New anthranilic and methylsulfonylpropenoic acid amides from thai Glycosmis species

Liebigs Annalen
1995.0

Abstract

<jats:title>Abstract</jats:title><jats:p>Five new methylsulfonylpropenamides were isolated from different <jats:italic>Glycosmis</jats:italic> species collected in Thailand. Four of these derivatives contain 4‐geranyloxy‐3‐hydroxy‐substituted phenethylamine moieties, Sakerine (<jats:bold>1</jats:bold>) has a simple geranyloxy side chain; sakerone (<jats:bold>2</jats:bold>), sakerol (<jats:bold>3</jats:bold>), and dihydroisosakerol (<jats:bold>4</jats:bold>) are characterized by different states of oxidation in the geranyloxy residue. Methylgerambullal (<jats:bold>5</jats:bold>) contains a 4‐geranyloxy‐substituted phenethylamine unit with a terminal formyl group. Two additional amides, doisuthine (<jats:bold>6</jats:bold>) and methoxydoisuthine (<jats:bold>7</jats:bold>), exhibit the structures of <jats:italic>N</jats:italic>‐methylanthranilic acid amides with phenethylamine and <jats:italic>p</jats:italic>‐methoxyphenethylamine as amine components. All structures were elucidated by IR, UV, <jats:sup>1</jats:sup>H‐, <jats:sup>13</jats:sup>C‐, 2D‐NMR spectroscopy, mass spectrometry, and CD spectroscopy.

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