Mass Spectra Analyses of Amides and Amide Dimers of Steviol, Isosteviol, and Steviolbioside

Author:

Lee Lin-Wen1,Lee Tzong-Huei2,Lin Ching-Tung3,Chen Tiffany4,Lin Pen-Yuan5

Affiliation:

1. Department of Microbiology and Immunology, College of Medicine, Taipei Medical University, 250 Wu-Hsing Street, Taipei 11031, Taiwan

2. Graduate Institute of Pharmacognosy, College of Pharmacy, Taipei Medical University, 250 Wu-Shing Street, Taipei 11031, Taiwan

3. Department of Chemistry, Tamkang University, 151 Yingzhuan Road, Danshui District, New Taipei City 25137, Taiwan

4. Departments of Biochemistry and Chemistry, University of Washington, 4311 11th Avenue NE, Seattle, WA 98105-4068, USA

5. Department of Medicinal Chemistry, College of Pharmacy, Taipei Medical University, 250 Wu-Shing Street, Taipei 11031, Taiwan

Abstract

The mass spectra of a series of stevioside analogues including the amide and dimer compounds of steviol, isosteviol, and steviolbioside were examined. Positive ion mass spectral fragmentation of new steviol, isosteviol, and steviolbioside amides and the amide dimers are reported and discussed. The techniques included their synthesis procedures, fast-atom bombardment (FAB), and LC/MS/MS mass spectra. Intense [M+H]+ and [M+Na]+ ion peaks were observed on the FAB and ESI spectra. LC/MS/MS also yielded ES+ and ES− ion peaks that fairly agreed with the results of the FAB and ESI studies. Mass spectral analysis of compounds 4p-q, 5a-g, 6, and 7 revealed the different cleavage pathway patterns that can help in identifying the structures of steviolbioside and its amide derivatives.

Publisher

Hindawi Limited

Subject

Rehabilitation,Physical Therapy, Sports Therapy and Rehabilitation,General Medicine

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