be administered (mg/mL).
Regarding topical administration, the preparation of cream from 5% and 10% extracts was conducted by incorporating 0.5 and 1 g of the studied extracts in 9.5 and 9 g of neutral cream, respectively. The topical administration was carried out by using cream from plant extracts (5% and 10%) [55].

4.4. Animals

Male adult Wistar rats (weighing 221 ± 22 g) and male Swiss mice (weighing 33 ± 3 g) were used to assess the pharmacological activities of plant samples. Animals were typically housed in cages (five animals/cage) in a temperature-controlled room with a 12/12 h light/dark cycle and relative humidity of 55 ± 5%. The animals were given free access to food and water. The institutional ethical committee of care and use of the laboratory animals at the Faculty of Sciences Dhar El Mehraz, Sidi Mohamed Ben Abdallah Fez University, Morocco, reviewed and approved the present study under the ethical clearance number 04/2019/LBEAS.

4.5. Analgesic Activity of Samples Demonstrated by the Acetic Acid Method

The analgesic effect of different extracts was evaluated according to the method described by Ouédraogo et al. [56]. The mice were randomly divided into 14 groups, with five mice in each; each extract (roots, seeds, leaves, and capitula) was orally administered to mice in three different doses of 300, 500, and 1000 mg/kg with the time. The negative control group was treated with physiological water and the positive control group was treated with 100 mg/kg of paracetamol. One hour after the administration of each extract, the pain was provoked by an intraperitoneal injection of acetic acid solution at 0.6% (10 mL/kg) in each mouse. Five minutes after the injection, the number of contortions was counted for 30 min in each mouse. The percentage of pain inhibition was calculated according to the following formula:
Inhibition   % = ( 1 − C T C T n ) × 100
where CTn means number of contortions in mice from the negative control lot and CT means number of contortions in mice from the treated lot.

4.6. Analgesic Activity of Samples Revealed by the Formaldehyde Method

In this work, the formaldehyde method was also used to evaluate the analgesic effect, as described in earlier work [57]. Briefly, one hour before the injection of 20 μL of formaldehyde solution (2.5%) under the plantar pad of the right hind leg, groups were orally treated with APPR (300 mg/kg), APPF (300 mg/kg), APPC (500 mg/kg), and APPG (500 mg/kg). Paracetamol (100 mg/kg) was used as a reference product. Immediately after the injection of formaldehyde solution, the licking time (in seconds) of the treated paw was determined in two phases. The first phase was from 0 to 5 min, and the second was from 15 to 30 min, with an intermediate period of 10 min. The pain inhibition percentage was determined according to the following formula:
Inhibition   % = ( Lc − Lt Lc ) × 100  
where Lc is the average amount of licking of the control per group and Lt is the average amount of licking of the test per group.

4.7. Anti-Inflammatory Activity

The anti-inflammatory activity was evaluated by cutaneous and oral methods, according to Winter et al. [58]. Rats were divided into six groups, with five in each group. The negative control group was treated with physiological water, and the positive control group was treated with 1% diclofenac. One hour before the induction of inflammation by carrageenan (1%; NaCl 0.9%) under the plantar fascia of the right hind leg of rats, the volume of the paw was measured. Afterward, the paw was measured within 1 h, 3 h, and 5 h following the carrageenan injection.
The inhibition percentage of the inflammation was determined by the following formula:
Inhibition   % =   [ ( PAPc   −   PAPt ) PAPc   ] ×   100
where PAPc is the percentage increase in paw weight of the control lot and PAPt is the percentage increase in paw weight of the treated lot.

4.8. Wound Healing Activity

The wound healing activity was evaluated according to the method described by Imtara et al. [59]. Wounds were created on the skin of the dorsal-omoplate region of each anesthetized rat. The animals were divided into six groups, with five in each group. All groups were treated daily with cream extracts at 5% and 10% by applying them over the wound previously cleaned with alcohol at 96 °C. The negative control group was treated with neutral cream (containing no anti-healing molecules), and the positive control group was treated with Madecassol cream. The edges of wounds were traced on polypropylene sheets, and photographs were taken every day up to 21 days. The wound healing was regularly observed on days 1, 3, 7, 12, 15, and 18. Each wound area was calculated using Adobe Illustrator CS5 NA image analysis software (version 5).

