RESUMEN
Two new norlignans together with two known phenylpropanoids were isolated from the whole herb of Anemone vitifolia. All compounds were reported from this plant for the first time. The structures of these compounds were identified by comprehensive HR-ESI-MS, 1D and 2D NMR spectroscopic data analysis and comparison with literature data. Additionally, bioactivity study results showed that two new compounds have potential anti-inflammatory activity. The plausible biosynthetic pathway for these compounds were also speculated in this article.
Asunto(s)
Anemone/química , Antiinflamatorios no Esteroideos/farmacología , Medicamentos Herbarios Chinos/farmacología , Lignanos/farmacología , Óxido Nítrico/antagonistas & inhibidores , Animales , Antiinflamatorios no Esteroideos/química , Antiinflamatorios no Esteroideos/aislamiento & purificación , Supervivencia Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/aislamiento & purificación , Lignanos/química , Lignanos/aislamiento & purificación , Lipopolisacáridos/antagonistas & inhibidores , Lipopolisacáridos/farmacología , Ratones , Estructura Molecular , Óxido Nítrico/biosíntesis , Propanoles/química , Propanoles/aislamiento & purificación , Propanoles/farmacología , Células RAW 264.7 , Relación Estructura-ActividadRESUMEN
A total of ten compounds were isolated from the 90% Et OH extract of Cassia siamea by using various chormatographic techniques,and their structures were established as( 2' S)-2-( propan-2'-ol)-5,7-dihydroxy-benzopyran-4-one( 1),chrobisiamone( 2), 2-( 2'-hydroxypropyl)-5-methyl-7-hydroxychromone( 3), 2,5-dimethyl-7-hydroxychromone( 4), 2-methyl-5-acetonyl-7-hydroxychromone( 5),3-O-methylquercetin( 6),3,5,7,3',4'-pentahydroxyflavonone( 7),luteolin-5,3'-dimethylether( 8),4-( trans)-acetul-3,6,8-trihydroxy-3-methyl-dihydronapht halenone( 9) and 6-hydroxymellein( 10) based on the spectroscopic data.Compound 1 was a new compound,and 3,4,6,8 were isolated from this plant for the first time.
Asunto(s)
Cassia , Senna , Luteolina , Análisis EspectralRESUMEN
A new naphthaldehyde derivative has been isolated from Comastoma pulmonarium by using various chromatographic techniques, including silica gel, Sephadex LH-20, MCI-gel resin and RP-HPLC. This compounds was determined as 5-methoxy-2-methyl-7-(2-oxopropyl)naphthalene-1-carbaldehyde(1) by NMR, MS, IR and UV spectra. This compound was also evaluated for its anti-tobacco mosaic virus (anti-TMV) activity. The result showed that it showed high anti-TMV activity with inhibition rate of 32.8%. The inhibition rate is close to that of positive control (ningnanmycin).
Asunto(s)
Aldehídos/farmacología , Antivirales/farmacología , Gentianaceae/química , Naftalenos/farmacología , Virus del Mosaico del Tabaco/efectos de los fármacos , Aldehídos/aislamiento & purificación , Antivirales/aislamiento & purificación , Cromatografía Líquida de Alta Presión , Naftalenos/aislamiento & purificación , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , NicotianaRESUMEN
Four new diterpene glucosides, namely perovskiaditerpenosides A - D (1 - 4), were isolated from the BuOH extract of Perovskia atriplicifolia. Their structures were well elucidated by chemical methods and comprehensive spectroscopic analyses including MS, IR, and NMR (1D and 2D). The newly isolated compounds were screened for their cytotoxic activity against HepG2, NB4, HeLa, K562, MCF7, PC3, and HL60. The obtained results indicated that the new compounds possessed considerable cytotoxic activity.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Diterpenos/aislamiento & purificación , Glucósidos/aislamiento & purificación , Lamiaceae/química , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Butanoles , Línea Celular Tumoral , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Estructura Molecular , Extractos Vegetales , Análisis EspectralRESUMEN
Three new xanthones (1-3), together with five known ones (4-8), were isolated from whole herb of Swertia bimaculata. Their structures were established on the basis of detailed spectroscopic analysis (1D- and 2D-NMR, HRESIMS, UV, and IR) and comparison with data reported in the literature. New isolates were evaluated for their anti-5α-reductase activity. The results revealed that all new compounds showed weak activity with reductase inhibitions of 40.5 ± 2.8, 38.6 ± 2.5, and 48.9 ± 3.0%, respectively.
