Choisyaternatine, a New Alkaloid Isolated from Choisya ternata

Wahab, Ikarastika Rahayu Abdul; Wong, Nikki Siu Hai; Boylan, Fábio

doi:10.1055/s-0032-1315044

Cited by 4 publications

(4 citation statements)

References 13 publications

(18 reference statements)

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“…Based on previous results by our group [ 14 , 15 , 37 ], we decided to evaluate the non volatile chemical composition and the possible central antinociceptive effect for C . Aztec- Pearl leaves, using the central model of pain (the hot plate).…”

Section: Resultsmentioning

confidence: 99%

Quinoline Alkaloids Isolated from Choisya Aztec-Pearl and Their Contribution to the Overall Antinociceptive Activity of This Plant

et al. 2016

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Choisya ‘Aztec-Pearl’, a hybrid of Choisya ternata and Choisya dumosa var. arizonica, had the antinociceptive activity in the ethanol extract (EECA) of its leaves evaluated. Two quinoline alkaloids, anhydroevoxine (A) and choisyine (C), isolated from these leaves were also tested. The results obtained pointed out to a very high antinociceptive activity measured by the hot plate model for EECA (at doses of 10, 30 and 100 mg/kg) as well as for A and C (at doses of 1, 3 and 10 mg/kg). The magnitude of the activity was two-fold higher than the one observed for the morphine treated animals for the higher doses of extracts/compounds (30, 100 mg/kg and 3, 10 mg/kg respectively). The mechanism of action for this activity was also investigated and it seems that for EECA as well as A and C, the opiate system plays an important role. Results have also shown that the nitric oxide (NO) system also play a pivotal role in the case of EECA and A while for C it seems that the cholinergic system have some involvement. The acute toxicity was evaluated for EECA with results showing no important toxic effect.

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Section: Resultsmentioning

confidence: 99%

Quinoline Alkaloids Isolated from Choisya Aztec-Pearl and Their Contribution to the Overall Antinociceptive Activity of This Plant

et al. 2016

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“…The identification of C . ternata EO and solvent extract constituents has been described before [ 14 , 15 ]. The EO of C .…”

Section: Methodsmentioning

confidence: 99%

“…Recently, our research group has isolated a new compound from the hexane extract of C . ternata leaves, choisyaternatine, together with the known compounds tecleamaniensine A, lup-20(29)-en-3β-ol (lupeol), lup-20(29)-en-3β,24-diol, β-sitosterol glucoside and skimmianine [ 14 ]. We also demonstrated the identification of a new alkaloid (isopropyl N -methylanthranilate, named ternanthranin) obtained from the EO of C .…”

Section: Introductionmentioning

confidence: 99%

Anti-Inflammatory Activity of Choisya ternata Kunth Essential Oil, Ternanthranin, and Its Two Synthetic Analogs (Methyl and Propyl N-Methylanthranilates)

et al. 2015

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Choisya ternata Kunth (Rutaceae) is native to North America where it is popularly known as “Mexican orange”. In this study, the anti-inflammatory effects of the essential oil (EO) obtained from the leaves of C. ternata, one of its minor components (ternanthranin—ISOAN) and its two synthetic analogues (methyl and propyl N-methylanthranilate – MAN and PAN) were evaluated. Mice pretreated with the EO (EO) obtained from C. ternata leaves (3–100 mg/kg, p.o.), ISOAN, MAN or PAN (1–30 mg/kg, p.o.) and the reference drugs, morphine (1 mg/kg, p.o.) and acetylsalicylic acid (ASA, 100 mg/kg, p.o.), were evaluated in inflammation models such as formalin and subcutaneous air pouch models, with measurement of cell migration, exudate volume, protein extravasation, nitric oxide and pro-inflammatory cytokines. The EO from C. ternata significantly inhibited the time that the animals spent licking the formalin-injected paw in the second phase of the model at their higher doses (30 and 100 mg/kg, respectively). An inhibition of the inflammatory reaction induced after subcutaneous carrageenan injection into air pouch was also observed. In this model, the EO significantly reduced cell migration, exudate volume, protein extravased, and the increase in levels of inflammatory mediators (nitric oxide, TNF-α and IL-1β). ISOAN, MAN and PAN behaved in the same fashion at much smaller doses. Also, these molecules were able to show significant effects in the reduction of paw edema (at all tested doses) when the phlogistic agent was carrageenan, bradykinin, 5-HT, PGE2, C48/80 or 12-O-tetradecanoylphorbol-acetate (TPA). None of the tested doses had any effect in reducing histamine-induced edema. Our results indicate that the EO from C. ternata and anthranilate derivatives demonstrates an anti-inflammatory effect.

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“…Choisya ternata is an ornamental plant with leaves and white flowers which resemble an orange tree. Due to this, its English name is “Mexican orange”; however, in Mexican culture can be identified by other popular namesm such as “flor de clavo”, “clavillo” or “clavo de olor” [ 106 ]. As a peculiarity, this plant is a member of the Rutaceae family and is native to the central and southern mountains of México [ 85 ].…”

Section: Preclinical Studies Of Mexican Medicinal Plants Used In Inflammatory and Neuropathic Pain Treatmentmentioning

confidence: 99%

Mexican Plants and Derivates Compounds as Alternative for Inflammatory and Neuropathic Pain Treatment—A Review

Quiñonez-Bastidas

Navarrete

2021

Plants

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Despite the availability of many anti-pain drugs, in the form of NSAIDs, steroids, gabapentinoids, opioids, and antidepressants, in this study we address the natural compounds belonging to the group of Mexican medicinal plants or “Mexican folk medicine”, used for pain management in Mexico. Our interest in this subject is due to the growing idea that “natural is harmless” and to the large number of side effects exhibited in pharmacotherapy. The objective of this review was to document the scientific evidence about Mexican medicinal plants and their derivatives used for inflammatory and neuropathic pain treatment, as well as the mechanisms of action implicated in their antinociceptive effects, their possible adverse effects, and the main pharmacological aspects of each plant or compound. Our data review suggested that most studies on Mexican medicinal plants have used inflammatory experimental models for testing. The anti-pain properties exerted by medicinal plants lack adverse effects, and their toxicological assays report that they are safe to consume; therefore, more studies should be performed on preclinical neuropathic pain models. Moreover, there is no convincing evidence about the possible mechanisms of action involved in the anti-pain properties exerted by Mexican plants. Therefore, the isolation and pharmacological characterization of these plant derivatives’ compounds will be important in the design of future preclinical studies.

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Choisyaternatine, a New Alkaloid Isolated from Choisya ternata

Cited by 4 publications

References 13 publications

Quinoline Alkaloids Isolated from Choisya Aztec-Pearl and Their Contribution to the Overall Antinociceptive Activity of This Plant

Quinoline Alkaloids Isolated from Choisya Aztec-Pearl and Their Contribution to the Overall Antinociceptive Activity of This Plant

Anti-Inflammatory Activity of Choisya ternata Kunth Essential Oil, Ternanthranin, and Its Two Synthetic Analogs (Methyl and Propyl N-Methylanthranilates)

Mexican Plants and Derivates Compounds as Alternative for Inflammatory and Neuropathic Pain Treatment—A Review

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