- Prevention of Marine Biofouling Using the Natural Allelopathic Compound Batatasin-III and Synthetic Analogues
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The current study reports the first comprehensive evaluation of a class of allelopathic terrestrial natural products as antifoulants in a marine setting. To investigate the antifouling potential of the natural dihydrostilbene scaffold, a library of 22 syn
- Moodie, Lindon W. K.,Trepos, Rozenn,Cervin, Gunnar,Brathen, Kari Anne,Lindgard, Bente,Reiersen, Rigmor,Cahill, Patrick,Pavia, Henrik,Hellio, Claire,Svenson, Johan
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p. 2001 - 2011
(2017/08/04)
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- MOLECULARLY IMPRINTED POLYMERS
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The present invention provides methods of designing molecularly imprinted polymers (MIPs) which have applications in extracting bioactive compounds from a range of bioprocessing feedstocks and wastes. The present invention is further directed to MIPs designed by the methods of the present invention.
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- Spasmolytic Effects, Mode of Action, and Structure-Activity Relationships of Stilbenoids from Nidema boothii
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A CH2Cl2-MeOH (1:1) extract prepared from the whole plant of Nidema boothii inhibited spontaneous contractions (IC50 = 6.26 ± 2.5 μg/mL) of the guinea-pig ileum. Bioassay-guided fractionation of the active extract led to t
- Hernandez-Romero, Yanet,Rojas, Juana-Isela,Castillo, Rafael,Rojas, Alejandra,Mata, Rachel
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p. 160 - 167
(2007/10/03)
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- Simple synthesis of 5-substituted resorcinols: A revisited family of interesting bioactive molecules
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The reaction of 3,5-dimethoxybenzyl trimethylsilyl ether (3) with different aldehydes (n-PrCHO, n-C11H23CHO, MeCHO, PhCHO) in the presence of lithium powder and a catalytic amount of naphthalene (4 mol %) gave, after hydrolysis, the expected alcohols 4 in moderate yields. The dehydroxylation of these compounds through the corresponding mesylates 5 or directly from benzylic derivatives by catalytic hydrogenation, afforded compounds 6, which are finally demethylated to yield 5-alkyl-3,5-dihydroxyresorcinols, such as olivetol (7a), grevillol (7b), 1,3-dihydroxy-5-propylbenzene (7c), or dihydropinosilvine (7d). Dehydration of alcohol derivatives 4 followed by demethylation led to hydroxylated stilbene-type structures, such as pinosilvine (9d), resveratrol (9e), or piceatannol (9f), which in some cases can be hydrogenated to give saturated molecules such as combretastanin B-4 tetramethyl ether (6f) or chrysotobibenzyl (6g). Finally, when the naphthalene-catalyzed lithiation of compound 3 was performed in the presence of other electrophiles [Me3SiCl, t-BuCHO, CH3(CH2)4CHO, 4-Me3SiOC6H4CHO, (CH2)5CO, PhN = C = O, PhN = CHPh], the expected reaction products 12 were isolated, after hydrolysis.
- Alonso, Emma,Ramon, Diego J.,Yus, Miguel
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p. 417 - 421
(2007/10/03)
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- Synthesis and nematocidal activity of hydroxystilbenes
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Various (E)-hydroxystilbenes were synthesized from (E)/(Z) mixtures of methoxystilbenes through a new (Z)-(E) isomerization method followed by demethylation. The nematocidal activity appears when methoxystilbenes are demethylated to hydroxystilbenes. For this activity, a hydroxy group at the C-2 or C-3 position is necessary. Thus, 2-hydroxy-, 3-hydroxy-, 2,6-dihydroxy-, 3,4-dihydroxy-, 3,5-dihydroxy-, 2,2'-dihydroxy-, 3,3'-dihydroxy-, 3,4'dihydroxy-, 2-hydroxy-4-methoxy-, 5-hydroxy-2-methoxy-, 2-hydroxy-6-methoxy-, 6-allyloxy-2-hydroxy-, 3-hydroxy-5-methoxy-, and 5-allyloxy-3-hydroxystilbenes showed rather potent nematocidal activity. The activity of 5-allyloxy-3-hydroxystilbene was the strongest [minimal lethal concentration (MLC) = 30 μM]. The activities of the (E) and (Z) isomers were comparable. The activities were also retained, though they were weaker, in the dihydro derivatives, hydroxybibenzyls.