Asunto(s)
Inhibidores de 5-alfa-Reductasa/aislamiento & purificación , Medicamentos Herbarios Chinos/aislamiento & purificación , Medicamentos Herbarios Chinos/farmacología , Swertia/química , Xantonas/aislamiento & purificación , Xantonas/farmacología , Inhibidores de 5-alfa-Reductasa/química , Inhibidores de 5-alfa-Reductasa/farmacología , Medicamentos Herbarios Chinos/química , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Xantonas/químicaRESUMEN
Three previously unreported anthraquinones, fistulaquinones A-C (1-3), together with three known ones (4-6) were isolated from the twigs of Cassia fistula. Their structures were determined by means of extensive NMR and MS spectroscopic analyses. All the isolated compounds were tested for their anti-tobacco mosaic virus (anti-TMV) activity, and compound 3 showed significant activity with inhibition rate of 34.5% at 20 µM concentration, even more potent than positive control. Additionally, compounds 1-6 exhibited moderate cytotoxicity with IC50 values ranging from 2.8 to 9.4 µM for some tested human tumor cell lines.
Asunto(s)
Antraquinonas/aislamiento & purificación , Antraquinonas/farmacología , Antivirales/aislamiento & purificación , Antivirales/farmacología , Cassia/química , Medicamentos Herbarios Chinos/aislamiento & purificación , Medicamentos Herbarios Chinos/farmacología , Virus del Mosaico del Tabaco/efectos de los fármacos , Antraquinonas/química , Antivirales/química , Citidina/análogos & derivados , Citidina/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Medicamentos Herbarios Chinos/química , Humanos , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Paclitaxel/farmacología , Hojas de la Planta/química , Tallos de la Planta/químicaRESUMEN
Biotransformation of trans-resveratrol and synthetic (±)-ε-viniferin in aqueous acetone using horseradish peroxidase and hydrogen peroxide as oxidants resulted in the isolation of two new resveratrol trimers (3 and 4), one new resveratrol derivative (5) with a dihydrobenzofuran skeleton, together with two known stilbene trimers (6 and 7), and six known stilbene dimers (8-13). Their structures and relative configurations were identified through spectral analysis and possible formation mechanisms were also discussed. Among these oligomers, trimers 6 and 7 were obtained for the first time through direct transformation from resveratrol. Results indicated that this reaction is suitable for the preparation of resveratrol oligomers with a complex structure.
Asunto(s)
Biomimética/métodos , Peroxidasa de Rábano Silvestre/metabolismo , Estilbenos/química , Estilbenos/síntesis química , Benzofuranos/química , Biocatálisis , Peróxido de Hidrógeno/química , Espectroscopía de Resonancia Magnética , Estructura Molecular , Oxidación-Reducción , ResveratrolRESUMEN
Oryzaeins A-D (1-4), four new isocoumarin derivatives, along with five known ones (5-9) were isolated from solid cultures of an endophytic fungus Aspergillus oryzae. Their structures were elucidated by detailed spectroscopic analysis and by comparison with reported data of related derivatives. Among them, compounds 1 and 2 represent the first examples of isocoumarins possessing an unusual 2-oxopropyl group and a rare 3-hydroxypropyl group. Compounds 1 and 2 displayed moderate anti-tobacco mosaic virus activities with inhibition rates of 28.4% and 30.6%, respectively, at the concentration of 20 µM. The new compounds showed moderate inhibitory activities against several human tumor cell lines with IC50 values in the range of 2.8-8.8 µM. Supporting information available online at http://www.thieme-connect.de/products.
