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New anthranilic and methylsulfonylpropenoic acid amides from thai Glycosmis species
Author(s) -
Hofer Otmar,
Zechner Gabriela,
Vajrodaya Srunya,
Lutz Gerda,
Greger Harald
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199510250
Subject(s) - phenethylamine , chemistry , anthranilic acid , residue (chemistry) , amine gas treating , stereochemistry , mass spectrometry , organic chemistry , chromatography
Five new methylsulfonylpropenamides were isolated from different Glycosmis species collected in Thailand. Four of these derivatives contain 4‐geranyloxy‐3‐hydroxy‐substituted phenethylamine moieties, Sakerine ( 1 ) has a simple geranyloxy side chain; sakerone ( 2 ), sakerol ( 3 ), and dihydroisosakerol ( 4 ) are characterized by different states of oxidation in the geranyloxy residue. Methylgerambullal ( 5 ) contains a 4‐geranyloxy‐substituted phenethylamine unit with a terminal formyl group. Two additional amides, doisuthine ( 6 ) and methoxydoisuthine ( 7 ), exhibit the structures of N ‐methylanthranilic acid amides with phenethylamine and p ‐methoxyphenethylamine as amine components. All structures were elucidated by IR, UV, 1 H‐, 13 C‐, 2D‐NMR spectroscopy, mass spectrometry, and CD spectroscopy.