4.9. Identification of Phytochemical Compounds

The determination of phytochemical compounds was carried out according to the silylation method described by Kabran and al. [31]. In short, 50 g of each sample (treated with petroleum ether and 250 mL of 2 N (HCl) was heated under reflux for two hours. After cooling, the hydrolysate was treated with 3 × 250 mL of ethyl acetate. The organic fractions were grouped, dried on anhydrous MgSO4, and then concentrated under vacuum. Afterward, 200 μL of N-methyl-N-trimethylsilyl trifluoroacetamide (MSTFA) was added to 3 mg of the resulting fraction and then heated at 37 °C for 30 min. Next, 0.1 μL of the sample was injected for analysis using a gas chromatograph coupled to a mass spectrophotometer (Brand Agilent Technologies Model 5973 with an Agilent column 19091S-433 HP-5MS, 30 m long, 0.25 mm inside diameter, and 0.25 μm film thickness of the stationary phase, (Helsinki, Finland) in positive mode. Helium was used as a carrier gas, with a typical pressure range (psi) of 0.9 mL/sec. The oven temperature program was set to 60–300 °C for 10 min and then maintained at 300 °C for 20 min. The detector temperature was set to 250 °C and the injector temperature to 260 °C. Identification of the silylated compounds was conducted by comparing the retention times with those of the standards obtained from the database.

4.10. Statistical Analysis

The results were expressed as means ± SEM. The analysis was performed via GraphPad Prism Software 6. Statistical processing was carried out by analysis of variance (ANOVA), followed by the Tukey multiple comparison test. A significant difference was considered at p < 0.05.

5. Conclusions

Different parts of Anacyclus pyrethrum (L) have important therapeutic activities, in terms of analgesic, anti-inflammatory, and healing activity, as described in this work. The A. pyrethrum capitula fraction was the most active extract in terms of the studied activities. Based on the results obtained in the present work, we may confirm that Anacyclus pyrethrum (L) possesses interesting natural chemical compounds that may serve society as analgesic, anti-inflammatory, and wound-healing agents.

Author Contributions

F.Z.J. and M.B.: writing—original draft; A.E.M., H.I., H.M., and I.E.-S.: formal analysis; R.U., E.E., G.A.M., A.G. and S.I.: revision and editing; D.B. and A.B.: methodology and supervision. All authors have read and agreed to the published version of the manuscript.

Funding

This research was funded by the research supporting project at King Saud University via grant number RSP/2020/45. The research was also supported by European project Horizon 2020 MSCA-RISE-2016-734759-VAHVISTUS.

Acknowledgments

Authors are thankful to King Saud University for their financial support via the research supporting project number (RSP/2020/45). The research was also supported by European project Horizon 2020 MSCA-RISE-2016-734759-VAHVISTUS.

Conflicts of Interest

The authors declare that they have no conflict of interest.

Abbreviation

APPRAnacyclus pyrethrum (L) roots
APPGAnacyclus pyrethrum (L) seeds
APPFAnacyclus pyrethrum (L) leaves
APPCAnacyclus pyrethrum (L) capitula

