TY - JOUR
T1 - Characterization of a bioactive derivative of calophyllolide by 2D NMR and LC-MS/MS
AU - Kalyanaraman, L.
AU - Sree Ganesh, K. K.
AU - Kumar, R. Mohan
AU - Pichai, R.
AU - Vyas, K.
PY - 2014/5/9
Y1 - 2014/5/9
N2 - This study details the characterization of a novel and an unexpected cyclization reduction product of Calophyllolide (I), by using sodium borohydride. The structure of the derivative (II) was established as 6,10,11-tetramethyl-4-phenyl-6, 10-dihydro-2H-dipyrano [2, 3-f: 2′, 3′-h] chromen-2-one by 2D NMR experiments such as 1H-1H gCOSY, gHSQC, gHMBC, and LC-MS/MS along with 1H and 13C NMR spectra. A reversed-phase HPLC method and a chiral HPLC method were developed to evaluate the purity and chirality. A reaction mechanism for II was proposed. The synthesized compound was showing significant antimicrobial activity than the parent compound (I) when tested against various pathogenic bacteria and fungus.
AB - This study details the characterization of a novel and an unexpected cyclization reduction product of Calophyllolide (I), by using sodium borohydride. The structure of the derivative (II) was established as 6,10,11-tetramethyl-4-phenyl-6, 10-dihydro-2H-dipyrano [2, 3-f: 2′, 3′-h] chromen-2-one by 2D NMR experiments such as 1H-1H gCOSY, gHSQC, gHMBC, and LC-MS/MS along with 1H and 13C NMR spectra. A reversed-phase HPLC method and a chiral HPLC method were developed to evaluate the purity and chirality. A reaction mechanism for II was proposed. The synthesized compound was showing significant antimicrobial activity than the parent compound (I) when tested against various pathogenic bacteria and fungus.
KW - LC-MS/MS
KW - bioactive derivative
KW - calophyllolide
KW - chiral HPLC
KW - cyclization mechanism
KW - two-dimensional NMR characterization
UR - http://www.scopus.com/inward/record.url?scp=84894188076&partnerID=8YFLogxK
U2 - 10.1080/10826076.2013.765463
DO - 10.1080/10826076.2013.765463
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AN - SCOPUS:84894188076
SN - 1082-6076
VL - 37
SP - 1087
EP - 1093
JO - Journal of Liquid Chromatography and Related Technologies
JF - Journal of Liquid Chromatography and Related Technologies
IS - 8
ER -