Analysis of MS/MS Fragmentation of Taxoids

The fragmentation pathways of seven types of taxoids were investigated by using a LC-MS/MS method, namely: (1) neutral taxoids with a C-4(20) double bond; (2) taxoids with a C-4(20) double bond and oxygenation at C-14; (3) 5-cinnamoyl taxoids with a C-4(20) double bond; (4) a basic taxoid with a C-4...

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Bibliographic Details
Published in:Natural product communications 2010-10, Vol.5 (10), p.1551-1556
Main Authors: Morikawa, Kouhei, Tanaka, Ken, Li, Feng, Awale, Suresh, Tezuka, Yasuhiro, Nobukawa, Takahiro, Kadota, Shigetoshi
Format: Article
Language:English
Subjects:
Chromatography, Liquid
Spectrometry, Mass, Electrospray Ionization
Tandem Mass Spectrometry
Taxoids - chemistry
Taxoids - isolation & purification
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Summary:The fragmentation pathways of seven types of taxoids were investigated by using a LC-MS/MS method, namely: (1) neutral taxoids with a C-4(20) double bond; (2) taxoids with a C-4(20) double bond and oxygenation at C-14; (3) 5-cinnamoyl taxoids with a C-4(20) double bond; (4) a basic taxoid with a C-4(20) double bond; (5) a taxoid with a C-4(20) epoxide; (6) taxoids with an oxetane ring; and (7) taxoids with an oxetane ring and a phenylisoserine C-13 side chain. Depending on the class of core structure and the substitution pattern, each taxoid gave either the molecular adduct ion [M+NH4]+ or [M+H]+. In the MS/MS, the molecular adduct ion gave characteristic product ions corresponding to the loss of water, acetic acid, benzoic acid, and cinnamic acid or the phenylisoserine group. These could reflect the difference of the substitutions and structural modifications and should be utilized for the structure elucidation of taxoids by LC-MS.
ISSN:1934-578X
1555-9475
DOI:10.1177/1934578X1000501007