RESUMEN
Three new bis-formyl phloroglucinol-meroterpenoids (1-3), three new euglobal type formyl phloroglucinol-meroterpenoids (4-6), and one new dimeric formyl phloroglucinol (7) were isolated from the leaves of Eucalyptus camaldulensis. Camaldulensal A (1) is the first bis-isovaleryl-formyl-phloroglucinol-sesquiterpenoid. It features a novel 6/6/10/3/6/6 fused ring system and contains six stereogenic centers. Camaldulensals B (2) and C (3) are the first bis-isovaleryl-formyl-phloroglucinols, each conjugated to a monoterpene. Formyl phloroglucinol compounds (FPCs) containing two spatially separated formyl phloroglucinols conjugated to a terpene core such as 1-3 have not been reported previously. The structures of these compounds were elucidated by spectroscopic methods and computational analysis. Camaldulensals B (2) and C (3) exhibited significant antibacterial activity against methicillin-susceptible and methicillin-resistant Staphylococcus aureus. Structure activity relationships are discussed in relation to previously reported antibacterial activities of other molecules from the FPC structure class.
Asunto(s)
Eucalyptus , Staphylococcus aureus Resistente a Meticilina , Terpenos/química , Eucalyptus/química , Floroglucinol/farmacología , Floroglucinol/química , Hojas de la Planta/química , Estructura MolecularRESUMEN
Three new dihydrobenzophenantridine alkaloids, zanthoisobutylamides A-C (2-4), consisting of a rare 6-alkylamide dihydrochelerythrine moiety, and two new small molecules of the unsaturated alkylamide, zanthoxylumamide J (1) and of phenylpropanoid, methyl 2-hydroxy-3,4-dimethoxycinnamate (5) together with 44 known compounds were isolated from the roots of Zanthoxylum nitidum. The structures of these compounds were established by analysis of spectroscopic data and comparison of their spectroscopic data with those previously published data. Some isolated compounds were evaluated for their cytotoxic activities.
Asunto(s)
Alcaloides , Zanthoxylum , Zanthoxylum/química , Estructura Molecular , Alcaloides/química , Raíces de Plantas/química , AmidasRESUMEN
Two undescribed sesquiterpenoids, namely dysoticans A and B, and three undescribed sesquiterpenoid dimers, namely dysoticans C-E, together with six analogs, were isolated from the stem bark of Dysoxylum parasiticum (Osbeck) Kosterm. (Meliaceae), growing in West Java, Indonesia. Their structures were elucidated based on extensive spectroscopic analysis and theoretical simulations of ECD spectra and 13C NMR shifts. Dysoticans A and B possessed undescribed cadinanes with minor modifications, while C and D featured unprecedented pseudo-sesquiterpenoid dimers through O-ether linkages of cadinanes and guaianes, respectively. Dysotican E was also characterized as the true-sesquiterpenoid dimer featuring eudesmane-germacrene hybrid framework from the Meliaceae family. Furthermore, A-C and E showed moderate activities against the human breast cancer MCF-7 and cervical cancer HeLa cell lines with IC50 values ranging from 22.15 to 45.14 µM. D selectively exhibited significant cytotoxicity against the HeLa cell line with an IC50 value of 13.00 ± 0.13 µM.
Asunto(s)
Células HeLa , Humanos , IndonesiaRESUMEN
A new alkaloid, 2-acetyl-4-methoxyfuro[2,3-b]quinoline (1), and a new benzaldehyde derivative, (2'S)-4-(2'-hydroxy-3'-methyl-3'-butenoxy)benzaldehyde (2), were isolated from the twig of Zanthoxylum rhetsa (Roxb.) DC. along with twenty-six known compounds (3-28). Their structures were determined by spectroscopic analysis (1D and 2D NMR spectroscopy and HRMS analysis) and comparison with data reported in the literature. Thirteen of the known compounds were evaluated for their cytotoxic activities against human cancer cell lines that included MDA-MB-231, SW1353, A549, and HCT116. (±)-8-Acetonyldihydronitidine (15) showed moderate cytotoxicity toward the SW1353 cancer cell line with an IC50 value of 18.90±0.39 µg/mL, and exhibited weak cytotoxic activity against MDA-MB-231, A549 and HCT116 cell lines with IC50 values of 49.86-71.32 µg/mL.
RESUMEN
Acylphloroglucinols are well-known Eucalyptus secondary metabolites which exhibit a variety of structures and bioactivities. The investigation of a crude acetone extract of Eucalyptus camaldulensis leaves led to the isolation of two new acylphloroglucinols, eucalypcamals O and P (1 and 2) together with seven phloroglucinols (3-9), and a benzene derivative (10). Their chemical structures were elucidated by 1D and 2D nuclear magnetic resonance (NMR) spectroscopy and mass spectroscopy. The absolute configurations of compounds 1 and 2 were established by comparison of experimental and calculated electronic circular dichroism (ECD) data. In the putative biosynthetic pathway, eucalypcamals O and P should be derived from hetero-Diels-Alder reaction between grandinol and trans-isoeugenol.
