Isolation of jacaranone, a sedative constituent extracted from the flowers of the Mexican tree Ternstroemia pringlei

Lozada-Lechuga, Jorge; Villarreal, Marı́a Luisa; Fliniaux, Marc‐André; Bensaddek, Lamine; F, Mesnard; Gutiérrez, María del Carmen; Cardoso-Taketa, Alexandre

doi:10.1016/j.jep.2009.11.020

Cited by 23 publications

(11 citation statements)

References 18 publications

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“…), which is traditionally used as a tranquilizer and to diminish insomnia and fear in Mexico, is widely employed and commercially exploited [34]. In 2010, Lozada et al .…”

Section: Resultsmentioning

confidence: 99%

Herbal Insomnia Medications that Target GABAergic Systems: A Review of the Psychopharmacological Evidence

Shi¹,

Dong²,

Zhao³

et al. 2014

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Insomnia is a common sleep disorder which is prevalent in women and the elderly. Current insomnia drugs mainly target the γ-aminobutyric acid (GABA) receptor, melatonin receptor, histamine receptor, orexin, and serotonin receptor. GABAA receptor modulators are ordinarily used to manage insomnia, but they are known to affect sleep maintenance, including residual effects, tolerance, and dependence. In an effort to discover new drugs that relieve insomnia symptoms while avoiding side effects, numerous studies focusing on the neurotransmitter GABA and herbal medicines have been conducted. Traditional herbal medicines, such as Piper methysticum and the seed of Zizyphus jujuba Mill var. spinosa, have been widely reported to improve sleep and other mental disorders. These herbal medicines have been applied for many years in folk medicine, and extracts of these medicines have been used to study their pharmacological actions and mechanisms. Although effective and relatively safe, natural plant products have some side effects, such as hepatotoxicity and skin reactions effects of Piper methysticum. In addition, there are insufficient evidences to certify the safety of most traditional herbal medicine. In this review, we provide an overview of the current state of knowledge regarding a variety of natural plant products that are commonly used to treat insomnia to facilitate future studies.

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“…), which is traditionally used as a tranquilizer and to diminish insomnia and fear in Mexico, is widely employed and commercially exploited [34]. In 2010, Lozada et al .…”

Section: Resultsmentioning

confidence: 99%

Herbal Insomnia Medications that Target GABAergic Systems: A Review of the Psychopharmacological Evidence

Shi¹,

Dong²,

Zhao³

et al. 2014

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“…On the other hand, jacaranone was identified as the sedative principle in T. pringlei (Lozada-Lechuga et al, 2010). However, Xu and coworkers reported neurotoxic effects for this natural quinone that lead to death of mice in 30-90 min, with a LD 50 of 150-200 mg/kg (Xu et al, 2003).…”

Section: Discussionmentioning

confidence: 99%

“…Fruits of T. sylvatica have sedative effects more than anxiolytic effects in rats (Aguilar-Santamaría & Tortoriello, 1996;Molina et al, 1999;Tortoriello & Romero, 1992). Recently, the isolation of jacaranone as a sedative substance from T. pringlei was reported (Lozada-Lechuga et al, 2010). Phytochemical studies of Ternstroemia species have reported the isolation of oleanane-and ursane-type triterpenoids, triterpenoid glycosides, triterpenoid saponins, carotenoids, monoterpenoids, tannins and other aromatic compounds (Balderas et al, 2008;Ikuta et al, 2003;Jo et al, 2005;Kikuchi & Yamaguchi, 1974;Shin et al, 2003;Tori et al, 2005).…”

Section: Introductionmentioning

confidence: 99%

Toxic rather than neuropharmacological effect ofTernstroemia sylvaticafruits and identification of 28-O-[β-l-6-rhamnopyranosyl]-R₁-barrigenol as a new compound with toxic effects in mice

