RESUMEN
Four new pavine alkaloids, (+)-eschscholtzidine-N-oxide (1), (-)-12-hydroxycrychine (2), (-)-12-hydroxy-O-methylcaryachine (3), and (-)-N-demethylcrychine (4), and four new proaporphine alkaloids, isocryprochine (5), prooxocryptochine (6), isoamuronine (7), and (+)-8,9-dihydrostepharine (8), together with nine known compounds were isolated from an ethanol extract of the wood of Cryptocarya chinensis. Their structures were elucidated by spectral analysis (NMR and MS), and the structures of 2 and 5 were confirmed by X-ray crystallography.
Asunto(s)
Alcaloides/aislamiento & purificación , Medicamentos Herbarios Chinos/aislamiento & purificación , Lauraceae/química , Alcaloides/química , Cristalografía por Rayos X , Medicamentos Herbarios Chinos/química , Espectrometría de Masas , Medicina Tradicional China , Conformación Molecular , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Plantas Medicinales/química , Espectroscopía Infrarroja por Transformada de Fourier , Taiwán , MaderaRESUMEN
Two new tetranortriterpenoids, 7-isovaleroylcycloseverinolide (1) and 7-isovaleroylcycloepiatalantin (2), together with 28 known compounds, were isolated and characterized from the root bark of Severinia buxifolia collected in Hainan. The structures of 1 and 2 were elucidated on the basis of spectral evidence including 2D NMR and X-ray techniques. The cytotoxicity of several acridone alkaloid isolates (3-8) was evaluated against a small tumor cell panel.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Medicamentos Herbarios Chinos/aislamiento & purificación , Plantas Medicinales/química , Triterpenos/aislamiento & purificación , Acridinas/química , Acridinas/farmacología , Acridonas , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Carcinoma Hepatocelular , Neoplasias del Colon , Cristalografía por Rayos X , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/farmacología , Humanos , Células KB , Espectroscopía de Resonancia Magnética , Estructura Molecular , Raíces de Plantas/química , Taiwán , Triterpenos/química , Triterpenos/farmacología , Células Tumorales Cultivadas/efectos de los fármacos , Células Tumorales Cultivadas/metabolismoRESUMEN
Two new triterpenoids, lucidenic acid N (1) and methyl lucidenate F (2), together with four known compounds, lucidenic acid A, lucidenolactone, lucidenic acid C, and ganoderic acid E, were isolated from the dried fruiting bodies of Ganoderma lucidum. Their structures were elucidated by spectral and chemical transformation studies. Among them, lucidenic acid N (1), lucidenic acid A, and ganoderic acid E showed significant cytotoxic activity against Hep G2, Hep G2,2,15, and P-388 tumor cells.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Medicamentos Herbarios Chinos/aislamiento & purificación , Polyporaceae/química , Triterpenos/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/farmacología , Humanos , Células KB/efectos de los fármacos , Espectroscopía de Resonancia Magnética , Estructura Molecular , Espectrofotometría Ultravioleta , Triterpenos/química , Triterpenos/farmacología , Células Tumorales Cultivadas/efectos de los fármacosRESUMEN
Five new constituents including a flavonoid, artemisidin A (1), and four coumarins, artemicapins A (2), B (3), C (4) and D (5), together with 70 known compounds (6-75), have been isolated and characterized from the aerial part of Artemisia capillaris. The structures of these compounds were determined from spectral analyses and/or chemical evidence. Among them, 15 compounds (3, 6, 10, 18. 30-32, 38-41, 44, 45, 51, and 55) showed antiplatelet aggregation activity and three compounds (10, 17, and 51) demonstrated significant activity against HIV replication in H9 lymphocytic cells.
Asunto(s)
Acetileno/análogos & derivados , Fármacos Anti-VIH/aislamiento & purificación , Artemisia/química , Plantas Medicinales , Inhibidores de Agregación Plaquetaria/aislamiento & purificación , Acetileno/farmacología , Animales , Plaquetas/efectos de los fármacos , Ácidos Cafeicos/farmacología , Cumarinas/farmacología , Espectroscopía de Resonancia Magnética , Estructura Molecular , Inhibidores de Agregación Plaquetaria/farmacología , Conejos , EspectrofotometríaRESUMEN
Five new sesquiterpenes, mandolins R (1), S (2), U (3), W (4), and X (5), together with 39 known compounds, were isolated from the dried roots and stems of Aristolochia mollissima. Their structures were determined by spectroscopic methods.