Asunto(s)
Antineoplásicos/farmacología , Antivirales/farmacología , Aspergillus oryzae/química , Isocumarinas/farmacología , Virus del Mosaico del Tabaco/efectos de los fármacos , Antibacterianos/farmacología , Antineoplásicos/aislamiento & purificación , Antivirales/aislamiento & purificación , Línea Celular Tumoral , China , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Estructura MolecularRESUMEN
Five new icetexane diterpenoids, namely, perovskatones B-D (1, 3, 4), 1α-hydroxybrussonol (2), and 1α-hydroxypisiferanol (5), were isolated from Perovskia atriplicifolia, together with a new natural product (6) and two known compounds, przewalskin E (7) and brussonol (8). The structures of the new compounds were elucidated by detailed analyses of their MS, IR, 1D, and 2D NMR data. Compounds 1-8 were assayed for their inhibitory hepatitis B virus activities in the HepG 2.2.15 cell line. The results suggested that compounds 1 and 2 possessed noticeable anti-hepatitis B virus activity in vitro, suppressing the replication of hepatitis B virus DNA with selectivity index values of 154.3 and 137.7, respectively.
Asunto(s)
Antivirales/farmacología , Diterpenos/farmacología , Virus de la Hepatitis B/efectos de los fármacos , Lamiaceae/química , Extractos Vegetales/farmacología , Antivirales/química , Antivirales/aislamiento & purificación , Antivirales/uso terapéutico , Diterpenos/química , Diterpenos/aislamiento & purificación , Diterpenos/uso terapéutico , Células Hep G2 , Hepatitis B/tratamiento farmacológico , Hepatitis B/virología , Humanos , Estructura Molecular , Fitoterapia , Extractos Vegetales/química , Extractos Vegetales/uso terapéuticoRESUMEN
A novel and highly selective electrochemical method for the synthesis of diverse quinazolinone oximes via direct electrooxidation of primary amines/C(sp2)-H functionalization of oximes has been developed. The reaction is conducted in an undivided cell under constant current conditions and is oxidant-free, open-air, and eco-friendly. Notably, the protocol shows good functional group tolerance, providing versatile quinazolinone oximes in good yields. Moreover, the mechanism is investigated through control experiments and cyclic voltammogram (CV) experiments.
RESUMEN
Nine pairs of undescribed enantiomers, (±)-styraxoids A-I (1-9), were isolated from the resin of Styrax tonkinensis, and their structures were assigned by spectroscopic and computational methods. Compounds (±)-1 are a pair of degraded lignans, and the remaining compounds (±)-(2-9) are phenylpropanoid skeletons. Compounds (±)-8 and (±)-9 feature a 1,3-dioxolane moiety. The biological evaluation showed that both enantiomers of 1 could inhibit LPS-induced INOS and COX-2 in RAW264.7 cells in a dose-dependent manner.
Asunto(s)
Lignanos , Styrax , Styrax/química , Antiinflamatorios/farmacología , Lignanos/farmacología , Resinas de Plantas/químicaRESUMEN
Seven new chromones, siamchromones A-G (1-7), and 12 known chromones (8-19) were isolated from the stems of Cassia siamea. Compounds 1-19 were evaluated for their antitobacco mosaic virus (anti-TMV) and anti-HIV-1 activities. Compound 6 showed antitobacco mosaic virus (anti-TMV) activity with an inhibition rate of 35.3% and IC50 value of 31.2 µM, which is higher than that of the positive control, ningnamycin. Compounds 1, 10, 13, and 16 showed anti-TMV activities with inhibition rates above 10%. Compounds 4, 6, 13, and 19 showed anti-HIV-1 activities with therapeutic index values above 50.
Asunto(s)
Antivirales/farmacología , Cassia/química , Cromonas/aislamiento & purificación , Cromonas/farmacología , Medicamentos Herbarios Chinos/aislamiento & purificación , Medicamentos Herbarios Chinos/farmacología , VIH-1/efectos de los fármacos , Virus del Mosaico del Tabaco/efectos de los fármacos , Cromonas/química , Medicamentos Herbarios Chinos/química , Estructura Molecular , Tallos de la Planta/químicaRESUMEN
A new chromone glycoside, 8-O-ß-D-Glucopyranosyl-2-methylchromone (1), together with eight known compounds (2-9) were isolated from the Tibetan medicine plant of Swertia punicea. All compounds of this plant were reported for the first time. The structures of these metabolites were elucidated by analysis of their HR-ESI-MS, 1D and 2D NMR spectroscopic data and comparison with data reported in the literature. In vitro test, all compounds were evaluated for their anti-inflammatory activity through the determination of nitric oxide production. Compounds 1-2 were evaluated for cytotoxic activities against three human cancer cell lines (HeLa, MDA-MB-231 and A375) by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) method. Furthermore, the chemotaxonomic significance of these compounds has also been described.