References

  1. Ekor, M. The growing use of herbal medicines: Issues relating to adverse reactions and challenges in monitoring safety. Front. Pharmacol. 2014, 4, 177. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  2. Chabrier, J.-Y. Plantes médicinales et formes d’utilisation en phytothérapie. Ph.D. Thesis, Universite Henri Poincare—Nancy 1, Nancy, France, 2010. [Google Scholar]
  3. Verpoorte, R. La pharmacognosie du nouveau millénaire: Pistes et biotechnologie. In Des Sources du Savoir Aux Médicaments du Future; Fleurentin, J., Mazars, G., Pelt, J.-M., Eds.; IRD Éditions: Marseille, France, 2014; pp. 263–274. [Google Scholar]
  4. Fennane, M. Eléments pour un Livre rouge de la flore vasculaire du Maroc. Fasc. 3. Asteraceae. Tela-Botanica 2017, 3. Available online: https://www.tela-botanica.org/wp-content/uploads/2017/05/Tela-Bot_LivreR-FVM_Fasc-3-avril-2017.pdf (accessed on 18 October 2020).
  5. Fennane, M.; Ibn Tattou, J.M.; Oualidi, E. Flore Pratique du Maroc; Institut Scientifique: Rabat, Morocco, 2014; Volume 3. [Google Scholar]
  6. Humphries, C.J. A revision of the genus Anacyclus, L. (Compositae: Anthemidaea). Bull. Br. Mus. Nat. Hist. 1979, 7, 83–142. [Google Scholar]
  7. Ouarghidi, A.; Powell, B.; Martin, G.J.; Abbad, A. Traditional Sustainable Harvesting Knowledge and Distribution of a Vulnerable Wild Medicinal Root (A. pyrethrum var. pyrethrum) in Ait M’hamed Valley, Morocco. Econ. Bot. 2017, 71, 83–95. [Google Scholar] [CrossRef]
  8. Macheteau, S.; Desvaux, C. Miraculeuses Plantes d’Hildegarde de Bingen; Rustica: Paris, France, 2017. [Google Scholar]
  9. Patel, V.K.; Patel, R.V.; Venkatakrishna-Bhatt, H.; Gopalakrishna, G.; Devasankariah, G. A clinical appraisal ofAnacyclus pyrethrum root extract in dental patients. Phytotherapy Res. 1992, 6, 158–159. [Google Scholar] [CrossRef]
  10. Zaidi, S.M.A.; Pathan, S.A.; Singh, S.; Jamil, S.; Ahmad, F.J.; Khar, R.K. Anticonvulsant, Anxiolytic and Neurotoxicity Profile of Aqarqarha (Anacyclus pyrethrum) DC (Compositae) Root Ethanolic Extract. Pharmacol. Pharm. 2013, 4, 535–541. [Google Scholar] [CrossRef] [Green Version]
  11. Shahraki, M.R.; Shahraki, S.; Arab, M.R.; Shahrakipour, M. The effects of aqueous extract of anacyclus pyrethrum on sperm count and reproductive organs in adult male rats. Zahedan J. Res. Med. Sci. 2015, 17, 5. [Google Scholar]
  12. Sharma, V.; Thakur, M.; Chauhan, N.S.; Dixit, V.K. Evaluation of the Anabolic, Aphrodisiac and Reproductive Activity of Anacyclus Pyrethrum DC in Male Rats. Sci. Pharm. 2009, 77, 97–110. [Google Scholar] [CrossRef] [Green Version]
  13. Bendjeddou, D.; Lalaoui, K.; Satta, D. Immunostimulating activity of the hot water-soluble polysaccharide extracts of Anacyclus pyrethrum, Alpinia galanga and Citrullus colocynthis. J. Ethnopharmacol. 2003, 88, 155–160. [Google Scholar] [CrossRef]
  14. Sharma, V.; Thakur, M.; Chauhan, N.S.; Dixit, V.K. Immunomodulatory activity of petroleum ether extract ofAnacyclus pyrethrum. Pharm. Biol. 2010, 48, 1247–1254. [Google Scholar] [CrossRef]
  15. Annalakshmi, R.; Uma, R.G.; Chandran, S.; Muneeswaran, A. A treasure of medicinal herb—Anacyclus pyrethrum A review. Indian J. Drugs Dis. 2012, 3, 9. [Google Scholar]
  16. Gautam, O.P.; Verma, S.; Jain, S.K. Anticonvulsant and myorelaxation activity of anacyclus pyrethrum dc. (akarkara) root extract. Pharmacologyonline 2011, 1, 121–125. [Google Scholar]
  17. Amine, D.; Mohamed, B.; Jamal, I.; Laila, N. Antibacterial Activity of Aqueous Extracts of Anacyclus Pyrethrum (L) Link and Corrigiola Telephiifolia Pourr. From the Middle Atlas Region-Morocco. Eur. Sci. J. ESJ 2017, 13, 116. [Google Scholar] [CrossRef] [Green Version]
  18. Jalayer, N.N.; Niakan, M.; Khodadadi, E. Determination of Antibacterial Activity of Anacyclus Pyrethrum Extract against Some of the Oral Bacteria: An In Vitro Study. J. Dent Shiraz Univ. Med. Scien. 2012, 13, 5. [Google Scholar]
  19. Elazzouzi, H.; Soro, A.; Elhilali, F.; Bentayeb, A.; Belghiti, M.A.E. Phytochemical study of Anacyclus pyrethrum (L.) of Middle Atlas (Morocco), and in vitro study of antibacterial activity of pyrethrum. Adv. Nat. Appl. Sci. 2014, 10, 131–141. [Google Scholar]
