Amaryllidaceae and Sceletium alkaloids

Lewis, J. R.

doi:10.1039/np9920900183

Cited by 14 publications

(14 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…These cover cardiovascular activity, immunostimulatory activity, antibacterial activity, antifertility activity, emetic and diaphoretic activity [7], [8], [9], [10]. Other effects also cover analgesic, central nervous system, antitumour and antiviral responses [11]. Recently, we reported the acetylcholinesterase inhibitory effects of these alkaloids [12] and affinity to the serotonin transporter (SERT) was reported for two Amaryllidaceae alkaloids, buphanidrine and buphanamine [13].…”

mentioning

confidence: 98%

Inhibition of [³ H]Citalopram Binding to the Rat Brain Serotonin Transporter by Amaryllidaceae Alkaloids

et al. 2006

View full text Add to dashboard Cite

Twenty-one Amaryllidaceae alkaloids isolated from different Amaryllidaceae species were investigated for their affinity to the serotonin reuptake transport protein and for GABA(A)-benzodiazepine receptor binding. Cherylline (21), crinamine (7), crinine (1), epibuphanisine (2), epivittatine (6), maritidine (11), O-methylmaritidine (12), powelline (3), 1-O-acetyllycorine (18) and tazettine ( 13) showed affinity to the serotonin reuptake transport protein. Cherylline (21) and epivittatine (6) yielded the highest activity among the group. No GABA(A)-benzodiazepine receptor binding activity was exhibited by the alkaloids tested.

show abstract

mentioning

confidence: 98%

Inhibition of [³ H]Citalopram Binding to the Rat Brain Serotonin Transporter by Amaryllidaceae Alkaloids

et al. 2006

View full text Add to dashboard Cite

show abstract

“…caranine, crinine, galanthamine and galanthine 31,32 . Haemanthidine and lycorine are also analgesics and antiinflammatory with activities greater than aspirin 33 and indomethacin 34 , respectively, while narwedine and vittatine could potentiate the analgesic effects of caffeine and morphine 33 .…”

Section: Analgesic and Anti-inflammatory Activitiesmentioning

confidence: 99%

“…Similarly, the aqueous leaves' extract of C. bulbispermum (1, 1.5 and 3 g/Kg, orally) significantly and markedly impaired the four parameters of rat hold-board test indicating its sedative properties 20 . Narwedine has been found to potentiate the pharmacological effects of caffeine, carbazole, arecoline and nicotine, in laboratory animals 33 .…”

Section: Analgesic and Anti-inflammatory Activitiesmentioning

confidence: 99%

“…Galanthamine is a tertiary amine and would be expected to be sufficiently lipid-soluble to cross the blood-brain barrier and act on the central nervous system. It exhibited reversible muscarinic and anticholinesterase activities and can be useful as a treatment for nervous diseases, neurological injuries, paralysis syndrome, schizophrenia, mania, and other forms of dementia as well as Alzheimer's disease [35][36][37] . This alkaloid acts by restocking acetylcholine levels in brain areas lacking cholinergic neurons by binding to the enzyme acetylcholinesterase.…”

Section: Analgesic and Anti-inflammatory Activitiesmentioning

confidence: 99%

“…It aided recovery after an overdose of the centrally acting muscarinic antagonist hyoscine (scopolamine) 41 . Moreover, it is also known to inhibit traumatic shock and has been patented for use in treatment of nicotine dependence 37 .…”

