73010-80-7Relevant academic research and scientific papers
Efficient synthesis of the sponge alkaloids cyclostellettamines A-F
Baldwin, Jack E.,Spring, David R.,Atkinson, Catherine E.,Lee, Victor
, p. 13655 - 13680 (1998)
The total synthesis of cyclostellettamines A-F is reported. The synthetic cyclostellettamines were reduced to the neutral bis- tetrahydropyridine compounds, and exact mass measurements of these reduced products provided unequivocal evidence for the cyclos
(11Z,13E)-hexadecadien-1-yl acetate: Sex pheromone of the grass webworm Herpetogramma licarsisalis - Identification, synthesis, and field bioassays
Gibb, Andrew R.,Suckling, D. Max,El-Sayed, Ashraf M.,Bohman, Bjoern,Unelius, C. Rikard,Dymock, Jennifer J.,Larsen, Michelle L.,Willoughby, Bruce E.
, p. 839 - 847 (2007)
The grass webworm Herpetogramma licarsisalis (Lepidoptera: Crambidae), which has recently established in pasture in Northland, New Zealand, is an important pest of many tropical and subtropical grasses. Two pheromone components, (Z)-11-hexadecen-1-yl acet
Asymmetric synthesis of the marine alkaloid (-)-(S)-nakinadine C
Davies, Stephen G.,Roberts, Paul M.,Shah, Rushabh S.,Thomson, James E.
, p. 6423 - 6426 (2013/11/19)
The first asymmetric synthesis of the marine alkaloid (-)-(S)-nakinadine C is described. This synthesis employs the conjugate addition of lithium dibenzylamide to an N-α-phenylacryloyl SuperQuat derivative followed by diastereoselective protonation of the intermediate enolate using 2-pyridone as the key step to introduce the stereochemistry. (-)-(S)-Nakinadine C was isolated in 13% yield over 9 steps from commercially available atropic acid, 98:2 dr [(Z):(E) ratio] and >99% ee.
The synthesis of (11R,12S)-lactobacillic acid and its enantiomer
Coxon, Geoffrey D.,Al-Dulayymi, Juma R.,Baird, Mark S.,Knobl, Stefan,Roberts, Evan,Minnikin, David E.
, p. 1211 - 1222 (2007/10/03)
(11R,12S)-Lactobacillic acid has been prepared from 2,3-O-isopropylidene-D-glyceraldehyde, in a sequence involving asymmetric cyclopropanation, and from cis-cyclopropane-1,2-dimethanol, using enzymatic desymmetrisation. The key step in the former route wa
Cuticular hydrocarbons and novel alkenediol diacetates from wheat stem sawfly (Cephus cinctus): Natural oxidation to pheromone components
Bartelt, Robert J.,Cosse, Allard A.,Petroski, Richard J.,Weaver, David K.
, p. 385 - 405 (2007/10/03)
The cuticular lipids of the wheat stem sawfly Cephus cinctus (Hymenoptera: Cephidae) were investigated as part of a chemical ecology project with this species. The major cuticular lipids were n-alkenes and n-alkanes. Alkenes were the most abundant and exhibited dramatic sexual dimorphism. (Z)-9-Tricosene accounted for about half of the total hydrocarbon in males but was nearly absent from females. The dominant alkenes in females were (Z)-9-pentacosene and (Z)-9-heptacosene. The alkane profiles were similar in both sexes, with n-tricosane being the most abundant, followed by n-pentacosane and n-heptacosane. In both sexes, there were minor amounts of alkanes and alkenes with other chain lengths and n-alkadienes of 29 and 31 carbons. In males, about one tenth of the surface lipids consisted of (Z)-9-alkene-1, ω-diol diacetates with 22-, 24-, and 26-carbon chains. The same compounds were also detected from females but in much smaller amounts. The structures of these novel diacetates were proven by synthesis. By analogy to methyl oleate, a well-studied food lipid, the alkenes and diacetates were expected to undergo slow oxidation in air to release specific aldehydes and other volatile products, and these were generally detected in volatiles collected from living sawflies. Atmospheric oxidation of the diacetates was also demonstrated in the absence of sawflies. One product from the diacetates, 9-acetyloxynonanal, was shown in other research to be particularly active electrophysiologically and was also attractive in the field. Aldehydes from the alkenes also showed strong electrophysiological activity. The concept of volatile pheromones originating from heavy, unsaturated cuticular lipids is discussed.
Selective antiproliferative activity of caffeic acid phenethyl ester analogues on highly liver-Metastatic murine colon 26-L5 carcinoma cell line
Nagaoka, Takema,Banskota, Arjun H,Tezuka, Yasuhiro,Saiki, Ikuo,Kadota, Shigetoshi
, p. 3351 - 3359 (2007/10/03)
Caffeic acid phenethyl ester (CAPE, 2) and its 20 analogues (1, 3-21) were prepared. These esters were tested by MTT assay on growth of murine colon 26-L5 carcinoma, murine B16-BL6 malonoma, murine Lewis lung carcinoma, human HT-1080 fibrosarcoma, human lung A549 adenocarcinoma, and human cervix HeLa adenocarcinoma cell lines. It was found that CAPE analogues possessed selective antiproliferative activity toward highly liver-metastatic murine colon 26-L5 carcinoma cell line. Among them, 4-phenylbutyl caffeate (4), (Z)-8-phenyl-7-octenyl (10a) and (E)-8-phenyl-7-octenyl (10b) caffeate showed the most potent antiproliferative activity (EC50 value, 0.02μM). In addition, CAPE (2) induced DNA fragmentation at concentrations of 1 to 10μg/mL towards murine colon 26-L5 carcinoma cells. Copyright
Development of Chemical Substances Regulating Biofilm Formation
Yamada, Akihiro,Kitamura, Hitomi,Yamaguchi, Kaori,Fukuzawa, Seketsu,Kamijima, Chiyuki,Yazawa, Kazunaga,Kuramoto, Makoto,Wang, Gui-Yang-Sheng,Fujitani, Yasuyuki,Uemura, Daisuke
, p. 3061 - 3069 (2007/10/03)
The chemical substances which regulate biofilm formation were examined, and a bioassay system which uses marine bacteria with adhering properties was developed. This bioassay system is suitable for screening crude extracts from marine organisms. Using this system, those substances which regulate biofilm formation were isolated from marine organisms. For example, bis(deacetyl)solenolide D was obtained from the marine sponge Psammaplysilla purpurea. Novel nitroalkanes were also isolated from the Okinawan sponge Callyspongia sp. Ethyl N-(2-phenylethyl)carbamate isolated from the marine bacteria SCRC3P79 (Cytophaga sp.) inhibited biofilm formation. Furthermore, the N,N-dichloro, isocyanide, isothiocyanate, and dithiocarbamate derivatives of 2-(4-nitrophenyl)ethylamine, significantly inhibited the growth of marine attaching bacteria. Interestingly, most of the marine sponges examined contained anti-biofilm compounds, such as benzoic acid, aeroplysinin-I, and bromoageliferin.
Three novel anti-microfouling nitroalkyl pyridine alkaloids from the Okinawan marine sponge Callyspongia sp
Wang, Gui-Yang-Sheng,Kuramoto, Makoto,Uemura, Daisuke,Yamada, Akihiro,Yamaguchi, Kaori,Yazawa, Kazunaga
, p. 1813 - 1816 (2007/10/03)
Three novel nitroalkyl pyridine alkaloids, untenines A, B and C, with anti-microfouling activity, were first isolated from the Okinawan marine sponge Callyspongia sp. Their structures were elucidated on the basis of spectroscopic methods. The synthesis of
