RESUMEN
Bioassay-guided isolation of the stems of Garcinia paucinervis led to one new adamantane-type polycyclic polyprenylated acylphloroglucinols (PPAPs), (-)-garpauvinin A (1), and four known analogues (2-5). The structure and absolute configuration of 1 was established via spectroscopic techniques and ECD method. All the isolates displayed moderate antiproliferative activity against HL-60, PC-3 and Caco-2 human cancer cell lines with IC50 values ranging from 0.81 to 19.92 µM, and exhibited low toxicity on WPMY-1 normal human cells, showing selectivity between normal and malignant prostate cells. The biosynthetic pathways of the isolated PPAPs were proposed.
Asunto(s)
Garcinia , Hypericum , Humanos , Estructura Molecular , Células CACO-2 , Garcinia/química , Células HL-60 , Floroglucinol , Hypericum/químicaRESUMEN
Stilbenes (based on the 1,2-diphenylethylene skeleton) are a class of plant polyphenols with rich structural and bioactive diversity. Twenty-six stilbenes, including five undescribed compounds (7,8-dioxy-4,3',5'-trihydroxystilbene, trans-13'-methoxygnetin H, suffruticosol E, paestibenetrimerols A and B), were isolated from the seedcases of Paeonia suffruticosa Andrews. Their structures were elucidated by spectroscopic analyses and comparison with previously reported data. The absolute configurations of trans-13'-methoxygnetin H, suffruticosol E, paestibenetrimerols A and B were assigned from their respective electronic circular dichroism (ECD) spectra. Additionally, the structures of known compounds suffruticosols A, B and rockiol B were revised and the absolute configurations of them, and along with (+)-davidiol A, were also further determined by ECD. The isolated compounds, trans-gnetin H, cis-gnetin H and suffruticosol E, were found to have potent cytotoxicity against the DU-145 and MDA-MB-231 cell lines with IC50 values of 4.89-8.61 µM. The preliminary antitumor structure-activity relationship of these stilbenes is discussed as well.
Asunto(s)
PaeoniaRESUMEN
Two new dimers of ambuic acid, pestaloversicoloric acids A (1) and B (2), and a known derivative, 13(S)-hydroxyambuic acid (3), were isolated from the static fermentation product of Pestalotiopsis versicolor. The structural identification was accomplished via analyses on the data of HR-MS, 1 D and 2 D NMR, and ECD. Different from the well-known exo-type dimer, torreyanic acid, compounds 1 and 2 represent the first example of endo-type product derived from the intermolecular Diels-Alder reaction of two molecules of ambuic acid derivative with the identical absolute stereochemistry.
Asunto(s)
Ciclohexanonas , Estructura Molecular , Reacción de Cicloadición , Ciclohexanonas/químicaRESUMEN
The chemical constituents from the roots of Thalictrum cultratum and T. baicalense were investigated. By various isolation methods, such as silica gel, aluminium oxide, ODS, and Sephadex LH-20 column chromatographies, and semi-preparative HPLC, 11 simple isoquinoline alkaloids were isolated from the ethanol extract of the roots of these two plants, including a new compound, named dehydrothalflavine(1), and ten known ones(2-11): N-methylcorydaline(2), N-methylthalidaldine(3), thaliflavine(4), oxyhydrastinine(5), noroxyhydrastinine(6), dimethoxyisoquinolone(7), thalactamine(8), dehydronoroxyhydrastinine(9), 6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline(10), and isopicnarrhine(11). Their structures were elucidated on the basis of HR-ESI-MS and 1 D and 2 D NMR techniques. Compound 1 was a new isoquinoline alkaloid. Compound 11 was obtained from Tha-lictrum plant for the first time. All compounds did not show cytotoxic activities against HL-60, U937, HCT116, Caco-2, and HepG2 cancer cell lines.
