Characterization and online detection of aromatic alkaloids in the ascidian <i>Lissoclinum</i> cf. <i>badium</i> by liquid chromatography/UV detection mass spectrometry

Liu, Hongwei; Gao, Hao; Namikoshi, Michio; Kobayashi, Haruo; Mangindaan, Remy E.P.; Wang, Nai‐Li; Yao, Xin‐Sheng

doi:10.1002/rcm.2833

Cited by 9 publications

(3 citation statements)

References 25 publications

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“…847 Cytotoxic activity of lissoclibadins 1-3 and related polysulfide alkaloids towards human solid tumours in vitro has been reported, 848 while methodology to achieve online detection of these alkaloids using HPLC-UV-ESI-MS has been described. 849 The absolute configurations of barrenazines A 909 and B 910 (unidentified ascidian) 850 were established by stereoselective synthesis. 851,852 Aplidium sp.…”

Section: Molluscsmentioning

confidence: 99%

Marine natural products

et al. 2009

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This review covers the literature published in 2007 for marine natural products, with 948 citations(627 for the period January to December 2007) referring to compounds isolated from marine microorganisms and phytoplankton, green algae, brown algae, red algae, sponges, cnidarians,bryozoans, molluscs, tunicates, echinoderms and true mangrove plants. The emphasis is on new compounds (961 for 2007), together with the relevant biological activities, source organisms and country of origin. Biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.1 Introduction, 2 Reviews, 3 Marine microorganisms and phytoplankton, 4 Green algae, 5 Brown algae, 6 Red algae, 7 Sponges, 8 Cnidarians, 9 Bryozoans, 10 Molluscs, 11 Tunicates (ascidians),12 Echinoderms, 13 Miscellaneous, 14 Conclusion, 15 References.

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Section: Molluscsmentioning

confidence: 99%

Marine natural products

et al. 2009

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“…Currently, high-perfromance liquid chromatography (HPLC) coupled to atmospheric pressure ionization sources, such as electrospray ionization (ESI) and atmospheric pressure chemical ionization (APCI), is routinely used in natural product analysis. [16][17][18][19][20][21][22][23][24] In recent years, tandem mass spectrometry techniques have been applied extensively to the structural analysis of organic compounds. A quadrupole ion-trap mass spectrometer equipped with an atmospheric pressure ionization source (ESI/APCI-ITMS) is an efficient tool for multistage tandem (MS [1][2][3][4][5][6][7][8][9][10] ) mass spectrometry, which provides useful information about the structures of analyte ions.…”

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confidence: 99%

A fragmentation study of podophyllotoxin and its 4′‐demethyl‐4β‐substituted derivatives by electrospray ionization ion‐trap time‐of‐flight tandem mass spectrometry

Yan

2007

Rapid Comm Mass Spectrometry

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High-resolution electrospray ionization multistage tandem mass spectrometry (MS(1-9)) was used to determine the accurate masses and the fragmentation pathways of protonated podophyllotoxin (1) and its corresponding 4'-demethyl-4beta-substituted derivatives (2-4). The protonated molecules, [M + H](+), of all the four compounds were observed in the conventional single-stage mass spectra. Two fragmentation pathways, that appear to be characteristic of the four compounds, are proposed on the basis of their multistage tandem mass spectrometric data. The characteristic elimination, from the precursor protonated ions, of the neutral groups 4-R(1)H, 1-ArH, CO, CH(2)O and C(4)H(4)O(2), in which R is located on C-4, is the common elimination, and the product ions at m/z 267, 239, 229, 181, 173, 153, 143 and 115 are the common diagnostic masses. The elimination of the R(1) group substituent located on the C-4 position of compounds 1-4 has a significant influence on the fragmentation pathway obtained in the conventional single-stage mass spectra. A large R(1) group would be unfavorable for this elimination, unless the collision energy is raised. Apart from the common fragmentations obtained for the protonated molecules 1-4, significant additional product ions were detected in the various multistage tandem mass spectrometric analyses, particularly in the case of the product ions derived initially from the phenolic hydroxyl group of 2-4, which are different from those of 1. Based on these additional formed product ions, several additional fragmentation pathways for 1 or 2-4 are also presented.

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“…Drugs from marine sources are an important part of TCM, and are gaining popularity in the recent years. A number of active components were found in various marine medicinal organisms 2. Nucleosides, nucleobases, and their analogs are known for their pharmacological properties such as anti‐tumor 3, 4 and anti‐viral activities 4–9.…”

Section: Introductionmentioning

confidence: 99%

Simultaneous determination nucleosides in marine organisms using ultrasound‐assisted extraction followed by hydrophilic interaction liquid chromatography–electrospray ionization time‐of‐flight mass spectrometry

Zhao

Chen

Shi

et al. 2011

J of Separation Science

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A new method has been developed based on ultrasound-assisted extraction (UAE) followed by hydrophilic interaction chromatography (HILIC) and electrospray ionization time-of-flight mass spectrometry (ESI-TOF/MS) for the simultaneous determination of 16 nucleosides and nucleobases in medicinal extracts of various marine organisms. The separation was achieved on a Venusil HILIC column (250×4.6 mm id, 5 μm) and gradient elution using a solution of acetonitrile and buffer (0.20% formic acid and 20 mmol/L ammonium acetate) as the mobile phase. Identification of the 16 target nucleosides and nucleobases was based on the retention time, UV spectra, and mass measurements of the protonated molecules ([M+H](+)) and main fragment ions (ESI-TOF/MS). In addition, non-target compounds of 2'-deoxyinosine and four other amino acids were also tentatively identified by ESI-TOF/MS. The 16 target compounds were quantified by HILIC-ESI-TOF/MS under optimized mass conditions. All calibration curves showed good linearity (r(2)>0.9951). The recoveries were 84.72-124.10%, and the limits of detection of the 16 target compounds were 0.6-130.0 ng/mL. The developed method was applied to quantify the target compounds in 15 batches of various marine organisms. The method has potential applicability for the identification and determination of highly polar and low-concentration active compounds in marine organisms.

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Characterization and online detection of aromatic alkaloids in the ascidian Lissoclinum cf. badium by liquid chromatography/UV detection mass spectrometry

Cited by 9 publications

References 25 publications

Marine natural products

Marine natural products

A fragmentation study of podophyllotoxin and its 4′‐demethyl‐4β‐substituted derivatives by electrospray ionization ion‐trap time‐of‐flight tandem mass spectrometry

Simultaneous determination nucleosides in marine organisms using ultrasound‐assisted extraction followed by hydrophilic interaction liquid chromatography–electrospray ionization time‐of‐flight mass spectrometry

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