Sesquiterpenoids from Teucrium ramosissimum.
An antiplasmodial bioguided investigation of the EtOAc extract of the aerial parts of Teucrium ramosissimum led to isolation and identification of three sesquiterpenoids, teucmosin, 4alpha-hydroxy-homalomenol C, 1beta,4beta,7alpha-trihydroxy-8,9-eudesmene and two trinorsesquiterpenoids, 4beta-hydroxy-11,12,13-trinor-5-eudesmen-1,7-dione and 1beta,4beta-dihydroxy-11,12,13-trinor-8,9-eudesmen-7-one together with five known sesquiterpenoids, oplopanone, homalomenol C, oxo-T-cadinol, 1beta,4beta,6beta-trihydroxyeudesmane, 1beta,4beta,7alpha-trihydroxyeudesmane and four flavonoids, 5-hydroxy-7,4'-dimethoxyflavone, salvigenin, genkwanin and cirsimaritin. The structures and the relative stereochemistry were elucidated by extensive spectroscopic studies including 1D and 2D NMR and mass spectrometry (MS). Homalomenol C, 4beta-hydroxy-11,12,13-trinor-5-eudesmen-1,7-dione, oxo-T-cadinol and 1beta,4beta,6beta-trihydroxyeudesmane displayed a significant in vitro antiplasmodial activity against Plasmodium falciparum with IC(50) values ranging from 1.2 to 5.0 microg/ml. Furthermore, no cytotoxicity was observed upon the human diploid lung cell line MRC-5 for these compounds.
Henchiri
Hichem
H
FRE 3206 CNRS Molécules de Communication et Adaptation des Micro-organismes, Muséum National d'Histoire Naturelle, 61-63 rue Buffon, 75005 Paris, France.
Bodo
Bernard
B
Deville
Alexandre
A
Dubost
Lionel
L
Zourgui
Lazhar
L
Raies
Aly
A
Grellier
Philippe
P
Mambu
Lengo
L
D000818:Animals; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002460:Cell Line; D006801:Humans; D008168:Lung / Q000166:cytology / Q000187:drug effects; D015394:Molecular Structure; D035261:Plant Components, Aerial; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D010963:Plasmodium falciparum / Q000187:drug effects*; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D031367:Teucrium / Q000737:chemistry*
C545972:1beta,4beta,7alpha-trihydroxy-8,9-eudesmene; C545971:4alpha-hydroxy-homalomenol C; D000962:Antimalarials; D010936:Plant Extracts; D012717:Sesquiterpenes; C545970:teucmosin