246. Chemical correlation of the absolute configurations of salsolidine, salsoline, and calycotomine with the amino-acids

Battersby, Alan R.; Edwards, Tanya

doi:10.1039/jr9600001214

Cited by 54 publications

(17 citation statements)

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“…The (R)‐ and (S)‐enantiomers of SAL (1,2,3,4‐tetrahydro‐6,7‐dihydroxy‐1‐methylisoquinoline) and N‐methyl‐SAL and other catechol isoquinolines were either donated by Dr M. Strolin Benedetti (Zambon Group, Milan, Italy) or synthesized by us. (+/−)‐Salsolidine was prepared by Pictet–Spengler condensation of acetaldehyde with 3,4‐dimethoxyphenylethylamine (13). Salsolidine was O‐demethylated by hydrogen bromide treatment resulting in the desired (±)‐SAL hydrobromide (14).…”

Section: Methodsmentioning

confidence: 99%

Salsolinol is a Putative Endogenous Neuro‐intermediate Lobe Prolactin‐Releasing Factor

Tóth

Homicskó

Radnai

et al. 2001

J Neuroendocrinology

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The isolation and identification of a prolactin-releasing factor (PRF) from the neuro-intermediate lobe of the pituitary gland has been pursued for over a decade. Using high-pressure liquid chromatography with electrochemical detection (HPLC-ECD) and gas chromatography/mass spectrometry (GC/MS) (R)-salsolinol (SAL) (a dopamine-related stereo-specific tetrahydroisoquinoline) was found to be present in neuro-intermediate lobe as well as median eminence extracts of male, intact-, and ovariectomized female rats. Moreover, analysis of SAL concentrations in neuro-intermediate lobe revealed parallel increases with plasma prolactin in lactating rats exposed to a brief (10 min) suckling stimulus following 4-h separation. SAL appears to be a selective and potent stimulator of prolactin secretion in vivo and it was without effect on the secretion of other pituitary hormones. We have also found that SAL can elevate prolactin release, although to a lesser extent, in pituitary cell cultures as well as in hypophysectomized rats bearing anterior lobe transplants under the kidney capsule. Lack of interference of SAL with [3H]-spiperone binding to AP homogenates indicates that SAL does not act at the dopamine D2 receptor. Moreover, [3H]-SAL binds specifically to homogenate of AL as well as neuro-intermediate lobe obtained from lactating rats. Taken together, our data clearly suggest that SAL is synthesized in situ and this compound can play a role in the regulation of pituitary prolactin secretion.

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Section: Methodsmentioning

confidence: 99%

Salsolinol is a Putative Endogenous Neuro‐intermediate Lobe Prolactin‐Releasing Factor

Tóth

Homicskó

Radnai

et al. 2001

J Neuroendocrinology

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“…The absolute configurations of the chiral cactus alkaloids were unknown at the time of their original isolation. In 1960 Battersby and Edwards applied the somewhat uncertain comparison of the solvent-related changes in optical rotation with those of related compounds of known configuration to propose that the natural (-)anhalonine and (-)-lophophorine are both S isomers [21]. This was fortunately confirmed a few years later by X-ray crystallography and comparison of ORD and CD spectra and, contrary to expectation, the same configuration was similarly demonstrated for 1S-(+)-O-methylanhalonidine [22].…”

Section: The History Of Cactaceous Alkaloid Chemistry Begins With Louismentioning

confidence: 99%

Alkaloids of the Cactaceae — The Classics

Cassels

2019

Natural Product Communications

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Alkaloids of the Cactaceae have been studied for the last 120 years. The first half of that period provided the "classic" compounds, after which a large number of usually very similar analogs were isolated or determined with modern methods. Although some unusual synthetic approaches have been developed, their preparation is generally quite straightforward. Their biosynthesis has been studied but, particularly in the case of the isoquinoline compounds, important aspects have not been addressed. Due to its striking effects, the pharmacology of mescaline has been studied more intensely than that of the other phenethylamines present in cacti, followed only by hordenine. The many 1,2,3,4-tetrahydroisoquinoline alkaloids have attracted much less interest and have often been considered practically inactive. Nevertheless, some recorded activities of this group of compounds suggests a need for additional studies, especially in connection with their co-administration with mescaline, as in dried cacti and in beverages prepared from them.

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“…Because 1,2- DHIQs are attractive synthetic intermediates, our modified Pomeranz–Fritsch conditions provide entry into IQ and THIQ derivatives (Scheme ). For example, reduction of the double bond by hydrogenation over Pd/C followed by reductive removal of the triflate with lithium aluminum hydride (LiAlH 4 ) provided THIQ (±)-salsolidine ( 8 ) in a 63% yield over two steps . Alternatively, isohypsic elimination mediated by KO t Bu in DMSO afforded the aromatized IQ natural product nigellimine ( 9 ) in a 50% yield .…”

Section: Resultsmentioning

confidence: 67%

Synthesis of 1,2-Dihydroisoquinolines by a Modified Pomeranz–Fritsch Cyclization

Huang

Lumb

2019

J. Org. Chem.

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Isoquinolines (IQs) and their derivatives are present in many natural products and biologically active small molecules. Herein, we report a modified procedure for the classical Pomeranz-Fritsch protocol, which expands the scope of 1,2-dihydroisoquinoline (DHIQs) products. 1,2-DHIQs are an attractive branch point for the synthesis of IQs, but because of their innate reactivity, they have remained difficult to prepare. We demonstrate that the Fujioka/Kita conditions, combining trimethylsiyltriflate (TMSOTf) and an amine base, activate dimethylacetals required for Pomeranz-Fritsch cyclization under sufficiently mild conditions to prepare a broad range of 1,2-DHIQ products. We also demonstrate the synthetic value of these DHIQs by further functionalization to either reduced tetrahydroisoquinoline (THIQ) or fully aromatized IQ natural products. Scheme 1. A) Redox States of Isoquinoline Compounds. B) Unique properties of 1,2-DHIQ. C) This Work: An Improved Pomeranz-Fritsch Synthesis of 1,2-DHIQ and other isoquinoline compounds.

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246. Chemical correlation of the absolute configurations of salsolidine, salsoline, and calycotomine with the amino-acids

Cited by 54 publications

References 0 publications

Salsolinol is a Putative Endogenous Neuro‐intermediate Lobe Prolactin‐Releasing Factor

Salsolinol is a Putative Endogenous Neuro‐intermediate Lobe Prolactin‐Releasing Factor

Alkaloids of the Cactaceae — The Classics

Synthesis of 1,2-Dihydroisoquinolines by a Modified Pomeranz–Fritsch Cyclization

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