Chapter 1 The Tropane Alkaloids

Lounasmaa, Mauri

doi:10.1016/s0099-9598(08)60296-5

Cited by 17 publications

(16 citation statements)

References 162 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…16−19 In general, more than 150 tropane alkaloids, which have in common a structural element, the azabicyclo[3.2.1]octane system, have been isolated from different plants. 16,20 Among them, the main and most abundant alkaloid, detected in some species of Erythroxylum, is cocaine (methyl (1S,3S,4R,5R)-3benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylate, M = C 17 H 21 NO 4 ; M w = 303.4 Da; melting point 96−98 °C, and pKb = 5.4). 16−19 Chemical analyzes of E. coca leaves, not necessarily of the derived product, i.e., cocaine, are widely reported in the literature, such as the work of Johnson and Emche, in 1994, who used gas chromatography−mass spectrometry (GC−MS) to monitor eight alkaloidscocaine, methyl ecgonine, hygrine, tropinone, trans-cinnamoylcocaine, cis-cinnamoylcocaine, cuscohygrine, and tropacocainein coca leaves as a function of leaf growth.…”

Section: Introductionmentioning

confidence: 99%

“…The Erythroxylum coca plant, found mainly in South America, is chemically characterized by tropane alkaloids. − In general, more than 150 tropane alkaloids, which have in common a structural element, the azabicyclo[3.2.1]octane system, have been isolated from different plants. , Among them, the main and most abundant alkaloid, detected in some species of Erythroxylum , is cocaine (methyl (1 S ,3 S ,4 R ,5 R )-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylate, M = C 17 H 21 NO 4 ; M w = 303.4 Da; melting point 96–98 °C, and pKb = 5.4). − …”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Analysis of Erythroxylum coca Leaves by Imaging Mass Spectrometry (MALDI–FT–ICR IMS)

Santos

Almeida

Gonçalves

et al. 2021

J. Am. Soc. Mass Spectrom.

View full text Add to dashboard Cite

Matrix-assisted laser desorption/ionization imaging mass spectrometry (MALDI IMS) can determine the chemical identity and spatial distribution of several molecules in a single analysis, conserving its natural histology. However, there are no specific studies on the spatial distribution of alkaloids in Erythroxylum coca leaves by MALDI IMS, preserving the histology of the monitored compounds. Therefore, in this work, positive-ion mode MALDI Fourier-transform ion cyclotron resonance imaging mass spectrometry (MALDI(+)FT–ICR IMS) was applied to identify and analyze the distribution of alkaloids on the surface of coca leaves, evaluating the ionization efficiency of three matrices (α-cyano-4-hydroxycinnamic acid (CHCA), 2-mercaptobenzothiazole (MBT), and 2,5-dihydroxybenzoic acid (DHB)). The last was chosen as the best matrix in this study, and it was studied in five concentrations (0.5, 1.0, 2.0, 4.0, and 8.0 mg·mL–1), where 2 mg·mL–1 was the most efficient. The washing of coca leaves with the organic solvents (acetonitrile, methanol, toluene, and dichloromethane) tested did not improve the performance of the ionization process. Finally, a tissue section, 50 μm thick, was used to study the inner part of the leaf tissue, where alkaloids and flavonoid molecules were detected.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Analysis of Erythroxylum coca Leaves by Imaging Mass Spectrometry (MALDI–FT–ICR IMS)

Santos

Almeida

Gonçalves

et al. 2021

J. Am. Soc. Mass Spectrom.

View full text Add to dashboard Cite

show abstract

“…The pharmaceutical, hyoscyamine (atropine), is the major tropane alkaloid produced by a wide range of solanaceous genera [1,2]. The biosynthesis of this alkaloid involves the esterification of tropine (tropan-30~-ol), a putrescine-derived amine, with a unit of phenylalanine-derived tropic acid (Fig.…”

Section: Introductionmentioning

confidence: 99%

The formation of 3α‐ and 3β‐acetoxytropanes byDatura stramonium transformed root cultures involves two acetyl‐CoA‐dependent acyltransferases

1991

FEBS Letters

View full text Add to dashboard Cite

Tropine (tropan-3~-ol) is an intermediate in the formation of hyoscyamine. An acyltransferase activity that can acetylate tropine using acetylcoenzyme A as cosubstrate has been found in translbrmed root cultures of Datura sfr(mtonit#n. A further acyltransferase activity that acetylates pseudotropine (tropan-3fl-ol) with acetyl-coeuzyme A is also present. These two activities can be partially resolved by anion-exchange chromatography, some fractions containing only the pseudotropine-utilizing activity. The basic properties of these two enzymes are reported and their roles in lbrming the observed alkaloid spectrum of D. stramoltium roots discussed.

