Neutral Fragment Filtering for Rapid Identification of New Diester-diterpenoid Alkaloids in Roots of Aconitum Carmichaeli by Ultra-high-pressure Liquid Chromatography Coupled with Linear Ion Trap-orbitrap Mass Spectrometry

Overview

Journal PLoS One

Specialties General Medicine
Science

Date 2013 Jan 4

PMID 23285005

Citations 9

Authors

Jing Zhang

Zhi Hai Huang

Xiao Hui Qiu

Yi Ming Yang

Da Yuan Zhu

Wen Xu

Affiliations

Soon will be listed here.

Abstract

A rapid and effective method was developed for separation and identification of diester-diterpenoid alkaloids (DDA) in the roots of Aconitum carmichaeli by ultra-high-pressure liquid chromatography coupled with high resolution LTQ-Orbitrap tandem mass spectrometry (UHPLC-LTQ-Orbitrap-MS(n)). According to accurate mass measurement and the characteristic neutral loss filtering strategy, a total of 42 diester-diterpenoid alkaloids (DDA) were rapidly detected and characterized or tentatively identified. Meanwhile, the proposed fragmentation pathways and the major diagnostic fragment ions of aconitine, mesaconitine and hypaconitine were investigated to trace DDA derivatives in crude plant extracts. 23 potential new compounds were successfully screened and characterized in Aconitum carmichaeli, including 16 short chain fatty acyls DDA, 4 N-dealkyl DDA and several isomers of aconitine, mesaconitine and hypaconitine.

Citing Articles

Multi-Omics on Traditional Medicinal Plant of the Genus : Current Progress and Prospect.

Wang T, Rangji C, Liu W, Ma J, Zhou R, Leng L Molecules. 2025; 30(1.

PMID: 39795175 PMC: 11722372. DOI: 10.3390/molecules30010118.

Metabolite Profiling Analysis of the Tongmai Sini Decoction in Rats after Oral Administration through UHPLC-Q-Exactive-MS/MS.

Zheng X, Zhan Y, Peng M, Xu W, Deng G Metabolites. 2024; 14(6).

PMID: 38921468 PMC: 11205536. DOI: 10.3390/metabo14060333.

Unveiling Dynamic Changes of Chemical Constituents in Raw and Processed Fuzi With Different Steaming Time Points Using Desorption Electrospray Ionization Mass Spectrometry Imaging Combined With Metabolomics.

Liu Y, Yang X, Zhou C, Wang Z, Kuang T, Sun J Front Pharmacol. 2022; 13:842890.

PMID: 35359875 PMC: 8960191. DOI: 10.3389/fphar.2022.842890.

Applying Four-Step Characteristic Ion Filtering with HPLC-Q-Exactive MS/MS Spectrometer Approach for Rapid Compound Structures Characterization and Major Representative Components Quantification in Modified Tabusen-2 Decoction.

Zhao Y, Dong X, Wang Z, Dong R, Bu R, Feng Q Evid Based Complement Alternat Med. 2022; 2021:9255305.

PMID: 35003312 PMC: 8741372. DOI: 10.1155/2021/9255305.

Insight into chemical basis of traditional Chinese medicine based on the state-of-the-art techniques of liquid chromatography-mass spectrometry.

Yu Y, Yao C, Guo D Acta Pharm Sin B. 2021; 11(6):1469-1492.

PMID: 34221863 PMC: 8245813. DOI: 10.1016/j.apsb.2021.02.017.

References

Shim S, Kim J, Kang S . Norditerpenoid alkaloids from the processed tubers of Aconitum carmichaeli. Chem Pharm Bull (Tokyo). 2003; 51(8):999-1002. DOI: 10.1248/cpb.51.999. View

Wu W, Liang Z, Zhao Z, Cai Z . Direct analysis of alkaloid profiling in plant tissue by using matrix-assisted laser desorption/ionization mass spectrometry. J Mass Spectrom. 2006; 42(1):58-69. DOI: 10.1002/jms.1138. View

Ameri A . The effects of Aconitum alkaloids on the central nervous system. Prog Neurobiol. 1998; 56(2):211-35. DOI: 10.1016/s0301-0082(98)00037-9. View

Wang Y, Liu Z, Song F, Liu S . Electrospray ionization tandem mass spectrometric study of the aconitines in the roots of aconite. Rapid Commun Mass Spectrom. 2002; 16(22):2075-82. DOI: 10.1002/rcm.828. View