Asunto(s)
Raíces de Plantas/química , Tallos de la Planta/química , Plantas Medicinales/química , Sesquiterpenos/aislamiento & purificación , China , Espectroscopía de Resonancia Magnética , Sesquiterpenos/química , Espectrofotometría Infrarroja , Espectrofotometría Ultravioleta , Espectroscopía Infrarroja por Transformada de FourierRESUMEN
Three new phenanthrene derivatives, aristoliukine-C, aristofolin-E and aristolochic acid-Ia methyl ester, and one new sesquiterpene, madolin-P, together with 58 known compounds were isolated from the stem and root of Aristolochia kaempferi. The structures of these compounds were determined by spectral analysis. The cytotoxicity and antiplatelet activity of the isolated compounds are also discussed.
Asunto(s)
Plantas Medicinales/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Técnicas In Vitro , Espectroscopía de Resonancia Magnética , Fenantrenos/análisis , Fenantrenos/aislamiento & purificación , Extractos Vegetales/química , Extractos Vegetales/farmacología , Raíces de Plantas/química , Tallos de la Planta/química , Inhibidores de Agregación Plaquetaria/farmacología , Sesquiterpenos/análisis , Sesquiterpenos/aislamiento & purificación , Espectrometría de Masa Bombardeada por Átomos Veloces , Espectrofotometría Infrarroja , Espectrofotometría Ultravioleta , TaiwánRESUMEN
One new biphenyl ether, aristogin C (1), and two new porphyrins, aristophylls A (2) and B (3), as well as 11 known compounds, were isolated from the leaves of Aristolochia elegans. Their structures were elucidated according to the spectroscopic (NMR and MS) analyses or by comparison with literature values.
Asunto(s)
Éteres Fenílicos/química , Plantas Medicinales/química , Porfirinas/química , Cromatografía Líquida de Alta Presión , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Éteres Fenílicos/aislamiento & purificación , Hojas de la Planta/química , Porfirinas/aislamiento & purificación , Espectrofotometría Infrarroja , Espectrofotometría UltravioletaRESUMEN
The structures of two new dimeric acridone alkaloids, glycobismine-D (1) and -E (2), having a novel linkage as binary acridones, three monomeric acridones, glycocitrine-IV (3), -V (4), and -VI (5), and three quinolone alkaloids, glycocitlone-A (6), -B (7), and -C (8) from Glycosmis citrifolia (Willd.) Lindl. (Rutaceae) have been elucidated by spectrometric studies.
Asunto(s)
Acridinas/química , Alcaloides/química , Plantas Medicinales/química , Quinolonas/química , Cromatografía en Capa Delgada , Espectroscopía de Resonancia Magnética , Epidermis de la Planta/química , Raíces de Plantas/química , Espectrofotometría UltravioletaRESUMEN
Eight new acridone alkaloids, buxifoliadines-A--H together with nine known acridone compounds, were isolated and characterized from the root bark of Severinia buxifolia which was collected in Hainan province, China. Their structures were determined by spectroscopic methods. The relationship between acridone alkaloids with collecting area is discussed. The 13C-NMR spectra of the prenyl substituents at C-2 and/or C-4 of N-unsubstituted acridone alkaloids are also discussed.
Asunto(s)
Acridinas/aislamiento & purificación , Alcaloides/aislamiento & purificación , Plantas Medicinales/química , China , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Epidermis de la Planta/química , Raíces de Plantas/química , Solventes , Espectrofotometría Infrarroja , Espectrofotometría UltravioletaRESUMEN
Seven new compounds, sodium aristolochate-VII (1), aristolactam-CIV (2), madolin-I (3), -J (4), -K (5), -L (6) and -M (7) together with 71 known compounds were isolated and characterized from the fresh root and stem of Aristolochia heterophylla Hemsl. Their structures were determined by spectral methods. Compound 8 was revised as aromadendrane-4beta, 10beta-diol by spectral data and single-crystal X-ray analysis.
