Quaternary isoquinoline alkaloids from Xylopia parviflora

Nishiyama, Yumi; Moriyasu, Masataka; Ichimaru, Momoyo; Iwasa, Kinuko; Kato, Atsushi; Mathenge, Simon G.; Mutiso, Patrick B. Chalo; Juma, Francis D.

doi:10.1016/j.phytochem.2003.12.010

Cited by 57 publications

(34 citation statements)

References 21 publications

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“…Due to lack of standards and no literature data about the ESI-MS of these compounds, their identification was not obtained. These compounds were also discovered from Xylopia parviflora (Annonaceae), 27 with which dominant protoberberine and aporphine alkaloids coexisted.…”

Section: Simple Isoquinoline Alkaloidsmentioning

confidence: 99%

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

Zhang

Shi

et al. 2006

Rapid Comm Mass Spectrometry

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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.

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Section: Simple Isoquinoline Alkaloidsmentioning

confidence: 99%

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

Zhang

Shi

et al. 2006

Rapid Comm Mass Spectrometry

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“…Based on the direct comparison of the HPLC retention time, MS n values and UV spectra with those of the reference standards, 11 compounds were unambiguously identifi ed as neo-chlorogenic acid, 3-O-feruloylquinic acid, 5-O-feruloylquinic acid, methyl-3-Oferuloyl quinate, magnofl orine, phellodendrine, menisperine, tetrahydropalmatine, jatrorrhizine, palmatine and berberine, respectively. Other constituents were only tentatively character- ized by comparing their MS n fragmentation behaviors and UV spectra with the literatures (Table 1) (Yoshida et al, 2005;Yoshiteru et al, 1994;Nishiyama et al, 2004;Ye et al, 2005;Han et al, 2008;Jacquemond-Collet et al, 2000). It could be seen that although most of the alkaloids could be detected in both of the CP species, only nine phenols were detected in the tested PCS sample.…”

Section: Identifi Cation Of the Major Chemical Constituents In Cp Sammentioning

confidence: 99%

Quality assessment of Cortex Phellodendri by high‐performance liquid chromatography coupled with electrospray ionization mass spectrometry

Sze

et al. 2009

Biomedical Chromatography

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A simple method based on liquid chromatography coupled with diode array detection and electrospray ionization mass spectrometry (LC-DAD-ESI-MS) was developed for the quality assessment of Cortex Phellodendri (CP), which was mainly derived from two species of Phellodendron chinense Schneid and Phellodendron amurense Rupr. Total 41 compounds, including 14 phenols, 24 alkaloids and three liminoidal triterpenes were identified or tentatively characterized from the 75% methanol extract of CP samples by online ESI-MS(n) fragmentation and UV spectra analysis. Among them, two phenols and six alkaloids were simultaneously quantified using HPLC-DAD method. The validated HPLC-DAD method showed a good linearity, precision, repeatability and accuracy for the quantification of eight marker compounds. Furthermore, the plausible fragmentation pathway of the representative compounds were proposed in the present study. The differences of the chemical constituents content and the comprehensive HPLC profiles between the two CP species using LC-DAD-ESI-MS method are reported for the first time, indicating that the CP drugs from different resources should be used separately in the clinic.

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“…1). It was already isolated in Xylopia parviflora (Nishiyama et al, 2004), Nandina domestica (Iwasa et al, 2008) and Anamirta cocculus (Satya et al, 2012).…”

Section: Resultsmentioning

confidence: 99%

A new natural indole and three aporphine alkaloids from Monodora bevipes Benth. (Annonaceae)

et al. 2017

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Four compounds were isolated from the leaves of Monodora brevipes Benth. (Annonaceae). Among them, one new natural indole named 5-formylindole (1) and three known aporphine alkaloids: (+)-roemeroline (2); (+)-corydine (3) and (+)-menispermine (4). They were isolated for the first time from this species. The structures of these compounds were established according to their spectral data (NMR, SM, IR and UV).Eric et al., International Current Pharmaceutical Journal, June 2017, 6(7): 40-43http://www.icpjonline.com/documents/Vol6Issue7/01.pdf

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Quaternary isoquinoline alkaloids from Xylopia parviflora

Cited by 57 publications

References 21 publications

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

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

Quality assessment of Cortex Phellodendri by high‐performance liquid chromatography coupled with electrospray ionization mass spectrometry

A new natural indole and three aporphine alkaloids from Monodora bevipes Benth. (Annonaceae)

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