Anthraquinones of Certain Egyptian Asphodelus Species

Hammouda, Faiza M.; Rizk, Sameh A.; El-Nasr, M. M. Seif; Asr, El-N

doi:10.1515/znc-1974-7-807

Cited by 12 publications

(12 citation statements)

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“…The complete list of the identified phytoconstituents is as follows: ( 1 ) apigenin-7- O -glucosyl ( m / z 431.3), which was never reported in A. tenuifolius but reported previously from Asphodelus ramosus by Reynaud et al [ 42 ]; ( 3 ) tamgermanetin ( m / z 312.2) reported by Faidi et al [ 17 ] from A. tenuifolius ; ( 5 ) luteolin ( m / z 284.9) reported in many plants of Asphodelus genus [ 4 , 8 , 17 , 43 ]; ( 6 ) apigenin ( m / z 269.0) found in A. tenuifolius by Faidi et al and Di Petrillo et al, from Asphodelus microcarpus [ 4 , 17 ]; ( 7 ) Ramosin ( m / z 671.0) reported only one time by Adinolfi et al from A. ramosus [ 44 ]; ( 8 ) Aloe-emodin ( m / z 269.0) described by Hammouda et al from Asphodelus fistulosus and van Oudtshoorn from Asphodelus albus [ 45 , 46 ]. Recently, Khalfaoui et al [ 47 ] found both compounds ( 10 ) P ,10′ S -oxanthrone-(10′)- β -glucopyranosyl asphodelin ( m / z 668.9) and ( 12 ) M ,10′ S -oxanthrone-(10′)- β -glucopyranosyl asphodelin ( m / z 668.9) from A .…”

Section: Resultsmentioning

confidence: 99%

“…Compounds ( 13 ) 10′ R -oxanthrone-(10′)- β -D-xylopyranoside asphodelin ( m / z 638.9), ( 14 ) 10′ S -oxanthrone-(10′)- β -D-xylopyranoside asphodelin ( m / z 639.0) and ( 15 ) 10′ S -oxanthrone-(10′)- β -L-arabinopyranoside asphodelin ( m / z 639.0) reported previously by Ghoneim et alfrom A. microcarpus [ 48 ]. Finally, ( 17 ) asphodelin ( m / z 505.0) reported in many studies from A. acaulis , A. albus , A. fistulosus and A. microcarpus [ 12 , 43 , 45 , 49 ]. However, compounds corresponding to peaks 2 , 4 , 9 , 11 and 16 are still unidentified.…”

Section: Resultsmentioning

confidence: 99%

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LC-ESI/MS-Phytochemical Profiling with Antioxidant, Antibacterial, Antifungal, Antiviral and In Silico Pharmacological Properties of Algerian Asphodelus tenuifolius (Cav.) Organic Extracts

et al. 2021

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Asphodelus tenuifolius Cav. (A. tenuifolius) is a medicinal plant with a long history of traditional use to treat ailments. In this study, total phenolic and flavonoid content evaluation using LC-ESI/MS analysis and various biological activities (antioxidant, antibacterial, antifungal, antiviral and cytotoxicity) of organic extracts from the aerial parts of A. tenuifolius were analyzed. ADME tools were used to predict the potential of the identified compounds from the most potent extract as specific drugs. As shown, LC-ESI/MS results of chloroformic extract allowed the tentative identification of 12 compounds. Chloroformic extract was rich in polyphenols and flavonoids and exhibited the highest antioxidant activity given by DPPH (IC50 = 25 µg/mL) as compared to the BHT standard (11.5 µg/mL) and β-carotene bleaching assays (IC50 = 95.692 µg/mL). Antibacterial activity results showed that chloroformic extract has a highest activity against Gram-positive and -negative bacteria, especially against Salmonella Typhimurium DT104 (IZ = 19.3 mm, MIC = 18.75 mg/mL, MBC = 37.5 mg/mL). The MBC/MIC ratio was evaluated to interpret the activity that was bacteriostatic rather than bactericidal. Conversely, weaker antifungal activity was registered, and no antiviral activity was observed for all extracts against Herpes Simplex Virus type 2 and Coxsakievirus B-3 viruses. Cytotoxic activity on VERO cell line results revealed that butanol extract was not toxic, with CC50 value of 1430 µg/mL, while chloroformic extract showed moderate cytotoxicity. Additionally, in silico studies performed proved promising pharmacokinetic and drug-likeness properties of the main compounds from the chloroformic extract. Taken together, this work highlights the potent bioactivity and acceptable drug-likeness of this plant, which supports its further preclinical development.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

