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Trypanocidal constituents in plants 4. Withanolides from the aerial parts of Physalis angulata.

The constituents of the aerial parts of Physalis angulata (Solanaceae) were investigated based on the plant's trypanocidal activity against epimastigotes of Trypanosoma cruzi, the etiologic agent for Chagas' disease. Four new withanolides were isolated, along with six known ones, from the active fraction. Their structures were determined by spectroscopic analysis. Trypanocidal activity against trypomastigotes, an infectious form of T. cruzi, was also estimated, as well as cytotoxic activity against human uterine carcinoma (HeLa) cells in vitro. Evaluation of trypanocidal activity using the colorimetric reagent Cell Counting Kit-8 was also examined.

Animals↗

Effect of seedling age and water depth on morphological and physiological aspects of transplanted rice under high temperature.

To study the effect of high temperature, rice seedlings 20, 30, 40 and 50 d were kept at 5, 10, 15 and 20 cm water depth in a water pool. Meteorological findings indicated that water temperature varied up to 10 cm but became stable below this depth. Deep water inflicted higher tiller mortality, minimal increase in dry weight of aerial parts and leaf area, decrease in root length, and decrease in root dry weight especially at 20 cm water depth and produced an unbalanced T/R ratio (top versus root dry weight). However, deep water tended to increase plant length. These parameters, however, excel in shallow water. Older seedlings, with the exception of root dry weight, could not perform well compared to young seedlings in all physiological and morphological aspects. The study revealed that seedlings, particularly young ones, stand well in shallow water and can cope with high temperature.

Desiccation↗

Clastogenic effect of Carthamus lanatus L. (Asteraceae).

The clastogenic effect of total dichloromethane, methanol and water extracts, four bioactive fractions and three individual constituents from Carthamus lanatus aerial parts were evaluated in mice by bone marrow chromosome aberration assay with mitomycin C as positive control. Significant differences in the percentage of aberrant mitosis of the extracts were observed. The dichloromethane extract exhibited a considerable clastogenic effect and the water extract a negligible one. Different types of chromosome aberrations and time-dependant effects for the active fractions and individual compounds were found.

Analysis of Variance↗

[Studies on the chemical constituents from the aerial parts of Cimicifuga dahurica].

AIM: To seek for new bioactive constituents from the aerial parts of Cimicifuga dahurica. METHODS: Various column chromatographic techniques were employed for the isolation and purification of the ingredients. The structures were elucidated on the basis of 1H, 13CNMR, 1H-1H COSY, HMQC, NOESY and HMBC spectra and chemical reactions. RESULTS: Two cyclolanostanol xylosides, cimidahuside C and D were isolated from the EtOAc section of EtOH extracts. CONCLUSION: Cimidahuside C(1) and D(2) are new triterpenoid xylosides.

Cimicifuga↗

A novel furostanol saponin from Tribulus terrestris of Bulgarian origin.

The phytochemical investigation of the aerial parts of Tribulus terrestris of Bulgarian origin has resulted in the isolation of the novel furostanol saponin 1, named tribol, together with the known spirostanol saponins 2 and 3 and sitosterol glucoside. The structure of tribol was determined as (25R)-furost-5(6)-ene-3beta,16,26-triol-3-O-alpha-rhamnopyranosyl-(1-->2)-[alpha-rhamnopyranosyl-(1-->4)]-beta-glucopyranoside (1) by spectral analysis, including extensive 1D and 2D-NMR experiments.

Bulgaria↗

A glycosidic isoflavonoid from Viola hondoensis W. BECKER et H. BOISSIEU (Violaceae), and its effect on the expression of matrix metalloproteinase-1 caused by ultraviolet irradiation in cultured human skin fibroblasts.

Isolation of the ethyl acetate soluble fraction from aerial parts of Viola hondoensis W. BECKER et H. BOISSIEU yielded one major isoflavonoid glycoside, tectoridin-4'-O-beta-D-glucoside. The structure of the compound was certainly determined by chemical analyses, as well as 1D- and 2D-NMR spectroscopy. The compound exhibited potent inhibitory activity against the expression of matrix metalloproteinase-1 caused by UV-irradiation in cultured human skin fibroblasts.

Animals↗

Anti-inflammatory activity of Leontopodium alpinum and its constituents.