- Ali,Kondo,Tsuda
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p. 1130 - 1136
(2007/10/02)
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- PRENYL BIBENZYLS FROM THE LIVERWORT RADULA KOJANA
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Fourteen new bibenzyl derivatives have been isolated from the liverwort Radula kojana together with two previously known bis(bibenzyls) and their structures characterized by spectral and chemical evidence.Seven new bibenzyls, 3,5-dihydroxy-2-(3-methyl-2-b
- Asakawa, Yoshinori,Kondo, Keiko,Tori, Motoo,Hashimoto, Toshihiro,Ogawa, Shunichi
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p. 219 - 234
(2007/10/02)
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- PRENYL BIBENZYLS FROM THE LIVERWORTS RADULA PERROTTETII AND RADULA COMPLANATA
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A new dihydrobenzofuran and a new chromene derivatives have been isolated from the liverwort Radula perrottetii, together with the known 3,5-dihydroxy-2-(3-methyl-2-butenyl)bibenzyl, 2(R)-2-isopropenyl-6,7-dihydroxy-4-(2-phenylethyl)dihydrobenzofuran, 2,2-dimethyl-7-hydroxy-5-(2-phenylethyl)chromene, 3,5-dihydroxy-6-carbomethoxy-2-(3-methyl-2-butenyl)bibenzyl, three bis(bibenzyls) and perrottetins E, F and G.The structures of the new compounds have been characterized as 2(R)-2-isopropenyl-6-hydroxy-4-(2-phenylethyl)dihydrobenzofuran and 2,2-dimethyl-7,8-dihydroxy-5-(2-phenylethyl)chromene by 1H and 13C NMR spectral analysis and synthesis.The structures of the previously reported chalcone and three prenyl bibenzyls, perrottetins A, B and C, and the other two bibenzyls, isolated from R. perrottetii are revised by analysis of their 1H and 13C NMR data, difference NOE experiments and synthesis of their derivatives.Radulanin L, a new bibenzyl with a dihydrooxepin skeleton was isolated from R. complanata together with 2- and 4-(3-methyl-2-butenyl)-3,5-dihydroxybibenzyls and its structure elucidated by comparison of 1H and 13C NMR spectral data with those of radulanins A and H.The structures of the previously reported radulanins A and H isolated from R. complanata are confirmed as correct by difference NOE.Some prenyl-containing bibenzyls showed 5-lipoxygenase and calmodulin inhibitory activity and vasopressin antagonist activity.R. perrottetii is a chemically isolated species in the Radulaceae.
- Asakawa, Yoshinori,Hashimoto, Toshihiro,Takikawa, Keiko,Tori, Motoo,Ogawa, Shunichi
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p. 235 - 251
(2007/10/02)
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- Synthesis of bryophyte components 2. Syntheses of prenylated bibenzyl derivatives
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Efficient and expeditious syntheses of the biologically active prenylated bibenzyl derivatives 1a-d are developed giving rise to their access on a preparative scale.
- Eicher,Tiefensee,Donig,Pick
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- Synthesis of Bibenzyl Cannabinoids, Hybrids of Two Biogenetic Series Found in Cannabis sativa
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Syntheses of a series of compounds which merge a m-dihydroxybibenzyl with a terpenoid structure, giving a series of hybrid cannabinoids in which products of two major biogenetic routes of Cannabis are united, are described.The compounds made are the biben
- Crombie, Leslie W.,Crombie, W. Mary L.,Firth, David F.
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p. 1263 - 1270
(2007/10/02)
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- Amorfrutin A and B, Bibenzyl Antimicrobial Agents From Amorpha Fruticosa
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Bioassay directed fractionation of the waxy fractions derived from the fruit of Amorpha fruticosa resulted in the isolation of amorfrutin A and B, active new antimicrobial agents. Spectroscopic studies, chemical degradation and synthesis showed them to be
- Mitscher, Lester A.,Park, Young Han,Al-Shamma, Ali,Hudson, P. Bryan,Haas, Thomas
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p. 781 - 786
(2007/10/02)
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- 9-Hydroxydibenzo[b,d]pyrans and intermediates
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9-Hydroxydibenzo[b,d]pyrans useful as analgesics, hypotensives, immunosuppressants, tranquilizers; as anti-secretory and anti-anxiety drugs; intermediates therefor and derivatives thereof having the formulae STR1 wherein R is hydrogen or alkanoyl having from one to five carbon atoms; R1 is hydrogen, alkanoyl having from one to five carbon atoms or --CO--(CH2)P --NR2 R3 wherein p is 0 or an integer from 1 to 4; each of R2 and R3 when taken individually is hydrogen or alkyl having from one to four carbon atoms; R2 and R3 when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrrolo, pyrrolidino, morpholino and N-alkylpiperazino having from one to four carbon atoms in the alkyl group; Each of R4 and R5 is hydrogen, methyl or ethyl; R0 is oxo or alkylenedioxy having from two to four carbon atoms; Z is (a) alkylene having from one to nine carbon atoms; (b) --(alk1)m --X--(alk2)n --wherein each of (alk1) and (alk2) has from 1 to 9 carbon atoms, with the proviso that the summation of carbon atoms in (alk1) plus (alk2) is not greater than 9; Each of m and n is 0 or 1; X is O, S, SO or SO2 ; and W is methyl, phenyl, p-chlorophenyl, p-fluorophenyl, pyridyl, piperidyl, cycloalkyl having from 3 to 7 carbon atoms, or monosubstituted cycloalkyl wherein the substituent is phenyl, p-chlorophenyl or p-fluorophenyl; With the proviso that when W is methyl, Z is --(alk1)m --X---(alk2)n --.
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