Negative ion electrospray mass spectrometry of neoflavonoids

• Published in: Phytochemistry (Oxford) 2005-12, Vol.66 (23), p.2766-2770
• Main Authors: Hulme, Alison N., McNab, Hamish, Peggie, David A., Quye, Anita
• Format: Article
• Language: English
• Subjects: Benzopyrans - chemistry; Biological and medical sciences; brazilin; Caesalpinia sappan; Chemical constitution; chemical structure; flavonoids; Flavonoids - chemistry; Fundamental and applied biological sciences. Psychology; Haematoxylum; hematoxylin; Hematoxylin - analogs & derivatives; Hematoxylin - chemistry; Indenes - chemistry; ion electrospray mass spectrometry; Mass spectrometry; Molecular Structure; Neoflavonoids; oxidation; Oxidation-Reduction; plant biochemistry; plant extracts; Plant physiology and development; reduction; Senescence and abscission; spectral analysis; Spectrometry, Mass, Electrospray Ionization - methods; Vegetative apparatus, growth and morphogenesis. Senescence
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2005.09.001

Negative ion electrospray ionisation (ESI) mass spectra of the neoflavonoids brazilin and hematoxylin under collision induced decomposition (CID) conditions show fragments characteristic of rings A and C. In their oxidised forms, the fragments are characteristic of rings B and D. The electrospray ionisation mass spectra of the neoflavanoids brazilin and hematoxylin are reported in both their reduced ( 1 and 2, respectively) and their oxidised forms ( 3 and 4, respectively). In the reduced forms, breakdown pathways under collision induced decomposition (CID) conditions produce fragments characteristic of rings A and C; in their oxidised forms, the fragments are characteristic of rings B and D. The structural assignments of the fragments are substantiated by recording the spectra after deuterium exchange at the hydroxyl groups.