  20. Muralikrishnan, K.; Asokan, S.; Geethapriya, P.; Ahmed, K.S.Z.; Ayyappadasan, G. Comparative Evaluation of the Local Anesthetic Activity of Root Extract of Anacyclus pyrethrum and its Interaction at the Site of Injection in Guinea Pigs. Anesthesia: Essays Res. 2017, 11, 444–448. [Google Scholar] [CrossRef] [Green Version]
  21. Manouze, H.; Bouchatta, O.; Gadhi, A.C.; Bennis, M.; Sokar, Z.; Ba-M’Hamed, S. Anti-inflammatory, Antinociceptive, and Antioxidant Activities of Methanol and Aqueous Extracts of Anacyclus pyrethrum Roots. Front. Pharmacol. 2017, 8, 598. [Google Scholar] [CrossRef] [Green Version]
  22. Rimbau, V.; Cerdan, C.; Vila, R.; Iglesias, J. Antiinflammatory activity of some extracts from plants used in the traditional medicine of North-African countries. Phytother. Res. 1999, 5, 421–423. [Google Scholar] [CrossRef]
  23. Manouze, H.; Bouchatta, O.; Bennis, M.; Sokar, Z.; Ba-M’Hamed, S. Anticonvulsive and neuroprotective effects of aqueous and methanolic extracts of Anacyclus pyrethrum root in kainic acid-induced-status epilepticus in mice. Epilepsy Res. 2019, 158, 106225. [Google Scholar] [CrossRef]
  24. Sujith, K.; Suba, V.; Darwin, C.R. Neuropharmacological profile of ethanolic extract of anacyclus Pyrethrum in Albino wistar rats. Int. J. Pharm. Sci. Res. 2011, 2, 6. [Google Scholar]
  25. Pahuja, M.; Mehla, J.; Reeta, K.H.; Tripathi, M.; Gupta, Y.K. Effect of Anacyclus pyrethrum on Pentylenetetrazole-Induced Kindling, Spatial Memory, Oxidative Stress and Rho-Kinase II Expression in Mice. Neurochem. Res. 2013, 38, 547–556. [Google Scholar] [CrossRef] [PubMed]
  26. Tyagi, S.; Mansoori, M.H.; Singh, N.K.; Shivhare, M.K.; Bhardwaj, P.; Singh, R.K. Antidiabetic effect of anacyclus pyrethrum DC in alloxan induced diabetic rats. Eur. J. Biol. Sci. 2011, 4, 117–120. [Google Scholar]
  27. Usmani, A.; Mujahid; Khushtar, M.; Siddiqui, H.H.; Rahman, A. Hepatoprotective effect of Anacyclus pyrethrum Linn. against antitubercular drug-induced hepatotoxicity in SD rats. J. Complement. Integr. Med. 2016, 13. [Google Scholar] [CrossRef]
  28. Sujith, K.; Darwin, C.R.; Sathish; Suba, V. Memory-enhancing activity of Anacyclus pyrethrum in albino Wistar rats. Asian Pac. J. Trop. Dis. 2012, 2, 307–311. [Google Scholar] [CrossRef]
  29. Atanasov, A.G.; Waltenberger, B.; Pferschy-Wenzig, E.-M.; Linder, T.; Wawrosch, C.; Uhrin, P.; Temml, V.; Wang, L.; Schwaiger, S.; Heiss, E.H.; et al. Discovery and resupply of pharmacologically active plant-derived natural products: A review. Biotechnol. Adv. 2015, 33, 1582–1614. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  30. Amresh, G.; Reddy, G.; Rao, C.; Singh, P. Evaluation of anti-inflammatory activity of Cissampelos pareira root in rats. J. Ethnopharmacol. 2007, 110, 526–531. [Google Scholar] [CrossRef] [PubMed]
  31. Gui, R.K.; Mamyrbékova-Békro, J.A.; Pirat, J.-L.; Bekro, Y.-A.; Sommerer, N.; Verbaere, A.; Meudec, E.; Kabran, G.R. Identification de composés phénoliques extraits de deux plantes de la pharmacopée ivoirienne. J. Soc. Ouest-Afr. Chim. 2014, 8, 57–63. [Google Scholar]
  32. Reanmongkol, W.; Noppapan, T.; Subhadhirasakul, S. Antinociceptive, antipyretic, and anti-inflammatory activities of Putranjiva roxburghii Wall. leaf extract in experimental animals. J. Nat. Med. 2009, 63, 290–296. [Google Scholar] [CrossRef] [PubMed]
  33. Liu, H.L.; Jiang, W.B.; Xie, M.X. Flavonoids: Recent advances as anticancer drugs. Recent Pat. Anti Cancer Drug Discov. 2010, 5, 152–164. [Google Scholar] [CrossRef] [PubMed]
  34. Arunachalam, K.; Parimelazhagan, T. Anti-inflammatory, wound healing and in-vivo antioxidant properties of the leaves of Ficus amplissima Smith. J. Ethnopharmacol. 2013, 145, 139–145. [Google Scholar] [CrossRef] [PubMed]
  35. Boonen, J.; Bronselaer, A.; Nielandt, J.; Veryser, L.; De Tré, G.; De Spiegeleer, B. Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides. J. Ethnopharmacol. 2012, 142, 563–590. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  36. Elufioye, T.O.; Habtemariam, S.; Adejare, A. Chemistry and Pharmacology of Alkylamides from Natural Origin. Rev. Bras. de Farm. 2020, 30, 1–19. [Google Scholar] [CrossRef] [PubMed]