Balderas-López

Alfaro-Romero

Monroy

et al. 2013

Pharmaceutical Biology

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Results: Crude extracts of T. sylvatica fruits, separated from seed and pericarp, showed sedative effect in mice. The aqueous (ED 50 ¼ 4.9 AE 0.8 mg/kg) seed extracts is the most active among them. This extract also decrease locomotor activity and disrupt motor coordination of mice. This extract was also the most toxic extract (LD 50 ¼ 5.0 AE 1.4 mg/kg; i.p.). The triterpene glycoside 28-O-[b-L-6-rhamnopyranosyl]-R 1 -barrigenol was identified in this extract as one of the active sedative compounds (ED 50 ¼ 0.12 AE 0.01 mg/kg) also with toxic effect (LD 50 ¼ 1.11 AE 0.23 mg/kg). Conclusion:The results suggest that T. sylvatica fruits has toxic activity rather than CNS depressant activity in mice and that this effect might be related to the presence of 28-O-[b-L-6-rhamnopyranosyl]-R 1 -barrigenol, one of the active principles of T. sylvatica fruits with sedative and toxic effect.

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“…Jacaronone and derivatives Concentrations [1]:0.055mM, [5]:0.033mM, [6]: 0.039mM, [7]:0.033mM These distinct types of cell death and their effect on immune response prompted a hypothesis where physiological cell death or apoptosis was considered as intrinsically tolerogenic, whereas pathological cell death or necrosis was considered inherently immunogenic, consequently producing inflammatory response [21]. The response of immune system has been considered as transcendental for the elimination of tumor cells after treatment with chemotherapeutic agents [22].…”

Section: % Necrosismentioning

confidence: 99%

Synthesis and Determination of Antitumor Activity of Jacaranone and Synthetic Analogs

Arias¹,

Corrales²,

Poveda³

et al. 2018

IJOC

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Natural product jacaranone, 1, and three analog derivatives were synthesized and their apoptotic and necrotic activity against four cancer cell lines was tested. One of these derivatives 7, was more active than the natural product, and exhibited an important necrotic effect against three of the cell lines tested (ovarian carcinoma, liver cancer and breast cancer cells). Derivative 6 was more active than the natural product, and showed a significant apoptotic activity against breast cancer and ovarian carcinoma cells. Some derivatives analyzed in this study showed promising anti-tumor results, nevertheless, further studies have to be done in order to determine their in vivo activity, their mechanism as well as their safety and stability.

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Isolation of jacaranone, a sedative constituent extracted from the flowers of the Mexican tree Ternstroemia pringlei

Cited by 23 publications

References 18 publications

Herbal Insomnia Medications that Target GABAergic Systems: A Review of the Psychopharmacological Evidence

Herbal Insomnia Medications that Target GABAergic Systems: A Review of the Psychopharmacological Evidence

Toxic rather than neuropharmacological effect ofTernstroemia sylvaticafruits and identification of 28-O-[β-l-6-rhamnopyranosyl]-R₁-barrigenol as a new compound with toxic effects in mice

Synthesis and Determination of Antitumor Activity of Jacaranone and Synthetic Analogs

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Isolation of jacaranone, a sedative constituent extracted from the flowers of the Mexican tree Ternstroemia pringlei

Cited by 23 publications

References 18 publications

Herbal Insomnia Medications that Target GABAergic Systems: A Review of the Psychopharmacological Evidence

Herbal Insomnia Medications that Target GABAergic Systems: A Review of the Psychopharmacological Evidence

Toxic rather than neuropharmacological effect ofTernstroemia sylvaticafruits and identification of 28-O-[β-l-6-rhamnopyranosyl]-R1-barrigenol as a new compound with toxic effects in mice

Synthesis and Determination of Antitumor Activity of Jacaranone and Synthetic Analogs

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Product

Resources

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Toxic rather than neuropharmacological effect ofTernstroemia sylvaticafruits and identification of 28-O-[β-l-6-rhamnopyranosyl]-R₁-barrigenol as a new compound with toxic effects in mice