Alkaloids from Eschscholzia californica and Their Capacity to Inhibit Binding of [3H]8-Hydroxy-2-(di-N-propylamino)tetralin to 5-HT1A Receptors in Vitro

Gafner, Stefan; Dietz, Birgit M.; McPhail, Kerry L.; Scott, Ian M.; Gliński, Jan A.; Russell, Fiona E.; McCollom, Megan; Budzinski, J.W.; Foster, Brian; Bergeron, Chantal; Rhyu, Mee-Ra; Bolton, Judy L.

doi:10.1021/np058114h

Cited by 30 publications

(23 citation statements)

References 23 publications

(37 reference statements)

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The presence of this alkaloid might explain anecdotal reports of “vivid dreams” and opioid-like activities observed in patients taking black cohosh [67], as well as explain its observed in vitro opioid activity [68]. Aporphine alkaloids exhibit strong serotonergic activity against the 5-HT 1A receptor [69, 70]. For example, N -methyllaurotetanine, which is an N -methyl analog of laurotetanine identified in this study, is a potent ligand for the 5-HT 1A receptor [70].…”

Section: Resultsmentioning

confidence: 99%

“…Aporphine alkaloids exhibit strong serotonergic activity against the 5-HT 1A receptor [69, 70]. For example, N -methyllaurotetanine, which is an N -methyl analog of laurotetanine identified in this study, is a potent ligand for the 5-HT 1A receptor [70]. Although it has been shown that small structural changes in the aporphine ring can lead to a large change in pharmacological activity, it is likely that some of the aporphines identified in this study contribute to the serotonergic activity of black cohosh [71].…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Mass spectrometric dereplication of nitrogen-containing constituents of black cohosh (Cimicifuga racemosa L.)

et al. 2012

View full text Add to dashboard Cite

Black cohosh preparations are popular dietary supplements among women seeking alternative treatments for menopausal complaints. For decades, triterpene glycosides and phenolic acids have dominated the phytochemical and biomedical research on this plant. In this study, we provide evidence that black cohosh contains an unexpected and highly diverse group of secondary nitrogenous metabolites previously unknown to exist in this plant. Using a dereplication approach that combines accurate mass measurements, database searches and general knowledge of biosynthetic pathways of natural products, we identified or tentatively identified 73 nitrogen-containing metabolites, many of which are new natural products. The identified compounds belong to several structural groups including alkaloids, amides or esters of hydroxycinnamic acids and betains. Among the alkaloids, several classes such as guanidino alkaloids, isoquinolines and β-carbolines were identified. Fragmentation patterns for major compound classes are discussed, which provides a framework for the discovery of these compounds from other sources. Identification of alkaloids as a well-known group of bioactive natural products represents an important advance in better understanding of the pharmacological profile of black cohosh.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Mass spectrometric dereplication of nitrogen-containing constituents of black cohosh (Cimicifuga racemosa L.)

et al. 2012

View full text Add to dashboard Cite

show abstract

“…It does contain many other isoquinoline alkaloids such as: protopine, cryptopine and α-cryptopine, chelerythrine californidine, escholtzine, N-methyllaurotetanine, caryachine, O-methylcaryachine, 6S,12S-neocaryachine, laurotetamine and N-methyl laurotetamine, Chelirubine, chelidonine and homochelidonine. 5 Which can interact with opioid receptors and ease opium withdrawal and helps pain through GABA and serotonin.…”

Section: About the Plant Eschscholzia Californicamentioning

confidence: 99%

Successful application of Eschscholzia californica to combat opioid addiction

Zampieron

2018

IJCAM

View full text Add to dashboard Cite

In 2002, a 34 y/o female amputated her finger in a large metal door. Her surgical repair was successful, but she was plagued with severe neuropathic from the episode.She was Prescribed Oxycodone (OxyContin, Roxicodone) by her surgeon. The pain continued to persist, and she was allowed to remain on the drug for 12months time. Unfortunately, she became addicted and her social and emotional life became seriously affected.The patient came to me (DrZ) at my clinic in Woodbury, CT, for help with this addiction, and to perhaps help with the chronic pain.Previous to this, DrZ read a citation in Mills/Bone a reference by Fundythus et al. that plants with chelerythrine reduce morphine dependence in animals. 3 AbstractIn the US today, a staggering 115 people die daily due to the tragedy of being addicted to opioids. 1 Some estimates are that this epidemic will cripple the economy with an 80-billion-dollar burden on taxpayers, who foot the bill for intervention, legal fees, and health for these individuals in the drug's insidious grip. 2 The crisis has permeated everywhere in our society…even into small towns across America, and into my practice in rural CT.In this editorial are two cases highlighting the power of botanical medicine, which assisted several patient's to beat this addiction.Citation: Zampieron ER. Successful application of Eschscholzia californica to combat opioid addiction. Int J Complement Alt Med.

show abstract

“…Among serotonergic activities, most interest has focused on 5-HT 1A and 5-HT 7 receptors, and natural aporphinoids have been used as model pharmacophores to develop novel synthetic analogs [79, 80]. For example, N -methyllaurotetanine, a methyl analog of laurotetanine identified in black cohosh, is a potent ligand against 5-HT 1A [81]. Interestingly, a recent study by de la Peña et al claims that magnoflorine possesses sedative and anxiolytic effects mediated by the GABAergic system [82].…”

Section: 5 Isoquinoline Alkaloidsmentioning

confidence: 99%

Nitrogen-Containing Constituents of Black Cohosh: Chemistry, Structure Elucidation, and Biological Activities

Nikolić

Lankin

Cisowska

et al. 2015

The Formation, Structure and Activity of Phytochemicals

View full text Add to dashboard Cite

The roots/rhizomes of black cohosh (Actaea racemosa L. syn. Cimicifuga racemosa [L]. Nutt., Ranunculaceae) have been used traditionally by Native Americans to treat colds, rheumatism, and a variety of conditions related to women’s health. In recent years black cohosh preparations have become popular dietary supplements among women seeking alternative treatments for menopausal complaints. The popularity of the plant has led to extensive phytochemical and biological investigations, including several clinical trials. Most of the phytochemical and biological research has focused on two abundant classes of compounds: the triterpene glycosides and phenolic acids. A third group of phytoconstituents that has received far less attention consists of the alkaloids and related compounds that contain nitrogen. This chapter summarizes the current state of knowledge of the chemistry and biological activities associated with this group of constituents and provides some perspective on their significance for future research on this interesting plant.

show abstract

Alkaloids from Eschscholzia californica and Their Capacity to Inhibit Binding of [³H]8-Hydroxy-2-(di-N-propylamino)tetralin to 5-HT_1A Receptors in Vitro

Cited by 30 publications

References 23 publications

Mass spectrometric dereplication of nitrogen-containing constituents of black cohosh (Cimicifuga racemosa L.)

Mass spectrometric dereplication of nitrogen-containing constituents of black cohosh (Cimicifuga racemosa L.)

Successful application of Eschscholzia californica to combat opioid addiction

Nitrogen-Containing Constituents of Black Cohosh: Chemistry, Structure Elucidation, and Biological Activities

Contact Info

Product

Resources

About