Asunto(s)
Plantas Medicinales/química , Cristalografía por Rayos X , Raíces de Plantas/química , Tallos de la Planta/química , Espectrofotometría UltravioletaRESUMEN
Three novel sesquiterpene esters of aristolochic acid, aristoloterpenate-II (2), -III (3), and-IV (4), together with known aristoloterpenate-I (1), were isolated and characterized from the root and stem of Aristolochia heterophylla. Their structures were elucidated by spectroscopic methods. The absolute configuration of these compounds at C-4' was determined as R by circular dichroic studies. These compounds showed cytotoxicity against hepatoma G2, 2, 2, 15 cells.
Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Ácidos Aristolóquicos , Medicamentos Herbarios Chinos/farmacología , Fenantrenos/farmacología , Sesquiterpenos/farmacología , Animales , Antineoplásicos Fitogénicos/aislamiento & purificación , Ensayos de Selección de Medicamentos Antitumorales , Medicamentos Herbarios Chinos/aislamiento & purificación , Neoplasias Hepáticas Experimentales/patología , Espectroscopía de Resonancia Magnética , Conformación Molecular , Fenantrenos/aislamiento & purificación , Raíces de Plantas/química , Tallos de la Planta/química , Sesquiterpenos/aislamiento & purificación , Células Tumorales CultivadasRESUMEN
Reinvestigation of the root of Rhinacanthus nasutus afforded, in addition to rhinacanthin-A to -D reported previously, two new dimethyldihydropyranonaphthoquinone esters (5, 6) and eight new 2-hydroxy-1,4-naphthoquinone esters (7-14) were isolated. The stereochemistry of rhinacanthin-A was determined as the R configuration. Compounds rhinacanthin-G to -N, belong to a class of 2-hydroxy-3-(3-hydroxy-2,2-dimethylpropyl)-1,4-naphthoquinone esters, and so far have been isolated only in this plant. Their biosynthesis is also discussed.
Asunto(s)
Antivirales/aislamiento & purificación , Ésteres/aislamiento & purificación , Naftoquinonas/aislamiento & purificación , Plantas Medicinales/química , Antihipertensivos/química , Antihipertensivos/aislamiento & purificación , Antivirales/química , Ésteres/química , Espectroscopía de Resonancia Magnética , Naftoquinonas/químicaRESUMEN
The continuing investigation of the root of Rhinacanthus nasutus afforded a 1,4-naphthoquinone ester, rhinacanthin-Q, accompanied by twenty-four known compounds. The structure was elucidated on the basis of spectroscopic analyses. The cytotoxicity and antiplatelet effect of this compound was also discussed.
Asunto(s)
Naftoquinonas/aislamiento & purificación , Naftoquinonas/farmacología , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Plantas Medicinales/química , Humanos , Células KB/efectos de los fármacos , Naftoquinonas/química , Resonancia Magnética Nuclear Biomolecular , Extractos Vegetales/química , Raíces de Plantas/química , Agregación Plaquetaria/efectos de los fármacos , Inhibidores de Agregación Plaquetaria/farmacologíaRESUMEN
Two related 1H-2,3,3a,8b-tetrahydrocyclopenta[b]benzofurans, aglafolin (1a) and rocaglamide (2), isolated from the stems of Aglaia elliptifolia, showed significant cytotoxicity in six cancer cell lines. Aglafolin (1a) was also found to completely block platelet aggregation caused by arachidonic acid and platelet-activating factor at 100 microM and 2 ng/mL, respectively.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Benzofuranos/aislamiento & purificación , Inhibidores de Agregación Plaquetaria/aislamiento & purificación , Animales , Antineoplásicos Fitogénicos/farmacología , Benzofuranos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Técnicas In Vitro , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Ratones , Extractos Vegetales/química , Agregación Plaquetaria/efectos de los fármacos , Inhibidores de Agregación Plaquetaria/farmacología , Conejos , Espectrofotometría Infrarroja , Espectrofotometría Ultravioleta , Células Tumorales CultivadasRESUMEN
Using antiplatelet aggregation as a guide to fractionation, seven aporphines, actinodaphnine (1), N-methylactinodaphnine (2), launobine (3), dicentrine (4), O-methylbulbocapnine (5), hernovine (7), and bulbocapnine (9), and two oxoaporphines, dicentrinone (6) and liriodenine (8), were isolated from the stems of Illigera luzonensis. Among them, compounds 2, 4, 5, 8, and 9 were isolated for the first time from this species. Moreover, compounds 1-5, and 8 showed significant antiplatelet aggregation and compounds 1 and 6 exhibited significant vasorelaxant activities, respectively.