Asunto(s)
Alcaloides , Thalictrum , Alcaloides/análisis , Células CACO-2 , Humanos , Isoquinolinas/farmacología , Raíces de Plantas/química , Thalictrum/químicaRESUMEN
Six alkaloids peharmalines F-K, along with 14 known ones, were isolated from the aerial part of Peganum harmala L.. The structures of the isolated compounds were determined based on their HR-ESI-MS data, extensive NMR spectroscopic analyses, and ECD calculations. 3-(4-Hydroxyphenyl)quinoline exhibited potent antiproliferative activity against the HepG-2 cell lines with an IC50 value of 3.05 µM. Norharmane displayed a moderate inhibition against A549 and HepG-2 cells with IC50 values of 16.45 µM and 17.27 µM, respectively.
Asunto(s)
Alcaloides , Antineoplásicos Fitogénicos , Peganum , Células A549 , Alcaloides/química , Antineoplásicos Fitogénicos/química , Células Hep G2 , Humanos , Peganum/química , Extractos Vegetales/químicaRESUMEN
Six new tirucallane-type triterpenoids (1-6), along with ten known triterpenoids, were isolated from methylene chloride extract of the resin of Boswellia carterii Birdw. By the application of the comprehensive spectroscopic data, the structures of the compounds were clarified. The experimental electronic circular dichroism spectra were compared with those calculated, which allowed to assign the absolute configurations. Compounds 5 and 6 possesed a 2, 3-seco tirucallane-type triterpenoid skeleton, which were first reported. Their inhibitory activity against NO formation in LPS-activated BV-2 cells were evaluated. Compound 9 showed appreciable inhibitory effect, with an IC50 value of 7.58 ± 0.87 µmol·L-1.
Asunto(s)
Boswellia , Triterpenos , Estructura Molecular , Resinas de Plantas , Triterpenos/farmacologíaRESUMEN
Baicalensines A (1) and B (2) were isolated from the roots of Thalictrum baicalense and structurally characterized using spectroscopic data, 13C NMR calculations, and the CASE algorithm. Compound 1, representing a new class of alkaloid dimers, contains berberine conjugated to a ring-opened isoquinoline. Compound 2 is the first reported natural benzylisoquinoline bearing a formyl group at C-3. Plausible biosynthetic pathways are proposed. Compound 1 exerted moderate cytotoxicity against the Caco-2 and HL-60 cell lines.
Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Berberina/farmacología , Thalictrum/química , Alcaloides/química , Alcaloides/aislamiento & purificación , Alcaloides/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Berberina/química , Berberina/aislamiento & purificación , Células CACO-2 , Células HL-60 , Humanos , Isoquinolinas/química , Isoquinolinas/aislamiento & purificación , Isoquinolinas/farmacología , Estructura Molecular , Raíces de Plantas/químicaRESUMEN
Inspired by the intriguing structures and bioactivities of polyprenylated xanthones, ten previously undescribed polyprenylated xanthones, nujiangxanthones G-P (1-10), and fifteen known ones (11-25) were isolated from the twigs and leaves of Garcinia nujiangensis. The structures of these compounds were established on the basis of spectroscopic data as well as comparison with the literature. Most of the isolates showed potent cytotoxicity against selected cancer cells. Compound 8 showed the highest effects against MDA-MB-231 and A549 cell lines with IC50 values of 4.12 and 2.67⯵M and 16 demonstrated the most potent activity against MCF-7 cell line with an IC50 value of 3.36⯵M.
Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Garcinia/química , Xantonas/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Estructura Molecular , Hojas de la Planta/química , Tallos de la Planta/química , Relación Estructura-Actividad , Xantonas/química , Xantonas/aislamiento & purificaciónRESUMEN
Two new lignanamides, majusamides A and B (1 and 2), and two new alkaloids, chelidoniumine (3) and tetrahydrocoptisine N-oxide (4), together with six known hydroxycinnamic acid amides (HCCA) were isolated from the 75% ethanol extract of Chelidonium majus through the silica gel, Sephadex LH-20, MCI, ODS column chromatography, and semi-HPLC. Their structures were determined on the basis of spectroscopic data and physico-chemical methods. The absolute configurations of 1-3 were determined by electronic circular dichroism (ECD) calculations. The anti-inflammatory activities of all the isolates on the NO production in lipopolysaccharide (LPS)-induced macrophages were evaluated. Compounds 7 and 9 exhibited moderate inhibitory activity with IC50 values of 25.3⯱â¯0.5 and 23.5⯱â¯1.7⯵M, respectively.