  37. Rajendran, R.; Narashimman, B.S.; Trivedi, V.; Chaturvedi, R. Isolation and quantification of antimalarial N -alkylamides from flower-head derived in vitro callus cultures of Spilanthes paniculata. J. Biosci. Bioeng. 2017, 124, 99–107. [Google Scholar] [CrossRef] [PubMed]
  38. Jiang, K.; Xing, Y.; Quan, Q.; Sun, Q.; Tian, J.; Liu, C.; Song, X.; Wang, X.; Liu, Y. Synthesis and biological evaluation of N-Alkylamide derivatives as anti-tumor agents. J. Tradit. Chin. Med Sci. 2020, 2095754820300892. [Google Scholar] [CrossRef]
  39. Rackemann, D.W.; Doherty, W.O. The conversion of lignocellulosics to levulinic acid. Biofuels, Bioprod. Biorefining 2011, 5, 198–214. [Google Scholar] [CrossRef] [Green Version]
  40. Aggarwal, N.; Mishra, P. Synthesis and evaluation of 4-substituted semicarbazones of levulinic acid for anticonvulsant activity. J. Zhejiang Univ. Sci. B 2005, 6, 617–621. [Google Scholar] [CrossRef]
  41. Licursi, D.; Antonetti, C.; Mattonai, M.; Pérez-Armad, L.; Rivas, S.; Ribechini, E.; Galletti, A.M.R. Multi-valorisation of giant reed (Arundo Donax L.) to give levulinic acid and valuable phenolic antioxidants. Ind. Crop. Prod. 2018, 112, 6–17. [Google Scholar] [CrossRef]
  42. Adeleye, A.T.; Hitler, L.; Akakuru, O.U.; Joseph, I.; Enudi, O.C.; Michael, D.P. A Review on the conversion of levulinic acid and its esters to various useful chemicals. AIMS Energy 2019, 7, 165–185. [Google Scholar] [CrossRef]
  43. Katariya, D.; Ashid, M.; Sharma, B.K.; Joshi, A. Synthesis, Characterization and Biological Activity of Some Indole Substituted Propanoic Acid. J. Chem. Chem. Sci. 2019, 9, 206–213. [Google Scholar] [CrossRef]
  44. Rao, P.V.; Gan, S.H. Cinnamon: A Multifaceted Medicinal Plant. Evidence-Based Complement. Altern. Med. 2014, 2014, 1–12. [Google Scholar] [CrossRef] [Green Version]
  45. Mollazadeh, H.; Hosseinzadeh, H. Cinnamon effects on metabolic syndrome: A review based on its mechanisms. Iran. J. Basic. Med. Sci. 2016, 19, 1258–1270. [Google Scholar] [PubMed]
  46. Sahib, A.S. Antidiabetic and Antioxidant Effect of Cinnamon in poorly Controlled Type-2 Diabetic Iraqi Patients: A Randomized, Placebo-Controlled Clinical Trial. J. Intercult. Ethnopharmacol. 2016, 5, 108–113. [Google Scholar] [CrossRef] [PubMed]
  47. Ku, S.-K.; Lee, I.-C.; Kim, J.A.; Bae, J.-S. Antithrombotic activities of pellitorine in vitro and in vivo. Fitoterapia 2013, 91, 1–8. [Google Scholar] [CrossRef]
  48. Ee, G.C.L.; Lim, C.M.; Rahmani, M.; Shaari, K.; Bong, C.F.J. Pellitorine, a Potential Anti-Cancer Lead Compound against HL60 and MCT-7 Cell Lines and Microbial Transformation of Piperine from Piper Nigrum. Molecules 2010, 15, 2398–2404. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  49. Lee, W.; Ku, S.-K.; Min, B.-W.; Lee, S.; Jee, J.-G.; Kim, J.A.; Bae, J.-S. Vascular barrier protective effects of pellitorine in LPS-induced inflammation in vitro and in vivo. Fitoterapia 2014, 92, 177–187. [Google Scholar] [CrossRef]
  50. Leland, D.L.; Kotick, M.P. Analgesic narcotic antagonists. 4.′ 7-Met hyl-N-(cycloalkylmet hyl) -3- hydroxymorp hinan-6-ones and -isomorphinan-6-ones. J. Med. Chem. 1980, 23, 1427–1431. [Google Scholar] [CrossRef]
  51. Ben Haddou, T.; Malfacini, D.; Calo’, G.; Aceto, M.D.; Harris, L.S.; Traynor, J.R.; Coop, A.; Schmidhammer, H.; Spetea, M. Exploring Pharmacological Activities and Signaling of Morphinans Substituted in Position 6 as Potent Agonists Interacting with the μ Opioid Receptor. Mol. Pain 2014, 10, 48. [Google Scholar] [CrossRef] [Green Version]
  52. Awasthi, K. An Investigation into Anti-Dyslipidemic Activity of Isovaleric Acid in Wistar Rats Fed Fructose-Rich High Fat Diet. J. Med Sci. Clin. Res. 2019, 7. [Google Scholar] [CrossRef]
  53. Eadie, M.J. Could Valerian Have Been the First Anticonvulsant? Epilepsia 2004, 45, 1338–1343. [Google Scholar] [CrossRef]
  54. El Moussaoui, A.; Bourhia, M.; Jawhari, F.Z.; Mechchate, H.; Slighoua, M.; Bari, A.; Ullah, R.; Mahmood, H.M.; Ali, S.S.; Ibenmoussa, S.; et al. Phytochemical Identification, Acute, and Sub-Acute Oral Toxicity Studies of the Foliar Extract of Withania frutescens. Molecules 2020, 25, 4528. [Google Scholar] [CrossRef]
