Expedient preparative isolation and tandem mass spectrometric characterization of C-seco triterpenoids from neem oil

TitleExpedient preparative isolation and tandem mass spectrometric characterization of C-seco triterpenoids from neem oil
Publication TypeJournal Article
Year of Publication2014
AuthorsHaldar, S, Mulani, FA, Aarthy, T, Dandekar, DS, Thulasiram, HV
JournalJournal of Chromatography A
Volume1366
Pagination1-14
Date PublishedOCT
ISSN0021-9673
KeywordsESI(+)-quadrupole/orbitrap-MS/MS, MPLC, Neem oil, Preparative isolation, Salannin, Triterpenoids
Abstract

C-seco triterpenoids are widely bioactive class of natural products with high structural complexity and diversity. The preparative isolation of these molecules with high purity is greatly desirable, although restricted due to the complexity of natural extracts. In this article we have demonstrated a Medium Pressure Liquid Chromatography (MPLC) based protocol for the isolation of eight major C-seco triterpenoids of salannin skeleton from Neem (Azadirachta indica) oil. Successive application of normal phase pre-packed silica-gel columns for the fractionation followed by reverse phase in automated MPLC system expedited the process and furnished highly pure metabolites. Furthermore, eight isolated triterpenoids along with five semi-synthesized derivatives were characterized using ultra performance liquid chromatography-electrospray ionization-quadrupole/orbitrap-MS/MS spectrometry as a rapid and sensitive identification technique. The structure-fragment relationships were established on the basis of plausible mechanistic pathway for the generation of daughter ions. The MS/MS spectral information of the triterpenoids was further utilized for the identification of studied molecules in the complex extract of stem and bark tissues from Neem. (C) 2014 Elsevier B.V. All rights reserved.

DOI10.1016/j.chroma.2014.09.006
Type of Journal (Indian or Foreign)

Foreign 

Impact Factor (IF)

2.86 

Divison category: 
Organic Chemistry