RESUMEN
Nineteen triterpenoids, including five previously unknown (four triucallane-type derivatives and one highly oxidized A, B-seco limonoids), together with fourteen known triterpenoids, were isolated from the fruits of Aphanamixis polystachya. Their structures were elucidated by extensive spectroscopic analysis. All isolates were evaluated their anti-inflammatory activities. The result showed that all compounds inhibit LPS-induced nitric oxide production in RAW264.7 macrophages with their IC50 value ranging from 95 to 1332 uM, and compound 6 exhibited obvious anti-inflammatory activity comparable to that of the positive control, with IC50 values of 94.96 uM.
Asunto(s)
Meliaceae , Triterpenos , Frutas/química , Triterpenos/farmacología , Óxido Nítrico , Estructura Molecular , Meliaceae/química , Antiinflamatorios/farmacologíaRESUMEN
Two new sesquiterpenoids, including a kessane-type sesquiterpenoid (1) and one bisabolane derivative (2), together with fourteen known sesquiterpenoids (3-16), were isolated from the roots and rhizomes of Valeriana amurensis. The structures of new compounds were established on the basis of extensive spectroscopic analysis. All isolates were evaluated for their effects on nerve growth factor (NGF)-mediated neurite outgrowth in pheochromocytoma (PC12) cells. As a results, four compounds including 10-12 and 15 showed potent promoting effects at the concentration of 10 µM on NGF-induced neurite outgrowth in PC12 cells with the differentiation rate of 11.84%, 12.21%, 13.77% and 12.16%, respectively.
Asunto(s)
Factor de Crecimiento Nervioso/farmacología , Proyección Neuronal/efectos de los fármacos , Raíces de Plantas/química , Rizoma/química , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/farmacología , Valeriana/química , Animales , Espectroscopía de Resonancia Magnética con Carbono-13 , Factor de Crecimiento Nervioso/metabolismo , Células PC12 , Espectroscopía de Protones por Resonancia Magnética , Ratas , Sesquiterpenos/químicaRESUMEN
Two unusual dendrobine-type alkaloids, findlayines E and F (1, 2), along with five known dendrobine-type alkaloids (3-7), were isolated from the stems of Dendrobium findlayanum Par. et Rchb. f. Compound 1 is the first example of dendrobine-type alkaloids with a 2-ethoxy-2-oxoethyl group attaching to the C-2, and compound 2 is a nor-dendrobine-type alkaloid, featuring a 5-decarboxylated structure. The structures of compounds 1 and 2 were elucidated by means of extensive spectroscopic analyses, and their absolute configuration were confirmed by electronic circular dichroism (ECD) calculations. All isolates were evaluated for their cytotoxicity against HL-60, SMMC-7721, A-549 and MCF-7 human cancer cells.
Asunto(s)
Alcaloides/farmacología , Dendrobium/química , Tallos de la Planta/química , Células A549 , Alcaloides/aislamiento & purificación , China , Células HL-60 , Humanos , Células MCF-7 , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacologíaRESUMEN
Three new sesquiterpene glycosides with alloaromadendrane and ylangene-derived type aglycones, named dendrofindlayanosides A-C (1-3), one new cyclopacamphane type sesquiterpene named dendrofindlayanobilin A (4), together with five known compounds have been isolated from stems of Dendrobium findlayanum. Their structures were determined on the basis of spectroscopic and chemical methods.
Asunto(s)
Dendrobium/química , Plantas Medicinales/química , Sesquiterpenos/química , Sesquiterpenos/aislamiento & purificación , China , Espectroscopía de Resonancia Magnética , Estructura Molecular , Tallos de la Planta/químicaRESUMEN
Four new monoterpenoids, including two new acyclic monoterpenoids (2R, 6R)-2, 6-dimethyl-8-isovaleroxyoctan-1-ol (1) and (2S, 6S)-2, 6-dimethyl-8-isovaleroxyoctan-1-ol (2), as well as two new iridoids stenopterins F-G (3 and 4), together with fifteen known compounds (5-19), were isolated from whole dried material of Valeriana stenoptera. Stenopterin F was the first reported iridoids with n-butoxyl in the Valerianaceae family. The structures of new compounds were established on the basis of extensive spectroscopic analysis.
