Valerian extract and valerenic acid are partial agonists of the 5-HT5a receptor in vitro

Dietz, Birgit M.; Mahady, Gail B.; Pauli, Guido F.; Farnsworth, Norman R.

doi:10.1016/j.molbrainres.2005.04.009

Cited by 126 publications

(80 citation statements)

References 43 publications

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“…Assim como os valepotriatos e o borneol, o ácido valerênico também contribui para a ação depressora do SNC e para os efeitos calmantes descritos para extratos de valeriana (Ortiz et al, 1999). Dietz et al (2005) realizaram estudo com o objetivo de investigar os efeitos de extratos de valeriana e de ácido valerênico sobre receptores serotoninérgicos 5-HT 5a . Nesse trabalho foi demonstrado que duas frações do extrato bruto de valeriana, diclorometano (DCM) e éter de petróleo (EP), apresentaram alta afinidade de ligação a esse subtipo de receptor, sendo a afinidade da fração EP maior que a da fração DCM (a concentração de ácido valerênico na fração EP é mais alta que na fração DCM).…”

Section: Sesquiterpenóides áCido Valerênicounclassified

Terpenóides com atividade sobre o Sistema Nervoso Central (SNC)

Passos¹,

Arbo²,

Rates³

et al. 2009

Rev. bras. farmacogn.

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RESUMO:Os terpenóides constituem um vasto grupo de metabólitos secundários com ações sobre o SNC, destacando-se suas atividades sedativa, ansiolítica, antinociceptiva, anticonvulsivante, pró-convulsivante e alucinógena. Neste trabalho foi realizada uma revisão bibliográfica sobre terpenóides com ações descritas no SNC, enfocando moléculas e sistemas neurotransmissores relacionados com sua atividade. As substâncias abordadas encontram-se divididas em mono, sesqui, di, tri e meroterpenóides e incluem compostos isolados e plantas que apresentam ação principalmente sobre os sistemas neurotransmissores GABAérgico, glutamatérgico, dopaminérgico e opióide.Unitermos: Terpenóides, sistema nervoso central, neurotransmissores.ABSTRACT: "Terpenoids with activity in the Central Nervous System (CNS)". The terpenoids are a large group of secondary metabolites which display many activities in the CNS, such as sedative, ansiolytic, antinociceptive, anticonvulsant, pro-convulsant and hallucinogenic. In this work we performed a research on terpenoids that exert effects on the CNS, focusing molecules and neurotransmitter systems related to their actions. The substances approached were classified as mono, sesqui, di, tri and meroterpenoids and include isolated compounds and plants which exert activities mainly on GABAergic, glutamatergic, dopaminergic and opioid neurotransmitter systems.

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Section: Sesquiterpenóides áCido Valerênicounclassified

Terpenóides com atividade sobre o Sistema Nervoso Central (SNC)

Passos¹,

Arbo²,

Rates³

et al. 2009

Rev. bras. farmacogn.

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“…1, has been isolated in a small quantity from the roots of Nardostachys chinensis 1,2) and Valeriana officinalis L., 3,4) and is a bicyclic sesquiterpene that has recently been shown to dose-dependently reduce the locomotor activity of mice with a particularly profound effect, the strongest sedative activity being observed at a dose of 0.06%. 1) The unique aspect for the pharmacological activity of this compound is that it can be administered via inhalation; the compound is naturally volatile at room temperature and bears a pleasant smell.…”

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Concise Synthesis of Valerena-4,7(11)-diene, a Highly Active Sedative, from Valerenic Acid

Kitayama

Kawabata

Ito

2010

Bioscience, Biotechnology, and Biochemistry

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A concise synthesis of valerena-4,7(11)-diene with potent sedative activity was achieved in three steps involving, reduction of carboxylic acid, bromination of the resulting alcohol, and reduction of the bromide from valerenic acid in a 63% total yield. This synthetic method makes it possible to provide further materials for biological testing to realize comprehensive SAR studies.Key words: valerena-4,7(11)-diene; valerenic acid; sedative activity; sesquiterpene Valerena-4,7(11)-diene ((2S,5R,6R)-5,9-dimethyl-2-(2-methyl-1-propenyl)bicyclo[4.3.0]non-1(9)-ene, 1) as shown in Fig. 1, has been isolated in a small quantity from the roots of Nardostachys chinensis 1,2) and Valeriana officinalis L., 3,4) and is a bicyclic sesquiterpene that has recently been shown to dose-dependently reduce the locomotor activity of mice with a particularly profound effect, the strongest sedative activity being observed at a dose of 0.06%. 1)The unique aspect for the pharmacological activity of this compound is that it can be administered via inhalation; the compound is naturally volatile at room temperature and bears a pleasant smell.1) It may hopefully be developed as a less-harmful remedy for attention deficit hyperactivity disorder (ADHD) and for the confused elderly. An efficient total synthesis of 1 therefore appears to be of importance, as more extensive and elaborate structural variations are envisaged. Structure-activity relationship (SAR) studies of this natural product would not only be able to elucidate the intrinsic mechanism of action, but would also open a new avenue for exploring the possible mode of action of this compound. However, an efficient method for synthesizing 1 is required before comprehensive SAR studies can become a reality.Valerenic acid 2, which has been isolated as the main component of Valeriana officinalis and previously synthesized by Mulzer et al. 5) and Altmann et al.,6) was purchased from EXTRASYNTHÈ SE (France) as an optically active compound (½ D À115 (c 0.13, CHCl 3 ). 2 has tranquilizing and/or sedative activity from animal experiments, 7) and the activation of adenosine receptors has been implicated in the action of valerian ingredients.8) We present here the first concise synthesis of valerena-4,7(11)-diene 1 from valerenic acid 2 as the starting material via the reduction of ,-unsaturated carboxylic acid to allylic alcohol with LiAlH 4 , bromination of the resulting primary alcohol with CBr 4 /PPh 3 , and reduction of the bromide with super hydride.Scheme 1 shows how the concise synthesis of target compound 1 was achieved in three steps from valerenic acid 2.Treatment of valerenic acid 2 with LiAlH 4 (LAH) at 0 C for 3 h gave valerenol 3 in a 93% yield without reduction of the conjugated olefin. 9) Alcohol 3 was reacted with triphenylphosphine and then exposed to tetrabromomethane at À10 C for 45 min to afford 4 in an 83% yield. Bromide 4 was converted to desired compound 1 as soon as possible since 4 easily decomposed. Bromide 4 was reacted with LiBHEt 3 at À20 C for 1 h to afford target...

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“…Известно, что компоненты валерианы связываются со множеством нейротрансмиттерных рецепторов [23], включая серотониновые 5-HT 5A -рецепторы [24], что оказывает эффект на циркадные ритмы и уровень тре-воги. Компоненты валерианы также являются аллосте-рическими модуляторами субъединице-специфических ГАМК-А-каналов [25] и аденозиновых А1-рецепторов [26].…”

Section: валериана (Valeriana Officinalis)unclassified