Antimycobacterial compounds from Piper sanctum.
Bioassay-guided chromatographic separation of the antimycobacterial extract of the leaves of Piper sanctum afforded 14 new compounds, identified as 2-oxo-12-(3',4'-methylenedioxyphenyl)dodecane (1), 2-oxo-14-(3',4'-methylenedioxyphenyl)tetradecane (2), 2-oxo-16-(3',4'-methylenedioxyphenyl)hexadecane (3), 2-oxo-18-(3',4'-methylenedioxyphenyl)octadecane (4), 2-oxo-14-(3',4'-methylenedioxyphenyl)-trans-13-tetradecene (5), 2-oxo-16-(3',4'-methylenedioxyphenyl)-trans-15-hexadecene (6), 2-oxo-18-(3',4'-methylenedioxyphenyl)-trans-17-octadecene (7), 2-oxo-16-phenyl-trans-3-hexadecene (8), methyl [6-(10-phenyldecanyl)tetrahydropyran-2-yl]acetate (9), methyl 2-(6-tridecyltetrahydro-2H-pyran-2-yl)acetate (10), methyl 2-(5-tetradecyltetrahydro-2-furanyl)acetate (11), 2-oxo-14-(3',4'-methylenedioxyphenyl)-trans-3-tetradecene (12), 2-oxo-16-(3',4'-methylenedioxyphenyl)-trans-3-hexadecene (13), and 2-oxo-16-phenyl-3-hexadecane (14). In addition, p-eugenol (15), methyleugenol (16), Z-piperolide (17), demethoxyyangonin (18), 5,6-dehydro-7,8-dihydromethysticin (19), cepharanone B (20), piperolactam A (21), cepharadione B (22), N-trans-feruloyltyramine (23), and N-trans-(p-coumaroyl)tyramine (24) were obtained from the anti-TBC stem extract of the plant. GC-MS and HPLC analyses of the essential oils of the leaves and stem revealed that safrol (25) was the major component of the oils. Compounds 2, 3, 6, 18-21, and 24 inhibited the growth of Mycobacterium tuberculosis when tested by the MABA assay, with MIC values ranging from 4 to 64 microg/mL.
Mata
Rachel
R
Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México, México City 04510, Mexico. rachel@servidor.unam.mx
Morales
Iliana
I
Pérez
Olga
O
Rivero-Cruz
Isabel
I
Acevedo
Laura
L
Enriquez-Mendoza
Isolda
I
Bye
Robert
R
Franzblau
Scott
S
Timmermann
Barbara
B
D000473:Alkanes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D000995:Antitubercular Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001555:Benzene Derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002522:Chlorocebus aethiops; D018360:Crystallography, X-Ray; D008800:Mexico; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D031701:Piper / Q000737:chemistry*; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism; D014709:Vero Cells
D000473:Alkanes; D000995:Antitubercular Agents; D001555:Benzene Derivatives