show abstract

“…In 1988, Tepfer et al (1988 reported the presence of a group of compounds in underground organs and root exudates of Culystegiu sepium (Convolvulaceae). Systematic screening of a number of plant species, representing 26 families, revealed their presence in Convolvulus arvensis (Convolvulaceae) and Atropa helladoizrza (Solanaceae) as well (Tepfer et al, 1988).…”

mentioning

confidence: 99%

“…However, the greatest number of plant species producing calystegines belong to the family Solanaceae. Tropane alkaloids, bearing a methyl substituent on the nitrogen atom, are a wellrecognized group of structurally related natural products and include such important medicinal alkaloids as cocaine, scopolamine and atropine (Lounasmaa, 1988 ;Lounasmaa and Tamminen, 1993). Tropane alkaloids have long been known to have anticholinergic, antiemetic, parasympatholytic, anesthetic and many other pharmacological actions.…”

mentioning

confidence: 99%

Specific α‐Galactosidase Inhibitors, N‐Methylcalystegines Structure/Activity Relationships of Calystegines from Lycium Chinense

Asano

Kato

Miyauchi

et al. 1997

European Journal of Biochemistry

View full text Add to dashboard Cite

An examination of the roots of Lycium chinense (Solanaceae) has resulted in the discovery of 14 calystegines, a cycloheptane bearing an amino group and three hydroxyl groups, and two polyhydroxylated piperidine alkaloids. Calystegines A, and B,, in addition to the previously known calystegines A,, A,, A,, B,, B,, B,, B4, C,, C, and N,, were isolated and determined as lu,2P,4u-trihydroxy-nortropane and lu,2a,4a,7a-tetrahydroxy-nortropane, respectively. L. chinense also had two polyhydroxytropanes bearing a methyl group on the nitrogen atom, unlike the previously reported nortropane alkaloids. They were established as N-methylcalystegines B, and C,, and their N-methyl groups were found to be axially oriented from NOE experiments. IP-Amino-3P,4P,5u-trihydroxycycloheptane was also present in L. chinense and may be a biosynthetic precursor of the calystegines that occur in this plant. Two polyhydroxypiperidine alkaloids, fagomine and 6-deoxyfagomine, were isolated. Calystegine B, is a potent competitive inhibitor of almond P-glucosidase (K, = 1.9 pM) and coffee bean a-galactosidase ( K L = 0.86 pM), while N-methylcalystegine B, was a more potent competitive inhibitor of the latter enzyme (K, = 0.47 pM) than the parent compound but showed a marked lack of inhibitory activities towards most other glycosidases.Since this compound is a very specific inhibitor of a-galactosidase and inhibits rat liver lysosomal agalactosidase with a K, of 1.8 pM, it may provide a useful experimental model for the lysosomal storage disorder, Fabry's disease. The addition of a hydroxyl group at Cbexo, as in calystegines B, and C,, enhances the inhibitory potential towards P-glucosidase and P-galactosidase but markedly lowers or abolishes inhibition towards a-galactosidase. Hence, the N-methylation of calystegine C , did not enhance its inhibition of u-galactosidase. The chemical N-methylation of calystegines A, and B, markedly enhanced inhibition of coffee bean a-galactosidase, with K, values of 5.2 pM and 36 pM, respectively, but almost eliminated their inhibitory potential towards P-glucosidase and trehalase, respectively. Thus, methylation of the nitrogen atom significantly altered the specificity of the inhibitors.Keywords: Lyciiim chinense ; u-galactosidase inhibitor; N-methylcalystegine ; chemical N-methylation ; alteration of specificity. In 1988, Tepfer et al. (1988 reported the presence of a group of compounds in underground organs and root exudates of Culystegiu sepium (Convolvulaceae). Systematic screening of a number of plant species, representing 26 families, revealed their presence in Convolvulus arvensis (Convolvulaceae) and Atropa helladoizrza (Solanaceae) as well (Tepfer et al., 1988). These compounds were named calystegines and proposed as nutritional mediators for rhizosphere bacteria, establishing and maintaining specific plant-bacterium relationships. Calystegines were characterized as nortropane alkaloids with a high degree of hydroxylation and an unusual aminoketal functionality at the bridgeCorrespondence fu N. Asano,

show abstract

Chapter 1 The Tropane Alkaloids

Cited by 17 publications

References 162 publications

Analysis of Erythroxylum coca Leaves by Imaging Mass Spectrometry (MALDI–FT–ICR IMS)

Analysis of Erythroxylum coca Leaves by Imaging Mass Spectrometry (MALDI–FT–ICR IMS)

The formation of 3α‐ and 3β‐acetoxytropanes byDatura stramonium transformed root cultures involves two acetyl‐CoA‐dependent acyltransferases

Specific α‐Galactosidase Inhibitors, N‐Methylcalystegines Structure/Activity Relationships of Calystegines from Lycium Chinense

Contact Info

Product

Resources

About

Chapter 1 The Tropane Alkaloids

Cited by 17 publications

References 162 publications

Analysis of Erythroxylum coca Leaves by Imaging Mass Spectrometry (MALDI–FT–ICR IMS)

Analysis of Erythroxylum coca Leaves by Imaging Mass Spectrometry (MALDI–FT–ICR IMS)

The formation of 3α&#x2010; and 3β&#x2010;acetoxytropanes byDatura stramonium transformed root cultures involves two acetyl&#x2010;CoA&#x2010;dependent acyltransferases

Specific α‐Galactosidase Inhibitors, N‐Methylcalystegines Structure/Activity Relationships of Calystegines from Lycium Chinense

Contact Info

Product

Resources

About

The formation of 3α‐ and 3β‐acetoxytropanes byDatura stramonium transformed root cultures involves two acetyl‐CoA‐dependent acyltransferases