Asunto(s)
Alcaloides/farmacología , Amidas/farmacología , Antiinflamatorios/farmacología , Chelidonium/química , Lignanos/farmacología , Óxido Nítrico/metabolismo , Alcaloides/aislamiento & purificación , Amidas/aislamiento & purificación , Animales , Antiinflamatorios/aislamiento & purificación , Línea Celular , China , Lignanos/aislamiento & purificación , Ratones , Microglía/efectos de los fármacos , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Componentes Aéreos de las Plantas/químicaRESUMEN
Three new compounds, ascotrichols A-B (1-2) and ascotrichrone A (3), along with two known isocoumarin derivatives (4-5), were isolated from the solid culture of a sea mud-derived fungus, Ascotricha sp. ZJ-M-5 on rice media. The structures were elucidated by extensive spectroscopic analyses, including 1D and 2D NMR data, and the absolute configurations were determined by electronic circular dichroism and biogenetic correlation.
Asunto(s)
Policétidos/química , Xylariales/química , Dicroismo Circular , Espectroscopía de Resonancia Magnética , Estructura Molecular , Espectrometría de Masa por Ionización de ElectrosprayRESUMEN
The structures of pestalrones A-B were revised via reinterpretation of the NMR data and a brief chemical transformation from the co-occurring polyketides, in our investigation on the secondary metabolites of Pestalotiopsis zonata, which also afforded a new α-pyrone derivative, pestazonatic acid, and four known analogs.
Asunto(s)
Policétidos/química , Pironas/química , Xylariales/química , Modelos Moleculares , Estructura MolecularRESUMEN
A new hybrid of dehydroergosterol and nitrogenous alternariol derivative, pestauvicomorpholine A (1), and three alternariol analogues (2-4) including a new aminated one, pestauvicolactone A (2), were isolated from the fermentation product of the fungus Pestalotiopsis uvicola on rice media. Compounds 1 and 2 represent the first example of aza-alternariol and aza-alternariol-steroid derived from transamination followed by intermolecular hetero-Diels-Alder reaction.
Asunto(s)
Ergosterol/análogos & derivados , Lactonas/química , Lactonas/metabolismo , Xylariales/química , Xylariales/metabolismo , Ergosterol/química , Ergosterol/metabolismo , Estructura Molecular , Nitrógeno/química , Nitrógeno/metabolismo , EstereoisomerismoRESUMEN
With bioassay- and chemistry-guided fractionation, seven new caged prenylxanthones including two scalemic mixtures, epiisobractatin (1), 13-hydroxyisobractatin (2), 13-hydroxyepiisobractatin (3), 8-methoxy-8,8a-dihydrobractatin (4), 8-ethoxy-8,8a-dihydrobractatin (5), garcibracteatone (6), and 8-methoxy-8,8a-dihydroneobractiatin (7), and the eight known compounds 8-15 were isolated from the leaves of Garcinia bracteata. The structures were unambiguously elucidated through analysis of spectroscopic data. The 2D structures and relative configurations of 1 and 5 were confirmed by X-ray crystallographic analysis. The separation of the enantiomers of 1-5 was accomplished by chiral-phase HPLC. The absolute configurations of the enantiomers of 1 and 5 were assigned by comparison of the experimental and calculated electronic circular dichroism (ECD) spectra. The absolute configurations of the related compounds were determined via comparisons of their ECD data with those of the enantiomers of 1 and 5, respectively. Notably, compound 7, with a neo caged skeleton, is the first representative of a novel type of caged xanthone lacking a Δ8(8a) double bond. The isolated compounds exhibited significant cell growth inhibitory activities in vitro against human leukemic HL-60 and K562 cell lines, with GI50 values ranging from 0.2 to 8.8 µM. A preliminary structure-activity relationship is discussed.