  55. Martini, M.-C. Introduction à la Dermopharmacie et à la Cosmétologie; Médicales Internationales: Cachan, France, 2011. [Google Scholar]
  56. Ouedraogo, N.; Lompo, M.; Sawadogo, R.W.; Tibiri, A.; Hay, A.-E.; Koudou, J.; Dijoux, M.-G.; Guissou, I.P. Étude des activités anti-inflammatoire, analgésique et antipyrétique des décoctés aqueux des feuilles et des racines de Pterocarpus erinaceus Poir. (Fabaceae). Phytothérapie 2012, 10, 286–292. [Google Scholar] [CrossRef]
  57. Ridtitid, W.; Sae-Wong, C.; Reanmongkol, W.; Wongnawa, M. Antinociceptive activity of the methanolic extract of Kaempferia galanga Linn. in experimental animals. J. Ethnopharmacol. 2008, 118, 225–230. [Google Scholar] [CrossRef] [PubMed]
  58. Winter, C.A.; Risley, E.A.; Nuss, G.W. Carrageenin-Induced Edema in Hind Paw of the Rat as an Assay for Antiinflammatory Drugs. Exp. Biol. Med. 1962, 111, 544–547. [Google Scholar] [CrossRef] [PubMed]
  59. Imtara, H.; Al-Waili, N.; Bakour, M.; Al-Waili, W.; Lyoussi, B. Evaluation of antioxidant, diuretic, and wound healing effect of Tulkarm honey and its effect on kidney function in rats. Veter-World 2018, 11, 1491–1499. [Google Scholar] [CrossRef] [Green Version]
Molecules 25 05469 g001 550
Figure 1. Chromatographic profile of different extracts (roots, seeds, leaves, and capitula) of A. pyrethrum (L).
Figure 1. Chromatographic profile of different extracts (roots, seeds, leaves, and capitula) of A. pyrethrum (L).
Molecules 25 05469 g001
Table
Table 1. Analgesic activity results of different parts of Anacyclus pyrethrum (L) on abdominal contractions induced in mice by acetic acid injection.
Table 1. Analgesic activity results of different parts of Anacyclus pyrethrum (L) on abdominal contractions induced in mice by acetic acid injection.
SamplesDoses, mg/kgNumber of ContortionsCramp Inhibition, %
Roots (APPR)30011.6 ± 4.35 ***94.10 ± 4.35
50017.2 ± 6.13 ***91.25 ± 6.13
100051.6 ± 14.79 ***73.75 ± 14.79
Seeds (APPG)30041.6 ± 11.79 ***78.84 ± 11.79
50040.4 ± 13.21 ***79.45 ± 13.23
100024.4 ± 7.95 ***87.59 ± 7.95
Leaves (APPF)300116.4 ± 8.91 **40.79 ± 8.91
500173 ± 5.2712.00 ± 5.27
1000141 ± 11.29 *28.28 ± 11.29
Capitula (APPC)30066 ± 6.50 ***66.42 ± 6.50
50058.4 ± 4.27 ***70.29 ± 4.27
1000104.6 ± 4.49 **46.79 ± 4.49
Control-196.6 ± 10.70-
Diclofenac100111.8 ± 22.47 **43.13 ± 22.47
* Correlation is significant at p < 0.05. ** Correlation is significant at p < 0.01. *** Correlation is significant at p < 0.001. Values are expressed as the mean ± SEM.
Table
Table 2. Analgesic activity results of different parts of A. pyrethrum (L) and the effect of diclofenac (100 mg/kg) on the pain (licking time) induced by the injection of formaldehyde solution.
Table 2. Analgesic activity results of different parts of A. pyrethrum (L) and the effect of diclofenac (100 mg/kg) on the pain (licking time) induced by the injection of formaldehyde solution.
SamplesFirst Phase (0–5 min)Second Phase (15–30 min)
Duration of
Nociceptive
Response (sec)		% InhibitionDuration of
Nociceptive
Response (sec)		% Inhibition
Roots (APPR) (300 mg/kg)16.2 ± 1.28 ***88.31 ± 1.2813.8 ± 0.96 ***88.87 ± 0.96
Seeds (APPG) (500 mg/kg)22.6 ± 5.83 ***83.69 ± 5.8329.2 ± 6.09 ***76.45 ± 6.09
Leaves (APPF) (300 mg/kg)8.2 ± 2.26 ***94.08 ± 2.2615.2 ± 2.22 ***87.74 ± 2.22
Capitula (APPC) (500 mg/kg)44.4 ± 2.50 ***67.96 ± 2.5010.8 ± 2.51 ***91.29 ± 2.51
Control (Nacl)138.6 ± 13.4-124 ± 2.23-
Diclofenac (100 mg/kg)97.8 ± 8.85 **29.44 ± 8.8567.4 ± 2.42 **45.65 ± 2.42
** Correlation is significant at p < 0.01. *** Correlation is significant at p < 0.001. Values are expressed as the mean ± SEM.
Table
Table 3. Anti-inflammatory activity of different parts of A. pyrethrum (L) and the effect of diclofenac by oral and dermal administration on carrageenan-induced paw edema in rats.
Table 3. Anti-inflammatory activity of different parts of A. pyrethrum (L) and the effect of diclofenac by oral and dermal administration on carrageenan-induced paw edema in rats.
Samples Oral AdministrationDermal Administration
Oedema Volume (ΔmL)% InhibitionOedema Volume (ΔmL)% Inhibition
1 h3 h5 h1 h3 h5 h1 h3 h5 h1 h3 h5 h
Roots (APPR) (300 mg/kg)0.32 ± 0.04 ***0.2 ± 0.03 ***0.06 ± 0.02 ***61.90 ± 4.4573.68 ± 4.1691.18 ± 3.600.22 ± 0.06 ***0.14 ± 0.05 ***0.04 ± 0.02 ***76.09 ± 6.3484.78 ± 5.5496 ± 2.45