LC-ESI/MS-Phytochemical Profiling with Antioxidant, Antibacterial, Antifungal, Antiviral and In Silico Pharmacological Properties of Algerian Asphodelus tenuifolius (Cav.) Organic Extracts

et al. 2021

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“…Polyphenols including trans-N-feruloyltyramine, luteolin, luteolin-7-O--D-glycopyranoside, apigenin, chrysoeriol (Khaled et al, 2014), vanillin, rutin and caffeic acid (Eddine et al, 2015) have been identified in various extracts of the plant. Anthraquoinones including chrysophanol, aloe-emodin, anhydrorugulosin; three other bianthraquinones and chrysophanol-8-mono--Dglucoside have been isolated from the plant (Basaif and Abdel-Mogib, 2002;Hammouda et al, 1974). Seeds contain considerable amount of fixed oils consisting of glycerides of myristic, palmitic, stearic, oleic and linoleic acids along with a non saponifiable component, fucosterol (Khaqn et al, 1961).…”

Section: Introductionmentioning

confidence: 99%

Hypotensive and diuretic activities of aqueous-ethanol extract of Asphodelus tenuifolius

Aslam

Janbaz

Jabeen

2016

Bangladesh J Pharmacol

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In order to rationalize the traditional uses of Asphodelus tenuifolius in cardiovascular complaints, aqueous-ethanol extract of the plant was investigated for hypotensive and diuretic activities using in vivo and in vitro models. Intravenous administration of the extract in anesthetized rats produced 14.5 (95% CI; 13.3–15.6), 24.5 (95% CI; 21.3-27.9) and 35.3% (95% CI; 32.0–42.5) fall in mean arterial blood pressure at the doses of 3, 10 and 30 mg/kg, respectively. The extract increased the urine volume and electrolytes excretion significantly at the doses of 300 and 500 mg/kg in rats. In rabbit’s isolated aorta preparations, the extract, like verapamil, relaxed K+ (80 mM)-induced contractions more potently than phenylephrine (1 µM)–induced contractions, indicating Ca2+ antagonistic activity. The extract produced dose-dependent stimulant followed by depressant effects in spontaneously contracting rabbit’s paired atria preparations. The results suggest that the extract of A. tenuifolius has hypotensive and diuretic effects in animals.

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“…It is even more promising by the fact that it is found in most different classes of organisms: It has been found to occur in fungi (Thomson 1997), in higher plants (Hammouda et al 1974), in lichens (Mishchenko et al 1980), and even in insects (Howard et al 1982;Hilker and Schulz 1991)-but always only in eukaryotes, never in streptomycetes or other prokaryotes.…”

Section: Introductionmentioning

confidence: 99%

Acetogenic anthraquinones: biosynthetic convergence and chemical evidence of enzymatic cooperation in nature

Bringmann¹,

Irmer²

2008

Phytochem Rev

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Phenylanthraquinones belong to the quite rare class of fully unsymmetric biaryls, consisting of two different molecular portions, an anthraquinone part, chrysophanol, and a phenyl part, 2,4-dihydroxy-6-methoxyacetophenone, linked together by phenol-oxidative coupling. The biosynthesis of these two moieties, from eight and four acetate units, respectively, bears some unique features: Chrysophanol is the first example of an acetogenic natural product that is, in an organismspecific manner, formed via more than one folding mode: In eukaryotes, like, e.g., in fungi, in higher plants, and in insects, it is formed via folding mode F, while in prokaryotes it originates through mode S. It has, more recently, even been found to be synthesized by a third pathway, which we have named mode S 0 . It is thus the first example of biosynthetic convergence in polyketide biosynthesis. The monocyclic ''southern'' portion of the molecule, which is much simpler (arising from only four acetate units and without decarboxylation), unexpectedly does not show the anticipated randomization of the C 2 -labeling in the aromatic ring, but has clearly localized C 2 units, excluding any symmetric intermediate like, e.g., 2,4,6-trihydroxyacetophenone. This is confirmed by competitive feeding experiments with specifically 13 C 2 -labeled acetophenones, showing the O-methylation to be the decisive symmetry-preventing step, which hints at a close collaboration of the participating enzymes. The results make knipholone an instructive example of structure, function, and evolution of polyketide synthases and O-methyltransferases, and their cooperation.

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Anthraquinones of Certain Egyptian Asphodelus Species

Cited by 12 publications

References 0 publications

LC-ESI/MS-Phytochemical Profiling with Antioxidant, Antibacterial, Antifungal, Antiviral and In Silico Pharmacological Properties of Algerian Asphodelus tenuifolius (Cav.) Organic Extracts

LC-ESI/MS-Phytochemical Profiling with Antioxidant, Antibacterial, Antifungal, Antiviral and In Silico Pharmacological Properties of Algerian Asphodelus tenuifolius (Cav.) Organic Extracts

Hypotensive and diuretic activities of aqueous-ethanol extract of <i>Asphodelus tenuifolius</i>

Acetogenic anthraquinones: biosynthetic convergence and chemical evidence of enzymatic cooperation in nature

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