Alkaloids from the roots of Stemona aphylla.
Three known compounds, stemofoline (1), (2'S)-hydroxystemofoline (2), and (11Z)-1',2'-didehydrostemofoline (3), along with two new alkaloids, stemaphylline (4) and stemaphylline-N-oxide (5), have been isolated from a root extract of Stemona aphylla. The structures of these alkaloids were determined on the basis of their spectroscopic data. The analysis of the crude dichloromethane extract by GC-MS in the EIMS mode showed the presence of alkaloids 1-4, the alkaloid 11, and stilbostemin R (12). The crude dichloromethane extract and 4 were tested for their comparative biological activities. The results of their acetylcholinesterase (AChE) inhibitory activities showed that the crude extract had higher activity than that of 4. The insecticidal properties of the crude extract and 4, using a topical application, showed that 4 had an activity similar to the positive control, methomyl, whereas the crude extract had much lower activity. Their antimicrobial activity against Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923, Pseudomonas auruginosa ATCC 27853, and Candida albicans ATCC 90028 was weak (MIC 62.5-125 microg/mL, MBC 125-250 microg/mL, MFC 125 microg/mL) but much higher than that of the crude extract.
Department of Chemistry, University of Wollongong, Wollongong, New South Wales 2522, Australia. pitchaya@uow.edu.au
Pitchaya
P
Mungkornasawakul
Sukanda
S
Chaiyong
Thanapat
T
Sastraruji
Araya
A
Jatisatienr
Chaiwat
C
Jatisatienr
Stephen G
SG
Pyne
Alison T
AT
Ung
John
J
Korth
Wilford
W
Lie
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D002176:Candida albicans / Q000187:drug effects; D002800:Cholinesterase Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004926:Escherichia coli / Q000187:drug effects; D008401:Gas Chromatography-Mass Spectrometry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry / Q000302:isolation & purification; D007306:Insecticides / Q000302:isolation & purification / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009036:Moths / Q000187:drug effects; D019906:Nuclear Magnetic Resonance, Biomolecular; D010084:Oxidation-Reduction; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D013211:Staphylococcus aureus / Q000187:drug effects; D041901:Stemonaceae / Q000737:chemistry*; D013237:Stereoisomerism; D013785:Thailand
D000470:Alkaloids; D002800:Cholinesterase Inhibitors; D006576:Heterocyclic Compounds, 4 or More Rings; D007306:Insecticides; C550786:stemaphylline; C550787:stemaphylline-N-oxide; C430220:stemofoline