Asunto(s)
Monoterpenos/química , Valeriana/química , Estructura MolecularRESUMEN
The roots and rhizomes of Valeriana jatamansi have long been used as folk medicine in Asia and usually named as "Zhizhuxiang" in Chinese for the treatment of abdominal distention and pain. However, its active ingredients and molecular targets for treatment of abdominal pain remain unrevealed. Inhibitors of Cav2.2 N-type voltage-gated calcium channels (VGCCs) are actively sought after for their potential in treating pain, especially chronic pain. As far as we know, the method used for seeking analgesic active ingredient from plant material has rarely been reported. The analgesic potentials of the EtOH extract (0.01 mg/ml) of the roots and rhizomes of V. jatamansi and its EtOAc, n-BuOH and H2O soluble parts (0.01 mg/ml, respectively) were tested herein on Cav2.2, using whole-oocyte recordings in vitro by tow-electrode voltage clamp. The results indicated that the EtOAc-soluble part exhibited the most potent inhibition of Cav2.2 peak current (20 mv). The EtOAc-soluble part was then subjected to silica gel column chromatography (CC) and giving 9 fractions. Phytochemical studies were carried out by repeated CC and extensive spectroscopic analyses after the fraction (0.01 mg/ml) was identified to be active and got seventeen compounds (1-17). All isolates were then sent for further bioactive verification (1 and 3 at concentration of 10 µM, others at 30 µM). In addition, the selectivity of the active compounds 1 and 3 were tested on various ion channels including Cav1.2, Cav2.1 and Cav3.1 VGCCs and Kv1.2, Kv2.1, Kv3.1 and BK potassium channels. The results indicated that compound 1 and 3 (an abundant compound) inhibited Cav2.2 with an EC50 of 3.3 and 4.8 µM, respectively, and had weaker or no effect on Cav1.2, Cav2.1 and Cav3.1 VGCCs and Kv1.2, Kv2.1, Kv3.1 and BK potassium channels. Compounds 1 and 3 appear to act as allosteric modulators rather than pore blockers of Cav2.2, which may play crucial role in attenuating nociception. The results of present research indicated that the ethnopharmacological utilization of V. jatamansi for relieving the abdominal distention and pain may mediate through Cav2.2 channel. Our work is the first demonstration of inhibition of Cav2.2 by iridoids, which may provide a fresh source for finding new analgesics.
RESUMEN
Four new glucosides, named as gigantol-5-O-ß-d-glucopyranoside (1), 9,10-dihydro-aphyllone A-5-O-ß-d-glucopyranoside (2), ficusal-4-O-ß-d-glucopyranoside (3), botrydiol-15-O-ß-d-glucopyranoside (4), together with eight known compounds (5-12) were isolated from the n-BuOH extract of the stems of Dendrobium fimbriatum Hook. Their structures were elucidated by the analyses of spectroscopic data.
Asunto(s)
Dendrobium/química , Glicósidos/química , Glucósidos/química , Glicósidos/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Estructura Molecular , Extractos Vegetales/química , Tallos de la Planta/químicaRESUMEN
Five new oleanane-type triterpene saponins including steganogenin 3-O-ß-D-glucopyranoside (1), steganogenin 3-O-α-L-rhamnopyranosyl-(1â2)-ß-D-glucopyranoside (2), steganogenin 3-O-ß-D-glucopyranosyl-(1â2)-ß-D-glucopyranoside (3), chichipegenin 3-O-α-L-rhamnopyranosyl-(1â2)-ß-D-glucopyranoside (4) and chichipegenin 3-O-ß-D-glucopyranosyl-(1â2)-ß-D-glucopyranoside (5), along with four known oleanane-type triterpenes and triterpene saponins (6-9) were isolated from EtOH extract of the whole plant of Hydrocotyle nepalensis. To the best of our knowledge, oleanane-type triterpenes possessing skeleton with 17, 22-seco-backbone (1-3) are not common in natural products. Compound 8 was isolated as a new natural product. The structures of new compounds were elucidated by extensive spectroscopic methods and chemical evidence. Moreover, the cytotoxic activity of all the isolates against five selected human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW480) was evaluated and the results indicated that compounds 6 and 7 show stronger cytotoxic activity.
Asunto(s)
Antineoplásicos Fitogénicos/química , Centella/química , Ácido Oleanólico/química , Saponinas/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Línea Celular Tumoral/efectos de los fármacos , Humanos , Estructura Molecular , Ácido Oleanólico/aislamiento & purificación , Saponinas/aislamiento & purificaciónRESUMEN
Twenty-one compounds (nine iridoids and twelve sesquiterpenoids), including ten previously unknown (five iridoids and five sesquiterpenoids) were isolated from whole dried material of Valeriana stenoptera. Structures were established on the basis of extensive spectroscopic analysis and the relative stereochemistry of 13-hydroxypatchoulol A was further confirmed by X-ray crystallographic data. All isolates were evaluated for their effects on nerve growth factor (NGF)-mediated neurite outgrowth in pheochromocytoma (PC12) cells and seven compounds showed potent promoting effects.
