Absolute configuration of the alpha-methylbutyryl residue in longipinene derivatives from Stevia pilosa.
The absolute configuration of the alpha-methylbutyryl residue in (4R,5S,7S,8S,9S,10R,11R,2''S)-7-angeloyloxy-9-hydroxy-8-(alpha-methylbutyryloxy)-longipin-2-en-L-one and (4R,5S,7S,8R,10R,11R,2''S)-7-angeloyloxy-8-(alpha-methylbutyryloxy)- longipin-2-en-L-one was determined by chemical correlation with (S)-(+)-benzyl alpha-methylbutyrate prepared from authentic (S)-(+)-alpha-methylbutyric acid. Both compounds were isolated from the hexane extracts of roots of Stevia pilosa Lag. together with four other longipinene derivatives. The developed correlation method is useful to ascertain the chirality of natural alpha-methylbutyryl esters found in nature and to reinforce the hypotheses on the biogenetic origin of these residues.
Alvarez-García
Rocío
R
Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Hidalgo, Apartado 1-622, Pachuca, Hidalgo 42001, Mexico.
Torres-Valencia
J Martín
JM
Román
Luisa U
LU
Hernández
Juan D
JD
Cerda-García-Rojas
Carlos M
CM
Joseph-Nathan
Pedro
P
D008968:Molecular Conformation; D015394:Molecular Structure; D018517:Plant Roots / Q000737:chemistry; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification*; D036625:Stevia / Q000737:chemistry*
C501186:(4R,5S,7S,8R,10R,11R,2''S)-7-angeloyloxy-8-(alpha-methylbutyryloxy)- longipin-2-en-L-one; C501185:(4R,5S,7S,8S,9S,10R,11R,2''S)-7-angeloyloxy-9-hydroxy-8-(alpha-methylbutyryloxy)-longipin-2-en-L-one; D012717:Sesquiterpenes; C410907:longipinene