TY - JOUR
T1 - A new longipinene diester from Stevia monardifolia Kunth
AU - Rojas-Pérez, Rodrigo E.
AU - Cedillo-Portugal, Ernestina
AU - Joseph-Nathan, Pedro
AU - Burgueño-Tapia, Eleuterio
PY - 2009
Y1 - 2009
N2 - Nonpolar and medium polarity fractions from whole plant methanolic extracts of Stevia monardifolia afforded the new 7β-angeloyloxy-8 α-isovaleroyloxylongipin-2-en-1-one 1 along with known 7β,8α-diangeloyloxylongipin-2-en-1-one 2 and 7β,8α- diangeloyloxylongipinan-1-one 3. Alkaline hydrolysis of a mixture of 1 and 2 gave 7β,8α-dihydroxylongipin-2-en-1-one 4 which was subjected to a single crystal X-ray diffraction study. The new compound 1, which is the third 7β,8α-dihydroxylongipin-2-en-1-one diester natural product isolated from a Stevia especies, was fully characterized by oneand two-dimensional NMR spectroscopy and its absolute configuration was confirmed as the 4R,5S,7S,8S,10R,11R enantiomer by vibrational circular dichroism (VCD) measurements in comparison to calculation at the B3LYP/DGDZVP level of theory.
AB - Nonpolar and medium polarity fractions from whole plant methanolic extracts of Stevia monardifolia afforded the new 7β-angeloyloxy-8 α-isovaleroyloxylongipin-2-en-1-one 1 along with known 7β,8α-diangeloyloxylongipin-2-en-1-one 2 and 7β,8α- diangeloyloxylongipinan-1-one 3. Alkaline hydrolysis of a mixture of 1 and 2 gave 7β,8α-dihydroxylongipin-2-en-1-one 4 which was subjected to a single crystal X-ray diffraction study. The new compound 1, which is the third 7β,8α-dihydroxylongipin-2-en-1-one diester natural product isolated from a Stevia especies, was fully characterized by oneand two-dimensional NMR spectroscopy and its absolute configuration was confirmed as the 4R,5S,7S,8S,10R,11R enantiomer by vibrational circular dichroism (VCD) measurements in comparison to calculation at the B3LYP/DGDZVP level of theory.
KW - Absolute configuration
KW - Longipinene
KW - NMR
KW - Stevia monardifolia
KW - Vibrational circular dichroism
UR - http://www.scopus.com/inward/record.url?scp=69849100052&partnerID=8YFLogxK
U2 - 10.1177/1934578x0900400603
DO - 10.1177/1934578x0900400603
M3 - Artículo
SN - 1934-578X
VL - 4
SP - 757
EP - 762
JO - Natural Product Communications
JF - Natural Product Communications
IS - 6
ER -