Section: Analgesic and Anti-inflammatory Activitiesmentioning

confidence: 99%

See 2 more Smart Citations

Untitled

2013

IJPSR

View full text Add to dashboard Cite

Progress in the Development of Methods for Asymmetric Organic Synthesis

Schultz

1994

J Chinese Chemical Soc

View full text Add to dashboard Cite

Methods for the enanticselecuve synthesis of chiral cyclohexane derivatives from aromatic carboxylic acids are presented. Birch reduction-alkylation of chiral benzamides of type 1 occur with high diastereoselectivities to give 1,4-cyclohexadiene derivatives with quaternary centers located at C(6). Early applications of this chemistry provided target structures with a quaternary center derived from C( I) of the starting benzoic acid derivative. Herein are described 1) the development of a more versatile Birch reduction-alkylation, 2) a practical "asymmetric linkage" between aromatic carboxylic acids and chiral acyclic structures, and 3) asymmetric syntheses of unnatural alkaloids; applications to opiate receptor pharmacology. INTRODUC'TlONWehavebeen involved with the development of enanuosetectivc methods for lhe synthesis of chiral cyclohexane derivatives from aromatic carboxylic acids? The inexpensive amino acid L-proline and the product of reduction with LiAll-4, Lsprclinol, serve as chiral auxiliaries to provide good to outstanding stereocontrol. As indicated in Scheme I, a wide range of substitucnts R on the benzoic acid nucleus is tolerated; subsutuents X at C(2) may take the form of alkyl, aryl, alkoxy and ttirnethylsily]. Although 2-dialky-Iamino substituents arc problematic in the chemistry shown in Scheme I, anthranilic adds may be successfully utilized by modiflcauon of the methodology (see Scheme V). Scheme IBirch reduction of the aryl nucleus provides a chiral amide enolate; enolate alkylations occur with high diastcreoselecuvitics to give 1,4-cycJohexadiene derivatives with quaternary centers located at C(6). This process in-volves l,4-chirality transfer from a stereogenic center associated with the chiral auxiliary to an Sp2 center located in the substrate. Jt is believed that enolate alkylations occur by the SN2 mechanism. Product yields are excellent even for sterically demanding alkylation reagents because the enolate center is Ilanked by three Sp2 hybridized carbon atoms (sec enolate 2). In rare cases where electron-transfer appears to be operating, intense colorations are observed and the enolate is converted to the starting bonzamide rather than the alkylated 1,4-cyclohexadiene.Hydrolysis of the enol ether (X =OMe) provides 2,2disubstituted cyclohex-S-cn-l-onca for a variety of synthetic applications.' It also is possible to generate 2,4-cyctonexadien-Lones, which have found utility in Diels-Alder' and 1,3-dipolar 4 cycloadditions.Chiral 2-substituted cyclchex-z-en-j-ones are available by Birch reduction followed by enol ether hydrolysis and double bond migration. Diastereoselective conjugate additions (1,5~hirality transfer) with organometallic reagents,' enol trimethylsHyl ethers" (the Mukaiyama-Michael addition) and allyl silanes" (the Sakurai reaction) provide tertiary stercocenters at CO) of the cyclohexanone ring; additional manipulations give access to trans-2,3disubstituted cyclohexanoncs with high enamiomcric purity.The chiral 2-substituted cyclohcx-2-en-l-one also can be prepared fro...

show abstract

Amaryllidaceae and Sceletium alkaloids

Abstract: 1 Occurrence and Structural Studies 2 Synthesis 3 ReferencesThe crystal structure of eugenine ( 14) a constituent of Narcissus eugeniae has been determined by X-ray crystal-10graphy.~ This alkaloid is far from planar, only the benzene ring being so.

Cited by 14 publications

References 10 publications

Inhibition of [³ H]Citalopram Binding to the Rat Brain Serotonin Transporter by Amaryllidaceae Alkaloids

Inhibition of [³ H]Citalopram Binding to the Rat Brain Serotonin Transporter by Amaryllidaceae Alkaloids

Untitled

Progress in the Development of Methods for Asymmetric Organic Synthesis

Contact Info

Product

Resources

About

Amaryllidaceae and Sceletium alkaloids

Abstract: 1 Occurrence and Structural Studies 2 Synthesis 3 ReferencesThe crystal structure of eugenine ( 14) a constituent of Narcissus eugeniae has been determined by X-ray crystal-10graphy.~ This alkaloid is far from planar, only the benzene ring being so.

Cited by 14 publications

References 10 publications

Inhibition of [3 H]Citalopram Binding to the Rat Brain Serotonin Transporter by Amaryllidaceae Alkaloids

Inhibition of [3 H]Citalopram Binding to the Rat Brain Serotonin Transporter by Amaryllidaceae Alkaloids

Untitled

Progress in the Development of Methods for Asymmetric Organic Synthesis

Contact Info

Product

Resources

About

Inhibition of [³ H]Citalopram Binding to the Rat Brain Serotonin Transporter by Amaryllidaceae Alkaloids

Inhibition of [³ H]Citalopram Binding to the Rat Brain Serotonin Transporter by Amaryllidaceae Alkaloids