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Characterization of isoquinoline alkaloids, diterpenoids and steroids in the Chinese herb Jin-Guo-Lan (Tinospora sagittata and Tinospora capillipes) by high-performance liquid chromatography/electrospray ionization with multistage mass spectrometry.
Rapid Commun Mass Spectrom. 2006; 20(15):2328-42.RC

Abstract

This study sought to determine the primary components (isoquinoline alkaloids, diterpenoids and steroids) in crude extracts of the Chinese herb Jin-Guo-Lan, prepared from the roots of Tinospora sagittata and T. capillipes, by liquid chromatography/electrospray ionization multistage mass spectrometry coupled with diode-array detection (LC-DAD/ESI-MS(n)). After separation on a reversed-phase C(18) column using gradient elution, positive and negative ESI-MS experiments were performed. In positive ion mode, the three types of compounds showed very different characteristic ions: strong [M](+) or [M+H](+) ions were observed for isoquinoline alkaloids; [M+NH(4)](+) and/or [M+H-CO(2)](+) for diterpenoids; [M+H-nH(2)O](+) (n=1-3) for steroids. These adduct ions and/or fragments were used to deduce the mass and categories of known and unknown components in crude extracts, and their structures were further confirmed by ESI-MS(n) in positive ion mode. Moreover, UV absorption peaks obtained from DAD provided useful functional group information to aid the MS(n)-based identification. As a result, 11 compounds were unambiguously identified by comparing with standard compounds and 13 compounds were tentatively identified or deduced according to their MS(n) data. Two of these compounds (13-hydroxycolumbamine and 13-hydroxyjatrorrhizine) were found to be new compounds and another one (13-hydroxypalmatine) was detected for the first time as a natural product. In addition, a [M-*CH(3)-H(2)O](*+) ion in MS(2) of [M](+) after in-source collision-induced dissociation was used to differentiate positional isomers of protoberberine alkaloids, columbamine and jatrorrhizine. Although the roots of T. sagittata and T. capillipes contain almost identical compounds, the content of the compounds in them is dramatically different, suggesting the necessity for further comparison of the bioactivities of the two species.

Authors+Show Affiliations

Pharmaceutical Informatics Institute, Zhejiang University, Hangzhou 310027, P.R. China.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

16817243

Citation

Zhang, Yufeng, et al. "Characterization of Isoquinoline Alkaloids, Diterpenoids and Steroids in the Chinese Herb Jin-Guo-Lan (Tinospora Sagittata and Tinospora Capillipes) By High-performance Liquid Chromatography/electrospray Ionization With Multistage Mass Spectrometry." Rapid Communications in Mass Spectrometry : RCM, vol. 20, no. 15, 2006, pp. 2328-42.
Zhang Y, Shi Q, Shi P, et al. Characterization of isoquinoline alkaloids, diterpenoids and steroids in the Chinese herb Jin-Guo-Lan (Tinospora sagittata and Tinospora capillipes) by high-performance liquid chromatography/electrospray ionization with multistage mass spectrometry. Rapid Commun Mass Spectrom. 2006;20(15):2328-42.
Zhang, Y., Shi, Q., Shi, P., Zhang, W., & Cheng, Y. (2006). Characterization of isoquinoline alkaloids, diterpenoids and steroids in the Chinese herb Jin-Guo-Lan (Tinospora sagittata and Tinospora capillipes) by high-performance liquid chromatography/electrospray ionization with multistage mass spectrometry. Rapid Communications in Mass Spectrometry : RCM, 20(15), 2328-42.
Zhang Y, et al. Characterization of Isoquinoline Alkaloids, Diterpenoids and Steroids in the Chinese Herb Jin-Guo-Lan (Tinospora Sagittata and Tinospora Capillipes) By High-performance Liquid Chromatography/electrospray Ionization With Multistage Mass Spectrometry. Rapid Commun Mass Spectrom. 2006;20(15):2328-42. PubMed PMID: 16817243.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Characterization of isoquinoline alkaloids, diterpenoids and steroids in the Chinese herb Jin-Guo-Lan (Tinospora sagittata and Tinospora capillipes) by high-performance liquid chromatography/electrospray ionization with multistage mass spectrometry. AU - Zhang,Yufeng, AU - Shi,Qirong, AU - Shi,Peiying, AU - Zhang,Weidong, AU - Cheng,Yiyu, PY - 2006/7/4/pubmed PY - 2007/8/24/medline PY - 2006/7/4/entrez SP - 2328 EP - 42 JF - Rapid communications in mass spectrometry : RCM JO - Rapid Commun Mass Spectrom VL - 20 IS - 15 N2 - This study sought to determine the primary components (isoquinoline alkaloids, diterpenoids and steroids) in crude extracts of the Chinese herb Jin-Guo-Lan, prepared from the roots of Tinospora sagittata and T. capillipes, by liquid chromatography/electrospray ionization multistage mass spectrometry coupled with diode-array detection (LC-DAD/ESI-MS(n)). After separation on a reversed-phase C(18) column using gradient elution, positive and negative ESI-MS experiments were performed. In positive ion mode, the three types of compounds showed very different characteristic ions: strong [M](+) or [M+H](+) ions were observed for isoquinoline alkaloids; [M+NH(4)](+) and/or [M+H-CO(2)](+) for diterpenoids; [M+H-nH(2)O](+) (n=1-3) for steroids. These adduct ions and/or fragments were used to deduce the mass and categories of known and unknown components in crude extracts, and their structures were further confirmed by ESI-MS(n) in positive ion mode. Moreover, UV absorption peaks obtained from DAD provided useful functional group information to aid the MS(n)-based identification. As a result, 11 compounds were unambiguously identified by comparing with standard compounds and 13 compounds were tentatively identified or deduced according to their MS(n) data. Two of these compounds (13-hydroxycolumbamine and 13-hydroxyjatrorrhizine) were found to be new compounds and another one (13-hydroxypalmatine) was detected for the first time as a natural product. In addition, a [M-*CH(3)-H(2)O](*+) ion in MS(2) of [M](+) after in-source collision-induced dissociation was used to differentiate positional isomers of protoberberine alkaloids, columbamine and jatrorrhizine. Although the roots of T. sagittata and T. capillipes contain almost identical compounds, the content of the compounds in them is dramatically different, suggesting the necessity for further comparison of the bioactivities of the two species. SN - 0951-4198 UR - https://www.unboundmedicine.com/medline/citation/16817243/Characterization_of_isoquinoline_alkaloids_diterpenoids_and_steroids_in_the_Chinese_herb_Jin_Guo_Lan__Tinospora_sagittata_and_Tinospora_capillipes__by_high_performance_liquid_chromatography/electrospray_ionization_with_multistage_mass_spectrometry_ L2 - https://doi.org/10.1002/rcm.2593 DB - PRIME DP - Unbound Medicine ER -