Benzylisoquinoline Alkaloids from Gnetum parvifolium

Xu, Qun; Lin, Mao Tsun

doi:10.1021/np980472f

Cited by 40 publications

(28 citation statements)

References 16 publications

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“…Higenamine (1‐[(4‐Hydroxyphenyl)methyl]‐1,2,3,4‐tetrahydroisoquinoline‐6,7‐diol; HG), also known as dl‐demethylcoclaurine or norcoclaurine, is a benzyl isoquinoline alkaloid. It is widely found in Chinese medicinal materials as well as traditional food materials and additives including aconite roots, Tinospora crispa , Nandina domestica , Gnetum parvifolium , Asarum herb, and Chinese prickly ash . HG was extracted from aconite roots by Kosuge et al in 1978 for the first time .…”

Section: Introductionmentioning

confidence: 99%

A pharmacokinetics study of orally administered higenamine in rats using LC–MS/MS for doping control analysis

Wang

Xiong

Yang

et al. 2020

Drug Testing and Analysis

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According to WADA guidelines, the presence of Higenamine (HG) in urine should not be ≥10 ng/mL. HG is widely found in materials used in Chinese herbal medicines as well as food and additives. This paper is the first method wherein a rat model has been used to evaluate the pharmacokinetics of orally administered HG by LC–MS/MS and would be helpful in doping control analysis. The method was found to be linear over a concentration range of 0.5(lower limit of quantification, LLOQ)–500 ng/mL for plasma and 0.5(LLOQ)–1000 ng/mL for urine. The values for intra‐ and inter‐day accuracy and precision did not deviate by >12.25% for HG in plasma and 5.87% in urine. Extraction recoveries of HG were 70.30–86.71% from plasma and 74.93%–79.29% from urine. HG was stable in plasma and urine after the extraction process and when exposed to different storage conditions. The findings of this study could provide some reference value for the assessment of HG misuse and for the control of intake and external application of HG‐related materials (foods and medicinal herbs). Our key findings are that high levels of external application or oral administration of HG‐rich materials may lead to a positive urine test for HG in athletes.

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Section: Introductionmentioning

confidence: 99%

A pharmacokinetics study of orally administered higenamine in rats using LC–MS/MS for doping control analysis

Wang

Xiong

Yang

et al. 2020

Drug Testing and Analysis

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“…NC was isolated as the racemate (namely, higenamine) from several higher plant sources, including aconite root, asiasari radix, the leaves of Annona squamosa , and the lianas of Gnetum parvifolium ; the single enantiomers were instead obtained from Nelumbo nucifera , upon extraction of different plant sources: the seed embryo yielded the dextrorotatory (+)‐enantiomer, to which it was later assigned the absolute ( R )‐configuration, while the leaves supplied the ( S )‐(–)‐enantiomer …”

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confidence: 99%

Occurrence of Enantioselectivity in Nature: The Case of (S)‐Norcoclaurine

et al. 2016

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This review article is aimed at providing a monographic overview on (S)-norcoclaurine (NC) alkaloid from three diverse points of view, collected all together for the first time: 1) the synthetic one, where the compound is seen as a target chiral molecule to be obtained in the highest optical purity and as a starting point for the development of biocatalytic asymmetric syntheses of tetrahydroisoquinoline alkaloids; 2) the chromatographic one, which addresses the HPLC separation of the two NC enantiomers; and 3) the biochemical one, for which a thorough understanding of the topology and mechanism of action of norcoclaurine synthase (NCS) enzyme is still a matter of debate. Special emphasis on the most recent studies in the field is given by discussing the results published by the main research groups who are working on NC and NCS.

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“…Both the FT-IR and the FT-Raman spectra exhibit a great 4 1.317 N 3 -C 4 -C 5 129.8 N 3 -C 4 -C 5 -C 7 1.9 C 4 -C 5 1.373 C 4 -C 5 -C 7 116.3 C 4 -C 5 -C 7 -N 8 0.6 C 5 -C 7 1.446 Both the FT-IR and the FT-Raman spectra exhibit a great 4 1.317 N 3 -C 4 -C 5 129.8 N 3 -C 4 -C 5 -C 7 1.9 C 4 -C 5 1.373 C 4 -C 5 -C 7 116.3 C 4 -C 5 -C 7 -N 8 0.6 C 5 -C 7 1.446…”

Section: Infrared and Raman Spectramentioning

confidence: 99%

Vibrational spectra and quantum chemical calculations of uracilyl–pyridinium mesomeric betaine

Schmidt¹,

Lindner²,

Casado³

et al. 2007

J Raman Spectroscopy

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Modified nucleobases (MNs) are promising molecules with potential application in non-linear optic (NLO) and drug design against a wide number of diseases. In the present paper we report studies on a cross-conjugated mesomeric betaine, which can act as a MN, formed by the covalent union of a 4-dimethylamino pyridinium and a uracilyl groups. The molecule thus formed must be presented by a dipolar canonical formulae in which positive and negative charges are delocalized within separated moieties. Quantum chemistry density functional theory (DFT) calculations, at the B3PW91/6-31G * * level, and Fourier transform (FT) infrared and Raman spectra of this molecule and its N-deuterated derivative were performed. The calculated structural properties over the ground state optimized structure evidenced a strong separation between the two conjugated systems. Comparison with previous results obtained for the cationic species indicated that N-protonation clearly affects the degree of conjugation. Assignments of the FT-IR and FT-Raman spectra were supported by the DFT wavenumbers, intensities and normal modes, which also evidenced the separation of the two conjugated systems. Significant deviations were found for the stretching force constants of the inter-ring and the uracilyl skeletal bonds when comparing this molecule with its N-protonated species.

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Benzylisoquinoline Alkaloids from Gnetum parvifolium

Cited by 40 publications

References 16 publications

A pharmacokinetics study of orally administered higenamine in rats using LC–MS/MS for doping control analysis

A pharmacokinetics study of orally administered higenamine in rats using LC–MS/MS for doping control analysis

Occurrence of Enantioselectivity in Nature: The Case of (S)‐Norcoclaurine

Vibrational spectra and quantum chemical calculations of uracilyl–pyridinium mesomeric betaine

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