Persicaline, A New Antioxidant Sulphur-Containing Imidazoline Alkaloid from Salvadora persica Roots

Farag, Mohamed A.; Abdel‐Mageed, Wael M.; Basudan, Omer A.; El‐Gamal, Ali A.

doi:10.3390/molecules23020483

Cited by 21 publications

(8 citation statements)

References 19 publications

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“…S. persica stem was also reported to act as a protectant against the pentylenetetrazol-induced convulsions in humans by extending the sleeping period and decreasing the induction time induced by sodium pentobarbital [36]. Moreover, Persicaline, a sulphur-containing imidazoline alkaloid, and three furan derivatives with hydroxyl groups were identified from the root of S. persica, which showed promising antioxidant activity as compared to ascorbic acid [48,49].…”

Section: Resultsmentioning

confidence: 99%

Phytochemical, Cytotoxic, and Antimicrobial Evaluation of the Fruits of Miswak Plant, Salvadora persica L.

Bratty

Makeen

Alhazmi

et al. 2020

Journal of Chemistry

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Salvadora persica L. (Salvadoraceae) is an evergreen shrub growing in the Middle East, Africa, and Southern Asia. It is traditionally known as “miswak” and used as toothbrushes and for the treatment of toothache, gum diseases, boils, chest infection, gonorrhea, headache, spleen troubles, stomachache, and ulcers. To the best of our knowledge, this is the first study aimed at conducting phytochemical, cytotoxic, and antimicrobial investigations of the fruits (berries) of S. persica collected from the Jazan region of Saudi Arabia. Analysis of the ethanol extract of S. persica fruits using GC-MS showed the presence of six esters (20.71%), seven alkanes (15.47%), tetracosamethyl-cyclododecasiloxane (9.91%), eicosamethyl-cyclodecasiloxane (7.27%), and 1-monolinoleoylglycerol (5.17%). The predominant constituents were acetyl dasycarpidan-1-methanol (10.47%), tetracosamethyl-cyclododecasiloxane (9.91%), eicosamethyl-cyclodecasiloxane (7.27%), and 1-monolinoleoylglycerol (5.17%). The petroleum ether extract of the fruits contained mainly eicosamethyl-cyclodecasiloxane (23.81%), 1-monolinoleoylglycerol (11.78%), (Z,Z,Z)-9,12,15-octadecatrienoic acid ethyl ester derivative (10.56%), and tetracosamethyl-cyclododecasiloxane (9.91%). The cytotoxic properties of the ethanol extract were investigated by MTT assay against the breast MCF7, ovary A2780, and colon HT29 cells. The fruit extract of S. persica was selective against the ovarian and colon cancer cells compared to normal fibroblast cells (MRC5) as it showed IC50 values 17.50, 8.35, and 5.12, against MCF7, A2780, and HT29 cells, respectively. Interestingly, the fruit extract was also found to possess selective antimicrobial activity for Streptococcus mutans isolates with minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values of 3.12 and 6.25 mg/mL, respectively. Interestingly, it was found to be ineffective against other Gram-positive as well as Gram-negative microorganisms. This study provides insight into the bioactive components present in the fruits of the plant that can be utilized for its cytotoxic and antimicrobial properties.

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Section: Resultsmentioning

confidence: 99%

Phytochemical, Cytotoxic, and Antimicrobial Evaluation of the Fruits of Miswak Plant, Salvadora persica L.

Bratty

Makeen

Alhazmi

et al. 2020

Journal of Chemistry

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“…Based on our phytochemical analyses of S. persica extract, antioxidant activity can be attributed to its polyphenol (5%) [ 64 ] and fatty acid (23%) content [ 65 ]. Farag et al (2018) examined the antioxidant activities of S. persica ethanol extract and some isolated compounds called persicaline [ 66 ]. Essentially, antioxidants have been reported to play an important role in expediting wound healing by reducing oral mucosa inflammation, thus decreasing the risk of developing precancerous lesions [ 67 ].…”

