RESUMEN
Bioassay-guided fractionation of the active AcOEt-soluble fraction from the roots of Piper taiwanense has led to the isolation of two new phenylpropanoids, taiwanensols A and B (1 and 2, resp.), a new natural product, taiwanensol C (3), and 3-acetoxy-4-hydroxy-1-allylbenzene (4). The compounds were obtained as two isomer mixtures (1/2 and 3/4, resp.). Their structures were elucidated by spectroscopic analyses, including 1D- and 2D-NMR spectroscopy and mass spectrometry, and by the comparison of their NMR data with those of related compounds. Compounds 1-4 were evaluated for their antiplatelet and antitubercular activities. The mixtures 1/2 and 3/4 showed potent inhibitory activities against platelet aggregation induced by collagen, with IC50 values of 35.2 and 8.8 µM, respectively. In addition, 1/2 and 3/4 showed antitubercular activities against Mycobacterium tuberculosis H37Rv, with MIC values of 30.0 and 48.0 µg/ml, respectively.
Asunto(s)
Compuestos Alílicos/química , Antituberculosos/química , Derivados del Benceno/química , Fenilalanina/análogos & derivados , Piper/química , Inhibidores de Agregación Plaquetaria/química , Compuestos Alílicos/aislamiento & purificación , Compuestos Alílicos/farmacología , Antituberculosos/aislamiento & purificación , Antituberculosos/farmacología , Derivados del Benceno/aislamiento & purificación , Derivados del Benceno/farmacología , Humanos , Pruebas de Sensibilidad Microbiana , Mycobacterium tuberculosis/efectos de los fármacos , Fenilalanina/aislamiento & purificación , Fenilalanina/farmacología , Raíces de Plantas/química , Agregación Plaquetaria/efectos de los fármacos , Inhibidores de Agregación Plaquetaria/aislamiento & purificación , Inhibidores de Agregación Plaquetaria/farmacología , Tuberculosis/tratamiento farmacológicoRESUMEN
Bioassay-guided fractionation of roots from Piper taiwanense led to isolation of three neolignans, diallylcatechol (1) and neotaiwanensols A, B (2, 3), two diphenylpropanoid ethers, taiwandimerols A, B (4, 5), with one phenylpropanoid, 2,3-diacetoxy-1-methoxy-5-allylbenzene (6), previously unknown in nature, together with 18 known compounds (7-24). Their structures were elucidated by spectroscopic evidence. Among the isolates, hydroxychavicol acetate (7), and 4-allylcatechol (8) showed potent inhibitory activities against platelet aggregation induced by collagen, with IC50 values of 2.1, and 5.3 µM, respectively. Hydroxychavicol acetate (7), 4-allylcatechol (8), and trans-caffeicaldehyde (9) showed antitubercular activities against Mycobacterium tuberculosis H37Rv, with MIC values of 30.3, 27.6, and 25.5 µg/mL, respectively.
Asunto(s)
Anticoagulantes/farmacología , Antituberculosos/farmacología , Lignanos/farmacología , Mycobacterium tuberculosis/efectos de los fármacos , Fenilpropionatos/farmacología , Piper/química , Anticoagulantes/química , Anticoagulantes/aislamiento & purificación , Antituberculosos/química , Antituberculosos/aislamiento & purificación , Plaquetas/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Humanos , Lignanos/química , Lignanos/aislamiento & purificación , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Fenilpropionatos/química , Fenilpropionatos/aislamiento & purificación , Raíces de Plantas/química , Agregación Plaquetaria/efectos de los fármacos , Relación Estructura-ActividadRESUMEN
Bioassay-guided fractionation of stems of Engelhardia roxburghiana led to isolation of: four diarylheptanoids, engelheptanoxides A-D (1-4); two cyclic diarylheptanoids, engelhardiols A (5) and B (6); one naphthoquinone dimer, engelharquinonol (7); and one 1-tetralone, (4S)-4,6-dihydroxy-1-tetralone (8), along with 24 known compounds (9-32). The structures of 1-8 were by spectroscopic analysis. Compounds 5, 6, 13, 22, and 23 showed antitubercular activity against Mycobacterium tuberculosis H(37)Rv with MIC values of 72.7, 62.1, 9.1, 15.3, and 70.1µM, respectively.
Asunto(s)
Antituberculosos/metabolismo , Antituberculosos/farmacología , Juglandaceae/metabolismo , Extractos Vegetales/metabolismo , Extractos Vegetales/farmacología , Tallos de la Planta/metabolismo , Antituberculosos/química , Juglandaceae/química , Pruebas de Sensibilidad Microbiana , Mycobacterium tuberculosis/efectos de los fármacos , Extractos Vegetales/química , Tallos de la Planta/químicaRESUMEN
Investigation of the leaves extract of Cinnamomum philippinense (Merr.) Chang (Lauraceae) led to the isolation of one novel compound, cinnamophilin D. Its structure was determined through in-depth spectroscopic and mass-spectrometric analyses.
Asunto(s)
Cinnamomum/química , Hojas de la Planta/química , Guayacol/análogos & derivados , Guayacol/química , Lignanos/química , Espectroscopía de Resonancia Magnética , Estructura MolecularRESUMEN
Investigation of leaf extract of Cinnamomum tenuifolium (Lauraceae) led to the isolation of one new nitrobenzoate, ethyl 3,5-dihydroxy-4-nitrobenzoate (1), along with four known compounds. This is the first report of Cinnamomum metabolites with a nitro benzenoid derivative. Their structures were determined through in-depth spectroscopic and mass spectrometric analyses.
Asunto(s)
Cinnamomum/química , Nitrobenzoatos/aislamiento & purificación , Hojas de la Planta/química , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Espectrofotometría UltravioletaRESUMEN
Ficumone, a 2-oxetanone isolated from the fruits of Synsepalum dulcificum, has been characterised as (R*)-4-hydroxy-2-oxetanone by means of spectroscopic methods.
Asunto(s)
Frutas/química , Extractos Vegetales/química , Synsepalum/química , Espectroscopía de Resonancia Magnética , Estructura MolecularRESUMEN
Six new prenylcoumarins, (+)-fatouain A (1), (-)-fatouain B (2), (+)-fatouain C (3), (-)-fatouain D (4), (+)-fatouain E (5), and (-)-fatouain F (6), along with two new bis-prenylcoumarins, (+)-fatouain G (7) and (+)-fatouain H (8), have been isolated from whole plants of Fatoua pilosa. The relative configurations of 1, 3, and 4 were confirmed by their acetonides on the basis of NOEDIF experiments, the results providing additional support for the relative configurations of 2, 5, 6, 7, and 8.
Asunto(s)
Cumarinas/aislamiento & purificación , Moraceae/química , Cumarinas/química , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , EstereoisomerismoRESUMEN
Five novel alkaloids, zanthomuurolanine ( 1), epi-zanthomuurolanine ( 2), zanthocadinanines A ( 3) and B ( 4), and epi-zanthocadinanine B ( 5), composed of dihydrochelerythrine and a cadinane-type sesquiterpene linked by a methylene bridge, have been isolated from stem bark of Zanthoxylum nitidum. These structures were elucidated by spectroscopic techniques (UV, IR, MS, CD, 1H NMR, 13C NMR, DEPT, COSY, NOESY, HSQC, and HMBC analyses). Single-crystal X-ray diffraction studies confirmed the relative configurations of 1 and 4 and provided additional support for the structures of 2, 3, and 5.