The aerial parts and roots of Leontopodium alpinum Cass. (Asteraceae) were investigated for their in vivo topical anti-inflammatory activity using the inhibition of Croton oil-induced ear dermatitis in mice. For both of the plant parts, the dichloromethane extract induced a dose-dependent oedema reduction, being more active than the methanol and 70% aqueous methanol ex-tracts. Moreover, the dichloromethane extract of the aerial parts was more active than that of the roots (ID50 = 221 and 338 pg/cm2, respectively). Fatty acids make a significant contribution to the anti-oedema activity of the dichloromethane extract of the aerial parts, whereas bisabolane sesquiterpenes, tricyclic sesquiterpenes, coumarins and lignans are involved in the activity of the root extract. Two bisabolane derivatives reduced also the polymorphonuclear neutrophil leukocytes accumulation in the inflamed tissue, while a 7a-silphiperfol-5-ene type sesquiterpene and a coumarin derivative inhibited the in vitro chemotaxis of these inflammatory cells.

Animals↗

[Chemical constituents of the aerial parts of Rhamnus crenatus].

AIM: To study chemical constituents of the aerial parts of Rhamnus crenatus sieb. et zucc. METHODS: The chemical constituents were isolated by chromatographic methods and their structures were elucidated on the basis of spectral analysis. RESULTS: Five compounds were isolated and their structures were identified as crenatoside (1), torachrysone (2), emodin (3), emodin-1-O-beta-D-glucopyranoside (4) and beta-sitosterol (5) respectively. CONCLUSION: Compound 1 is a new compound and the others were isolated from Rhamnus crenatus for the first time.

Caffeic Acids↗

Antiprotozoal activity of the constituents of Teloxys graveolens.

Antiprotozoal activity-guided fractionation of a methanol extract of the aerial parts of Teloxys graveolens led to the isolation of one coumarinic acid derivative, melilotoside, and five flavonoids, pinocembrine, pinostrobin, chrysin, narcissin and rutin. Among them, melilotoside exhibited the most potent activity toward Entamoeba histolytica and Giardia lamblia (IC(50) 12.5 and 16.8 micro g/mL, respectively). Narcissin showed selectivity against E. histolytlica (IC(50) 17.2 micro g/mL). The results support data for the traditional use of T. graveolens in some gastrointestinal diseases.

Amaranthaceae↗

Cytotoxic saponins from Schefflera rotundifolia.

Eight new oleanane and lupane saponins (1-8) as well as two new benzyl glycosides (9 and 10) were isolated from the aerial parts of Schefflera rotundifolia (Ten) Frodin (Araliaceae) together with two known benzyl glycosides. Their structures were established using 1D- and 2D-NMR spectroscopy and mass spectrometry. The antiproliferative activity of all compounds was evaluated using three continuous murine and human culture cell lines J774.A1, HEK-293, and WEHI-164. Compounds 7 and 8, having betulinic acid as aglycone, were the most active constituents.

Animals↗

Antiprotozoal activity of the constituents of Rubus coriifolius.

Extraction of the aerial parts of Rubus coriifolius, a medicinal plant used by the Maya communities in Southern Mexico to treat bloody diarrhoea, resulted in the isolation of seven known compounds (-)-epicatechin, (+)-catechin, hyperin, nigaichigoside F1, beta-sitosterol 3-O-beta-d-glucopyranoside, gallic acid and ellagic acid. All compounds were tested for their antiprotozoal activity against Entamoeba histolytica and Giardia lambia. Epicatechin was the main responsible for the antiprotozoal activity of the extract against both protozoa, its activity was comparable to emetine, but no exceeded that of metronidazole.

Animals↗

Neuroprotective flavonoids from Flemingia macrophylla.

Using an Abeta-induced neurotoxicity blocking assay to direct fractionation, three new flavonoids, fleminginin (1), flemingichromone (2), and flemingichalcone (3), and twenty known compounds were isolated from the active fractions of the aerial parts of Flemingia macrophylla. The structures of 1 - 3 were elucidated on the basis of spectroscopic data. When tested for neuroprotective activity, compound 2, osajin ( 4), 5,7,4'-trihydroxy-6,8-diprenylisoflavone (5), 5,7,4'-trihydroxy-6,3'-diprenylisoflavone (6), and aureole (7) protected neuronal cells from Abeta-induced damage with EC50 values of 31.43 +/- 3.16, 5.01 +/- 1.28, 11.25 +/-1.51, 4.47 +/- 0.65, 12.09 +/- 2.55 microM, respectively.

Alzheimer Disease↗

Daturametelins H, I, and J: three new withanolide glycosides from Datura metel L.