Asunto(s)
Swertia , Cromonas , Glicósidos/farmacología , Humanos , Medicina Tradicional Tibetana , Estructura MolecularRESUMEN
Two new secolignans and one new neolignan, named feddeiphenols A-C (1-3), together with eight known compounds (4-11), were isolated from the leaves and stems of Daphne feddei. Their structures were established on the base of spectroscopic methods, mainly extensive NMR, UV spectroscopy, and MS spectrometry. Compounds 1-11 were tested for their anti-human immunodeficiency virus (HIV)-1 activity and cytotoxicity. The results revealed that compounds 1, 2, 3, 7, and 9 showed therapeutic index (TI) values above 30, respectively, and the other compounds also showed weak anti-HIV-1 activity. Compound 1 showed modest cytotoxic activity. The other compounds also showed weak cytotoxic activity.
Asunto(s)
Fármacos Anti-VIH/química , Fármacos Anti-VIH/farmacología , Daphne/química , Lignanos/química , Extractos Vegetales/química , Extractos Vegetales/farmacología , Fármacos Anti-VIH/aislamiento & purificación , Línea Celular Tumoral , VIH-1/efectos de los fármacos , Humanos , Lignanos/aislamiento & purificación , Lignanos/toxicidad , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Conformación Molecular , Extractos Vegetales/aislamiento & purificación , Hojas de la Planta/química , Tallos de la Planta/química , Espectrofotometría UltravioletaRESUMEN
Five new ent-kaurane diterpenoids, isodonhenrins A-E (1-5), together with thirteen known ones were isolated from the aerial parts of Isodon henryi. Their structures were identified by means of extensive spectroscopic analysis, and the absolute configurations of 1 were determined by single-crystal X-ray diffraction. Most of the diterpenoids were evaluated for their cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW480 cell lines. Compound 17 showed significant inhibitory effects on five cell lines, and compounds 6, 9, 10, 11, 12 and 16 exhibited selective activity.
Asunto(s)
Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Diterpenos de Tipo Kaurano/química , Diterpenos de Tipo Kaurano/farmacología , Isodon/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Línea Celular Tumoral , Cristalografía por Rayos X , Diterpenos de Tipo Kaurano/aislamiento & purificación , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Modelos Moleculares , Neoplasias/tratamiento farmacológico , Componentes Aéreos de las Plantas/químicaRESUMEN
OBJECTIVE: To study the alkaloids from Corydalis impatiens. METHODS: The alkaloids were isolated and purified by chromatography and their structures were identified by spectral data and others methods. RESULTS: Seven alkaloids were isolated and identified as bicuculline(1), ochotensine(2), ochotensimine(3), ochrobirine(4), tetrahydrothalifendine(5), norochotensimine(6), N-methylactinodaphnine(7). CONCLUSION: All these compounds are isolated from this plant for the first time.
Asunto(s)
Alcaloides/aislamiento & purificación , Corydalis/química , Dioxolanos/aislamiento & purificación , Plantas Medicinales/química , Alcaloides/química , Bicuculina/química , Bicuculina/aislamiento & purificación , Cromatografía en Capa Delgada , Dioxolanos/química , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Raíces de Plantas/químicaRESUMEN
Three new phenylacetamide glycosides (1-3) together with one known phenylacetamide glycoside (4) and two known flavonoid glycosides (5-6) were isolated from whole plants of Dracocephalum tanguticum. The structure of all compounds were elucidated based on spectroscopic data analysis and comparison with data reported in related literature. Compounds (1-3) were evaluated for their anti-hyperglycemic and anti-fungal (Candida albicans) activities, the results revealed that all of them showed moderate activity with 3T3-L1 adipocytes glucose consumption rate of 20.80 ± 1.47%, 21.48 ± 2.44%, and 21.57 ± 1.35%, respectively at the final concentration of 25 µM. However, none of them showed obvious Candida albicans inhibitory activity.