Turabekova M, Rasulev B . A QSAR toxicity study of a series of alkaloids with the lycoctonine skeleton. Molecules. 2007; 9(12):1194-207. PMC: 6147334. DOI: 10.3390/91201194. View

Chan T . Aconite poisoning. Clin Toxicol (Phila). 2009; 47(4):279-85. DOI: 10.1080/15563650902904407. View

Chan T . Aconite poisoning presenting as hypotension and bradycardia. Hum Exp Toxicol. 2009; 28(12):795-7. DOI: 10.1177/0960327109353056. View

Werner E, Croixmarie V, Umbdenstock T, Ezan E, Chaminade P, Tabet J . Mass spectrometry-based metabolomics: accelerating the characterization of discriminating signals by combining statistical correlations and ultrahigh resolution. Anal Chem. 2008; 80(13):4918-32. DOI: 10.1021/ac800094p. View

Wang F, Chen Q, Liu X . Diterpenoid alkaloids. Nat Prod Rep. 2010; 27(4):529-70. DOI: 10.1039/b916679c. View

10.

Malik A, Blasco C, Pico Y . Liquid chromatography-mass spectrometry in food safety. J Chromatogr A. 2010; 1217(25):4018-40. DOI: 10.1016/j.chroma.2010.03.015. View

11.

Mitamura M, Horie S, Sakaguchi M, Someya A, Tsuchiya S, Van de Voorde J . Mesaconitine-induced relaxation in rat aorta: involvement of Ca2+ influx and nitric-oxide synthase in the endothelium. Eur J Pharmacol. 2002; 436(3):217-25. DOI: 10.1016/s0014-2999(01)01623-5. View

12.

Hu R, Zhao J, Qi L, Li P, Jing S, Li H . Structural characterization and identification of C(19)- and C(20)-diterpenoid alkaloids in roots of Aconitum carmichaeli by rapid-resolution liquid chromatography coupled with time-of-flight mass spectrometry. Rapid Commun Mass Spectrom. 2009; 23(11):1619-35. DOI: 10.1002/rcm.4038. View

13.

Liu X, Jian X, Cai X, Chao R, Chen Q, Chen D . Cardioactive C₁₉-diterpenoid alkaloids from the lateral roots of Aconitum carmichaeli "Fu Zi". Chem Pharm Bull (Tokyo). 2012; 60(1):144-9. DOI: 10.1248/cpb.60.144. View

14.

Lim H, Chen J, Sensenhauser C, Cook K, Subrahmanyam V . Metabolite identification by data-dependent accurate mass spectrometric analysis at resolving power of 60,000 in external calibration mode using an LTQ/Orbitrap. Rapid Commun Mass Spectrom. 2007; 21(12):1821-32. DOI: 10.1002/rcm.3024. View

15.

Sleno L, Volmer D, Marshall A . Assigning product ions from complex MS/MS spectra: the importance of mass uncertainty and resolving power. J Am Soc Mass Spectrom. 2005; 16(2):183-98. DOI: 10.1016/j.jasms.2004.10.001. View

16.

Bello-Ramirez A, Nava-Ocampo A . A QSAR analysis of toxicity of Aconitum alkaloids. Fundam Clin Pharmacol. 2004; 18(6):699-704. DOI: 10.1111/j.1472-8206.2004.00280.x. View

17.

Konno C, SHIRASAKA M, Hikino H . Cardioactive principle of aconitum carmichaeli roots. Planta Med. 1979; 35(2):150-5. DOI: 10.1055/s-0028-1097196. View

18.

Turabekova M, Rasulev B, Dzhakhangirov F, Salikhov S . Aconitum and Delphinium alkaloids "Drug-likeness" descriptors related to toxic mode of action. Environ Toxicol Pharmacol. 2011; 25(3):310-20. DOI: 10.1016/j.etap.2007.10.035. View

19.

Murayama M, Ito T, Konno C, Hikino H . Mechanism of analgesic action of mesaconitine. I. Relationship between analgesic effect and central monoamines or opiate receptors. Eur J Pharmacol. 1984; 101(1-2):29-36. DOI: 10.1016/0014-2999(84)90027-x. View

20.

Tai Y, But P, Young K, Lau C . Cardiotoxicity after accidental herb-induced aconite poisoning. Lancet. 1992; 340(8830):1254-6. DOI: 10.1016/0140-6736(92)92951-b. View