Asunto(s)
Alcaloides/aislamiento & purificación , Plantas Medicinales/química , Inhibidores de Agregación Plaquetaria/aislamiento & purificación , Alcaloides/farmacología , Animales , Técnicas In Vitro , Contracción Muscular/efectos de los fármacos , Músculo Liso Vascular/efectos de los fármacos , Tallos de la Planta/química , Inhibidores de Agregación Plaquetaria/farmacología , Conejos , RatasRESUMEN
Five new carbazole alkaloids, clausines B, E, H, I and K, as well as 22 known compounds, were isolated from the stem bark of Clausena excavata. The structures were established from spectral data and chemical transformation. These compounds showed significant inhibition of rabbit platelet aggregation and caused vasocontraction. The crude methanol extract, partitioned layers and chromatographic fractions revealed the presence of promotive and inhibitive constituents, simultaneously. These results might explain the philosophy of use in Chinese medicine, in that the dose and content variation in a prescription produced different, promotive or inhibitive, effects on therapy.
Asunto(s)
Alcaloides/aislamiento & purificación , Plantas Medicinales/química , Inhibidores de Agregación Plaquetaria/aislamiento & purificación , Vasoconstrictores/aislamiento & purificación , Alcaloides/química , Alcaloides/farmacología , Animales , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Medicina Tradicional China , Estructura Molecular , Inhibidores de Agregación Plaquetaria/química , Inhibidores de Agregación Plaquetaria/farmacología , Conejos , Espectrofotometría Ultravioleta , Vasoconstrictores/química , Vasoconstrictores/farmacologíaRESUMEN
In the present study, we extracted Angelica pubescens (AP) with various solvents in order to find the bioactive constituents that demonstrated analgesic and anti-inflammatory effects. The results were obtained as follows: (1) Methanol-, chloroform-, and ethyl acetate-extracts effectively reduced the pain that was induced by 1% acetic acid and a hot plate. (2) Methanol-, chloroform-, and ethyl acetate-extracts reduced the edema that was induced by 3% formalin or 1.5% carrageenan. (3) Sixteen compounds have been isolated and identified from the roots of AP. Among these compounds, columbianadin, columbianetin acetate, bergapten, umbelliferone, and caffeic acid significantly demonstrated anti-inflammatory and analgesic activities at 10 mg/kg. However, only osthole and xanthotoxin revealed anti-inflammatory activity. Isoimperatorin only demonstrated an analgesic effect. These results revealed that the anti-inflammatory and analgesic constituents from roots of AP were related to peripheral inhibition of inflammatory substances and to the influence on the central nervous system.
Asunto(s)
Analgésicos/farmacología , Antiinflamatorios/farmacología , Medicamentos Herbarios Chinos/química , Animales , Masculino , Ratones , Ratones Endogámicos ICR , Raíces de Plantas/química , Ratas , Ratas Sprague-DawleyRESUMEN
The effects of beta-carotene (beta C) or vitamin A (VA) administration for 8 consecutive weeks were compared in male Wistar rats submitted to the resistant hepatocyte model (RH model) of hepatocarcinogenesis. Animals treated with corn oil (CO), instead of carotenoid or retinoid, served as controls. At the end of the study, beta C treatment resulted in a substantial reduction in the hepatocyte nodule incidence, total number of nodules and in the nodule multiplicity, as well as in the number and size of hepatic gamma-glutamyltranspeptidase (gamma GT)-positive foci. In contrast, animals administered with VA presented a 100% nodule incidence and only a moderate decrease in the total number of hepatocyte nodules. These showed to be in the great majority larger than nodules observed after beta C treatment. Moreover, VA administration resulted in similar number and size of gamma GT-positive foci than controls. In addition, the hepatic concentrations of total VA increased in both, beta C and VA treated animals. However, as expected, increases in the hepatic carotenoid concentrations could be only observed after beta C application. Therefore, changes in the hepatic levels of beta C, and not of VA, resulted in appreciable inhibitory effects on preneoplastic lesions of the liver. The evidence implies that the chemopreventive property of beta C is unrelated to its provitamin A activity.
