TY - JOUR A1 - Coy-Barrera, Ericsson David A1 - Cuca-Sußrez, Luis Enrique A1 - Sefkow, Michael T1 - PAF-antagonistic bicyclo[3.2.1]octanoid neolignans from leaves of Ocotea macrophylla Kunth (Lauraceae) N2 - Di-nor-benzofuran neolignan aldehydes, Delta(7)-3,4-methylenedioxy-3'-methoxy-8',9'-dinor- 4',7-epoxy-8,3'-neolignan-7'-aldehyde (ocophyllal A) 1, Delta(7)-3,4,5,3'-tetramethoxy- 8',9'-dinor-4',7-epoxy-8,3'-neolignan-7'-aldehyde (ocophyllal B) 2, and macrophyllin-type bicyclo[3.2.1]octanoid neolignans (7R, 8R, 3'S, 4'S, 5'R)-Delta(8)'-4'-hydroxy-5'- methoxy-3,4-methylenedioxy-2',3'.4',5'-tetrahydro-2'-oxo-7.3',8.5'-neolignan (ocophyllol A) 3, (7R, 8R, 3'S, 4'S, 5'R)-Delta 8'-4'-hydroxy-3,4,5'-trimethoxy- 2',3',4',5'-tetrahydro-2'-oxo-7.3',8.5'-neolignan (ocophyllol B) 4, (7R, 8R, 3'S, 4'S, 5'R)-Delta(8)'-4'-hydroxy-3,4,5,5'-tetramethoxy- 2',3',4',5'-tetrahydro-2'-oxo-7.3',8.5'-neolignan (ocophyllol C) 5, as well as 2'-epi-guianin 6 and (+)-licarin B 7, were isolated and characterized from leaves of Ocotea macrophylla (Lauraceae). The structures and configuration of these compounds were determined by extensive spectroscopic analyses. Inhibition of platelet activating factor (PAF)-induced aggregation of rabbit platelets were tested with neolignans 1-7. Although compound 6 was the most potent PAF-antagonist, compounds 3-5 showed some activity. Y1 - 2009 UR - http://www.sciencedirect.com/science/journal/00319422 U6 - https://doi.org/10.1016/j.phytochem.2009.07.010 SN - 0031-9422 ER - TY - JOUR A1 - Coy-Barrera, Ericsson David A1 - Cuca-Sußrez, Luis Enrique A1 - Sefkow, Michael T1 - COX, LOX and platelet aggregation inhibitory properties of Lauraceae neolignans N2 - The anti-inflammatory potential of 26 neolignans (14 of the bicyclooctane-type and 12 of the benzofuran-type), isolated from three Lauraceae species (Pleurothyrium cinereum, Ocotea macrophylla and Nectandra amazonum), was evaluated in vitro through inhibition of COX-1, COX-2, 5-LOX and agonist-induced aggregation of rabbit platelets. Benzofuran neolignans were found to be selective COX-2 inhibitors, whereas bicyclooctane neolignans inhibit selectively the PAF- action as well as COX-1 and 5-LOX. The neolignan 9-nor-7,8-dehydro-isolicarin B 15 and cinerin C 7 were found to be the most potent COX-2 inhibitor and PAF-antagonist, respectively. Nectamazin C 10 exhibited dual 5-LOX/COX-2 inhibition. Y1 - 2009 UR - http://www.sciencedirect.com/science/journal/0960894X U6 - https://doi.org/10.1016/j.bmcl.2009.10.069 SN - 0960-894X ER - TY - JOUR A1 - Coy-Barrera, Ericsson David A1 - Cuca-Sußrez, Luis Enrique A1 - Sefkow, Michael T1 - Macrophyllin-type bicyclo[3.2.1]octanoid neolignans from the leaves of Pleurothyrium cinereum N2 - 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'RYS,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 cinercum. 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 mu g mL(-1). Compounds 1-5 showed no significant inhibitory activity against some Gram-positive and Gram-negative bacteria by the agar-well diffusion method. Y1 - 2009 UR - http://pubs.acs.org/journal/jnprdf U6 - https://doi.org/10.1021/Np9000569 SN - 0163-3864 ER - TY - JOUR A1 - Coy-Barrera, Ericsson David A1 - Cuca-Sußrez, Luis Enrique A1 - Sefkow, Michael T1 - PAF-antagonist 7.3 '.8.5 '-connected bicyclo[3.2.1]octane neolignans obtained from three colombian Lauraceae species and their synthesis Y1 - 2009 SN - 0032-0943 ER - TY - JOUR A1 - David Coy, Ericsson A1 - Enrique Cuca, Luis A1 - Sefkow, Michael T1 - Pd-NHC catalyzed biaryl coupling by direct C-H Activation-A Novel strategy for the synthesis of dibenzocyclooctane lignans JF - Synthetic communications : an international journal for rapid communication of synthetic organic chemistry N2 - Cross-coupling reactions, such as Buchwald-Hartwig arylamination and direct intramolecular biaryl coupling by C-H activation, were carried out using various Palladium-N-heterocyclic carbenes (Pd-NHC) as catalysts. The yields were good to excellent. The latter strategy was adopted to transform two dibenzylbutane lignans, isolated from the leaves of Ocotea macrophylla (Lauraceae), into the corresponding dibenzocyclooctane lignans in good overall yields. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file. KW - Cross-coupling reactions KW - dibenzylbutane KW - dibenzocyclooctane KW - lignans KW - N-heterocyclic carbenes (NHC) Y1 - 2011 U6 - https://doi.org/10.1080/00397910903531755 SN - 0039-7911 VL - 41 IS - 1 SP - 41 EP - 51 PB - Taylor & Francis Group CY - Philadelphia ER -