Seeds (APPG) (500 mg/kg)0.24 ± 0.07 ***0.14 ± 0.06 ***0.04 ± 0.02***71.43 ± 8.9181.58 ± 7.8994.12 ± 3.600.16 ± 0.04 ***0.1 ± 0.031 ***0.039 ± 0.02 ***82.61 ± 4.3589.13 ± 3.4496 ± 2.45
Leaves (APPF) (300 mg/kg)0.24 ± 0.02 ***0.12 ± 0.02 ***0.06 ± 0,02 ***71.43 ± 2.9284.21 ± 2.6391.18 ± 3.600.36 ± 0.05 ***0.26 ± 0.02 **0.2 ± 0.04 **60.87 ± 5.5471.74 ± 2.6680 ± 4.47
Capitula (APPC) (500 mg/kg)0.28 ± 0.06 ***0.14 ± 0.05 ***0.04 ± 0.02 ***66.67 ± 6.9481.58 ± 6.7194.12 ± 3.600.28 ± 0.05 ***0.14 ± 0.05 ***0.02 ± 0.02 ***69.57 ± 6.3484.78 ± 5.5498 ± 2
Control (Nacl)0.9 ± 0.030.98 ± 0.040.94 ± 0.050000.92 ± 0.020.92 ± 0.051 ± 0.04000
Diclofenac (100 mg/kg) or cream 1%0.64 ± 0.08 *0.26 ± 0.04 **0.14 ± 0.04 **23.81 ± 8.9165.79 ± 5.2679.41 ± 5.880.52 ± 0.08 **0.28 ± 0.07 **0.04 ± 0.02 ***38.10 ± 9.5263.18 ± 9.6794.12 ± 3.60
* Correlation is significant at p < 0.05. ** Correlation is significant at p < 0.01. *** Correlation is significant at p < 0.001. Values are expressed as the mean ± SEM.
Table
Table 4. The results of the wound healing activity of different parts of A. pyrethrum (doses of 5% and 10%) and Madecasol compared to the negative control.
Table 4. The results of the wound healing activity of different parts of A. pyrethrum (doses of 5% and 10%) and Madecasol compared to the negative control.
SamplesDosesDay 1Day 3Day 7Day 12Day 14Day 16Day 18
Roots (APPR)5%017.52 ± 3.0074.45 ± 2.0899.81 ± 0.19100 ± 0100 ± 0100 ± 0
10%010.73 ± 1.8459.35 ± 4.9498.23 ± 0.7599.84 ± 0.16100 ± 0100 ± 0
Seeds (APPG)5%010.08 ± 1.0555.93 ± 1.2196.07 ± 0.2699.5 ± 0.04100 ± 0100 ± 0
10%014.26 ± 0.4660.71 ± 3.2298.93 ± 0.11100 ± 0100 ± 0100 ± 0
Leaves (APPF)5%010.15 ± 1.2844.74 ± 1.8786.19 ± 1.9595.46 ± 0.5299.04 ± 0.29100 ± 0
10%011.69 ± 1.6741.79 ± 4.0579.16 ± 2.4494.17 ± 2.2199.58 ± 0.22100 ± 0
Capitula (APPC)5%014.47 ± 1.7856.29 ± 1.4098.89 ± 0.422100 ± 0100 ± 0100 ± 0
10%016.09 ± 3.0173.54 ± 6.43100 ± 0100 ± 0100 ± 0100 ± 0
Control-05.90 ± 0.6234.57 ± 2.9366.14 ± 2.4875.25 ± 2.5084.88 ± 1.4092.73 ± 1.66
Diclofenac 1%-012.54 ± 2.2244.15 ± 4.3177.47 ± 3.3489.14 ± 1.5896.22 ± 1.31100 ± 0
Values are expressed as the mean ± SEM.
Table
Table 5. Chemical composition of different parts (roots, seeds, leaves, and capitula) of A. pyrethrum (L).
Table 5. Chemical composition of different parts (roots, seeds, leaves, and capitula) of A. pyrethrum (L).
N°RTm/z Quasi-Molecular PeakStructural FormulaCompounds% Area
Anacyclus pyrethrum (L)
Roots (APPR)Seeds (APPG)Leaves (APPF)Capitula (APPC)
14.35231 (M + H)+C15H19NO(2,4)-N-isobutyl-2,4-undecadiene-8,10-diynamide0.970.762.29-
24.92246 (M)+C16H25ONN-isobutyl-dodeca-2,4,8,10-tetraenamide6.794.449.4515.91
36.12 241 (M)+C9H14F3NO3 Sarcosine, N-(trifluoroacetyl)-, butyl ester 2.650.654.26-
46.98193 (M + H)+C12H17ONN-isobutyl-2,4-octadiene-6- monoynamide0.760.680.680.74
57.71116 (M)+C5H8O3Levulinic acid37.4750.457.013.66
68.43 104 (M)+C3H4O4propanedioic acid8.486.3916.866.50
78.77177 (M)+C11H15ONN-isobutyl-2,4-heptadiene-6- monoynamide-1.526.29-
89.38256 (M)+C16H32O2Palmitic Acid2.852.753.178.34
99.65285 (M)+C17H19NO3Morphinan-6-One, 4,5.Alpha.-Epoxy-3-Hydroxy-17-Methyl2.171.312.864.93
1010.62147 (M)+C9H8O2Cinnamic acid--10.53-
1110.75278 (M + H)+C18H31NO2,4-undecadiene-8,10-diyne-N-tyramide11.095.3416.5046.07
1211.64271 (M)+C18H25NON-isobutyl-dodeca-2,4,8,10-tetraenamide (Anacycline)2.948.63--
1312.12221 (M)+C14H23NON-isobutyl-2,6,8-decatrienamide0.63-2.06-
1412.61223 (M)+C14H25NO(2E,4E)-N-(2-methylpropyl)deca-2,4-dienamide (Pellitorine)1.166.040.78-
1512.94274 (M + H)+C18H27NOTetradeca-2E-diny-8,10-diynoic acid IBA0.77-0.592.72
1613.39270 (M + H)+C18H23NOTetradeca-2E,4E, nE-trienoic-8,10-diynoic acid IBA-2.851.86-
1713.67102 (M)+C5H10O2Isovaleric acid1.284.134.14-
1814.10313 (M)+C20H27NO2Dodeca-2E,4E, nE-trienoic acid 4-hydroxyphenylethylamide3.541.151.582.08
1914.57251 (M)+C16H29NO2,8-N-isobutyl-2,8-dodecadienamide0.87-1.191.19
2015.15341 (M)+C22H31NO2Tetradeca-2E,4E,8Etrienoic acid 4-hydroxyphenylethylamide0.61-0.82-
Sample Availability: Samples of the compounds are not available from the authors.
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Share and Cite

