title: Macrophyllin-type bicyclo[3.2.1]octanoid neolignans from the leaves of Pleurothyrium cinereum.
abstract: Four new macrophyllin-type bicyclo[3.2.1]octanoid neolignans, (7S,8R,3'S,5'R)-Delta(8')-5,5',3'-trimethoxy-3,4-methylenedioxy-2',3',4',5'-tetrahydro-2',4'-dioxo-7.3',8.5'-neolignan (cinerin A), 1, (7R,8R,3'S,4'R,5'R)-Delta(8')-4'-hydroxy-5,5'-dimethoxy-3,4-methylenedioxy-2',3',4',5'-tetrahydro-2'-oxo-7.3',8.5'-neolignan (cinerin B), 2, (7S,8R,3'R,4'S,5'R)-Delta(8')-4'-hydroxy-5,5',3'-trimethoxy-3,4-methylenedioxy-2',3',4',5'-tetrahydro-2'-oxo-7.3',8.5'-neolignan (cinerin C), 3, and (7S,8R,2'R,3'S,5'R)-Delta(8')-2'-hydroxy-5,5'-dimethoxy-3,4-methylenedioxy-2',3',4',5'-tetrahydro-4'-oxo-7.3',8.5'-neolignan (cinerin D), 4, along with the known diterpene kaurenoic acid 5, were isolated from the leaves of Pleurothyrium cinereum. The structures and configuration of these compounds were determined by extensive spectroscopic analysis. Cinerins A-D (1-4) were tested for their inhibition efficacy of platelet activating factor (PAF)-induced aggregation of rabbit platelets. Compound 3 was the most potent PAF antagonist. Compounds 1-5 were tested against Mycobacterium tuberculosis (H(37)Rv strain) using the MABA method. Compound 5 induced 91.3% growth inhibition at 50 microg mL(-1). Compounds 1-5 showed no significant inhibitory activity against some Gram-positive and Gram-negative bacteria by the agar-well diffusion method.
authors: Departamento de Quimica, Facultad de Ciencias, Universidad Nacional de Colombia, AA 14490, Bogota D.C., Colombia.
authors: Ericsson D
authors: ED
authors: Coy
authors: Luis E
authors: LE
authors: Cuca
authors: Michael
authors: M
authors: Sefkow
mesh_terms: D000818:Animals; D000995:Antitubercular Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D003105:Colombia; D019770:Lauraceae / Q000737:chemistry*; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D010972:Platelet Activating Factor / Q000037:antagonists & inhibitors*; D011817:Rabbits; D013237:Stereoisomerism
chemical_list: D000995:Antitubercular Agents; D019086:Bridged Bicyclo Compounds, Heterocyclic; D017705:Lignans; D010972:Platelet Activating Factor