New sesquiterpene derivatives from the red alga Laurencia scoparia. Isolation, structure determination, and anthelmintic activity.
Eleven sesquiterpenes (1-11) and one long chain aldehyde (12) have been isolated from the dichloromethane extract of the red alga Laurencia scoparia. Four of them are new natural products. Scopariol (1) is a new natural product with an unusual rearranged chamigrane-type structure. The other three are beta-chamigrenes: isorigidol (2), (+)-3-(Z)-bromomethylidene-10 beta-bromo-beta-chamigrene (3), and (-)-3-(E)-bromomethylidene-10 beta-bromo-beta-chamigrene (4). The in vitro activity of compounds 1-12 against the parasitant stage of Nippostrongylus brasiliensis (L4) has been studied.
Davyt
D
D
Cátedra de Química Farmacéutica, Facultad de Química, Universidad de la República, Avenida Gral. Flores 2124, Montevideo, Uruguay.
Fernandez
R
R
Suescun
L
L
Mombrú
A W
AW
Saldaña
J
J
Domínguez
L
L
Coll
J
J
Fujii
M T
MT
Manta
E
E
D000818:Animals; D000871:Anthelmintics / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001938:Brazil; D002855:Chromatography, Thin Layer; D066298:In Vitro Techniques; D008968:Molecular Conformation; D015394:Molecular Structure; D009559:Nippostrongylus / Q000187:drug effects*; D019906:Nuclear Magnetic Resonance, Biomolecular; D000461:Rhodophyta / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D017550:Spectroscopy, Fourier Transform Infrared; D013141:Spiro Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C446684:3-bromomethylidene-10-bromochamigren; C428926:8-bromo-3,7,7-trimethyl-11-methylenespiro(5.5)-undec-1-ene-3,9-diol; D000871:Anthelmintics; D012717:Sesquiterpenes; D013141:Spiro Compounds; C446683:scopariol