Asunto(s)
Antifúngicos/aislamiento & purificación , Glicósidos/farmacología , Hipoglucemiantes/aislamiento & purificación , Lamiaceae/química , Animales , Antifúngicos/química , Antifúngicos/farmacología , Candida albicans/efectos de los fármacos , Línea Celular , Flavonoides/química , Flavonoides/aislamiento & purificación , Flavonoides/farmacología , Glucosa/farmacocinética , Glicósidos/química , Glicósidos/aislamiento & purificación , Hipoglucemiantes/química , Hipoglucemiantes/farmacología , Ratones , Estructura Molecular , Análisis EspectralRESUMEN
Two new xanthone glycosides (1-2), together with seven known analogues (3-9), were isolated from whole herb of Swertia punicea. The structures of these metabolites were established on the basis of detailed spectroscopic analysis and comparison with data reported in the literature. In an in vitro test, all isolates were evaluated for their anti-inflammatory activity. The results revealed that all of them showed significant anti-inflammatory activity with IC50 values ranging from 1.237 to 3.319 mM. Compounds 3, 4, and 5 (IC50 values in the range 1.237-1.987 mM) displayed more potent anti-inflammatory activity than the positive control, indomethacin (IC50 value of 2.004 mM).
Asunto(s)
Antiinflamatorios no Esteroideos/química , Antiinflamatorios no Esteroideos/farmacología , Swertia/química , Xantonas/química , Animales , Evaluación Preclínica de Medicamentos , Medicamentos Herbarios Chinos/química , Glicósidos/química , Espectroscopía de Resonancia Magnética , Ratones , Estructura Molecular , Células RAW 264.7RESUMEN
OBJECTIVE: To study the chemical constituents of Swertia mussotii. METHODS: The constituents were isolated by various column chromatography methods, and their structures were identified by physico-chemical properties and spectral analysis. RESULTS: Eleven compounds were isolated and identified as 1,3, 8-trihydroxy-7-methoxyxanthone (I), 2,8-dihydroxy-1,6-dimethyoxyxanthone (II), 1,8-dihydroxy-2,6-dimethoxyxanthone (III), 1,2,8-trimethoxyxanthone (IV), 1,3,5,6-tetrohyroxyxanthone (V), 1,8-dihydroxy-3,7-dimethoxyxanthone (VI), beta-daucosterol (VII), clerosterol 3beta-O-[6'-o-hydro-benzene-beta-D-glucoside] (VIII), ursolicacid (IX), 3beta,28-dihydroxylup-20 (29) -ene (X), erythrocentaurin (XI). CONCLUSION: Compounds VIII, IX and X are isolated from Swertia mussotii for the first time.
Asunto(s)
Plantas Medicinales/química , Swertia/química , Triterpenos/aislamiento & purificación , Xantonas/aislamiento & purificación , Estructura Molecular , Control de Calidad , Sitoesteroles/química , Sitoesteroles/aislamiento & purificación , Triterpenos/química , Xantonas/químicaRESUMEN
Diverse terpenoids including a novel sesquiterpenoidal lactam, commipholactam A (1), and a structurally related new cadinane sesquiterpenoid, commiphorane H (2), a new eudesmane sesquiterpenoid, commiphorane I (4), a new guaiane sesquiterpenoid, commiphorane J (5), and two new nor-abietane diterpenoids, commiphoranes K1 and K2 (6 and 7) along with two known terpenoids (3 and 8), were isolated from Resina Commiphora. Their structures with absolute configurations were characterized by spectroscopic methods and calculated electronic circular dichroism (ECD). Notably, commipholactam A represents the first example of cadinane sesquiterpene alkaloids isolated from Resina Commiphora. Biological assessment toward human cancer cells showed that the IC50 values of 1 against HepG2 and A549 cells were 21.73⯵M and 128.50⯵M, respectively.