The Absolute Configuration of Hyperforin, an Antibiotic from Hypericum perforatum L., Based on the Crystal Structure Determination of its p-Bromobenzoate Ester.

Brondz, Ilia; Greibrokk, Tyge; Groth, P.; Aasen, Arne J.; Seip, Ragnhild; Brunvoll, J.

doi:10.3891/acta.chem.scand.37a-0263

Cited by 43 publications

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“…+41 [2] ". Figure 13 shows the structure presented by Shimizu et al [21] and that of the structure published [16], for comparison. Proving that the X-ray structure of hyperforin in [16] is identical to that of the synthetic structures in [20] and provides the best evidence for the accuracy of the structure given in [16].…”

Section: Stereochemistry Of Hyperforin Proposed By Brondzmentioning

confidence: 99%

“…The actual instrumentation used here for GC-MS with SMB was based on a Varian 1200 GC-MS system (Varian, Middleburg, The Netherlands); details are described in [19]. Separation of substances and resolution of isomers was carried Figure 7 shows the structure of the p-bromobenzoate ester of hyperforin [16] Hyperforin in free form is a keto-enol molecule, which is subjected to keto- Rapid tautomeric equilibrium between a keto form (a ketone or an aldehyde) and an enol (an alcohol) (see Figure 8), which contains a pair of doubly bonded carbon atoms adjacent to a hydroxyl (−OH) group, is highly thermodynamically driven (see Figure 9) and specific pH can favor one of the tautomeric forms.…”

Section: Methodsmentioning

confidence: 99%

“…The above sample of transparent white crystals of the p-bromobenzoate ester of hyperforin (described in [16]) (1.0 mg) was dissolved in n-hexane (1 mL; analytical grade reagent, Merck, Darmstadt, Germany). GC-MS analysis with supersonic molecular beams (SMB) instrumentation enabling the separation and analysis of thermolabile substances is described in detail in [17] and [18].…”

Section: Methodsmentioning

confidence: 99%

“…The oxidative analysis of crystals gave 95% and 97% compliance with dinitro-benzoate of hyperforin [15] and p-bromobenzoate of hyperforin [16], respectively. Quantities of impurities present in crystals did not interfere with the results of X-ray analysis.…”

Section: Introductionmentioning

confidence: 99%

“…Using X-ray crystallography, the relative and absolute stereochemistry of hyperforin has been elucidated, as reported in [15] and [16], respectively. Figure 3 shows the structure of the p-bromobenzoate ester of hyperforin (1) and hyperforin (2).…”

Section: Introductionmentioning

confidence: 99%

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Super Antibiotics, Part IV. Hyperforin, Relative and Absolute Stereochemistry Elucidated by Gas-Chromatography Mass-Spectrometry with Supersonic Molecular Beams

Brondz¹

2017

IJAMSC

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Relative and absolute stereochemistry for hyperforin has been proposed by Brondz et al. was supported and new isomer of hyperforin-perforatrin has been discovered. Relative and absolute stereochemistry for perforatrin was proposed and elucidated by using gas-chromatography mass-spectrometry with supersonic molecular beams (SMB). The possibility of the existence of ambiguities in chirality as a hypothesis for the existence, and a new understanding, of chiral substances with shifting chirality is presented.

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Section: Stereochemistry Of Hyperforin Proposed By Brondzmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Super Antibiotics, Part IV. Hyperforin, Relative and Absolute Stereochemistry Elucidated by Gas-Chromatography Mass-Spectrometry with Supersonic Molecular Beams

Brondz¹

2017

IJAMSC

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Catalytic Asymmetric Total Synthesis of ent‐Hyperforin

et al. 2010

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Neurotrophe Naturstoffe – ihre Chemie und Biologie

Lacoske

Theodorakis

2013

Angewandte Chemie

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Neurodegenerative Erkrankungen und Rückenmarksverletzungen betreffen weltweit etwa 50 Millionen Menschen und verursachen Gesundheitskosten von insgesamt mehr als 600 Milliarden Dollar pro Jahr. Nervenwachstumsfaktoren, d. h. Neurotrophine, sind potenzielle Therapeutika für diese Erkrankungen, denn sie können die Regeneration von Nerven fördern. Durchschnittlich 500 Publikationen jährlich belegen die Bedeutung der Neurotrophine in den biomedizinischen Wissenschaften und ihr Potenzial für therapeutische Anwendungen. Allerdings ist die klinische Verwendung von Neurotrophinen wegen ihres schlechten pharmakokinetischen Profils stark eingeschränkt. Niedermolekulare Verbindungen, die die neurotrophe Aktivität modulieren, bieten hingegen einen vielversprechenden Therapieansatz bei neurologischen Erkrankungen. Die Natur hat für eine beeindruckende Zahl von Naturstoffen mit starken neurotrophen Wirkungen gesorgt. Die aktuellen Strategien zur Synthese dieser Verbindungen sowie deren Fähigkeit, das Wachstum und die Erneuerung von Nervenzellen zu induzieren, bilden den Schwerpunkt dieses Aufsatzes. Es ist davon auszugehen, dass neurotrophe Naturstoffe nicht nur als Leitstrukturen in der Wirkstoffentwicklung genutzt werden können, sondern auch für das nächste große Projekt der Biomedizin: die Kartierung der Hirnaktivität (BAM, Brain Activity Map).

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The Absolute Configuration of Hyperforin, an Antibiotic from Hypericum perforatum L., Based on the Crystal Structure Determination of its p-Bromobenzoate Ester.

Cited by 43 publications

References 0 publications

Super Antibiotics, Part IV. Hyperforin, Relative and Absolute Stereochemistry Elucidated by Gas-Chromatography Mass-Spectrometry with Supersonic Molecular Beams

Super Antibiotics, Part IV. Hyperforin, Relative and Absolute Stereochemistry Elucidated by Gas-Chromatography Mass-Spectrometry with Supersonic Molecular Beams

Catalytic Asymmetric Total Synthesis of ent‐Hyperforin

Neurotrophe Naturstoffe – ihre Chemie und Biologie

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