TY - JOUR
T1 - Structure and absolute configuration of a visamminol derivative using IR and vibrational circular dichroism
AU - Burgueño-Tapia, Eleuterio
AU - Ordaz-Pichardo, Cynthia
AU - Buendía-Trujillo, Abigail I.
AU - Chargoy-Antonio, Francisco J.
AU - Joseph-Nathan, Pedro
N1 - Funding Information:
Partial financial support from Conacyt Mexico (Grants 62213 , 152994 and 168066 ), and SIP-IPN (Grants 20101395 and 20110391 ) is acknowledged. EBT and COP are fellows of COFAA and EDI of IPN. We thank Dr. Edith López Villafranco (Facultad de Estudios Superiores Iztacala-UNAM) for identifying the plant material.
PY - 2012/12
Y1 - 2012/12
N2 - The aerial parts of Arracacia tolucensis (Kunth) Hemsl. (Apiaceae) provided the new visamminol derivative (S)-(+)-4′-O-angeloylvisamminol (1), along with the known angular pyranocoumarin 2. Analysis of HMBC NMR correlations did not allow distinction of the linear dihydrofurochromone 1 from pyranochromone 5. The structure and S absolute configuration of (+)-1 was therefore established by comparison of the IR and vibrational circular dichroism spectra of the natural product with the DFT B3LYP/DGDZVP calculated spectra for (S)-1 and (S)-5. Structural verification followed by single crystal X-ray diffraction of (+)-1 and chemical correlation.
AB - The aerial parts of Arracacia tolucensis (Kunth) Hemsl. (Apiaceae) provided the new visamminol derivative (S)-(+)-4′-O-angeloylvisamminol (1), along with the known angular pyranocoumarin 2. Analysis of HMBC NMR correlations did not allow distinction of the linear dihydrofurochromone 1 from pyranochromone 5. The structure and S absolute configuration of (+)-1 was therefore established by comparison of the IR and vibrational circular dichroism spectra of the natural product with the DFT B3LYP/DGDZVP calculated spectra for (S)-1 and (S)-5. Structural verification followed by single crystal X-ray diffraction of (+)-1 and chemical correlation.
KW - 4′-O-Angeloylvisamminol
KW - Absolute configuration
KW - Arracacia tolucensis
KW - Vibrational circular dichroism
UR - http://www.scopus.com/inward/record.url?scp=84869508243&partnerID=8YFLogxK
U2 - 10.1016/j.phytol.2012.09.006
DO - 10.1016/j.phytol.2012.09.006
M3 - Artículo
SN - 1874-3900
VL - 5
SP - 804
EP - 808
JO - Phytochemistry Letters
JF - Phytochemistry Letters
IS - 4
ER -