Asunto(s)
Garcinia/química , Hojas de la Planta/química , Xantonas/química , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Bioensayo/métodos , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Cromatografía Líquida de Alta Presión , Dicroismo Circular/métodos , Cristalografía por Rayos X/métodos , Células HL-60 , Humanos , Células K562 , Relación Estructura-Actividad , Xantonas/farmacologíaRESUMEN
Bioassay-guided fractionation of the dichloromethane-soluble portion of the stems of Garcinia paucinervis led to the isolation of eight new xanthones, including three pairs of enantiomers, (+) and (-) paucinervins L-N (1a-3a, and 1b-3b), one optically pure compound, (-) paucinervin O (4), and one new analogue, paucinervin P (5), as well as thirteen known xanthones (6-18). Their structures were established by detailed analysis of extensive spectroscopic data. The absolute configurations of 1-4 were confirmed by ECD calculations. All the isolates 1-18 displayed antiproliferative effect against HL-60 with IC50 values ranging from 0.87 to 29.14⯵M, of which compound 5 was the most active. Compounds 6, and 14 exhibited potential inhibitory activity against PC-3 cells, while compounds 5-7, 14, and 16-17 displayed cytotoxic potency against Caco-2 cells. A preliminary structure-activity relationship was also discussed.
Asunto(s)
Antineoplásicos Fitogénicos/química , Garcinia/química , Xantonas/química , Células CACO-2 , Células HL-60 , Humanos , Estructura Molecular , Tallos de la Planta/química , Relación Estructura-ActividadRESUMEN
Five pairs of new 2-oxoindole alkaloids, (±)-peganumalines A-E (1-5), and a new indole alkaloid, peganumaline F (6), along with two known analogues, were isolated from the seeds of Peganum harmala. Their structures and absolute configurations were elucidated through spectroscopic analyses and quantum chemistry calculations. Notably, (±)-peganumalines A (1) represent a pair of rare 2-oxoindole dimeric alkaloid enantiomer with the hitherto unknown carbon skeleton. All isolates were tested for antiproliferative and antibacterial activities.
Asunto(s)
Alcaloides Indólicos/química , Peganum/química , Semillas/química , Línea Celular Tumoral , Humanos , Alcaloides Indólicos/aislamiento & purificación , Pruebas de Sensibilidad Microbiana , Estructura MolecularRESUMEN
Three new diterpenoids, ebractenoids O~Q (1-3), and a new phenolic glucoside, γ-pyrone-3-O-ß-d-(6-galloyl)-glucopyranoside (4), together with 6 known compounds, were isolated from the 95% ethanol extract of the roots of Euphorbia ebracteolata, and their structures were elucidated on the basis of spectroscopic data. The absolute configurations of 1-3 were determined by electronic circular dichroism (ECD) calculations. The inhibitory effects of all the isolates with exception of compounds 8 and 10 on the NO production in lipopolysaccharide (LPS)-induced macrophages were evaluated. All of them exhibited significant inhibitory activity.
Asunto(s)
Diterpenos/química , Euphorbia/química , Glucósidos/química , Fenoles/química , Animales , Diterpenos/aislamiento & purificación , Glucósidos/aislamiento & purificación , Lipopolisacáridos , Macrófagos/efectos de los fármacos , Ratones , Estructura Molecular , Óxido Nítrico/metabolismo , Fenoles/aislamiento & purificación , Raíces de Plantas/química , Células RAW 264.7RESUMEN
Seventeen quinazoline alkaloids and derivatives, containing two pairs of new epimers, named as (S)- and (R)-1-(2-aminobenzyl)-3-hydroxypyrrolidin-2-one ß-d-glucopyranosyl-(1â¯ââ¯6)-ß-d-glucopyranoside (1, 2), (S)- and (R)-vasicinone ß-d-glucopyranosyl-(1â¯ââ¯6)-ß-d-glucopyranoside (3, 4), and a new enantiomer (12b), together with six known ones (5-8, 10, and 12a), and three pairs of known enantiomers (9, 11, and 13), were isolated from the ethanol extracts of the seeds of Peganum harmala L.. Their structures including the absolute configuration were elucidated by using 1D and 2D NMR, and ECD calculation approaches. The cytotoxic activities of all isolated compounds were evaluated. 11 showed moderate cytotoxicity against PC-3 cells with an IC50 value of 15.41⯵M.
