New sesquiterpene lactones from Elephantopus mollis and their leishmanicidal activities.
The leishmanicidal compounds isolated from whole plants of Elephantopus mollis H.B.K. were identified as follows. Three new sesquiterpenoid lactones, 2,5-epoxy-2beta-hydroxy-8alpha-(2-methylpropenoyloxy)-4(15),10(14),11(13)-germacratrien-12,6alpha-olide, (4betaH)-8alpha-(2-methylpropenoyloxy)-2-oxo-1(5),10(14), 11(13)-guaiatrien-12,6alpha-olide and (4betaH)-5alpha-hydroxy-8alpha-(2-methylpropenoyloxy)-1(10),11(13)-guaiadiene-12,6alpha-olide, were isolated from Peruvian and Brazilian collections together with four known sesquiterpenoids, molephantin, elephantopin, isoelephantopin and 2-deethoxy-2beta-methoxyphantomolin. They exhibited potent in vitro leishmanicidal activities against Leishmania major. The alpha-methylene-gamma-butyrolactone moiety was found to be essential to the potent leishmanicidal effect observed.
Fuchino
H
H
Division of Pharmacognosy and Phytochemistry, National Institute of Health Sciences, Kamiyoga 1-18-1, Setagaya-ku, Tokyo 158-8501, Japan. fuchino@nihs.go.jp
Koide
T
T
Takahashi
M
M
Sekita
S
S
Satake
M
M
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000494:pharmacology*; D000818:Animals; D000981:Antiprotozoal Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D019659:Asteraceae; D001938:Brazil; D020128:Inhibitory Concentration 50; D018320:Leishmania major / Q000187:drug effects*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010568:Peru; D010936:Plant Extracts / Q000494:pharmacology; D010946:Plants, Medicinal; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification; D045788:Sesquiterpenes, Germacrane; D045789:Sesquiterpenes, Guaiane
C440099:(4H)-5-hydroxy-8-(2-methylpropenoyloxy)-1(10),11(13)-guaiadiene-12,6-olide; C440097:(4H)-8-(2-methylpropenoyloxy)-2-oxo-1(5),10(14), 11(13)-guaiatrien-12,6-olide; C440096:2,5-epoxy-2-hydroxy-8-(2-methylpropenoyloxy)-4(15),10(14),11(13)-germacratrien-12,6-olide; D000981:Antiprotozoal Agents; D010936:Plant Extracts; D012717:Sesquiterpenes; D045788:Sesquiterpenes, Germacrane; D045789:Sesquiterpenes, Guaiane; C014096:alpha-methylene gamma-butyrolactone; D015107:4-Butyrolactone