Antitubercular natural products: berberine from the roots of commercial Hydrastis canadensis powder. Isolation of inactive 8-oxotetrahydrothalifendine, canadine, beta-hydrastine, and two new quinic acid esters, hycandinic acid esters-1 and -2.
Berberine (4) is responsible for the activity of an extract of a commercial root sample of Hydrastis canadensis against multiply drug resistant Mycobacterium tuberculosis. Two new quinic acid feruloyl esters, compounds 2 and 3, have been isolated from the same source along with canadine (1c), 8-oxotetrahydrothalifendine (1), and beta-hydrastine (5). These were found to be inactive. The structures of the new compounds were elucidated from spectral (1H, 13C, HMQC, HMBC, and H-H COSY) and chemical evidences.
Gentry
E J
EJ
PathoGenesis Corporation, 201 Elliott Avenue West, Suite 150, Seattle, Washington 98119, USA.
Jampani
H B
HB
Keshavarz-Shokri
A
A
Morton
M D
MD
Velde
D V
DV
Telikepalli
H
H
Mitscher
L A
LA
Shawar
R
R
Humble
D
D
Baker
W
W
D000470:Alkaloids / Q000302:isolation & purification; D000995:Antitubercular Agents / Q000737:chemistry / Q000494:pharmacology*; D044182:Benzylisoquinolines; D001599:Berberine / Q000031:analogs & derivatives / Q000302:isolation & purification / Q000494:pharmacology*; D001688:Biological Products / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D011801:Quinic Acid / Q000031:analogs & derivatives / Q000302:isolation & purification
C115552:8-oxotetrahydrothalifendine; D000470:Alkaloids; D000995:Antitubercular Agents; D044182:Benzylisoquinolines; D001688:Biological Products; C115554:hycandinic acid ester-1; C115555:hycandinic acid ester-2; D011801:Quinic Acid; D001599:Berberine; C013024:hydrastine; C004645:canadine