RESUMEN
Fourteen undescribed phloroglucinol-meroterpenoids, namely eucalypcamals A-N, were isolated from a CH2Cl2 extract of the leaves of Eucalyptus camaldulensis Dehnh. In addition, from the same extract, twelve known phloroglucinols, three known flavonoids, and four known phenolic compounds were also isolated. The structures of the undescribed compounds were analyzed by 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, and high resolution electrospray ionization mass spectrometry (HRESIMS). The assignments of the absolute configurations were performed by comparing the experimental electronic circular dichroism (ECD) data with the calculated values. Eucalyprobusal E was found to be cytotoxic against HCT116, Jurkat, and MDA-MB-231 cell lines with IC50 values of 17.6, 9.44, and 17.9 µM, respectively. Eucalrobusone F exhibited antibacterial activity against methicillin-resistant S. aureus (MRSA) and S. aureus with minimum inhibitory concentration/minimum bactericidal concentration (MIC/MBC) values of 4/4 µg/mL while euglobal Ia1 showed antifungal activity with MIC/MFC values of 16/16 µg/mL.
Asunto(s)
Eucalyptus , Staphylococcus aureus Resistente a Meticilina , Antibacterianos/farmacología , Eucalyptus/química , Pruebas de Sensibilidad Microbiana , Floroglucinol/química , Extractos Vegetales/química , Hojas de la Planta/química , Staphylococcus aureusRESUMEN
Five undescribed xanthones, 4-methoxypyranojacareubin, 4-hydroxy-3-prenylpyranoxanthone, 1-hydroxy-5,7-dimethoxyxanthone, 5-hydroxy-1,6,7-trimethoxyxanthone and 2-hydroxy-1,5-dimethoxyxanthone, together with thirty-three known xanthones were isolated from the roots of Mesua ferrea L. The structures of all isolated xanthones were elucidated based on spectroscopic methods. 5-Hydroxy-1,6,7-trimethoxyxanthone and 2-hydroxy-1,5-dimethoxyxanthone were also confirmed by X-ray diffraction data. In addition, the isolated compounds were determined for antibacterial, antioxidant and cytotoxic activities. The known 1,5,6-trihydroxyxanthone showed cytotoxicity against A375, PC-3 and HaCaT cell lines with IC50 values of 5.73⯵g/mL, 5.93⯵g/mL and 8.94⯵g/mL, respectively.
Asunto(s)
Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Magnoliopsida/química , Raíces de Plantas/química , Xantonas/química , Xantonas/farmacología , Línea Celular Tumoral , Humanos , Concentración 50 InhibidoraRESUMEN
A new alkylamide, named (2E,6E,8E)-N-(2-methylpropyl)-10-oxo-2,6,8-decatrienamide (1), together with 22 known compounds (2-23), were isolated from the stems of Zanthoxylum nitidum. Their structures were elucidated by spectroscopic methods, including 1D and 2D NMR spectroscopy. The isolated compounds exhibited slightly antioxidant activities through DPPH and ABTS radical scavenging assays but showed no antibacterial activity against Streptococcus mutans ATCC2517, a dental caries causing bacteria.
Asunto(s)
Antibacterianos/farmacología , Antioxidantes/farmacología , Alcamidas Poliinsaturadas/farmacología , Zanthoxylum/química , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Antioxidantes/química , Caries Dental/microbiología , Evaluación Preclínica de Medicamentos , Depuradores de Radicales Libres/química , Depuradores de Radicales Libres/farmacología , Humanos , Espectroscopía de Resonancia Magnética , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Extractos Vegetales/química , Tallos de la Planta/química , Alcamidas Poliinsaturadas/química , Alcamidas Poliinsaturadas/aislamiento & purificación , Estereoisomerismo , Streptococcus mutans/efectos de los fármacosRESUMEN
Seven new compounds constituted by three secoiridoids (1-3), two isocoumarins (4 and 5), an iridoid (6), and an aromatic derivative (7) in addition to 24 known compounds were isolated from the stem bark of Fagraea fragrans. The structures of the new compounds were determined on the basis of spectroscopic data analysis. The isolated compounds showed no antibacterial activity against Staphylococcus aureus and Escherichia coli. However, 5-formylisochromen-1-one (4), (-)-mellein (8), and swermacrolactone C (9) exhibited potent antimycobacterial activities against Mycobacterium smegmatis when used in combination with the antibiotic drug erythromycin.
