New phenylethanoids from Buddleja cordata subsp. cordata.
Bioassay-guided fractionation of a crude extract of the stem bark of Buddleja cordata subsp. cordata with significant antimycobacterial activity led to the isolation of a mixture composed by ten new long-chain esters of 2[4'-hydroxyphenyl]-ethanol (1-10), along with the lichen metabolites methyl beta-orcinolcarboxylate (11) and beta-orcinolcarboxylate (12). Extensive HPLC allowed the separation of the major components of the mixture, which were characterized by spectral means as 2[4'-hydroxyphenyl]-ethyl stearate (3), 2[4'-hydroxyphenyl]-ethyl behenate (6), and 2[4'-hydroxyphenyl]-ethyl lignocerate (8). The minor esters were identified as 2[4'-hydroxyphenyl]-ethyl palmitate (1), 2[4'-hydroxyphenyl]-ethyl heptadecanoate (2), 2[4'-hydroxyphenyl]-ethyl nonadecanoate (4), 2[4'-hydroxyphenyl]-ethyl arachidate (5), 2[4'-hydroxyphenyl]-ethyl tricosanoate (7), 2[4'-hydroxyphenyl]-ethyl pentacosanoate (9), and 2[4'-hydroxyphenyl]-ethyl hexacosanoate (10) by GC-MS analysis of the methyl esters derivatives of the fatty acids obtained by alkaline hydrolysis of the mixture. Compound 8 exhibited moderate antibacterial activity against Mycobacterium tuberculosis (MIC = 64 micrograms/ml).
Acevedo
L
L
Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México, D.F., México.
Martínez
E
E
Castañeda
P
P
Franzblau
S
S
Timmermann
B N
BN
Linares
E
E
Bye
R
R
Mata
R
R
D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D009162:Mycobacterium avium / Q000187:drug effects; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D010936:Plant Extracts / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D013057:Spectrum Analysis
D005960:Glucosides; D010936:Plant Extracts