Asunto(s)
Carotenoides/farmacología , Neoplasias Hepáticas Experimentales/patología , Vitamina A/farmacología , Animales , Carotenoides/uso terapéutico , Aceite de Maíz/farmacología , Modelos Animales de Enfermedad , Hígado/enzimología , Hígado/patología , Neoplasias Hepáticas Experimentales/enzimología , Neoplasias Hepáticas Experimentales/prevención & control , Masculino , Lesiones Precancerosas/patología , Ratas , Ratas Wistar , Vitamina A/uso terapéutico , beta Caroteno , gamma-Glutamiltransferasa/análisisRESUMEN
Clausine-D inhibited concentration-dependently the aggregation and release reaction of washed rabbit platelets induced by arachidonic acid and collagen, without affecting those induced by U46619, PAF and thrombin. The IC50 values of clausine-D on arachidonic acid- and collagen-induced platelet aggregation were calculated to be 9.0 +/- 1.1 and 58.9 +/- 0.9 microM, respectively. Thromboxane B2 and prostaglandin D2 formation in platelets caused by arachidonic acid were also suppressed. Clausine-D inhibited increased intracellular concentration of calcium in platelets caused by arachidonic acid and collagen, and also abolished the generation of inositol monophosphate caused by arachidonic acid, but not that by collagen, U46619, PAF and thrombin. In human citrated platelet-rich plasma, clausine-D inhibited the secondary phase, but not the primary phase, of aggregation induced by epinephrine and ADP. These results indicate that the antiplatelet effect of clausine-D is due to inhibition of the formation of thromboxane A2.
Asunto(s)
Alcaloides/aislamiento & purificación , Carbazoles/aislamiento & purificación , Extractos Vegetales/análisis , Inhibidores de Agregación Plaquetaria/aislamiento & purificación , Adenosina Difosfato/farmacología , Adenosina Trifosfato/metabolismo , Animales , Ácido Araquidónico/farmacología , Colágeno/farmacología , Epinefrina/farmacología , Fosfatidilinositoles/metabolismo , Prostaglandina D2/metabolismo , Conejos , Tromboxano B2/metabolismoRESUMEN
Girinimbine is an antiplatelet agent isolated from Murraya euchrestifolia. In washed rabbit platelets, it inhibited arachidonic acid (AA)-, collagen-, U46619- and platelet-activating factor (PAF)-induced aggregation and ATP release in a concentration-dependent manner with IC50 values of 9.1 +/- 1.5, 16.7 +/- 1.7, 60.0 +/- 5.1 and 71.9 +/- 5.6 microM, respectively. However, it did not apparently affect thrombin-induced aggregation and ATP release even when a concentration of 80 microM was used. In citrated human platelet-rich plasma (PRP), girinimbine selectively inhibited secondary aggregation and ATP release without appearing to affect the primary aggregation induced by epinephrine and ADP. The formation of both platelet thromboxane B2 (TxB2) and prostaglandin D2 (PGD2) caused by AA was inhibited by girinimbine concentration dependently, with a maximal effect at 20 microM. Girinimbine also inhibited cyclooxygenase activity as reflected by the attenuation of prostaglandin E2 (PGE2) formation after incubation of sheep vesicular gland microsomes with arachidonic acid. In myo-[3H]inositol-labeled and fura-2-loaded platelets, [3H]inositol monophosphate generation and the increase in intracellular Ca2+ ([Ca2+]i) stimulated by AA and collagen, but not that stimulated by U46619, PAF and thrombin, were inhibited by girinimbine (20 microM). Platelet cyclic AMP levels were elevated by high concentrations of girinimbine (20 and 80 microM). These data indicate that the antiplatelet effect of girinimbine is due to the inhibition of cyclooxygenase activity and elevation of the cyclic AMP level.