Asunto(s)
Antibacterianos/aislamiento & purificación , Antibacterianos/farmacología , Eritromicina/farmacología , Iridoides/aislamiento & purificación , Iridoides/farmacología , Isocumarinas/aislamiento & purificación , Isocumarinas/farmacología , Antibacterianos/química , Iridoides/química , Isocumarinas/química , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Mycobacterium smegmatis/efectos de los fármacos , Resonancia Magnética Nuclear Biomolecular , Corteza de la Planta/química , Staphylococcus aureus/efectos de los fármacos , TailandiaRESUMEN
A carbazole-pyranocoumarin conjugate, carbazomarin B (1), and two carbazole alkaloids, 6-methoxymukonidine (2) and 2-hydroxy-3-methoxycarbazole (3), together with 27 known compounds (4-30), were isolated from the stems of Clausena excavata. Their structures have been elucidated by spectroscopic analyses. Compound 2 showed moderate cytotoxicity to HuCCA-1, MOLT-3 and HepG2 cancer cell lines with IC50 values of 15.09-28.50 µg/mL, but none to A549 cell line. Heptaphylline (6) and nordentatin (23) were found to show moderate cytotoxic activity against HepG2 cell line with IC50 values of 12.33 and 11.33, respectively, while clausine K (27) exhibited strong cytotoxicity with IC50 value of 1.05 µg/mL, better than a standard drug (etoposide, IC50 13.40 µg/mL).
Asunto(s)
Antibacterianos/aislamiento & purificación , Antineoplásicos Fitogénicos/aislamiento & purificación , Carbazoles/aislamiento & purificación , Clausena/química , Piranocumarinas/aislamiento & purificación , Antibacterianos/química , Antibacterianos/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Carbazoles/química , Carbazoles/farmacología , Células Hep G2 , Humanos , Espectroscopía de Resonancia Magnética , Tallos de la Planta/química , Piranocumarinas/química , Piranocumarinas/farmacologíaRESUMEN
Five (1-5) and 15 known compounds were isolated from the acetone extract of the green fruits of Aegle marmelos. The structure of compounds 1-5, marmesiline (1), 6-(4-acetoxy-3-methyl-2-butenyl)-7-hydroxycoumarin (2), 6-(2-hydroxy-3-hydroxymethyl-3-butenyl)-7-hydroxycoumarin (3), marmelonine (4) and 8-hydroxysmyrindiol (5), were determined on the basis of spectroscopic analyses. Antifungal and antibacterial activities of selected compounds were also evaluated.
Asunto(s)
Aegle/química , Alcaloides/farmacología , Antibacterianos/farmacología , Antifúngicos/farmacología , Cumarinas/farmacología , Frutas/química , Alcaloides/química , Alcaloides/aislamiento & purificación , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Antifúngicos/química , Antifúngicos/aislamiento & purificación , Bacterias/efectos de los fármacos , Cumarinas/química , Cumarinas/aislamiento & purificación , Relación Dosis-Respuesta a Droga , Hongos/efectos de los fármacos , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Estereoisomerismo , Relación Estructura-ActividadRESUMEN
A new naphthoquinone, named eleuthinone A ( 8), two new anthraquinones, named eleuthraquinone A and B ( 12, 13), a naphthalene derivative, named eleucanarol ( 14) were isolated from the bulbs of ELEUTHERINE AMERICANA, together with two new natural products previously synthesized, and nine known compounds. Their structures were established based on spectroscopic evidence. Their antibacterial activities against STAPHYLOCOCCUS AUREUS ATCC25923 and ATCC27664, an enterotoxin producing strain were investigated.
Asunto(s)
Antraquinonas/aislamiento & purificación , Antibacterianos/farmacología , Iridaceae/química , Naftoquinonas/aislamiento & purificación , Extractos Vegetales/farmacología , Staphylococcus aureus/efectos de los fármacos , Antraquinonas/química , Antraquinonas/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Naftoquinonas/química , Naftoquinonas/farmacología , Extractos Vegetales/química , Raíces de PlantasRESUMEN
A structurally representative series of 1,2- and 1,3-cyclic sulfamidates react with enolates derived from methyl alpha-phenylthioacetate 9b to give 5- and 6-substituted alpha-phenylthio lactams 20-24. These products provide, via the corresponding sulfoxides, an entry to alpha,beta-unsaturated lactams e.g. 12, 27, 29 and their alpha-phenylthio analogues e.g. 26 and 30. With the enantiomerically pure 1,2-cyclic sulfamidates 10, 15 and 17, these reactions all proceed with no detectable loss of stereochemical integrity.
Asunto(s)
Lactamas/síntesis química , Sulfonas/química , Glicolatos/química , Lactamas/química , Estereoisomerismo , Ácidos Sulfónicos/químicaRESUMEN
[reaction: see text] 1,2-Cyclic sulfamidates undergo regiospecific nucleophilic displacement with either methyl thioglycolate or alpha-amino esters, followed by lactamization (thermal, base-mediated, or cyanide-catalyzed), to give thiomorpholin-3-ones and piperazin-2-ones.