Transtorine, a New Quinoline Alkaloid from <i>Ephedra transitoria</i>

Al-Khalil, Suleiman; Alkofahi, Ahmad S.; El-Eisawi, Dawud; Al-Shibib, A.

doi:10.1021/np9702998

Cited by 46 publications

(35 citation statements)

References 8 publications

(35 reference statements)

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“…Kynurenates-Kynurenic acid and several derivatives, namely 6-hydroxykynurenic acid, 6-methoxykynurenic acid, and 7-methoxykynurenic acid, are present in the photosynthetic stem tissue of many Ephedra species (Nawwar et al, 1985;Starratt and Caveney, 1996;Al-Khalil et al, 1998). Relatively low levels of 6-hydroxykynurenate are found in the seeds (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…In most species, it occurs in trace amounts only. For instance, a recent paper (Al-Khalil et al, 1998) reported the isolation from E. transitoria of small amounts (Ͻ0.01% dry mass) of ''transtorine,'' a compound for which the structure of kynurenic acid is assigned.…”

Section: Resultsmentioning

confidence: 99%

“…Kynurenates are related to the 4Ј-quinolones (quinoline-3-carboxylic acids), a group of compounds that are potent inhibitors of bacterial DNA gyrase, an enzyme involved in the incorporation of nascent DNA strands into the bacterial chromosome (Andriole, 1988). Kynurenic acid has reported activity against several Gram-positive and Gram-negative bacteria (Al-Khalil et al, 1998), although considerably less than ciprofloxacin. Kynurenic acid has reported activity against several Gram-positive and Gram-negative bacteria (Al-Khalil et al, 1998), although considerably less than ciprofloxacin.…”

Section: Discussionmentioning

confidence: 99%

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New observations on the secondary chemistry of world Ephedra (Ephedraceae)

Caveney

Charlet

Freitag

et al. 2001

American J of Botany

118

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For several millennia, stem extracts of Ephedra (Ephedraceae, Gnetales) have been used as folk medicines in both the Old and New World. Some species were used in treatments of questionable efficacy for venereal disease in North America during the last century. Many Eurasian species produce phenylethylamine alkaloids, mostly ephedrine and pseudoephedrine, that interact with adrenergic receptors in the mammalian sympathetic nervous system. Asian Ephedra have been used recently in the clandestine manufacture of a street drug, methamphetamine. Although ephedrine alkaloids are not detectable in New World species of Ephedra, together with Asian species they contain other nitrogen-containing secondary metabolites with known neuropharmacological activity. Many mesic and particularly xeric species worldwide accumulate substantial amounts of quinoline-2-carboxylic acids, or kynurenates, in their aerial parts. Many species of Ephedra accumulate cyclopropyl amino acid analogues of glutamate and proline in their stems and roots, and particularly in the seed endosperm. Mesic species synthesize substantial amounts of three L-2-(carboxycyclopropyl)glycine stereomers rarely seen in nature. A cyclopropyl analogue of proline with known antimicrobial activity, cis-3,4-methanoproline, is found in large amounts in the stems and seeds of many Ephedra species. The ability to synthesize cyclopropyl amino acids may be an ancestral feature in the taxon. The natural function in the taxon of these three groups of secondary compounds remains to be established.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

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New observations on the secondary chemistry of world Ephedra (Ephedraceae)

Caveney

Charlet

Freitag

et al. 2001

American J of Botany

118

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“…Similarly, the aqueous extract of the Ephedra aphylla is used as strong inhibiter against malarial parasitic protozoan, plasmodium falciparum [8], and the compounds which were isolated from Ephedra aphylla have no estrogenic activity but most of the Lignans exhibited moderate antioxidant activity without any cytotoxicity. Up to now, some species of genus ephedra were screened for antimicrobial activities including, E. altissima [9], E. transitoria [10], E. breana [11], and E. gerardiana (leaf) [12], while, as for their antioxidant potential, E. laristanica, E. sarcocarp [13], and E. gerardiana (ethanol extract) [14] were investigated. In the light of this previous study, we sought to evaluate the crude extracts and fractions of E. gerardiana (root and stem) for free radical scavenging potential and antimicrobial (fungal and bacterial) activities.…”