Section: Discussionmentioning

confidence: 99%

HPLC/MSn Profiling and Healing Activity of a Muco-Adhesive Formula of Salvadora persica against Acetic Acid-Induced Oral Ulcer in Rats

et al. 2021

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Salvadora persica L. (S. persica, Siwak) is an ethnic plant that is widely used for improving oral hygiene. This study aimed to provide a phytochemical profiling of S. persica ethyl acetate fraction (SPEAF) and to evaluate the healing activity of a muco-adhesive formula of the fraction against acetic acid-induced oral ulcers in rats. HPLC-ESI-QTOF-MS-MS analysis of SPEAF resulted in the tentative identification of 56 metabolites containing fatty acids (23%), urea derivatives (10.5%) and sulphur compounds (10%), in addition to several amides, polyphenols and organic acids (6.5%, 5% and 2%, respectively). For the first time, 19 compounds were identified from S. persica. In vitro and in vivo experiments indicated that the extract is non-toxic. SPEAF exhibited superior healing activities compared to both the negative and positive control groups on days 7 and 14 of tongue ulcer induction. This was confirmed by histopathological examinations of haematoxylin and eosin-stained (H&E) and Masson’s trichrome-stained tongue sections. Moreover, SPEAF showed potent anti-inflammatory activities, as evidenced by the inhibited expression of interleukin-6 (IL-6) and tumour necrosis alpha (TNF-α). Moreover, SPEAF exhibited potent antioxidant activity, as it prevented malondialdehyde (MDA) accumulation, reduced glutathione (GSH) depletion and superoxide dismutase (SOD) exhaustion. SPEAF significantly enhanced hydroxyproline tongue content and upregulated collagen type I alpha 1 (Col1A1) mRNA expression. SPEAF also improved angiogenesis, as shown by the increased mRNA expression of the angiopoietin-1 (Ang-1). In conclusion, S. persica has a wide range of secondary metabolites and ameliorates acetic acid-induced tongue ulcers in rats. This can be attributed, at least partly, to its anti-inflammatory, antioxidant, procollagen and angiogenic activities. These findings provide support and validity for the use of S. persica as a traditional and conventional treatment for oral disorders.

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“…Fortunately, the S. persica antioxidant potency has been demonstrated via an impressive collection of standard tests. A recent evidence has been obtained by ( Farag et al, 2018 ) who documented antioxidant activities of an ethanol extract, its many fractions, and some isolated compounds, in particular of a new compound, persicaline. Various in vitro assays, such as 1,1-diphenyl-2-picrylhydrazyl [DPPH], superoxide anion, and nitric oxide radical-scavenging methods, have been utilized to estimate the antioxidant activities of the fractions and isolated compounds.…”

Section: Health Benefits Of the Plant And Its Extractsmentioning

confidence: 99%

“…Interestingly, this majestic plant still yields new bioactive compounds until now. Our team ( Farag et al, 2018 ) recently has isolated a new antioxidant sulfur-containing imidazoline alkaloid, persicaline, from the roots.…”

Section: Phytochemical Profilementioning

confidence: 99%

Salvadora persica L.: Toothbrush tree with health benefits and industrial applications – An updated evidence-based review

Farag

Abdel‐Mageed

Gamal

et al. 2021

Saudi Pharmaceutical Journal

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Salvadora persica L. is also known as Arak (in Arabic) and Peelu (in Urdu). Its frequent use as a toothbrush (miswak) is highly recommended by Prophet Muhammad. With a long history in folk medicine for centuries, S. persica was used in oral hygiene, food, cosmetics, fuel, and even as a medicine. Previous phytochemical investigation of its different parts afforded different classes of secondary metabolites such as flavonoids, glycosides, sterols, terpenes, carbohydrates and alkaloids. Organic sulfur-containing compounds and elemental sulfur are also present. In addition, there is a huge research on its biological potentials and industrial applications. Many pharmacological activities were reported experimentally, including antimicrobial, antioxidant, analgesic, anthelmintic, anti-inflammatory, antiulcer, sedative, anticonvulsant, anti-osteoporosis, antidiabetic, hypo-lipidemic, in addition to wound-healing, antidepressant and antitumor activities. Recently, a possible activity against COVID-19 protease was documented by molecular docking. This review tries to provide a recent detailed documentation of folk and modern uses of S. persica, focusing on the possible relations between its chemical constituents, pharmacological properties, and industrial applications. Moreover, a brief about recent analytical and validation methods for the major antimicrobial component is reported.

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Persicaline, A New Antioxidant Sulphur-Containing Imidazoline Alkaloid from Salvadora persica Roots

Cited by 21 publications

References 19 publications

Phytochemical, Cytotoxic, and Antimicrobial Evaluation of the Fruits of Miswak Plant, Salvadora persica L.

Phytochemical, Cytotoxic, and Antimicrobial Evaluation of the Fruits of Miswak Plant, Salvadora persica L.

HPLC/MSn Profiling and Healing Activity of a Muco-Adhesive Formula of Salvadora persica against Acetic Acid-Induced Oral Ulcer in Rats

Salvadora persica L.: Toothbrush tree with health benefits and industrial applications – An updated evidence-based review

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