Three new withanolide glycosides named daturametelins H-J (1-3), together with two known ones, daturataturin A (4) and 7,27-dihydroxy-1-oxowitha-2,5,24-trienolide (5), were isolated from the MeOH extract of the aerial parts of Datura metel L. (Solanaceae). Their structures were determined mainly by spectroscopic techniques including 2D-NMR (HMBC, HMQC, (1)H,(1)H-COSY, NOESY) and MS experiments. Compounds 1-5 were tested for their antiproliferative activity towards the human colorectal carcinoma (HCT-116) cell line. The nonglycosidic compound 5 exhibited the highest activity of the tested withanolides, with an IC(50) value of 3.2+/-0.2 microM (Table 3).

Antineoplastic Agents, Phytogenic↗

Two new eremophilanolides from Xanthium sibiricum.

Two new eremophilanolides, sibiriolides A (1) and B (2), were isolated from the aerial parts of Xanthium sibiricum. The structures of the new compounds were identified as 4S,5R,7R,8R, 11R-2-oxo-1(10)-eremophilen-12,8-olide (1) and 4S,5R,7R,8R,11S-2-oxo-1(10)-eremophilen-12,8-olide (2) by HREIMS and NMR spectroscopic techniques in combination with X-ray crystallographic analysis and CD measurements.

China↗

Cytotoxic constituents from Plumbago zeylanica.

The bioassay-guided fractionation of the dichloromethane extract of aerial parts of Plumbago zeylanica led to the isolation of beta-sitosterol, beta-sitosteryl-3beta-glucopyranoside, beta-sitosteryl-3beta-glucopyranoside-6'-O-palmitate (1), lupenone, lupeol acetate, plumbagin and trilinolein. Compound 1 showed cytotoxic activity against MCF7 and Bowes cancer cell lines (IC50 113 microM and 152 microM, respectively), beta-sitosterol inhibited Bowes cell growth (IC50 36.5 microM) and plumbagin was cytotoxic against MCF7 and Bowes cells (IC50 1.28 microM and 1.39 microM, respectively).

Antineoplastic Agents, Phytogenic↗

Wound healing potential of Tephrosia purpurea (Linn.) Pers. in rats.

Tephrosia purpurea is a well-known herb for its hepatoprotective, anticancer, antiulcer, antibacterial and in healing bleeding piles, etc. The present study was aimed for wound healing potential of ethanolic extract of Tephrosia purpurea (aerial part) in the form of simple ointment using three types of wound models in rats as incision wound, excision wound and dead space wound. The results were comparable to standard drug Fluticasone propionate ointment, in terms of wound contraction, tensile strength, histopathological and biochemical parameters such as hydroxyproline content, protein level, etc. Histopathological study showed significant (P<0.05) increase in fibroblast cells, collagen fibres and blood vessels formation. All parameters were observed significant (P<0.05) in comparison to control group.

Androstadienes↗

Natural phenylpropanoids inhibit lipoprotein-induced endothelin-1 secretion by endothelial cells.

There is increasing evidence that oxidized low-density lipoproteins (Ox-LDL) might be involved in the pathogenesis of atherosclerosis and it has been reported that polyphenols inhibit LDL peroxidation and atherosclerosis. Endothelin-1 (ET-1) is a potent vasoconstrictor peptide isolated from endothelial cells and it induces smooth muscle cell proliferation. ET-1 secretion is increased in atheroma and induces deleterious effects such as vasospasm and atherosclerosis. The goal of this study was to test the effect of four natural phenolic compounds against copper-oxidized LDL (Cu-LDL)-induced ET-1 liberation by bovine aortic endothelial cells (BAEC). The tested compounds were phenylpropanoid glycosides previously isolated from the aerial parts of Marrubium vulgare L. (acteoside 1, forsythoside B 2, arenarioside 3 and ballotetroside 4). ET-1 secretion increased when cells were incubated with Cu-LDL but the compounds 1-4 inhibited this increase. These results were confirmed by quantitative-polymerase chain reaction (QPCR) analysis. Since ET-1 plays an important role in atherosclerosis development, our work suggests that the tested phenylpropanoids could have a beneficial effect in inhibiting atherosclerosis development.

Animals↗

8-hydroxydihydrochelerythrine and 8-hydroxydihydrosanguinarine with a potent acetylcholinesterase inhibitory activity from Chelidonium majus L.

Ethanol extract of the aerial portion of Chelidonium majus L. inhibited acetylcholinesterase (AChE) activity without a significant inhibition of butyrylcholinesterase (BuChE). Using mass spectrometry and NMR studies, three active constituents were isolated and identified: 8-hydroxydihydrochelerythrine (1), 8-hydroxydihydrosanguinarine (2), and berberine (3). Compounds 1-3 showed potent inhibitory activity against AChE, with IC50 (microM) values of 0.61-1.85. Compound 1 exhibited competitive and selective inhibition for AChE.

Acetylcholinesterase↗