MDPI and ACS Style

Jawhari, F.Z.; El Moussaoui, A.; Bourhia, M.; Imtara, H.; Mechchate, H.; Es-Safi, I.; Ullah, R.; Ezzeldin, E.; Mostafa, G.A.; Grafov, A.; et al. Anacyclus pyrethrum (L): Chemical Composition, Analgesic, Anti-Inflammatory, and Wound Healing Properties. Molecules 2020, 25, 5469. https://doi.org/10.3390/molecules25225469

AMA Style

Jawhari FZ, El Moussaoui A, Bourhia M, Imtara H, Mechchate H, Es-Safi I, Ullah R, Ezzeldin E, Mostafa GA, Grafov A, et al. Anacyclus pyrethrum (L): Chemical Composition, Analgesic, Anti-Inflammatory, and Wound Healing Properties. Molecules. 2020; 25(22):5469. https://doi.org/10.3390/molecules25225469

Chicago/Turabian Style

Jawhari, Fatima Zahra, Abdelfattah El Moussaoui, Mohammed Bourhia, Hamada Imtara, Hamza Mechchate, Imane Es-Safi, Riaz Ullah, Essam Ezzeldin, Gamal A. Mostafa, Andriy Grafov, and et al. 2020. "Anacyclus pyrethrum (L): Chemical Composition, Analgesic, Anti-Inflammatory, and Wound Healing Properties" Molecules 25, no. 22: 5469. https://doi.org/10.3390/molecules25225469

APA Style

Jawhari, F. Z., El Moussaoui, A., Bourhia, M., Imtara, H., Mechchate, H., Es-Safi, I., Ullah, R., Ezzeldin, E., Mostafa, G. A., Grafov, A., Ibenmoussa, S., Bousta, D., & Bari, A. (2020). Anacyclus pyrethrum (L): Chemical Composition, Analgesic, Anti-Inflammatory, and Wound Healing Properties. Molecules, 25(22), 5469. https://doi.org/10.3390/molecules25225469

Article Metrics

Back to TopTop