Biosynthesis of Hyoscyamine and Scopolamine in Datura stramonium

Underhill, E. W.; Youngken, Heber W.

doi:10.1002/jps.2600510208

Cited by 22 publications

(5 citation statements)

References 12 publications

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“…Alkaloids were extracted from the root cultures as described by KARAWYA et al [8]. Free alkamines were obtained by alkaline hydrolysis of these extracts [9].…”

Section: Methodsmentioning

confidence: 99%

Partial Purification and Properties of Tropine Dehydrogenase from Root Cultures ofDatura stramonium

Koelen¹,

Gross²

1982

Planta Med

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From sterile root cultures of Datura stramonium, an NADP(H)-specific tropine dehydrogenase has been isolated and characterized. The enzyme catalyzes the reversible and stereospecific oxidation of tropine and related tropane-3 alpha-ols to the corresponding ketone. Isomeric pseudotropine (tropane-3 beta-ol) is neither accepted as substrate nor produced in the reverse reaction. It is assumed that this dehydrogenase is involved in the biosynthesis of tropane alkaloids.

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“…Alkaloids were extracted from the root cultures as described by KARAWYA et al [8]. Free alkamines were obtained by alkaline hydrolysis of these extracts [9].…”

Section: Methodsmentioning

confidence: 99%

Partial Purification and Properties of Tropine Dehydrogenase from Root Cultures ofDatura stramonium

Koelen¹,

Gross²

1982

Planta Med

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“…Tables 1 and 2 show data gathered over two years. All three acids apparently serve as precursors for the tropic acid moieties of hyoscyamine [1] and hyoscine [2].…”

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confidence: 99%

“…Because we have been unable to trace details of the systematic degradation of hyoscyamine [1] or hyoscine [2] labeled by phenylpyruvate [4], hyoscyamine from the phenylalanine competitive feed was degraded using the excellent method of Leete (5).…”

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confidence: 99%

Competitive Feeding Experiments with Tropic Acid Precursors in Datura

Ansarin¹,

Woolley²

1993

J. Nat. Prod.

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Phenyl{ 1 -14C]alanine [31, phenyl[2-14C)pyruvate [4], and phenyl[ 1 -14C]lactate [51 were fed singly and in competition with unlabeled phenylalanine, phenyllactate, and phenylpyruvate to Datura stramonium. The activities recorded in the alkaloids hyoscyamine [11 and hyoscine (scopolamine) [21 suggested that phenyllactate [51 was the closest precursor for the tropic acid moiety of these alkaloids.Hyoscyamine [11, from plants fed with phenyl[2-14C}pyruvate [4l, was hydrolyzed, but the resultant tropic acid 7 contained only 21% of the activity, the remainder being located in the tropine. However, degradation of the tropic acid showed that the phenylpyruvate incorporated in a specific manner, although it is clearly not an efficient precursor.( -)-S-Tropic acid is the aromatic acid moiety of the important tropane ester alkaloids hyoscyamine [1] and hyoscine (scopolamine) (2], which are constituents of Datura spp. Its biosynthesis, which has aroused much interest, was first investigated in I960 when Leete (1) demonstrated that the label from phenyl[3-14C]alanine infiltrated into Datura stramoniumL. (Solanaceae) incorporated into C-2 of tropic acid [6], Underhill and Youngken (2) and Gross and Schutte (3) were able to confirm this result using intact D. stramonium and Datura metel isolated root cultures, respectively. The former workers reported that phenylacetic acid was also a good precursor but that the usual one-carbon sources (formate and serine), capable of extending the two-carbon side chain to three carbons, only labeled the tropane part of the ester alkaloids. Methionine and formaldehyde (1) also failed as additional one-carbon sources, but bicarbonate (4), although labeling other carbons, predominantly labeled the hydroxymethyl group of tropic acid, a result that favored the intermediacy of phenylacetate. However, it was later (5) demonstrated that all three carbons in the side chain of tropic acid [6} were derived from the side-chain carbons of phenylalanine [31 by means of a rearrangement (Scheme 1). The primary role of phenylalanine was confirmed when it was shown that after very careful purification, the alkaloids derived from phenylacetate feedings were devoid of activity 'Part 3 in the series "The Biosynthesis of Tropic Acid.' For Part 2, see Evans and Woolley ( 14). 2Dedicated to the memory of Professor Edward Leete.

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“…Tropine is finally converted to hyoscyamine by condensation with phenyllactate to form littorine, which is further oxidized and rearranged enzymatically to form hyoscyamine (Figure ). Scopolamine, on the other hand, is formed from hyoscyamine by the enzymatic activity of hyoscyamine-6β-hydroxylase. − Calystegines, a group of alkaloids with the nortropane skeleton, have also been reported in belladonna. They are derived via a tropane alkaloid biosynthetic pathway like that of the tropane alkaloids but with pseudotropine as the first metabolite in their biosynthesis .…”

Section: Pharmacotherapeutic Characterization Of Belladonnamentioning

confidence: 99%

Dark Classics in Chemical Neuroscience: An Evidence-Based Systematic Review of Belladonna

Maurya

Kumar

Kabir

et al. 2020

ACS Chem. Neurosci.

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Belladonna has diverse pharmacotherapeutic properties with a shadowy history of beauty, life, and death. Alkaloids present in belladonna have anti-inflammatory, anticholinergic, antispasmodic, mydriatic, analgesic, anticonvulsant, and antimicrobial activities, which makes it widely applicable for the treatment of various diseases. However, because of its associated toxicity, the medicinal use of belladonna is debatable. Therefore, an evidencebased systematic review was planned to elucidate the pharmacotherapeutic potential of belladonna. A comprehensive literature search was performed in PubMed, MEDLINE, the Cochrane database, Embase, and ClinicalTrials.gov using the keywords "belladonna", "belladonna and clinical trials", and "safety and efficacy of belladonna". Articles published from 1965 to 2020 showing the efficacy of belladonna in diverse clinical conditions are included. The quality of evidence was generated using the GRADE approach, and 20 studies involving 2302 patients were included for the systematic review. Our analyses suggest that belladonna treatment appears to be safe and effective in various disease conditions, including acute encephalitis syndrome, urethral stent pain, myocardial ischemia injury, airway obstructions during sleep in infants, climacteric complaints, irritable bowel syndrome, and throbbing headache. However, better understanding of the dosage and the toxicity of tropane alkaloids of belladonna could make it an efficient remedy for treating diverse medical conditions.

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Biosynthesis of Hyoscyamine and Scopolamine in Datura stramonium

Cited by 22 publications

References 12 publications

Partial Purification and Properties of Tropine Dehydrogenase from Root Cultures ofDatura stramonium

Partial Purification and Properties of Tropine Dehydrogenase from Root Cultures ofDatura stramonium

Competitive Feeding Experiments with Tropic Acid Precursors in Datura

Dark Classics in Chemical Neuroscience: An Evidence-Based Systematic Review of Belladonna

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