Asunto(s)
Alcaloides/farmacología , Antineoplásicos Fitogénicos/farmacología , Peganum/química , Quinazolinas/farmacología , Semillas/química , Alcaloides/química , Alcaloides/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Estructura Molecular , Quinazolinas/química , Quinazolinas/aislamiento & purificación , Relación Estructura-ActividadRESUMEN
Inspired by the intriguing structures and bioactivities of dimeric alkaloids, 11 new thalifaberine-type aporphine-benzylisoquinoline alkaloids, thalicultratines A-K, a tetrahydroprotoberberine-aporphine alkaloid, thalicultratine L, and five known ones were isolated from the roots of Thalictrum cultratum. Their structures were defined on the basis of NMR and HRESIMS data. The antiproliferative activities of compounds 1-17 were evaluated against human leukemia HL-60 and prostate cancer PC-3 cells. Most alkaloids showed potent cytotoxicity against selected cancer cells. Preliminary SARs are discussed. The most active new compound (3), with an IC50 value of 1.06 µM against HL-60 cells, was selected for mechanism of action studies. The results revealed that compound 3 induced apoptosis and arrested the HL-60 cell cycle at the S phase with the loss of mitochondria membrane potential. The nuclear morphological Hoechst 33258 staining assay was also carried out, and the results confirmed apoptosis.
Asunto(s)
Alcaloides/aislamiento & purificación , Alcaloides/farmacología , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Aporfinas/aislamiento & purificación , Aporfinas/farmacología , Medicamentos Herbarios Chinos/aislamiento & purificación , Medicamentos Herbarios Chinos/farmacología , Raíces de Plantas/química , Thalictrum/química , Alcaloides/química , Antineoplásicos Fitogénicos/química , Aporfinas/química , Alcaloides de Berberina , Medicamentos Herbarios Chinos/química , Células HL-60 , Humanos , Concentración 50 Inhibidora , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Relación Estructura-ActividadRESUMEN
Neobraclactones A-C (1-3), featuring an unprecedented further rearranged prenylxanthone skeleton with a unique octahydro-2H-1,3-dioxacyclopenta[c,d]inden-2-one scaffold, along with their biosynthesis-related known compound neobractatin (4), were isolated from the leaves of Garcinia bracteata. Their structures with absolute configurations were determined by extensive analyses of spectroscopic data and ECD calculations. Compounds 1 and 2 showed significant growth inhibition activities against the human leukaemia HL-60 and K562 cell lines with GI50 values from 0.40 to 0.86 µM.
Asunto(s)
Garcinia/química , Xantonas/aislamiento & purificación , Conformación Molecular , Xantonas/químicaRESUMEN
Two new amide compounds, mariamides A and B (1-2), were obtained together with fourteen known compounds from the seeds of milk thistle (Silybum marianum). Their structures were established on the basis of extensive 1D and 2D NMR analyses, as well as HR-ESI-MS data. Most of the compounds showed significant antioxidant activities than positive control in ABTS and FRAP assays. However, only amide compounds 1-4 showed moderate DPPH radical scavenging activity and compounds 7 and 16 showed the most potent activity against DPPH. Most of the compounds showed moderate to stronger α-glucosidase inhibitory activities. Nevertheless, only flavonoids showed strong PTP1B inhibitory activities. These results indicate a use of milk thistle seed extracts as promising antioxidant and antidiabetic agents.