Asunto(s)
Iridoides/aislamiento & purificación , Iridoides/farmacología , Neuritas/efectos de los fármacos , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/farmacología , Valeriana/química , Animales , Cristalografía por Rayos X , Iridoides/química , Conformación Molecular , Factor de Crecimiento Nervioso , Células PC12 , Raíces de Plantas/química , Ratas , Sesquiterpenos/químicaRESUMEN
Three new iridoids, jatamanvaltrates R-S (1-2) and jatamanin Q (3), as well as three new sesquiterpenoids, valeriananoids D-E (4, 5) and clovane-2ß-isovaleroxy-9α-ol (6), together with nine known compounds were isolated from the roots of Valeriana jatamansi Jones. Compound 2 was the first reported iridoid with fatty acid esters in the Valerianaceae family. The structures of new compounds were established on the basis of extensive spectroscopic analysis. Moreover, all the isolates were evaluated for inhibitory activity on acetylcholinesterase (AChE).
Asunto(s)
Inhibidores de la Colinesterasa/química , Iridoides/química , Raíces de Plantas/química , Sesquiterpenos/química , Valeriana/química , Inhibidores de la Colinesterasa/aislamiento & purificación , Iridoides/aislamiento & purificación , Estructura Molecular , Sesquiterpenos/aislamiento & purificaciónRESUMEN
One new phenanthrene, aphyllone A (1) and four new bibenzyl derivatives, aphyllone B (2) and aphyllals C-D (3-5), together with nine known compounds (6-14), were isolated from the stems of Dendrobium aphyllum (Roxb.) C. E. Fischer. The structures of these new compounds were elucidated by means of extensive spectroscopic analyses, and the absolute configuration of compound 1 was determined by single crystal X-ray diffraction and quantum calculations. Compounds 6, 8 and 14 inhibited NO production at the concentration of 25 µM in LPS-stimulated RAW264.7 cells with the inhibition (%) of 32.48, 35.68, and 38.50. Compound 2 possessed significant DPPH radical scavenging activity with scavenging percentage of 87.97% at the concentration of 100 µg/mL.
Asunto(s)
Dendrobium/química , Fenantrenos/química , Fenoles/química , Animales , Bibencilos/química , Bibencilos/aislamiento & purificación , Línea Celular , Línea Celular Tumoral , Depuradores de Radicales Libres/química , Depuradores de Radicales Libres/aislamiento & purificación , Humanos , Macrófagos/efectos de los fármacos , Ratones , Estructura Molecular , Óxido Nítrico/biosíntesis , Fenantrenos/aislamiento & purificación , Fenoles/aislamiento & purificación , Tallos de la Planta/químicaRESUMEN
ETHNOPHARMACOLOGICAL RELEVANCE: Various species of genus Passiflora have been used as traditional folk medicines owing to their sedative and anti-hypertensive properties. Passiflora edulis Sims most widely grown in the warm temperate for their fragrant fruits and their twigs and leaves are used as a folk medicine for treating both anxiety and nervousness in American countries. The present study was to evaluate the antidepressant-like effect and the active components of this plant. MATERIALS AND METHODS: The alcohol extracts of the stems (PES, 10 and 2 g/kg of the plant materials) and leaves (PEL, 10 and 2 g/kg of the plant materials) of Passiflora edulis Sims were orally administered to mice for 7 day. The animals were tested in the forced swim test (FST) and tail suspension test (TST). After behavioral assay of ethanol extract, phytochemical research of the stems and leaves (5.7 kg) of Passiflora edulis Sims were developed and further bioactive verification of monomeric compounds were conducted. RESULTS: There are mainly cycloartane triterpenoids and their saponins isolated from this plant, including two new cycloartane triterpenoid saponins named cyclopassifloside ХII (1) and ХIII (2), together with six known cycloartane triterpenoids, cyclopassifloic acids B and E, cyclopassiflosides II, VI, IX and XI. The ethanol extract of Passiflora edulis Sims together with isolated compounds cyclopassiflosides IX and XI may possess antidepressant-like effect. CONCLUSIONS: Cycloartane triterpenoid was one of the main compositions of Passiflora edulis Sims and possess antidepressant-like activity.