Antispasmodic effects and structure-activity relationships of labdane diterpenoids from Marrubium globosum ssp. libanoticum.
Marrubium globosum ssp. libanoticum is a medicinal plant used in Lebanon to reduce pain and smooth muscle spasms. A chloroform extract obtained from M. globosum aerial parts reduced acetylcholine-induced contractions in the isolated mouse ileum. The purification of this extract identified, among 12 isolated labdane diterpenoids, four new compounds, named 13-epicyllenin A (4), 13,15-diepicyllenin A (5), marrulibacetal (9), and marrulactone (11). Their structures were determined by spectroscopic methods. Compound 9, which exerted antispasmodic activity, is likely the active ingredient of the extract. Preliminary structure-activity relationships for this class of compounds are suggested.
Rigano
Daniela
D
Department of Chemistry of Natural Products, University of Naples Federico II, Via D. Montesano 49, 80131 Naples, Italy.
Aviello
Gabriella
G
Bruno
Maurizio
M
Formisano
Carmen
C
Rosselli
Sergio
S
Capasso
Raffaele
R
Senatore
Felice
F
Izzo
Angelo A
AA
Borrelli
Francesca
F
D000109:Acetylcholine / Q000494:pharmacology; D000818:Animals; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D007082:Ileum / Q000187:drug effects*; D007861:Lebanon; D008297:Male; D027522:Marrubium / Q000737:chemistry*; D051379:Mice; D015394:Molecular Structure; D009130:Muscle, Smooth / Q000187:drug effects*; D010276:Parasympatholytics / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D010946:Plants, Medicinal / Q000737:chemistry*; D013329:Structure-Activity Relationship
D004224:Diterpenes; D010276:Parasympatholytics; D010936:Plant Extracts; D000109:Acetylcholine