Paper · 2025 · Journal of Chemical Education

Studies on the Isolation and Structure Elucidation of Berberine, (−)-β-Hydrastine, and Jatrorrhizine from Goldenseal Root (Hydrastis canadensis L.) and Mahonia x media ‘Winter Sun’ Stem Bark

Minchao Guo; Muhammad Waleed Baig; Shane Carney; et al.

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claims
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verbatim quotes
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citations
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Open access · cc-by

Abstract

High Resolution Image Download MS PowerPoint Slide Goldenseal ( Hydrastis canadensis L., Ranunculaceae) is a traditional North American herbal medicine with a long history of use to treat various illnesses, primarily as a chemotherapeutic agent for microbial infections. Two of its alkaloid constituents, berberine and (−)-β-hydrastine, have well-defined pharmacological effects. In addition to its presence in goldenseal, berberine (and analogues) are found in other plant families. One such is the barberry family (Berberidaceae), encompassing various medicinal and decorative species, including those of the genus Mahonia ( Berberis ). This 3-h laboratory practical has been devised to allow undergraduate students to isolate berberine and (−)-β-hydrastine from a commercially available root sample of goldenseal, and both berberine and the closely related alkaloid, jatrorrhizine, from the bark of Mahonia x media ‘Winter sun’. Isolation is carried out on a miniature, sustainable and environmentally friendly scale using flash column chromatography. A gradient mobile phase is utilized for the isolation of (−)-β-hydrastine and berberine from goldenseal. A notable feature of the isolation of berberine and jatrorrhizine from Mahonia is the utilization of silica gel loaded with 10% w/w sodium carbonate. In this way, jatrorrhizine, an acidic alkaloid, is significantly retained while berberine elutes effortlessly from the column. A follow-on spectral assignment workshop is undertaken using 1- and 2-D NMR and IR spectra of the isolated alkaloids. Both formative and summative assessment of student comprehension takes place during the practical, workshop and end-of-semester college examinations. The experiment has been fully validated in the class setting, having been completed by circa 160 third year pharmacy students.

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Claims 3

Method / resourceobservedoriginal resultpositivemeasured

Claim · model-written summary

The alkaloid isolation experiment was fully validated in the class setting with about 160 third-year pharmacy students.

Taxon
Hydrastis canadensisHydrastis canadensise0
Outcome
validated in the class settinge3
Value
circa 160e3
Setting
class settinge3

Organisms pictured · Representative pictures of the matched species, not figures from the paper.

Hydrastis canadensis
Hydrastis canadensis · TaxonEric Hunt · CC BY-SA 4.0 · Wikimedia Commons ↗

Verbatim

e0

“Goldenseal ( Hydrastis canadensis L., Ranunculaceae) is a traditional North American herbal medicine”

✓ located verbatim in the source · abstract, characters 51–151 · show in text ↑
e3

“The experiment has been fully validated in the class setting, having been completed by circa 160 third year pharmacy students”

✓ located verbatim in the source · abstract, characters 1705–1830 · show in text ↑
Intervention effectobservedoriginal resultpositivemeasured

Claim · model-written summary

Jatrorrhizine is significantly retained on silica gel loaded with 10% w/w sodium carbonate while berberine elutes.

Taxon
MahoniaMahoniae1
Treatment
silica gel loaded with 10% w/w sodium carbonatee1
Compound
jatrorrhizinee2
Outcome
significantly retainede2
Direction
retainede2

Not reportedComparator

Organisms pictured · Representative pictures of the matched species, not figures from the paper.

Mahonia
Mahonia · Taxon · picture of the genus (one of its species)The original uploader was JoJan at English Wikipedia . · Public domain · Wikimedia Commons ↗

Verbatim

e1

“A notable feature of the isolation of berberine and jatrorrhizine from Mahonia is the utilization of silica gel loaded with 10% w/w sodium carbonate”

✓ located verbatim in the source · abstract, characters 1160–1308 · show in text ↑
e2

“In this way, jatrorrhizine, an acidic alkaloid, is significantly retained while berberine elutes effortlessly from the column”

✓ located verbatim in the source · abstract, characters 1310–1435 · show in text ↑
Observationobservedoriginal resultpositivemeasured

Claim · model-written summary

Berberine elutes effortlessly from the silica column in the Mahonia isolation.

Taxon
MahoniaMahoniae1
Compound
berberinee2
Outcome
elutes effortlesslye2

Organisms pictured · Representative pictures of the matched species, not figures from the paper.

Mahonia
Mahonia · Taxon · picture of the genus (one of its species)The original uploader was JoJan at English Wikipedia . · Public domain · Wikimedia Commons ↗

Verbatim

e1

“A notable feature of the isolation of berberine and jatrorrhizine from Mahonia is the utilization of silica gel loaded with 10% w/w sodium carbonate”

✓ located verbatim in the source · abstract, characters 1160–1308 · show in text ↑
e2

“In this way, jatrorrhizine, an acidic alkaloid, is significantly retained while berberine elutes effortlessly from the column”

✓ located verbatim in the source · abstract, characters 1310–1435 · show in text ↑