A Modified H-NMR Quantification Method of Ephedrine Alkaloids in Ephedrae Herba Samples

Overview

Journal Int J Mol Sci

Publisher MDPI

Specialties Biochemistry
Chemistry
Molecular Biology

Date 2023 Jul 29

PMID 37511036

Authors

Yue-Chiun Li

Chia-Hung Wu

Thi Ha Le

Qingjun Yuan

Luqi Huang

Guo-Fen Chen

Mei-Lin Yang

Sio-Hong Lam

Hsin-Yi Hung

Handong Sun

Yi-Hung Wu

Ping-Chung Kuo

Tian-Shung Wu

Affiliations

Soon will be listed here.

Abstract

A previous H-NMR method allowed the quantification of ephedrine alkaloids; however, there were some disadvantages. The cyclized derivatives resulted from the impurities of diethyl ether were identified and benzene was selected as the better extraction solvent. The locations of ephedrine alkaloids were confirmed with 2D NMR. Therefore, a specific H-NMR method has been modified for the quantification of ephedrine alkaloids. Accordingly, twenty Ephedrae Herba samples could be classified into three classes: (I) -like species; (II) -like species; (III) others (lower alkaloid contents). The results indicated that ephedrine and pseudoephedrine are the major alkaloids in plants, but the concentrations vary greatly determined by the plant species and the collection locations.

References

Abourashed E, El-Alfy A, Khan I, Walker L . Ephedra in perspective--a current review. Phytother Res. 2003; 17(7):703-12. DOI: 10.1002/ptr.1337. View

Kim H, Choi Y, Chang W, Verpoorte R . Quantitative analysis of ephedrine analogues from ephedra species using 1H-NMR. Chem Pharm Bull (Tokyo). 2003; 51(12):1382-5. DOI: 10.1248/cpb.51.1382. View

Frederich M, Choi Y, Verpoorte R . Quantitative analysis of strychnine and Brucine in Strychnos nux-vomica using 1H-NMR. Planta Med. 2004; 69(12):1169-71. DOI: 10.1055/s-2003-818014. View

Chan K, Pan R, Hsu M . Simultaneous quantification of six ephedrines in a Mahwang preparation and in urine by high-performance liquid chromatography. Biomed Chromatogr. 2005; 19(5):337-42. DOI: 10.1002/bmc.452. View

Schaneberg B, Khan I . Quantitative and qualitative HPLC analysis of thermogenic weight loss products. Pharmazie. 2004; 59(11):819-23. View

Zhang J, Tian Z, Lou Z . [Quality evaluation of twelve species of Chinese Ephedra (ma huang)]. Yao Xue Xue Bao. 1989; 24(11):865-71. View

Walker R, Wood D, Akmal M, Sharks E . Effects of oxazolidines derived from (-) ephedrine in the rat. Gen Pharmacol. 1992; 23(4):729-32. DOI: 10.1016/0306-3623(92)90156-e. View

Mateus-Avois L, Mangin P, Saugy M . Development and validation of a capillary zone electrophoresis method for the determination of ephedrine and related compounds in urine without extraction. J Chromatogr B Analyt Technol Biomed Life Sci. 2003; 791(1-2):203-16. DOI: 10.1016/s1570-0232(03)00222-8. View

Gonzalez-Juarez D, Escobedo-Moratilla A, Flores J, Hidalgo-Figueroa S, Martinez-Taguena N, Morales-Jimenez J . A Review of the genus: Distribution, Ecology, Ethnobotany, Phytochemistry and Pharmacological Properties. Molecules. 2020; 25(14). PMC: 7397145. DOI: 10.3390/molecules25143283. View

10.

Hurlbut J, CARR J, Singleton E, Faul K, Madson M, Storey J . Solid-phase extraction cleanup and liquid chromatography with ultraviolet detection of ephedrine alkaloids in herbal products. J AOAC Int. 1998; 81(6):1121-7. View

11.

Gentili S, Torresi A, Marsili R, Chiarotti M, Macchia T . Simultaneous detection of amphetamine-like drugs with headspace solid-phase microextraction and gas chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2002; 780(1):183-92. DOI: 10.1016/s1570-0232(02)00522-6. View

12.

Choi Y, Choi H, Hazekamp A, Bermejo P, Schilder Y, Erkelens C . Quantitative analysis of bilobalide and ginkgolides from Ginkgo biloba leaves and Ginkgo products using (1)H-NMR. Chem Pharm Bull (Tokyo). 2003; 51(2):158-61. DOI: 10.1248/cpb.51.158. View

13.

Sa-Ih N, Reakkamnuan C, Samerphob N, Cheaha D, Niyomdecha S, Kumarnsit E . Local field potential power spectra and locomotor activity following treatment with pseudoephedrine in mice. Acta Neurobiol Exp (Wars). 2020; 80(1):19-31. View

14.

Pauli G, Jaki B, Lankin D . Quantitative 1H NMR: development and potential of a method for natural products analysis. J Nat Prod. 2005; 68(1):133-49. DOI: 10.1021/np0497301. View

15.

Roman M . Determination of ephedrine alkaloids in botanicals and dietary supplements by HPLC-UV: collaborative study. J AOAC Int. 2004; 87(1):1-14. PMC: 2584348. View

16.

Gurley B, Wang P, Gardner S . Ephedrine-type alkaloid content of nutritional supplements containing Ephedra sinica (Ma-huang) as determined by high performance liquid chromatography. J Pharm Sci. 1999; 87(12):1547-53. DOI: 10.1021/js9801844. View

17.

Suedee R, Songkram C, Petmoreekul A, Sangkunakup S, Sankasa S, Kongyarit N . Direct enantioseparation of adrenergic drugs via thin-layer chromatography using molecularly imprinted polymers. J Pharm Biomed Anal. 2000; 19(3-4):519-27. DOI: 10.1016/s0731-7085(98)00248-9. View

18.

Li C, Lin C, Wu C, Lee K, Wu T . Efficient 1H nuclear magnetic resonance method for improved quality control analyses of Ginkgo constituents. J Agric Food Chem. 2004; 52(12):3721-5. DOI: 10.1021/jf049920h. View

19.

El-Haj B, Al-Amri A, Hassan M, Ali H, Bin Khadem R . The use of cyclohexanone as a "derivatizing" reagent for the GC-MS detection of amphetamines and ephedrines in seizures and the urine. Forensic Sci Int. 2003; 135(1):16-26. DOI: 10.1016/s0379-0738(03)00101-4. View

20.

Andraws R, Chawla P, Brown D . Cardiovascular effects of ephedra alkaloids: a comprehensive review. Prog Cardiovasc Dis. 2005; 47(4):217-25. DOI: 10.1016/j.pcad.2004.07.006. View