Section: Introductionmentioning

confidence: 99%

In Vitro Antioxidant and Antimicrobial Activities of Ephedra gerardiana (Root and Stem) Crude Extract and Fractions

Khan

Jan

Khan

et al. 2017

Evidence-Based Complementary and Alternative Medicine

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The utilization of medicinal plants to treat infectious disease is a common practice in developing countries worldwide. The present study was aimed at evaluating the crude extracts of Ephedra gerardiana (root and stem) with different chemicals for antioxidant and antimicrobial (fungal and bacterial) potential. The results revealed that the ethyl acetate fractions of E. gerardiana (root and stem) have significant free radical scavenging potential with values 2.96 ± 0.39 and 2.73 ± 0.84 while n-butanol and aqueous fractions showed IC502.69 ± 0.26 and 3.44 ± 0.69 µg/ml in stem. Furthermore, crude extract and fractions also revealed promising antibacterial activities against all tested microbial strains while aqueous fraction showed no activities against Bacillus subtilis, Kleibsiella pneumoniae, and Pseudomonas aeruginosa. Interestingly, all crude extracts and fractions were nonactive against fungal strain, Aspergillus niger and Aspergillus flavus, as compare to control. In summary, the Ephedra gerardiana (root and stem) extract and fraction possess antioxidant activities, which might be helpful in preventing or slowing the progress of various oxidative stresses, suggested to be a strong pharmaceutical agent.

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“…Transtorine, considered as a pharmacologically active compound of E. transitoria, was also identified. This quinoline alkaloid exhibited growth inhibitory activity against the common bacteria, E. cloaceae, E. coli, P. aeruginosa and S. aureus [3].…”

Section: Discussionmentioning

confidence: 98%

Study ofin vitroantimicrobial and antiproliferative activities of selected Saharan plants

Palici¹,

Liktor‐Busa²,

Zupkó³

et al. 2015

Acta Biologica Hungarica

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The aim of the present study was the evaluation of the antimicrobial and antiproliferative activities of selected Saharan species, which are applied in the traditional medicine but not studied thoroughly from chemical and pharmacological point of view. The studied plants, namely Anthyllis henoniana, Centropodia forskalii, Cornulaca monacantha, Ephedra alata var. alenda, Euphorbia guyoniana, Helianthemum confertum, Henophyton deserti, Moltkiopsis ciliata and Spartidium saharae were collected from remote areas of North Africa, especially from the Tunisian region of Sahara. After drying and applying the appropriate extraction methods, the plant extracts were tested in antimicrobial screening assay, performed on 19 Gram-positive and -negative strains of microbes. The inhibition zones produced by plant extracts were determined by disc-diffusion method. Remarkable antibacterial activities were exhibited by extracts of Ephedra alata var. alenda and Helianthemum confertum against B. subtilis, M. catarrhalis and methicillin-resistant and non-resistant S. aureus. Minimum inhibitory concentrations of these two species were also determined. Antiproliferative effects of the extracts were evaluated against 4 human adherent cell lines (HeLa, A431, A2780 and MCF7). Notable cell growth inhibition was found for extract of Helianthemum confertum and Euphorbia guyoniana. Our results provided data for selection of some plant species for further detailed pharmacological and phytochemical examinations.

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Transtorine, a New Quinoline Alkaloid from Ephedra transitoria

Cited by 46 publications

References 8 publications

New observations on the secondary chemistry of world Ephedra (Ephedraceae)

New observations on the secondary chemistry of world Ephedra (Ephedraceae)

In Vitro Antioxidant and Antimicrobial Activities of Ephedra gerardiana (Root and Stem) Crude Extract and Fractions

Study ofin vitroantimicrobial and antiproliferative activities of selected Saharan plants

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